Page last updated: 2024-10-15

guanosine

Description

ribonucleoside : Any nucleoside where the sugar component is D-ribose. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135398635
CHEMBL ID375655
CHEBI ID16750
SCHEMBL ID21217
SCHEMBL ID12212184
MeSH IDM0009684

Synonyms (123)

Synonym
guanine-9-beta-d-ribofuranoside
2-amino-1,9-dihydro-9-beta-d-ribofuranosyl-6h-purin-6-one
2(3h)-imino-9-beta-d-ribofuranosyl-9h-purin-6(1h)-one
CHEBI:16750 ,
2-amino-9-beta-d-ribofuranosyl-1,9-dihydro-6h-purin-6-one
guanosin
9-beta-d-ribofuranosyl-guanine
SGCUT00093
6h-purin-6-one, 2-amino-1,9-dihydro-9-beta-d-ribofuranosyl-
vernine (van)
guanine, 9-beta-d-ribofuranosyl- (van)
inosine, 2-amino- (van)
einecs 204-227-8
nsc 19994
9-.beta.-d-ribofuranosylguanine
2(3h)-imino-9-.beta.-d-ribofuranosyl-9h-purin-6(1h)-one
guanozin
usaf cb-11
.beta.-d-ribofuranoside, guanine-9
nsc-19994
inosine, 2-amino-
GUO ,
guanine-9:beta-d-ribofuranoside
guanine, 9.beta.-d-ribofuranosyl-
2-amino-9-.beta.-d-ribofuranosyl-9-h-purine-6(1h)-one
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1h-purin-6-one
9-beta-d-ribofuranosylguanine
ribofuranoside, guanine-9, beta-d-
ai3-52065
inosine, 2-amino
6h-purin-6-one, 2-amino-1,9-dihydro-9-beta-d-ribofuranosyl
gr
9-(beta-d-ribofuranosyl)guanine
beta-d-ribofuranoside, guanine-9
guanine, 9-beta-d-ribofuranosyl-
118-00-3
guanosine ,
ribonucleoside
guanine riboside
vernine
C00387
85-30-3
guanosine, >=98%
TO_000053
guanosine, suitable for cell culture, bioreagent
2FQX
1ODJ
DB02857
NCGC00142496-01
CHEMBL375655
BMSE000091
G0171
AKOS005622500
ST057098
9-[(4s,2r,3r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-aminohydropurin -6-one
AKOS007930368
12133jr80s ,
unii-12133jr80s
2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3h-purin-6-one
A818517
9-(ss--d-ribofuranosyl)guanine
guanine-9-ss--d-ribofuranoside
2-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-purin-6(9h)-one
BMSE001018
bdbm50366814
EPITOPE ID:141493
AKOS015896931
S2439
dl-guanosine
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1h-purin-6-one
gtpl4567
guanosine [inci]
guanosine [who-dd]
2-amino-9-.beta.-d-ribofuranosyl-1,9-dihydro-6h-purin-6-one
guanosine [usp impurity]
2-amino-9-.beta.-d-ribofuranosyl-9h-purine-6(1h)-one
guanosine [mi]
adenosine impurity h [ep impurity]
guanosine [mart.]
AM83933
SCHEMBL21217
2-amino-9-beta-d-ribofuranosyl-9h-purine-6(1h)-one
3h-guanosine
9-beta-d-ribofuranosyl guanine
[3h]-guanosine
ribofuranoside, guanine-9, .beta.-d-
2-amino-1,9-dihydro-9.beta.-d-ribofuranosyl-6h-purin-6-one
6h-purin-6-one, 2-amino-1,9-dihydro-9-.beta.-d-ribofuranosyl-
guanine-9-.beta.-d-ribofuranoside
Q-201301
SCHEMBL12212184
STR04471
9-b-d-ribofuranosylguanine
mfcd00010182
guanosine, >=97.0% (hplc)
guanosine, vetec(tm) reagent grade, >=98%
2-amino-9-beta-d-ribofuranosyl-1,9-dihydro-6h-purin-6-one (guanosine)
2-amino-9-beta-d-ribofuranosyl-1,9-dihydro-6h-purin-6-one; adenosine imp. h (ep); guanosine; adenosine impurity h
NCGC00142496-02
CS-W020018
9-b-d-ribofuranosyl-guanine
9-beta-delta-ribofuranosyl-guanine
2-amino-inosine
beta-delta-ribofuranoside guanine-9
2-amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6h-purin-6-one
b-d-ribofuranoside guanine-9
2-amino-1,9-dihydro-9-b-d-ribofuranosyl-6h-purin-6-one
HY-N0097
AKOS032949764
DTXSID00893055 ,
Q422462
(2r,3r,4s,5r)-2-(2-amino-6-hydroxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
2-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3h-purin-6(9h)-one
CCG-267277
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-purin-6-one
2-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxy-methyl)tetrahydrofuran-2-yl)-1h-purin-6(9h)-one
EN300-204342
Z1741979723
BP-58656
guanosine (mart.)
dtxcid601322998
adenosine impurity h (ep impurity)
guanosine (usp impurity)

Research Excerpts

Overview

Ganosine is a purinergic nucleoside that has been shown to have neuroprotective effects. This guanosine modification is an emerging biomarker for disease detection and determination of 8-OHG in human urine.

ExcerptReference
"Guanosine is a purinergic nucleoside that has been shown to have neuroprotective effects, mainly through its ability to modulate the glutamatergic system. "( Guanosine treatment prevents lipopolysaccharide-induced depressive-like behavior in mice.
da Silva Buss, Z; de Arruda, CM; de Lima Reis, SR; de Lima, E; de Matos, YAV; Doneda, DL; Dos Santos, RAL; Gibbert, PC; Rios Santos, F; Vandresen-Filho, S; Viola, GG, 2023
)
"This guanosine modification is an emerging biomarker for disease detection and determination of 8-OHG in human urine is favored because it is noninvasive to patients."( 8-Hydroxyguanosine as a possible RNA oxidative modification marker in urine from colorectal cancer patients: Evaluation by ultra performance liquid chromatography-tandem mass spectrometry.
Chen, J; Chen, Q; Guo, C; Hu, Y; Yu, J; Zhang, S; Zheng, S, 2020
)
"Guanosine is an endogenous nucleoside with important neuromodulatory and neuroprotective effects."( Guanosine modulates SUMO2/3-ylation in neurons and astrocytes via adenosine receptors.
Cimarosti, HI; Henley, JM; Tasca, CI; Wilkinson, KA; Zanella, CA, 2020
)
"Guanosine is a purine nucleoside that has been shown to exhibit antidepressant effects, but the mechanisms underlying its effect are not well established. "( Antidepressant-like effect of guanosine involves activation of AMPA receptor and BDNF/TrkB signaling.
Bettio, LEB; Dalsenter, Y; Fraga, DB; Freitas, AE; Heinrich, IA; Kaufmann, FN; Leal, RB; Moretti, M; Neis, VB; Platt, N; Rodrigues, ALS; Rosa, PB; Rosado, AF; Tavares, MK; Werle, I, 2021
)
"Guanosine (Guo) is a nucleotide metabolite that acts as a potent neuromodulator with neurotrophic and regenerative properties in neurological disorders. "( Neuroprotective Effects of Guanosine in Ischemic Stroke-Small Steps towards Effective Therapy.
Chojnowski, K; Kowianski, P; Nazar, W; Opielka, M; Smolenski, RT, 2021
)
"Guanosine (GUO) is an endogenous nucleoside involved in extracellular signaling that presents neuroprotective effects and also shows the effect of inducing differentiation in cancer cells."( Guanosine promotes cytotoxicity via adenosine receptors and induces apoptosis in temozolomide-treated A172 glioma cells.
Dal-Cim, TA; Lopes, FG; Nedel, CB; Oliveira, KA; Tasca, CI, 2017
)
"Guanosine is a natural product and an endogenous nucleoside that has shown to increase during myocardial ischemia. "( Guanosine exerts antiplatelet and antithrombotic properties through an adenosine-related cAMP-PKA signaling.
Alarcón, M; Badimon, L; Fuentes, E; Fuentes, F; Fuentes, M; Kachler, S; Klotz, KN; Padró, T; Palomo, I; Vilahur, G, 2017
)
"Guanosine is an important neuromodulator and neuroprotector in the brain and is involved in many pathological conditions, including ischemia and neuroinflammation. "( Subsecond detection of guanosine using fast-scan cyclic voltammetry.
Cryan, MT; Ross, AE, 2018
)
"Guanosine (GUO) is a guanine-based purine that has been extensively described in the literature as an endogenous nucleoside with participation in brain cell signalling pathways. "( Long lasting behavioral and electrophysiological action of early administration of guanosine: Analysis in the adult rat brain.
Abadie-Guedes, R; da Silva, JM; Gondim-Silva, KR; Guedes, RCA; Lopes-de-Morais, AAC, 2019
)
"Guanosine is an important building block for supramolecular gels owing to the unique self-assembly property that results from the unique hydrogen bond acceptors and donor groups. "( The Development and Lifetime Stability Improvement of Guanosine-Based Supramolecular Hydrogels through Optimized Structure.
Chen, M; Hong, L; Ji, N; Lin, W; Zhao, H, 2019
)
"Guanosine (GUO) is an endogenous modulator of glutamatergic excitotoxicity and has been shown to promote neuroprotection in in vivo and in vitro models of neurotoxicity. "( Guanosine controls inflammatory pathways to afford neuroprotection of hippocampal slices under oxygen and glucose deprivation conditions.
Dal-Cim, T; Egea, J; López, MG; Ludka, FK; Martins, WC; Parada, E; Reginato, C; Tasca, CI, 2013
)
"Guanosine is a pleiotropic molecule affecting multiple cellular processes, including cellular growth, differentiation and survival."( Guanosine exerts neuroprotective effects by reversing mitochondrial dysfunction in a cellular model of Parkinson's disease.
Chen, W; Dong, YH; Li, DW; Li, GR; Sun, BQ; Tang, MN; Yao, M, 2014
)
"Guanosine is a guanine-based purine that modulates glutamate uptake and exerts neurotrophic and neuroprotective effects. "( Guanosine prevents behavioral alterations in the forced swimming test and hippocampal oxidative damage induced by acute restraint stress.
Bettio, LE; Farina, M; Freitas, AE; Neis, VB; Ribeiro, CM; Rodrigues, AL; Rosa, PB; Santos, DB, 2014
)
"Guanosine is a purine nucleoside that occurs naturally in the central nervous system, exerting trophic effects. "( The antidepressant-like effect of chronic guanosine treatment is associated with increased hippocampal neuronal differentiation.
Bettio, LE; Brocardo, PS; Christie, BR; Gil-Mohapel, J; Neis, VB; Patten, AR; Pazini, FL; Rodrigues, AL, 2016
)
"Guanosine is a purine nucleoside thought to have neuroprotective properties. "( Guanosine and its role in neuropathologies.
Bettio, LE; Gil-Mohapel, J; Rodrigues, AL, 2016
)
"Guanosine is an important intercellular signalling molecule; it stimulates stem cell proliferation in vivo and affects cholesterol efflux in vitro through activation of ABCG transporter (ABCG1), raising the possibility that it might also affect ABCG2 and hence the SP."( Guanosine-induced decrease in side population of lung cancer cells: lack of correlation with ABCG2 expression.
Jiang, S; Picard, P; Rathbone, MP; Su, C,
)
"8-Oxoguanosine (8-oxoG) is a representative metabolite derived by the oxidation of guanosine (G) and is regarded as a marker of oxidative stress in the cells. "( Synthesis of new derivatives of 8-oxoG-clamp for better understanding the recognition mode and improvement of selective affinity.
Koga, Y; Li, Z; Nakagawa, O; Sasaki, S; Taniguchi, Y, 2010
)
"Guanosine is an extracellular signaling molecule implicated in the modulation of glutamatergic transmission and neuroprotection. "( Guanosine produces an antidepressant-like effect through the modulation of NMDA receptors, nitric oxide-cGMP and PI3K/mTOR pathways.
Bettio, LE; Budni, J; Colla, AR; Cunha, MP; Oliveira, Á; Pazini, FL; Rodrigues, AL, 2012
)
"Guanosine (Guo) is an endogenous neuroprotective molecule of the CNS, which has various acute and long-term effects on both neurones and astroglial cells. "( Guanosine promotes the up-regulation of inward rectifier potassium current mediated by Kir4.1 in cultured rat cortical astrocytes.
Benfenati, V; Caprini, M; Ferroni, S; Nobile, M; Rapisarda, C, 2006
)
"Guanosine appeared to be a specific substrate for N1, while this applies to thymidine for N2."( Characteristics of Na(+)-dependent intestinal nucleoside transport in the pig.
Grenacher, B; Rech, KS; Scharrer, E, 2002
)

Effects

Ganosine (GUO) has been shown to act as a neuroprotective agent against glutamatergic excitotoxicity by increasing glutamate uptake and decreasing its release. Guanosine has been reported to promote reflecting platelet formation in melanin-producing pigment cells.

ExcerptReference
"Guanosine has been reported to elicit antidepressant-like responses in rodents, but if these actions are associated with its ability to afford neuroprotection against glutamate-induced toxicity still needs to be fully understood. "( NMDA receptor-mediated modulation on glutamine synthetase and glial glutamate transporter GLT-1 is involved in the antidepressant-like and neuroprotective effects of guanosine.
Altê, GA; Camargo, A; Dalmagro, AP; Rodrigues, ALS; Tasca, CI; Zeni, ALB, 2023
)
"Guanosine has been shown to potentiate ketamine's antidepressant-like actions, although its ability to augment the anxiolytic effect of ketamine remains to be determined."( Low doses of ketamine and guanosine abrogate corticosterone-induced anxiety-related behavior, but not disturbances in the hippocampal NLRP3 inflammasome pathway.
Camargo, A; Dalmagro, AP; Fraga, DB; Kaster, MP; Rodrigues, ALS; Rosa, JM; Zeni, ALB, 2021
)
"Guanosine has been reported to promote reflecting platelet formation in melanin-producing pigment cells; however, the process of pigment organellogenesis is still unclear."( Unusual light-reflecting pigment cells appear in the Xenopus neural tube culture system in the presence of guanosine.
Fukuzawa, T; Kikuchi, Y, 2018
)
"Guanosine (GUO) has been shown to act as a neuroprotective agent against glutamatergic excitotoxicity by increasing glutamate uptake and decreasing its release. "( Neuroprotection Promoted by Guanosine Depends on Glutamine Synthetase and Glutamate Transporters Activity in Hippocampal Slices Subjected to Oxygen/Glucose Deprivation.
Coelho, V; Dal-Cim, T; Lanznaster, D; Martins, WC; Poluceno, GG; Tasca, CI; Thomaz, DT; Vandresen-Filho, S, 2016
)
"Guanosine has been reported to exert neuroprotective effects. "( Guanine-based purines modulate the effect of L-NAME on learning and memory in rats.
Ballerini, P; Buccella, S; Caciagli, F; Ciccarelli, R; Cicchitti, S; D'Alimonte, I; Di Iorio, P; Giuliani, P; Iacovella, G; Natale, S; Petragnani, N, 2012
)
"Two guanosine analogues have been designed and synthesized by connecting one (1) or three adamantane branches (2). "( From G-quartets to G-ribbon gel by concentration and sonication control.
Liu, K; Mao, Y; Meng, L; Mo, S; Yi, T, 2013
)
"Guanosine (GUO) has been shown to stimulate glutamate uptake in primary astrocyte cultures. "( Extracellular conversion of guanine-based purines to guanosine specifically enhances astrocyte glutamate uptake.
Antunes Soares, FA; Dall'Onder, LP; Frizzo, ME; Lara, DR; Souza, DO; Swanson, RA, 2003
)
"Guanosine has been demonstrated, by infrared and nuclear magnetic resonance spectroscopy, to have a keto-amino structure in neutral aqueous solution and to undergo protonation at N(7) in acid solution."( TAUTOMERISM AND PROTONATION OF GUANOSINE.
FRAZIER, J; HOWARD, FB; MILES, HT, 1963
)
"Guanosine has been shown to modulate glutamate system by stimulating astrocytic glutamate uptake. "( Guanosine selectively inhibits locomotor stimulation induced by the NMDA antagonist dizocilpine.
Dall'Igna, OP; Dietrich, MO; dos Anjos, GM; Lara, DR; Mantese, CE; Souza, DO; Tort, AB, 2004
)
"Guanosine (Guo) has been used in combination with acriflavina to potentiate the latter's antitumor activity, through still unknown mechanisms."( Guanosine promotes B16F10 melanoma cell differentiation through PKC-ERK 1/2 pathway.
Chammas, R; Donatti, L; Luvizon, AC; Mercadante, AF; Nakao, LS; Naliwaiko, K; Zanata, SM, 2008
)
"Isoguanosine has been incorporated into a 34-mer hammerhead ribozyme by the solid-phase phosphoramidite method, using an acetamidine base protecting group. "( Isoguanosine substitution of conserved adenosines in the hammerhead ribozyme.
Benseler, F; Eckstein, F; Ng, MM; Tuschl, T, 1994
)
"Guanosine has been reacted with triformylmethane (TFM) in refluxing pyridine. "( Condensation of triformylmethane with guanosine.
Koissi, N; Kronberg, L; Lönnberg, H; Munter, T; Neuvonen, K,
)
"The guanosine-binding site has been localized to the G264-C311 base pair of the Tetrahymena intron on the basis of analysis of mutations that change the specificity of the nucleophile from G (guanosine) to 2AP (2-aminopurine ribonucleoside) (F."( Mutations at the guanosine-binding site of the Tetrahymena ribozyme also affect site-specific hydrolysis.
Cech, TR; Celander, DW; Herschlag, D; Legault, P, 1992
)

Actions

Ganosine prevented the increase on spinal cord glutamate uptake induced by intraplantar capsaicin. Guanosine promoted an increase in Akt protein phosphorylation. Guanosine did not activate the purinergic P1 receptors.

ExcerptReference
"The guanosine-induced increase in global SUMO2/3-ylation was still observed in the presence of dipyridamole, which prevents guanosine internalization, demonstrating an extracellular guanosine-induced effect."( Guanosine modulates SUMO2/3-ylation in neurons and astrocytes via adenosine receptors.
Cimarosti, HI; Henley, JM; Tasca, CI; Wilkinson, KA; Zanella, CA, 2020
)
"As guanosine plays an important neuroprotective role in the central nervous system, the purpose of this study was to evaluate the neuroprotective effects of guanosine and putative cerebral events following the onset of permanent focal cerebral ischemia."( The potential therapeutic effect of guanosine after cortical focal ischemia in rats.
Almeida, RF; Delgado, CA; Hansel, G; Portela, LV; Quincozes-Santos, A; Ramos, DB; Souza, DG; Souza, DO, 2014
)
"Guanosine plays an important neuroprotective role in several cerebral ischemic models and is involved in the modulation of oxidative responses and glutamatergic parameters."( Guanosine Protects Against Cortical Focal Ischemia. Involvement of Inflammatory Response.
Achaval, M; Duarte, MMMF; Duarte, T; Guella, FL; Hansel, G; Oses, JP; Pettenuzzo, LF; Souza, DO; Tonon, AC, 2015
)
"Guanosine prevented the increase on spinal cord glutamate uptake induced by i.pl."( Spinal mechanisms of antinociceptive action caused by guanosine in mice.
Antunes, C; Böhmer, AE; Elisabetsky, E; Leke, R; Pereira, MS; Schallenberger, C; Schmidt, AP; Souza, DO; Wofchuk, ST, 2009
)
"Guanosine prevented the increase on spinal cord glutamate uptake induced by intraplantar capsaicin."( Mechanisms involved in the antinociception induced by systemic administration of guanosine in mice.
Antunes, C; Böhmer, AE; Elisabetsky, E; Schallenberger, C; Schmidt, AP; Souza, DO; Tavares, RG; Wofchuk, ST, 2010
)
"Guanosine promoted an increase in Akt protein phosphorylation."( Guanosine is neuroprotective against oxygen/glucose deprivation in hippocampal slices via large conductance Ca²+-activated K+ channels, phosphatidilinositol-3 kinase/protein kinase B pathway activation and glutamate uptake.
Dal-Cim, T; Martins, WC; Santos, AR; Tasca, CI, 2011
)
"5. Guanosine prevented the increase in propidium iodide incorporation into cortical slices induced by OGD, indicating a protective role against ischemic injury."( Guanosine enhances glutamate uptake in brain cortical slices at normal and excitotoxic conditions.
Frizzo, ME; Lara, DR; Prokopiuk, Ade S; Salbego, CG; Souza, DO; Vargas, CR; Wajner, M, 2002
)
"Guanosine also did not activate the purinergic P1 receptors, because the A2 receptor antagonists, 1,3-dipropyl-7-methylxanthine (DPMX) or C"( GTP and guanosine synergistically enhance NGF-induced neurite outgrowth from PC12 cells.
Gysbers, JW; Rathbone, MP, 1996
)

Treatment

Ganosine or L-NAME treatment prevented the impaired ATP production, lactate release, and glutamate uptake following OGD/R. Guanosine treatment also increased respiratory control ratio (RCR), an indicator of the state of mitochondrial coupling, which is related to the mitochondrial functionality.

ExcerptReference
"Guanosine or L-NAME treatment prevented the impaired ATP production, lactate release, and glutamate uptake following OGD/R."( Guanosine Neuroprotective Action in Hippocampal Slices Subjected to Oxygen and Glucose Deprivation Restores ATP Levels, Lactate Release and Glutamate Uptake Impairment: Involvement of Nitric Oxide.
Andreguetti, RR; Binder, LB; Corrêa, AW; Scheffer, DDL; Silva, FRMB; Tasca, CI; Thomaz, DT, 2020
)
"Guanosine treatment also increased respiratory control ratio (RCR), an indicator of the state of mitochondrial coupling, which is related to the mitochondrial functionality."( Guanosine protects against behavioural and mitochondrial bioenergetic alterations after mild traumatic brain injury.
Cassol, G; Courtes, AA; da Rosa, PC; de Carvalho, NR; Gonçalves, DF; Hartmann, DD; Royes, LFF; Soares, FAA, 2020
)
"Guanosine treatment also lowered interleukin-1β, interleukin-6, and tumor necrosis factor-α mRNA levels."( Preventive effects of guanosine on intestinal inflammation in 2, 4-dinitrobenzene sulfonic acid (DNBS)-induced colitis in rats.
Bellanca, A; Caldara, G; Di Carlo, M; Nuzzo, D; Serio, R; Zizzo, MG, 2019
)
"The guanosine treatment attenuated the changes in these inflammatory parameters and also reduced the infarct volume, PI incorporation, and number of FJC-positive cells, improving the functional recovery."( Guanosine Protects Against Cortical Focal Ischemia. Involvement of Inflammatory Response.
Achaval, M; Duarte, MMMF; Duarte, T; Guella, FL; Hansel, G; Oses, JP; Pettenuzzo, LF; Souza, DO; Tonon, AC, 2015
)
"Guanosine treatment reduced apoptosis, increased tyrosine hydroxylase-positive dopaminergic neurons and expression of tyrosine hydroxylase in the SNc, increased cellular proliferation in the SNc and subventricular zone, and ameliorated symptoms."( Guanosine improves motor behavior, reduces apoptosis, and stimulates neurogenesis in rats with parkinsonism.
Ballerini, P; Bau, C; Caciagli, F; Ciccarelli, R; D'Alimonte, I; Elfeki, N; Gabriele, J; Jiang, S; Su, C, 2009
)
"The guanosine-treated efferent connections from these animals showed a significant increase in the number and size of synaptic boutons along the efferent fibers when compared with controls."( Guanosine-induced synaptogenesis in the adult brain in vivo.
Gerrikagoitia, I; Martínez-Millán, L, 2009
)
"Guanosine pre-treatment decreased betaA-induced apoptosis (maximal effect after 24 h, 300 microM, p<0.05)."( Guanosine protects SH-SY5Y cells against beta-amyloid-induced apoptosis.
Bau, CJ; Caciagli, F; Ciccarelli, R; Kleywegt, S; Pettifer, KM; Ramsbottom, JD; Rathbone, MP; Vertes, E; Werstiuk, ES, 2004
)
"Guanosine pre-treatment did not affect total spontaneous locomotion in all experiments."( Guanosine selectively inhibits locomotor stimulation induced by the NMDA antagonist dizocilpine.
Dall'Igna, OP; Dietrich, MO; dos Anjos, GM; Lara, DR; Mantese, CE; Souza, DO; Tort, AB, 2004
)
"Pretreatment with guanosine was able to prevent LPS- induced depressive-like behaviors in the TST and FST."( Guanosine treatment prevents lipopolysaccharide-induced depressive-like behavior in mice.
da Silva Buss, Z; de Arruda, CM; de Lima Reis, SR; de Lima, E; de Matos, YAV; Doneda, DL; Dos Santos, RAL; Gibbert, PC; Rios Santos, F; Vandresen-Filho, S; Viola, GG, 2023
)
"Treatment with guanosine restored these parameters."( The potential therapeutic effect of guanosine after cortical focal ischemia in rats.
Almeida, RF; Delgado, CA; Hansel, G; Portela, LV; Quincozes-Santos, A; Ramos, DB; Souza, DG; Souza, DO, 2014
)
"Co-treatment with guanosine, a substrate in the salvage pathway of nucleotide biosynthesis, restored GTP levels and adipogenesis demonstrating the specificity of these effects."( Inhibition of inosine monophosphate dehydrogenase reduces adipogenesis and diet-induced obesity.
Connor, T; de Vries, M; Gunter, JH; Hutley, LJ; Molero, JC; Newell, FS; Prins, JB; Reizes, O; Segal, D; Su, H; Walder, K; Wanyonyi, S; Whitehead, JP, 2009
)
"Treatment with guanosine (1 mg/kg) in parallel with MMF completely reversed MMF activity in vivo, indicating that inhibition of inosine monophosphate dehydrogenase (IMPDH) was responsible for the observed suppressive effects."( Down-regulation of multiple low dose streptozotocin-induced diabetes by mycophenolate mofetil.
Maksimovic-Ivanic, D; Miljkovic, DJ; Mostarica Stojkovic, M; Stosic-Grujicic, S; Trajkovic, V, 2002
)
"Treatment of guanosine with n-propylnitrosourea yields 7-n-propylguanine (after acid hydrolysis) but O6-isopropylguanosine. "( n-Propyldiazonium ion alkylates O6 of guanine with rearrangement, but alkylates N-7 without rearrangement.
Ford, GP; Scribner, JD,
)

Toxicity

We have previously shown that deoxyguanosine (dGuo) is toxic to normal T and B lymphocytes, an effect mediated by intracellular accumulation of guanine ribonucleotides. Hydroxy-nitrobenzylthioguanosine (555) was a less potent inhibitor of 3H-thymidine uptake.

ExcerptReference
" While 10(-5) M MTX was rescued by 10(-3) M leucovorin, rescue of the toxic effect of 10(-4) M MTX by 10(-3) M leucovorin was not observed."( The reversal of methotrexate cytotoxicity to mouse bone marrow cells by leucovorin and nucleosides.
Bull, JM; Chabner, BA; Pinedo, HM; Zaharko, DS, 1976
)
" The combination dCF + cordycepin and alkylating agent mafosfamide were, however, toxic to all the cell lines at the concentrations employed, as well as to CFU-GM and CFU-GEMM."( Selective toxicity of purine nucleosides to human leukaemic cells.
Ganeshaguru, K; Green, ES; Hoffbrand, AV; Piga, A; Sheridan, B, 1989
)
" Hydroxy-nitrobenzylthioguanosine (555) was a less potent inhibitor of 3H-thymidine uptake and was toxic to normal lymphocytes at concentrations inhibiting 3H-thymidine uptake."( Potentiation of methotrexate lymphocytotoxicity in vitro by inhibitors of nucleoside transport.
Hughes, JM; Tattersall, MH, 1989
)
"We have previously shown that deoxyguanosine (dGuo) is toxic to normal T and B lymphocytes, an effect mediated by intracellular accumulation of guanine ribonucleotides."( Expression of deoxyadenosine and deoxyguanosine toxicity at different stages of lymphocyte activation.
Rijkers, GT; Scharenberg, JG; Staal, GE; Toebes, EA; Zegers, BJ, 1988
)
" The drug was found to be toxic to all of the cell lines tested."( Studies on the mechanism of cytotoxicity of 3-deazaguanosine in human cancer cells.
Jacobsen, SJ; Mangum, JH; Nyhan, WL; Page, T; Robins, RK; Scheele, J; Smejkal, RM, 1985
)
" GdR was found to be toxic to T-leukaemia cells."( Differential cytotoxicity of deoxyguanosine and 8-aminoguanosine for human leukemic cell lines and normal bone marrow progenitor cells.
de Fouw, NJ; Gray, DA; Hoffbrand, AV; Ma, DD; Michalevicz, R,
)
" Growth studies with various purine salvage pathway mutants and the ability of guanosine to prevent adenine toxicity indicated that adenine exerts its toxic effects by depleting guanine nucleotide pools."( Mechanism of adenine toxicity in Escherichia coli.
Levine, RA; Taylor, MW, 1982
)
"Ototoxicity is a typical dose-limiting side effect of cancer chemotherapy with cisplatin but much less so with carboplatin."( High accumulation of platinum-DNA adducts in strial marginal cells of the cochlea is an early event in cisplatin but not carboplatin ototoxicity.
Lautermann, J; Liedert, B; Seiler, F; Thomale, J; Thomas, JP, 2006
)
" This induced a toxic effect shown by up-regulation of the alarmin high-mobility group protein B1 and reduced responses in a MTT-assay."( Oligodeoxynucleotides inhibit Toll-like receptor 3 mediated cytotoxicity and CXCL8 release in keratinocytes.
Espevik, T; Grimstad, O; Pukstad, B; Stenvik, J, 2012
)
" Motion imaging analysis revealed the difference in cardiotoxicity between the cardiotoxic BMS-986094 and the less toxic sofosbuvir in hiPSC-CMs, with a minimum of 4 days of treatment."( Chronic cardiotoxicity assessment of BMS-986094, a guanosine nucleotide analogue, using human iPS cell-derived cardiomyocytes.
Hayashi, S; Kanda, Y; Ono, A; Satsuka, A; Yanagida, S, 2021
)
" The primary endpoint was frequency of adverse events and other safety outcomes."( Phase 1 safety, tolerability, pharmacokinetics and pharmacodynamics results of a long-acting C-type natriuretic peptide prodrug, TransCon CNP.
Breinholt, VM; Christoffersen, ED; Mygind, PH; Ota, S; Viuff, D; Will Charlton, R; Zhang, Y, 2022
)
" TransCon CNP was well-tolerated, with no serious treatment-emergent adverse events or discontinuations."( Phase 1 safety, tolerability, pharmacokinetics and pharmacodynamics results of a long-acting C-type natriuretic peptide prodrug, TransCon CNP.
Breinholt, VM; Christoffersen, ED; Mygind, PH; Ota, S; Viuff, D; Will Charlton, R; Zhang, Y, 2022
)

Pharmacokinetics

ExcerptReference
" Thus, the results of this pharmacokinetic study suggest that APD is likely to serve as a better prodrug of DXG and should be considered for clinical trials for antiviral therapy against human immunodeficiency virus and hepatitis B virus."( Pharmacokinetics of (-)-beta-D-2-aminopurine dioxolane and (-)-beta-D-2-amino-6-chloropurine dioxolane and their antiviral metabolite (-)-beta-D-dioxolane guanine in rhesus monkeys.
Boudinot, FD; Chen, H; Chu, CK; Mcclure, HM; Schinazi, RF, 1996
)
" Similar pharmacokinetic profiles for DXG were observed following either route of administration in serum, liver and brain."( Biotransformation and pharmacokinetics of prodrug 9-(beta-D-1,3-dioxolan-4-yl)-2-aminopurine and its antiviral metabolite 9-(beta-D-1,3-dioxolan-4-yl)guanine in mice.
Boudinot, FD; Chu, CK; Manouilov, KK; Manouilova, LS; Schinazi, RF, 1997
)
" A mass balance study of radiolabeled IDX184 and pharmacokinetic studies of IDX184 in portal vein-cannulated monkeys revealed relatively low IDX184 absorption but higher exposure of IDX184 in the portal vein than in the systemic circulation, indicating >90 % of the absorbed dose was subject to hepatic extraction."( Pharmacokinetics of IDX184, a liver-targeted oral prodrug of 2'-methylguanosine-5'-monophosphate, in the monkey and formulation optimization for human exposure.
Bhadresa, S; Bu, C; Cohen, ML; Gasparac, R; Good, SS; Gupta, K; Mayes, BA; Moussa, A; Pan-Zhou, XR; Rashidzadeh, H; Rush, R; Smith, S, 2016
)

Compound-Compound Interactions

O6-benzyl-N2-acetylguanosine (BNAG), an MGMT inhibitor, can be combined with cystemustine by intravenous administration. The increase in lifespan (ILS) of mice treated with 5'-DFUR was augmented by the combination with guanosine or inosine.

ExcerptReference
"Beta-thioguanine deoxyriboside (betaTGdR) is a purine nucleoside derivative which was studied alone or in combination with arabinosyl cytosine (Ara-C) in patients with solid tumors and acute leukemia."( Clinical studies of beta-thioguanine deoxyriboside alone and in combination with arabinosyl cytosine.
Bodey, GP; Freireich, EM; McCredie, KB; Whitecar, JP, 1976
)
" Deoxyguanosine or deoxyadenosine combined with HAG-IQ inhibited cell growth in an additive manner; three-drug combinations, HAG-IQ plus either deoxyguanosine/8-aminoguanosine or deoxyadenosine/deoxycoformycin, were strongly synergistic."( Effects of N-hydroxy-N'-aminoguanidine isoquinoline in combination with other inhibitors of ribonucleotide reductase on L1210 cells.
Cory, JG; Lien, EJ; Weckbecker, A; Weckbecker, G, 1988
)
" The increase in lifespan (ILS) of mice treated with 5'-DFUR was augmented by the combination with guanosine or inosine in a dose-dependent fashion, and the maximum ILS was about 160% with the combination, while that in the case of 5'-DFUR alone was only 48% in the P388 leukemia system."( Potentiation of the chemotherapeutic action of 5'-deoxy-5-fluorouridine in combination with guanosine and related compounds.
Iigo, M; Ishitsuka, H; Miwa, M; Nitta, K, 1987
)
"The anti-tumour activity of acriflavine in combination with guanosine has been evaluated in solid or ascitic tumour-implanted animal models."( Enhanced anti-tumour effects of acriflavine in combination with guanosine in mice.
Ahn, ET; Han, YB; Hong, EK; Kim, CW; Kim, SG; Lee, KY; Yoo, BI, 1997
)
" Previously, we have shown that O6-benzyl-N2-acetylguanosine (BNAG), an MGMT inhibitor, can be combined with cystemustine by intravenous administration, and increases the antitumour effect of cystemustine in resistant human melanoma."( Melanoma-cell toxicity of cystemustine combined with O6-benzyl-N2-acetylguanosine.
Buchdahl, C; Debiton, E; Glasser, AL; Laval, F; Madelmont, JC; Mounetou, E; Rolhion, C, 1998
)
"A simple, fast and inexpensive method based on dispersive solid phase extraction (DSPE) combined with LC-MS was developed for simultaneous determination of 7 nucleosides and nucleobases (i."( Determination of the nucleosides and nucleobases in Tuber samples by dispersive solid-phase extraction combined with liquid chromatography-mass spectrometry.
Li, HM; Li, YY; Liu, P; Tang, YJ; Wan, DJ, 2011
)

Bioavailability

ExcerptReference
" Pharmacokinetic analysis of BzDAG in the rat showed it to be 48% orally bioavailable (at a dose of 5 mg/kg)."( Purine nucleoside phosphorylase inhibitors: biochemical and pharmacological studies with 9-benzyl-9-deazaguanine and related compounds.
Allan, PW; Bennett, LL; Erion, MD; Montgomery, JA; Niwas, S; Noker, PE; Rose, LM, 1993
)
" Oral bioavailability of DAPD was estimated to be approximately 30%."( Pharmacokinetics of (-)-beta-D-dioxolane guanine and prodrug (-)-beta-D-2,6-diaminopurine dioxolane in rats and monkeys.
Boudinot, FD; Chen, H; Chu, CK; Gao, Z; McClure, HM; Rajagopalan, P; Schinazi, RF, 1999
)
" However, the combination of AZT with DXG or its orally bioavailable prodrug (-)-beta-D-2, 6-diaminopurine-dioxolane should be explored because of the suppressive effects of the K65R and L74V mutations on AZT resistance."( In vitro selection of mutations in the human immunodeficiency virus type 1 reverse transcriptase that decrease susceptibility to (-)-beta-D-dioxolane-guanosine and suppress resistance to 3'-azido-3'-deoxythymidine.
Bazmi, HZ; Cavalcanti, SC; Chu, CK; Hammond, JL; Mellors, JW; Schinazi, RF, 2000
)
" The modulation of transporters during differentiation could potentially regulate drug bioavailability and cytotoxicity and should be evaluated prior to combining differentiating agents with traditional nucleoside analogs in the treatment of APL."( Nucleoside transporter expression and activity is regulated during granulocytic differentiation of NB4 cells in response to all-trans-retinoic acid.
Flanagan, SA; Meckling, KA, 2007
)
" administration of the combination mixture, resulting in a 2 fold increase in the bioavailability (BA) of PRF The concentrations of TRF and PRF in all the tissues examined were similar in the groups given the mixture and ACF."( Effects of guanosine on the pharmacokinetics of acriflavine in rats following the administration of a 1:1 mixture of acriflavine and guanosine, a potential antitumor agent.
Chung, YB; Hong, JT; Lee, KM; Lee, PS; Moon, DC; Shin, DH; Song, S; Yoo, HS, 2007
)
" This study provides a direct link between oxidative stress and the enzymatic control of the NO bioavailability at the cellular level and endows with further insight into fundamental mechanisms underlying pancreatic disorders associated with disruptions in the L-arginine-NO-cGMP signalling enzyme cascade."( L-arginine-NO-cGMP signalling pathway in pancreatitis.
Bankfalvi, A; Boecker, W; Buchwalow, I; Neumann, J; Poremba, C; Samoilova, V; Schleicher, C; Schnekenburger, J; Tiemann, K, 2013
)
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)

Dosage Studied

The level of damaged RNA, measured by the content of 8-hydroxyguanosine (7,8-dihydro-8-oxoguanosine, 8-oxoG), increases depending on H2O2 dosage and is inversely correlated with cell viability. Guanosine-loaded microspheres could be prepared for once-a-week intravitreal injection.

ExcerptReference
" The same dosage of tolerogen did not reverse a strongly established anti-nucleoside antibody production after a tertiary response."( Nucleoside specificity in the carrier IgG-dependent induction of tolerance.
Borel, Y; Stollar, BD, 1976
)
" However, on increasing the concentrations of these agents, the reversing effect of guanylic acid decreased gradually, the dose-response curves for the two agents being similar."( Effect of bredinin and its aglycone on L5178Y cells.
Hayano, K; Ishida, N; Mizuno, K; Sakaguchi, K; Tsujino, M, 1975
)
" Moderate rhinovirus activity was observed for several compounds at nontoxic dosage levels."( Imidazo[1,2-a]-s-triazine nucleosides. Synthesis and antiviral activity of the N-bridgehead guanine, guanosine, and guanosine monophosphate analogues of imidazo[1,2-a]-s-triazine.
Allen, LB; Bartholomew, DG; Kim, SH; Revankar, GR; Robins, RK, 1978
)
" Preincubation of contracted artery rings with GTP (100 microM) or guanosine (100 microM) before eliciting relaxations with nitrovasodilators significantly shifted the dose-response curves of nitrocompounds to the left and augmented the increases in cyclic GMP."( Modification of nitrovasodilator effects on vascular smooth muscle by exogenous GTP and guanosine.
Laustiola, KE; Manninen, V; Metsä-Ketelä, T; Pörsti, I; Vapaatalo, H; Vuorinen, P, 1991
)
" Other findings of major interest to us were the different dosing characteristics of sulfinosine and 6TGR, the divergent efficiencies of the two drugs in generating cellular resistance, and the activity of sulfinosine against experimental leukemias refractory to 6TGR and other experimental or clinically used chemotherapeutic agents."( Chemotherapeutic characterization in mice of 2-amino-9-beta-D-ribofuranosylpurine-6-sulfinamide (sulfinosine), a novel purine nucleoside with unique antitumor properties.
Avery, TL; Finch, RA; Hanna, NB; Radparvar, S; Revankar, GR; Robins, RK; Vasquez, KM, 1990
)
" Dose-response profiles for inductive responses appear to correlate with apparent Kd values for low-affinity nucleoside binding sites; dose-response curves for antigen-dependent differentiative responses correlate with apparent Kd values for high-affinity binding sites."( B lymphocytes from hyporesponsive SJL mice contain aberrant nucleoside binding sites.
Goodman, MG, 1990
)
" BNU and N-methyl-N-nitrosourea dose-response curves for cell killing suggests that both AT and excision may be involved in the repair of cytotoxic lesions."( Evidence for the excision repair of O6-n-butyldeoxyguanosine in human cells.
Boyle, JM; Margison, GP; Saffhill, R, 1986
)
" As an adjuvant for in vitro antibody responses, however, 7m8oGuo achieves the same degree of immunoenhancement as 8MGuo but at approximately 10-fold lower concentrations, that is, the dose-response profile has been shifted to the left."( Distinct effects of dual substitution on inductive and differentiative activities of C8-substituted guanine ribonucleosides.
Goodman, MG; Hennen, WJ, 1986
)
" Unresponsiveness is not attributable to a shift in either the dose-response or kinetic profiles, nor can the presence of suppressor cells be demonstrated."( Dissociation of inductive from differentiative signals transmitted by C8-substituted guanine ribonucleosides to B cells from SJL mice.
Goodman, MG; Weigle, WO, 1985
)
" Dose-response experiments indicated that the GTP pool was significantly reduced (65% of control) at 25 microM ribavirin, and increasing concentrations of the drug caused only a small further reduction in the GTP pool (5-10% at 100 microM)."( Mode of action of ribavirin: effect of nucleotide pool alterations on influenza virus ribonucleoprotein synthesis.
Gilbert, BE; Knight, V; Noall, MW; Wray, SK, 1985
)
"The dose-response effects of intracerebroventricular (i."( Lack of effect of 1-methylisoguanosine on sleep in rats.
Crane, RC; Radulovacki, M; Rapoza, D; Virus, RM, 1985
)
" Dose-response curves to intravenously administered 1-methylisoguanosine and adenosine in anaesthetized rats demonstrated qualitatively similar decreases in blood pressure and heart rate, with 1-methylisoguanosine being two to three times more potent than adenosine."( The cardiovascular actions of 1-methylisoguanosine.
Marwood, JF,
)
" In murine B cells, two distinct binding activities have been characterized that have dissociation constants that parallel their distinctive dose-response profiles."( Topology of the loxoribine binding site. Studies with inactive loxoribine analogues.
Goodman, JH; Goodman, MG, 1994
)
" In spite of common gene dosage effects, unexpected and highly significant differences were noted between Down's syndrome patients without complications and those presenting with additional psychotic features."( Differences in purine metabolism in patients with Down's syndrome.
Cattaneo, F; Lejeune, J; Megarbane, A; Peeters, MA; Rethore, MO, 1993
)
"3 kb repeat units, and could thus give rise to double dosage levels of an X-linked gene."( Long-range sequence analysis in Xq28: thirteen known and six candidate genes in 219.4 kb of high GC DNA between the RCP/GCP and G6PD loci.
Burough, F; Chen, CN; Chen, EY; Ciccodicola, A; D'Urso, M; Heiner, C; Mazzarella, R; Repetto, M; Schlessinger, D; Zollo, M; Zuo, L, 1996
)
" Also, dosage with guanosine produces region-specific influences on the production of xanthophores from wild-type embryos."( Anterior/posterior influences on neural crest-derived pigment cell differentiation.
Gerard, P; Holder, S; Thibaudeau, G, 1998
)
" Guanosine-loaded microspheres could be prepared for once-a-week intravitreal injection with minimum required concentration maintained throughout the dosing interval."( Kinetics of a model nucleoside (guanosine) release from biodegradable poly(DL-lactide-co-glycolide) microspheres: a delivery system for long-term intraocular delivery.
Chowdhury, DK; Mitra, AK, 2000
)
" Peak concentrations of DXGTP were obtained 8 h after dosing and were measurable through 48 h postdose."( Enzymatic assay for measurement of intracellular DXG triphosphate concentrations in peripheral blood mononuclear cells from human immunodeficiency virus type 1-infected patients.
Back, DJ; Hart, R; Hoggard, PG; Kewn, S; Khoo, SH; MacNeela, JP; Rousseau, F; Wang, LH, 2003
)
" The complexity of these dose-response relationships is likely due to the dual role of peroxynitrite as both an oxidant and a nucleophile in competition with water."( Quantitation of four guanine oxidation products from reaction of DNA with varying doses of peroxynitrite.
Tannenbaum, SR; Venkatarangan, L; Wishnok, JS; Yu, H, 2005
)
" However, dosing with masked oral prodrugs of TLR7 agonists, such as ANA-975, limits the adverse events associated with the activation of responsive gastrointestinal immune tissue."( Masked oral prodrugs of toll-like receptor 7 agonists: a new approach for the treatment of infectious disease.
Averett, D; Fletcher, S; Steffy, K, 2006
)
" The level of damaged RNA, measured by the content of 8-hydroxyguanosine (7,8-dihydro-8-oxoguanosine, 8-oxoG), increases depending on H2O2 dosage and is inversely correlated with cell viability."( Human polynucleotide phosphorylase reduces oxidative RNA damage and protects HeLa cell against oxidative stress.
Li, Z; Wu, J, 2008
)
" A concentration of 100 micromol/L (50 mg/L) AcMPAG, which provided effective inhibition of cell proliferation according to dose-response curves, was selected for gene expression analysis on microarray, verified by quantitative real-time polymerase chain reaction on the LightCycler."( Regulation of IL2 and NUCB1 in mononuclear cells treated with acyl glucuronide of mycophenolic acid reveals effects independent of inosine monophosphate dehydrogenase inhibition.
Armstrong, VW; Heller, T; Hitt, R; Oellerich, M; Petrova, DT; Shipkova, M; Wieland, E, 2009
)
" Following oral dosing (3mg/kg) in Beagle dogs, high levels (>9."( Discovery of GS-9131: Design, synthesis and optimization of amidate prodrugs of the novel nucleoside phosphonate HIV reverse transcriptase (RT) inhibitor GS-9148.
Birkus, G; Boojamra, CG; Cihlar, T; Desai, MC; Douglas, JL; Gao, Y; Grant, D; Hui, HC; Laflamme, G; Lin, KY; Mackman, RL; Markevitch, DY; McDermott, M; Mishra, R; Pakdaman, R; Petrakovsky, OV; Ray, AS; Vela, JE; Zhang, L, 2010
)
" In this study, we have examined the dose-response relationship for the formation of the above four products arising in calf thymus DNA exposed to gamma irradiation, photoactivated rose bengal, and two sources of peroxynitrite."( Comparative analysis of four oxidized guanine lesions from reactions of DNA with peroxynitrite, singlet oxygen, and γ-radiation.
Cui, L; Dedon, PC; Prestwich, EG; Taghizadeh, K; Tannenbaum, SR; Wishnok, JS; Ye, W, 2013
)
" The most appropriate approach to use in low dose-response assessment must be approved on the basis of scientific judgment."( Qualitative and quantitative approaches in the dose-response assessment of genotoxic carcinogens.
Fukushima, S; Gi, M; Kakehashi, A; Matsumoto, M; Wanibuchi, H, 2016
)
"Safety and PD data from this phase 1 trial support that TransCon CNP is well tolerated, with a PK profile compatible with a once-weekly dosing regimen."( Phase 1 safety, tolerability, pharmacokinetics and pharmacodynamics results of a long-acting C-type natriuretic peptide prodrug, TransCon CNP.
Breinholt, VM; Christoffersen, ED; Mygind, PH; Ota, S; Viuff, D; Will Charlton, R; Zhang, Y, 2022
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fundamental metaboliteAny metabolite produced by all living cells.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
guanosinesAny purine ribonucleoside that is a derivative of guanosine.
purines D-ribonucleosideA purine ribonucleoside that is a purine derivative attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (19)

PathwayProteinsCompounds
guanine and guanosine salvage II17
guanine and guanosine salvage III010
purine nucleosides salvage II (plant)419
guanosine nucleotides degradation II125
superpathway of purines degradation in plants745
superpathway of guanosine nucleotides degradation (plants)227
guanosine nucleotides degradation I226
purine nucleotides degradation I (plants)334
Purine nucleotides and Nucleosides metabolism ( Purine nucleotides and Nucleosides metabolism )10577
Guanosine + Orthophosphate = Guanine + D-Ribose 1-phosphate ( Purine nucleotides and Nucleosides metabolism )13
Purine metabolism1336
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-20490
The impact of Nsp14 on metabolism (COVID-19 Disease Map)084
salvage pathways of purine nucleosides021
purine and pyrimidine metabolism032
salvage pathways of guanine, xanthine, and their nucleosides017
salvage pathways of purine nucleosides I027
Biochemical pathways: part I0466
Purine metabolism and related disorders2353

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency3.98110.125919.1169125.8920AID2549
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AdenosylhomocysteinaseHomo sapiens (human)Ki1,472.00000.00000.18991.9300AID199747
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Membrane lipoprotein tmpCTreponema pallidumKd0.07100.07100.18370.2700AID977611
Chain A, Membrane lipoprotein tmpCTreponema pallidumKd0.07100.07100.18370.2700AID977611
Chain A, Membrane lipoprotein tmpCTreponema pallidumKd0.07100.07100.18370.2700AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AdenosylhomocysteinaseHomo sapiens (human)Km844.00000.82001.66002.5000AID199751
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
urate biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of T cell proliferationPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of alpha-beta T cell differentiationPurine nucleoside phosphorylaseHomo sapiens (human)
allantoin metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nucleobase-containing compound metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyinosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyadenosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
purine ribonucleoside salvagePurine nucleoside phosphorylaseHomo sapiens (human)
IMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nicotinamide riboside catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
immune responsePurine nucleoside phosphorylaseHomo sapiens (human)
nucleotide biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
response to xenobiotic stimulusPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of interleukin-2 productionPurine nucleoside phosphorylaseHomo sapiens (human)
purine-containing compound salvagePurine nucleoside phosphorylaseHomo sapiens (human)
dAMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
one-carbon metabolic processAdenosylhomocysteinaseHomo sapiens (human)
S-adenosylmethionine cycleAdenosylhomocysteinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
nucleoside bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine nucleobase bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
phosphate ion bindingPurine nucleoside phosphorylaseHomo sapiens (human)
identical protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
guanosine phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
adenosylhomocysteinase activityAdenosylhomocysteinaseHomo sapiens (human)
protein bindingAdenosylhomocysteinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
extracellular regionPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
cytosolPurine nucleoside phosphorylaseHomo sapiens (human)
secretory granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
extracellular exosomePurine nucleoside phosphorylaseHomo sapiens (human)
ficolin-1-rich granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
nucleusAdenosylhomocysteinaseHomo sapiens (human)
endoplasmic reticulumAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
melanosomeAdenosylhomocysteinaseHomo sapiens (human)
extracellular exosomeAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (46)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID610952Neuroprotective activity against MPP+-induced neuronal cell death in human SH-SY5Y cells assessed as cell viability at 10 uM pretreated for 2 hrs before MPP+ administration measured after 4 hrs by MTT assay2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Bioactive neo-clerodane diterpenoids from the whole plants of Ajuga ciliata Bunge.
AID1296048Induction of phenotypic perturbation in human ONS cells assessed as decrease in EEA1-associated early endosomes level in at 10 uM after 24 hrs by EEA1 staining based assay relative to control2016Journal of natural products, Feb-26, Volume: 79, Issue:2
A Grand Challenge: Unbiased Phenotypic Function of Metabolites from Jaspis splendens against Parkinson's Disease.
AID1452128Inhibition of ATPgammaS-BODIPY binding to Thermotoga maritima His-tagged HK853 expressed in Escherichia coli BL21(DE3)pLysS Rosetta preincubated for 30 mins prior to ATPgammaS-BODIPY addition measured after 1 hr by coomassie staining-based SDS-PAGE analys2017Journal of medicinal chemistry, 10-12, Volume: 60, Issue:19
Rational Design of Selective Adenine-Based Scaffolds for Inactivation of Bacterial Histidine Kinases.
AID82319Inhibitory activity against cellular replication in hypoxanthine-guanine phosphoribosyltransferase (HGPRT-) HL-60 cells.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.
AID157569Antiviral activity against human peripheral blood mononuclear cells, infected with HIV-1(strain LAV)1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes.
AID584550Cytotoxicity against mouse J774A1 cells2010Antimicrobial agents and chemotherapy, Dec, Volume: 54, Issue:12
Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.
AID155467The compound was tested for toxicity in peripheral blood mononuclear cells1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes.
AID636717Neuroprotective activity against MPP+-induced human SH-SY5Y cell death assessed as cell viability at 3 uM pretreated for 2 hrs prior to MPP+ induction by MTT assay relative to control2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Bioactive myrsinol diterpenoids from the roots of Euphorbia prolifera.
AID199616Enzyme catalytic rate kinetic constant for S-adenosyl-L-homocysteine hydrolase2003Bioorganic & medicinal chemistry letters, Jun-16, Volume: 13, Issue:12
Unexpected inhibition of S-adenosyl-L-homocysteine hydrolase by a guanosine nucleoside.
AID199747Inhibitory activity against S-adenosyl-L-homocysteine hydrolase was determined2003Bioorganic & medicinal chemistry letters, Jun-16, Volume: 13, Issue:12
Unexpected inhibition of S-adenosyl-L-homocysteine hydrolase by a guanosine nucleoside.
AID278367Effect on metabolism of 40 ug/ml RBV in Vero E6 cells assessed as RBV-MP concentration at 10 ug/ml after 24 h2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID199751Enzyme kinetic constant for S-adenosyl-L-homocysteine hydrolase2003Bioorganic & medicinal chemistry letters, Jun-16, Volume: 13, Issue:12
Unexpected inhibition of S-adenosyl-L-homocysteine hydrolase by a guanosine nucleoside.
AID158514Activity against Plasmodium berghei in mice (Mus musculus)1980Journal of medicinal chemistry, Apr, Volume: 23, Issue:4
Synthesis of potential inhibitors of hypoxanthine-guanine phosphoribosyltransferase for testing as antiprotozoal agents. 1. 7-Substituted 6-oxopurines.
AID1136399Activity of human erythrocyte purine nucleoside phosphorylase assessed as ribose relase at 5 umol after 30 mins by orcinol reaction relative to guanosine1978Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
Stereoelectronic factors in the binding of substrate analogues and inhibitors to purine nucleoside phosphorylase isolated from human erythrocytes.
AID610951Neuroprotective activity against MPP+-induced neuronal cell death in human SH-SY5Y cells assessed as cell viability at 3 uM pretreated for 2 hrs before MPP+ administration measured after 4 hrs by MTT assay2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Bioactive neo-clerodane diterpenoids from the whole plants of Ajuga ciliata Bunge.
AID278357Increase in GTP level in Vero E6 cells at 35 uM after 24 hr relative to control2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID584547Antibacterial activity against Bacillus anthracis Sterne 34F2 infected in mouse J774A.1 cells assessed as protection against bacteria-induced cytotoxicity using propidium iodide staining after 3 hrs measured every hours for up to 7 hrs2010Antimicrobial agents and chemotherapy, Dec, Volume: 54, Issue:12
Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.
AID278356Inhibition of 1 ug/ml RBV-induced depression in intracellular GTP level in Vero E6 cells at 35 uM after 24 h2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID1296049Induction of phenotypic perturbation in human ONS cells assessed as decrease in autophagy markers level in at 10 uM after 24 hrs relative to control2016Journal of natural products, Feb-26, Volume: 79, Issue:2
A Grand Challenge: Unbiased Phenotypic Function of Metabolites from Jaspis splendens against Parkinson's Disease.
AID106497Compound was tested for its cytotoxicity against MGL-8 B -lymphoblasts1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
9-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)guanine: a metabolically stable cytotoxic analogue of 2'-deoxyguanosine.
AID666651Metabolic stability in Wistar rat liver homogenates assessed as increase in guanine formation by HPLC analysis2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis and in vitro stability of nucleoside 5'-phosphonate derivatives.
AID217743The compound was tested for toxicity in Vero cells1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes.
AID1136400Activity of human erythrocyte purine nucleoside phosphorylase assessed as ribose relase after 30 mins by Lineweaver-Burk plot analysis1978Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
Stereoelectronic factors in the binding of substrate analogues and inhibitors to purine nucleoside phosphorylase isolated from human erythrocytes.
AID217433Antiviral activity against Vero cells, infected with HSV-11991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes.
AID636715Neuroprotective activity against MPP+-induced human SH-SY5Y cell death assessed as cell viability at 30 uM pretreated for 2 hrs prior to MPP+ induction by MTT assay relative to control2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Bioactive myrsinol diterpenoids from the roots of Euphorbia prolifera.
AID636716Neuroprotective activity against MPP+-induced human SH-SY5Y cell death assessed as cell viability at 10 uM pretreated for 2 hrs prior to MPP+ induction by MTT assay relative to control2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Bioactive myrsinol diterpenoids from the roots of Euphorbia prolifera.
AID93194Ability to inhibit hypoxanthine-guanine phosphoribosyltransferase in crude extracts of H.Ep.-2 cells.1980Journal of medicinal chemistry, Apr, Volume: 23, Issue:4
Synthesis of potential inhibitors of hypoxanthine-guanine phosphoribosyltransferase for testing as antiprotozoal agents. 1. 7-Substituted 6-oxopurines.
AID71650Inhibitory activity against cellular replication in Friend erythroleukemia cells as growth inhibition.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.
AID610953Neuroprotective activity against MPP+-induced neuronal cell death in human SH-SY5Y cells assessed as cell viability at 30 uM pretreated for 2 hrs before MPP+ administration measured after 4 hrs by MTT assay2011Journal of natural products, Jul-22, Volume: 74, Issue:7
Bioactive neo-clerodane diterpenoids from the whole plants of Ajuga ciliata Bunge.
AID278355Inhibition of 40 ug/ml RBV-induced depression in intracellular GTP level in Vero E6 cells at 35 uM after 24 h2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID71649Inhibitory activity against cellular differentiation in Friend erythroleukemia cells as percentage of benzidine - positive cells.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.
AID584546Inhibition of inosine/L-alanine-induced Bacillus anthracis Sterne 34F2 spore germination pretreated for 15 mins before inosine/L-alanine challenge2010Antimicrobial agents and chemotherapy, Dec, Volume: 54, Issue:12
Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.
AID209954Compound was tested for its cytotoxicity against T- cell line1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
9-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)guanine: a metabolically stable cytotoxic analogue of 2'-deoxyguanosine.
AID613867Inhibition of N-terminal His6-tagged Trypanosoma brucei CTPS assessed as NH3-dependent CTP formation by continuous spectrophotometric assay2011Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18
Activation and inhibition of CTP synthase from Trypanosoma brucei, the causative agent of African sleeping sickness.
AID666648Half life in Wistar rat liver homogenates at 50 uM by HPLC analysis2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis and in vitro stability of nucleoside 5'-phosphonate derivatives.
AID278354Inhibition of MPA effect on viral RNA in HTNV 76-118-infected Vero E6 cells at 35 uM2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID278366Effect on metabolism of 10 ug/ml RBV in Vero E6 cells assessed as RBV-MP concentration at 10 ug/ml after 24 h2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID278376Effect on metabolism of 10 ug/ml RBV in Vero E6 cells assessed as RBV-TP concentration at 10 ug/ml after 24 h2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID278377Effect on metabolism of 40 ug/ml RBV in Vero E6 cells assessed as RBV-TP concentration at 10 ug/ml after 24 h2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activity of ribavirin against Hantaan virus correlates with production of ribavirin-5'-triphosphate, not with inhibition of IMP dehydrogenase.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2006The Journal of biological chemistry, Mar-24, Volume: 281, Issue:12
The PnrA (Tp0319; TmpC) lipoprotein represents a new family of bacterial purine nucleoside receptor encoded within an ATP-binding cassette (ABC)-like operon in Treponema pallidum.
AID1811Experimentally measured binding affinity data derived from PDB2006The Journal of biological chemistry, Mar-24, Volume: 281, Issue:12
The PnrA (Tp0319; TmpC) lipoprotein represents a new family of bacterial purine nucleoside receptor encoded within an ATP-binding cassette (ABC)-like operon in Treponema pallidum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4,280)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901444 (33.74)18.7374
1990's675 (15.77)18.2507
2000's1035 (24.18)29.6817
2010's838 (19.58)24.3611
2020's288 (6.73)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials26 (0.59%)5.53%
Reviews136 (3.06%)6.00%
Case Studies14 (0.32%)4.05%
Observational6 (0.14%)0.25%
Other4,260 (95.90%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]