Page last updated: 2024-10-15

8-hydroxyguanine

Description

7,8-dihydro-8-oxoguanine: was substituted for guanine at G(8), G(9), G(14), or G(15) in the human telomeric oligonucleotide 5'-d[AGGGTTAG(8)G(9)GTT AG(14)G(15)GTTAGGGTGT]-3' [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

7,8-dihydro-8-oxoguanine : An oxopurine that is guanine in which the hydrogen at position 8 is replaced by an oxo group and in which the nitrogens at positions 7 and 9 each bear a hydrogen. [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 CID135420630
CHEMBL ID1328799
CHEBI ID52617
SCHEMBL ID22144
MeSH IDM0083463

Synonyms (47)

Synonym
2-amino-6,8-dihydroxypurine
5614-64-2
nsc22720
nsc-22720
NCGC00096114-01
einecs 227-035-6
2-aminopurine-6,8-diol
8-hydroxyguanine
1h-purine-6,8-dione, 2-amino-7,9-dihydro-
nsc 22720
8-oxo-7,8-dihydroguanine
CHEBI:52617 ,
2-amino-7,9-dihydro-1h-purine-6,8-dione
2-amino-7,9-dihydro-3h-purine-6,8-dione
7,8-dihydro-8-oxoguanine
AKOS009157521
unii-v5wdn6hy4l
v5wdn6hy4l ,
C20155
AKOS024325917
AKOS006222063
AKOS016002066
FT-0611196
SCHEMBL22144
CHEMBL1328799
2-amino-9h-purine-6,8-diol #
CLGFIVUFZRGQRP-UHFFFAOYSA-N
W-203120
AC-32448
DTXSID10204673
cyclopropa[4,5]benzo[1,2-f]pyrido[1,2-b][1,2,5]thiadiazepine,1,5,6,7,8,8a,9,10-octahydro-,3,3-dioxide
2-amino-6,7,8,9-tetrahydro-1h-purine-6,8-dione
2-amino-purine-6,8-diol
1h-purine-6,8-dione, 2-amino-7,9-dihydro-1h-purine-6,8-dione
HY-113338
CS-0059641
discontinued see a604921
2-amino-1h-purine-6,8(7h,9h)-dione
Q27123514
hypophousphorous acid
2-amino-7h-purine-6,8-diol
E78514
A913728
2-amino-6.8-dihydroxypurine
rac norphenylephrine hydrochloride
(phenylephrine impurity a)
PD101894

Toxicity

ExcerptReference
" This mycotoxin is a frequent contaminant of human and animal food products, and is toxic to all animal species tested."( The role of oxidative stress in the ochratoxin A-mediated toxicity in proximal tubular cells.
de Groene, EM; Fink-Gremmels, J; Maas, RF; Nijmeijer, SM; Roestenberg, P; Schaaf, GJ, 2002
)
" For NTA, the low dose (9 mg/kg per day) was without adverse effect."( NTA and Fe(III)NTA: differential patterns of renal toxicity in subchronic studies.
Deckardt, K; Grundler, O; Jäckh, R; Leibold, E; Mellert, W; Potthoff-Karl, B, 2002
)

Pharmacokinetics

ExcerptReference
" A pharmacokinetic model incorporating separate compartments for O6BG and the O6-benzyl-8-oxoguanine metabolite, first-order conversion of O6BG to the metabolite, and additional first-order elimination rate constants for each compound, was simultaneously fitted to the parent drug and metabolite plasma concentration time data."( Plasma and cerebrospinal fluid pharmacokinetics of O6-benzylguanine and time course of peripheral blood mononuclear cell O6-methylguanine-DNA methyltransferase inhibition in the nonhuman primate.
Balis, FM; Berg, SL; Cole, DE; Gerson, SL; Godwin, K; Liu, L, 1995
)

Bioavailability

ExcerptReference
" In this study, we exposed primary cultured cortical neurons to pulsed RF electromagnetic fields at a frequency of 1800 MHz modulated by 217 Hz at an average special absorption rate (SAR) of 2 W/kg."( Exposure to 1800 MHz radiofrequency radiation induces oxidative damage to mitochondrial DNA in primary cultured neurons.
Chen, C; Chen, Y; He, M; Li, M; Wang, X; Wang, Y; Xu, S; Yu, Z; Zhang, G; Zhang, L; Zhang, W; Zhong, M; Zhou, Z, 2010
)
" In summary, this mechanistic study supports previous conclusions, namely that the repeated inhalation exposure of rats to highly respirable pigment-type iron oxides cause nonspecific pulmonary inflammation which shows a clear dependence on the particle volume-dependent lung overload rather than any increased dissolution and/or bioavailability of redox-active iron."( Siderite (FeCO₃) and magnetite (Fe₃O₄) overload-dependent pulmonary toxicity is determined by the poorly soluble particle not the iron content.
Pauluhn, J; Wiemann, M, 2011
)

Dosage Studied

ExcerptReference
" Data from correlation analysis of the log ratios for normal tissues from cancer were consistent with an age-dependent, dose-response relationship."( Age-related radical-induced DNA damage is linked to prostate cancer.
Barker, EA; Johnson, PM; Malins, DC; Polissar, NL; Vinson, MA; Wheeler, TM, 2001
)
"Recent changes in the risk assessment landscape underscore the need to be able to compare the results of toxicity and dose-response testing between a growing list of animal models and, quite possibly, an array of in vitro screening assays."( Toward a molecular equivalent dose: use of the medaka model in comparative risk assessment.
Deangelo, AB; Hobbie, KR; King, LC; Law, JM; Winn, RN, 2009
)
" The most significant protective effect was demonstrated when 1 mg/kg dosage of C(60)HyFn was administered before irradiation."( Peculiarities of the antioxidant and radioprotective effects of hydrated C60 fullerene nanostuctures in vitro and in vivo.
Andrievsky, GV; Bruskov, VI; Gudkov, SV; Tykhomyrov, AA, 2009
)
" The participating laboratories were successful in finding a dose-response of oxidatively damaged DNA in coded samples, but there remains a need to standardize the protocols to enable direct comparisons between laboratories."( An ECVAG trial on assessment of oxidative damage to DNA measured by the comet assay.
Allione, A; Azqueta, A; Charlton, AJ; Collins, AR; Forchhammer, L; Godschalk, RW; Johansson, C; Jones, GD; Kwok, RW; Langie, SA; Loft, S; Lumeij, S; Matullo, G; Möller, L; Møller, P; Palus, J; Phillips, DH; Porrini, M; Riso, P; Routledge, MN; Sozeri, O; Stepnik, M, 2010
)
" Still, there was linear dose-response relationship for 8-oxo-7,8-dihydroguanine in lung tissue without obvious signs of a threshold."( Oxidatively damaged DNA in animals exposed to particles.
Danielsen, PH; Jantzen, K; Loft, S; Møller, P; Roursgaard, M, 2013
)
", 4 years) treatment with coenzyme Q10 (ubiquinone) at the dosage of 4 mg/kg/d does not affect whole body DNA and RNA oxidation."( The effect of long-term treatment with coenzyme Q10 on nucleic acid modifications by oxidation in children with Down syndrome.
Bergholdt, HKM; Gabrielli, O; Henriksen, T; Larsen, EL; Littarru, GP; Orlando, P; Padella, L; Poulsen, HE; Santoro, L; Tiano, L, 2018
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
oxopurine
[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]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Microtubule-associated protein tauHomo sapiens (human)Potency39.81070.180013.557439.8107AID1468
[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)
Olfactory receptor 51E2Homo sapiens (human)EC50 (µMol)0.00000.00000.07800.5700AID1639697
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
adenylate cyclase-activating G protein-coupled receptor signaling pathwayOlfactory receptor 51E2Homo sapiens (human)
cell migrationOlfactory receptor 51E2Homo sapiens (human)
melanocyte differentiationOlfactory receptor 51E2Homo sapiens (human)
steroid hormone mediated signaling pathwayOlfactory receptor 51E2Homo sapiens (human)
positive regulation of blood pressureOlfactory receptor 51E2Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of smellOlfactory receptor 51E2Homo sapiens (human)
cellular response to fatty acidOlfactory receptor 51E2Homo sapiens (human)
melanocyte proliferationOlfactory receptor 51E2Homo sapiens (human)
positive regulation of renin secretion into blood streamOlfactory receptor 51E2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
nuclear steroid receptor activityOlfactory receptor 51E2Homo sapiens (human)
G protein-coupled receptor activityOlfactory receptor 51E2Homo sapiens (human)
olfactory receptor activityOlfactory receptor 51E2Homo sapiens (human)
signaling receptor activityOlfactory receptor 51E2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membraneOlfactory receptor 51E2Homo sapiens (human)
early endosome membraneOlfactory receptor 51E2Homo sapiens (human)
intracellular organelleOlfactory receptor 51E2Homo sapiens (human)
plasma membraneOlfactory receptor 51E2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (1,255)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (0.88)18.7374
1990's200 (15.94)18.2507
2000's509 (40.56)29.6817
2010's430 (34.26)24.3611
2020's105 (8.37)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 (%)
Trials14 (1.09%)5.53%
Reviews127 (9.85%)6.00%
Case Studies1 (0.08%)4.05%
Observational1 (0.08%)0.25%
Other1,146 (88.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]