Page last updated: 2024-12-06

aristeromycin

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Description

Aristeromycin is a naturally occurring nucleoside antibiotic produced by Streptomyces hygroscopicus. It is a potent inhibitor of adenosine deaminase (ADA), an enzyme that converts adenosine to inosine, and it has been studied extensively for its potential as an antiviral and antitumor agent. Aristeromycin is a structural analog of adenosine and can be synthesized by a variety of chemical methods. It was discovered in 1967 and has been shown to have a wide range of biological activities, including antiviral, antibacterial, and antitumor activity. Aristomycin has been shown to inhibit the growth of a variety of cancer cell lines in vitro and in vivo, and it has also been shown to be effective against a variety of viral infections, including herpes simplex virus, influenza virus, and HIV. The mechanism of action of aristomycin is thought to be related to its ability to inhibit the synthesis of DNA and RNA. Aristomycin has also been shown to have immunomodulatory properties and can stimulate the production of interferon, a protein that is important for the body's immune response. Aristomycin has been studied extensively for its potential as a therapeutic agent. It has been used in clinical trials for the treatment of a variety of diseases, including cancer, viral infections, and autoimmune diseases. However, aristomycin has shown significant toxicity in humans, and its clinical use has been limited. Despite its toxicity, aristomycin remains an important research tool and a potential lead compound for the development of new antiviral and antitumor agents.'

aristeromycin: RN given refers to (1R-(1alpha,2alpha,3beta,5alpha)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65269
CHEMBL ID49935
SCHEMBL ID692209
MeSH IDM0095338

Synonyms (24)

Synonym
1,2-cyclopentanediol, 3-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)-, (1r,2s,3r,5r)-
nsc 103526
19186-33-5
nsc103526
aristeromycin
cycloadenosine
(1r,2s,3r,5r)-3-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
avs-12219
(-)-.beta.-d-aristeromycin
(1r,2s,3r,5r)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
.beta.-d-carbocyclic adenosine
(1r,2s,3r,5r)-3-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
bdbm50088426
CHEMBL49935 ,
SCHEMBL692209
UGRNVLGKAGREKS-GCXDCGAKSA-N
(+/-)-(1r*,2s*,3r*,5r*)-3-(6-amino-9h-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
7cy ,
AKOS030616274
CS-0058742
HY-112639
MS-23749
AT33705
1,2-cyclopentanediol, 5-(6-amino-9h-purin-9-yl)-3-(hydroxymethyl)-, (1s,2r,3r,5r)-

Research Excerpts

Overview

Aristeromycin is a unique carbocyclic nucleoside antibiotic produced by Streptomyces citricolor.

ExcerptReferenceRelevance
"Aristeromycin is a unique carbocyclic nucleoside antibiotic produced by Streptomyces citricolor. "( Five-Membered Cyclitol Phosphate Formation by a myo-Inositol Phosphate Synthase Orthologue in the Biosynthesis of the Carbocyclic Nucleoside Antibiotic Aristeromycin.
Eguchi, T; Kudo, F; Takashima, M; Tsunoda, T, 2016
)
2.08

Effects

ExcerptReferenceRelevance
"Aristeromycin structure has major pharmacophoric motif as 5'-OH and adenosine base, which may have significant role in enzyme binding followed by activity and or toxicity."( Synthesis and anti-HBV activity of α-stereoisomer of aristeromycin based analogs.
Baba, M; Bal, C; Jha, AK; Kasula, M; Rozy, F; Samunuri, R; Sharon, A; Toyama, M; Yadav, M, 2016
)
1.41
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine deaminaseMus musculus (house mouse)Ki9.90001.00005.45009.9000AID33971
AdenosylhomocysteinaseHomo sapiens (human)IC50 (µMol)2.15770.00152.11118.7000AID1152849; AID1563199; AID318694
AdenosylhomocysteinaseHomo sapiens (human)Ki0.11000.00000.18991.9300AID199940
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki6.26000.00011.20929.9700AID32358
Adenosine receptor A3Rattus norvegicus (Norway rat)Ki110.00000.00030.91969.0000AID33337; AID33360
Adenosine receptor A2bHomo sapiens (human)Ki47.30000.00021.635210.0000AID33295
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki2.15000.00021.494010.0000AID32896
AdenosylhomocysteinasePlasmodium falciparum 3D7IC50 (µMol)57.00001.10002.43333.1000AID318695
[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)
NS5 Zika virusEC50 (µMol)0.64000.00870.54751.3000AID1563204
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
one-carbon metabolic processAdenosylhomocysteinaseHomo sapiens (human)
S-adenosylmethionine cycleAdenosylhomocysteinaseHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
positive regulation of chronic inflammatory response to non-antigenic stimulusAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A2bHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
positive regulation of chemokine productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of interleukin-6 productionAdenosine receptor A2bHomo sapiens (human)
mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
positive regulation of mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
relaxation of vascular associated smooth muscleAdenosine receptor A2bHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2bHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
vasodilationAdenosine receptor A2bHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
adenosylhomocysteinase activityAdenosylhomocysteinaseHomo sapiens (human)
protein bindingAdenosylhomocysteinaseHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2bHomo sapiens (human)
protein bindingAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor activityAdenosine receptor A2bHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
nucleusAdenosylhomocysteinaseHomo sapiens (human)
endoplasmic reticulumAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
melanosomeAdenosylhomocysteinaseHomo sapiens (human)
extracellular exosomeAdenosylhomocysteinaseHomo sapiens (human)
cytosolAdenosylhomocysteinaseHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A2bHomo sapiens (human)
presynapseAdenosine receptor A2bHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2bHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (43)

Assay IDTitleYearJournalArticle
AID1563204Inhibition of RNA-dependent RNA polymerase in ZIKV SL0612 infected in African green monkey Vero cells assessed as reduction in virus-induced cytopathic effect measured after 96 hrs post-infection by MTS assay
AID199459Kinetic constant against bovine liver S-adenosyl-L-homocysteine hydrolase (AdoHcy); reversibleinhibitor1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
4'-modified analogues of aristeromycin and neplanocin A: synthesis and inhibitory activity toward S-adenosyl-L-homocysteine hydrolase.
AID1563205Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability measured after 96 hrs by MTS assay
AID94708Percentage control of incorporation of [3H]thymidine into DNA of uninfected L-cell cultures after 72 hr exposure1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 9. 2',3'-Dialdehyde derivatives of carbocyclic purine nucleosides as inhibitors of S-adenosylhomocysteine hydrolase.
AID538978Antiparasitic activity against Trichomonas vaginalis T1 at 10 uL after 24 hrs by hemocytometric analysis2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
AdoHcy hydrolase of Trichomonas vaginalis: studies of the effects of 5'-modified adenosine analogues and related 6-N-cyclopropyl derivatives.
AID1695271Antiviral activity against Hepatitis B virus infected in human HepG2.2.15.7 assessed as reduction in HBV DNA level incubated for 9 days media replaced every 3 days once with test compound by RT-PCR analysis2020RSC medicinal chemistry, May-01, Volume: 11, Issue:5
Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin.
AID94560Percentage inhibition of plaque formation, after 72 hr of incubation in virus plaque assay, prepared from monolayer cultures of mouse L 929 cells1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 9. 2',3'-Dialdehyde derivatives of carbocyclic purine nucleosides as inhibitors of S-adenosylhomocysteine hydrolase.
AID113993Effective dose by 50% was evaluated1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Carbocyclic analogues of xylofuranosylpurine nucleosides. Synthesis and antitumor activity.
AID318695Inhibition of Plasmodium falciparum SAHH2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.
AID94707Percentage control of incorporation of [3H]thymidine into DNA of uninfected L-cell cultures after 36h exposure1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 9. 2',3'-Dialdehyde derivatives of carbocyclic purine nucleosides as inhibitors of S-adenosylhomocysteine hydrolase.
AID107455Compound was tested for antileukemic activity in P388 leukemia mice when administered a dose of 100 mg/kg/day; IA means inactive1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Carbocyclic analogues of xylofuranosylpurine nucleosides. Synthesis and antitumor activity.
AID1563215Selectivity index, ratio of CC50 for African green monkey Vero E6 cells to EC50 for inhibition of RNA-dependent RNA polymerase in CHIKV LS3 infected in African green monkey Vero E6 cells assessed as reduction in virus-induced cytopathic effect
AID538979Antitrypanosomal activity against Trichomonas vaginalis T12010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
AdoHcy hydrolase of Trichomonas vaginalis: studies of the effects of 5'-modified adenosine analogues and related 6-N-cyclopropyl derivatives.
AID33295Displacement of [3H]- ZM-241385 from human adenosine A2B receptor expressed in HEK cells2000Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11
Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists.
AID33971Compound was evaluated for competitive inhibition of adenosine deaminase and expressed as Ki1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Carbocyclic analogues of xylofuranosylpurine nucleosides. Synthesis and antitumor activity.
AID150433In vitro inhibition against P-388 mouse leukemia cells using growth inhibition assay at the concentration of 100 ug/mL1990Journal of medicinal chemistry, Apr, Volume: 33, Issue:4
Synthesis and biological evaluation of carbocyclic analogues of lyxofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines.
AID33360Displacement of [125I]- AB-MECA from rat adenosine A3 receptor expressed in CHO cells2000Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11
Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists.
AID199940Binding affinity against S-adenosyl-homocysteine hydrolase1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 9. 2',3'-Dialdehyde derivatives of carbocyclic purine nucleosides as inhibitors of S-adenosylhomocysteine hydrolase.
AID1563199Inhibition of human placental SAH hydrolase expressed in Escherichia coli JM109 using SAH as substrate preincubated for 10 mins followed by SAH addition and measured after 20 mins by DNTB reagent-based spectrophotometric method
AID31247Binding affinity determined on Adenosine A1 receptor in rat brain membranes by measuring displacement of specific [3H]PIA as radioligand.1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID199455Inhibitory activity against bovine liver S-adenosyl-L-homocysteine hydrolase (AdoHcy); reversibleinhibitor1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
4'-modified analogues of aristeromycin and neplanocin A: synthesis and inhibitory activity toward S-adenosyl-L-homocysteine hydrolase.
AID318699Metabolic stability in presence of calf intestinal adenosine deaminase assessed as compound remaining after 15 mins2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.
AID33765Binding affinity determined on Adenosine A2A receptor in rat striatal membranes by measuring displacement of specific [3H]-CGS- 21680 as radioligand.1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID1563209Selectivity index, ratio of CC50 for African green monkey Vero cells to EC50 for inhibition of RNA-dependent RNA polymerase in ZIKV SL0612 infected in African green monkey Vero cells assessed as reduction in virus-induced cytopathic effect
AID1563202Inhibition of RNA-dependent RNA polymerase in SARS-CoV Frankfurt1 infected in African green monkey Vero E6 cells assessed as reduction in virus-induced cytopathic effect measured after 72 hrs post-infection by MTS assay
AID152702Cytotoxicity against P388 mouse leukemia cells1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
Synthesis and biological evaluation of 5'-sulfamoylated purinyl carbocyclic nucleosides.
AID318698Selectivity ratio of IC50 for human SAHH to IC50 for Plasmodium falciparum SAHH2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.
AID1152849Inhibition of recombinant human AHCY using SAH as substrate assessed as formation of homocysteine after 10 mins2014Bioorganic & medicinal chemistry letters, Jun-15, Volume: 24, Issue:12
Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase.
AID32896Displacement of specific [3H]-CGS- 21680 binding to adenosine A2A receptor in rat striatal membranes2000Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11
Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists.
AID231299Relative binding affinity for Adenosine A1 and A3 receptors2000Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11
Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists.
AID1563203Cytotoxicity against African green monkey Vero E6 cells assessed as reduction in cell viability measured after 72 hrs by MTS assay
AID1563201Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability measured after 72 hrs by MTS assay
AID1563200Inhibition of RNA-dependent RNA polymerase in MERS-CoV EMC/2012 infected in African green monkey Vero cells assessed as reduction in virus-induced cytopathic effect measured after 72 hrs post-infection by MTS assay
AID33337Binding affinity determined by displacement of specific binding of [125I]N-(4-amino-3-iodophenethyl)-adenosine in membranes of CHO cells stably transfected with the rat adenosine A3 receptor1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID150434In vitro inhibition against P-388 mouse leukemia cells using growth inhibition assay at the concentration of 12.5 ug/mL1990Journal of medicinal chemistry, Apr, Volume: 33, Issue:4
Synthesis and biological evaluation of carbocyclic analogues of lyxofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines.
AID318694Inhibition of human SAHH2008Bioorganic & medicinal chemistry, Apr-01, Volume: 16, Issue:7
Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.
AID1563206Inhibition of RNA-dependent RNA polymerase in CHIKV LS3 infected in African green monkey Vero E6 cells assessed as reduction in virus-induced cytopathic effect measured after 96 hrs post-infection by MTS assay
AID1695272Cytotoxicity against human HepG2.2.15.7 cells assessed as reduction in cell viability2020RSC medicinal chemistry, May-01, Volume: 11, Issue:5
Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin.
AID150437In vitro inhibition against P-388 mouse leukemia cells using growth inhibition assay at the concentration of 6.25 ug/mL1990Journal of medicinal chemistry, Apr, Volume: 33, Issue:4
Synthesis and biological evaluation of carbocyclic analogues of lyxofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines.
AID32358Displacement of [3H]R-PIA from rat brain membrane Adenosine A1 receptor2000Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11
Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists.
AID150436In vitro inhibition against P-388 mouse leukemia cells using growth inhibition assay at the concentration of 50 ug/mL1990Journal of medicinal chemistry, Apr, Volume: 33, Issue:4
Synthesis and biological evaluation of carbocyclic analogues of lyxofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines.
AID199931Inhibition of bovine liver S-adenosyl-homocysteine hydrolase at 0.2 mM1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 9. 2',3'-Dialdehyde derivatives of carbocyclic purine nucleosides as inhibitors of S-adenosylhomocysteine hydrolase.
AID150435In vitro inhibition against P-388 mouse leukemia cells using growth inhibition assay at the concentration of 25 ug/mL1990Journal of medicinal chemistry, Apr, Volume: 33, Issue:4
Synthesis and biological evaluation of carbocyclic analogues of lyxofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (71)

TimeframeStudies, This Drug (%)All Drugs %
pre-199019 (26.76)18.7374
1990's17 (23.94)18.2507
2000's19 (26.76)29.6817
2010's15 (21.13)24.3611
2020's1 (1.41)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.88

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.88 (24.57)
Research Supply Index4.29 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index35.22 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.88)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (4.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other69 (95.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]