Page last updated: 2024-10-15

8-bromoguanosine

Cross-References

ID SourceID
PubMed CID135465599
CHEMBL ID3246762
CHEBI ID183722
SCHEMBL ID56018
MeSH IDM0107928

Synonyms (41)

Synonym
8 brguo
4016-63-1
8-bromoguanosine ,
2-amino-8-bromo-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one
8-bromo-guanosine
2-amino-8-bromo-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1h-purin-6-one
CHEBI:183722
2-amino-8-bromo-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-purin-6-one
2-amino-8-bromo-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one
2-amino-8-bromo-9-((2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1h-purin-6(9h)-onesc 174257; nsc 79211; ac1l5qrp
A824953
bg2 ,
AKOS015955615
guanosine, 8-bromo-
einecs 223-677-6
nsc 174257
nsc 79211
2-amino-8-bromo-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-purin-6(9h)-one
HG1301
c10h12brn5o5
CHEMBL3246762
SCHEMBL56018
J-700340
2-amino-8-bromo-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1h-purin-6(9h)-one
ASUCSHXLTWZYBA-UMMCILCDSA-N
8-bro-moguanosine
2-amino-8-bromo-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6h-purin-6-one
AC-32296
mfcd00037985
2-amino-8-bromo-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3h-purin-6(9h)-one
(2r,3r,4s,5r)-2-(2-amino-8-bromo-6-hydroxy-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
AS-19159
AM10154
Q27458387
EN300-30595405
2-amino-8-bromo-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1h-purin-6-one
nsc-816043
nsc816043
PD017498
(2r,3r,4s,5r)-2-(2-amino-8-bromo-6-hydroxy-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
AKOS040768044

Dosage Studied

ExcerptReference
" 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
)
" 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
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
purine nucleoside
[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 (1)

Other Measurements

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

Biological Processes (17)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID220073In vivo effect on murine NK cell activity in isolated CBA/CaJ mice spleen cells and cytotoxicity measured against YAC-1 cells at a targetor ratio 100:1.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
AID220075In vivo effect on murine NK cell activity in isolated CBA/CaJ mice spleen cells and cytotoxicity measured against YAC-1 cells at a targetor ratio 50:1.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
AID122230Effect against semliki forest virus infection in mice at an ip dose of 200 mg/kg; 2/111990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
AID110577Ability to activate CBA/CaJ Mice spleen cells to proliferate in vitro by measuring new DNA synthesis in a [3H]thymidine incorporation assay at 0.01 mM1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
AID118650Effect against semliki forest virus infection in mice at an ip dose of 100 mg/kg.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
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.
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.
AID122227Effect against semliki forest virus infection in mice at an ip dose of 100 mg/kg; 0/121990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
AID110580Ability to activate CBA/CaJ Mice spleen cells to proliferate in vitro by measuring new DNA synthesis in a [3H]thymidine incorporation assay at 0.40 mM1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
AID110579Ability to activate CBA/CaJ Mice spleen cells to proliferate in vitro by measuring new DNA synthesis in a [3H]thymidine incorporation assay at 0.20 mM1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
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.
AID139429Effect against semliki forest virus infection in mice at an ip dose of 200 mg/kg.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
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.
AID71651Inhibitory activity against cellular differentiation in Friend erythroleukemia cells as optimal concentration required for maximum activity.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.
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.
AID110461Ability to activate CBA/CaJ Mice spleen cells to proliferate in vitro by measuring new DNA synthesis in a [3H]thymidine incorporation assay at 0 mM1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
AID110578Ability to activate CBA/CaJ Mice spleen cells to proliferate in vitro by measuring new DNA synthesis in a [3H]thymidine incorporation assay at 0.05 mM1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-199024 (48.98)18.7374
1990's6 (12.24)18.2507
2000's11 (22.45)29.6817
2010's8 (16.33)24.3611
2020's0 (0.00)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 (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other51 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]