Compounds > 8-thioguanosine
Page last updated: 2024-10-15

8-thioguanosine

Description

8-thioguanosine: lymphocyte activator [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135457302
CHEMBL ID2311184
SCHEMBL ID54408
MeSH IDM0112328

Synonyms (34)

Synonym
nsc-79216
26001-38-7
8-mercaptoguanosine
8-thioguanosine
2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanylidene-6,7,8,9-tetrahydro-1h-purin-6-one
AKOS001714888
mfcd01081756
b0t9fow56n ,
unii-b0t9fow56n
einecs 247-402-4
7,8-dihydro-8-thioxoguanosine
nsc 79216
SCHEMBL54408
KZELNMSPWPFAEB-UMMCILCDSA-N
29836-03-1
CHEMBL2311184
686300-03-8
guanosine, 7,8-dihydro-8-thioxo-
sq 12760
guanosine, 8-mercapto-
AC-32333
AKOS030489379
DTXSID00365121
AS-61194
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanylidene-6,7,8,9-tetrahydro-1h-purin-6-one
sr-01000147753
SR-01000147753-1
2-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-thioxo-8,9-dihydro-1h-purin-6(7h)-one
2-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-mercapto-1h-purin-6(9h)-one
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanylidene-1,7-dihydropurin-6-one
Q27274231
nsc-817320
nsc817320
2-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-thioxo-1,7,8,9-tetrahydro-6h-purin-6-one

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

Bioassays (21)

Assay IDTitleYearJournalArticle
AID220084Ability to stimulate the natural killer response in murine in vitro cell assays1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Small-molecule immunostimulants. Synthesis and activity of 7,8-disubstituted guanosines and structurally related compounds.
AID142466Ability to act as B-cell mitogens1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Small-molecule immunostimulants. Synthesis and activity of 7,8-disubstituted guanosines and structurally related compounds.
AID140780Percent of maximum response was tested to augment the antibody response of B cells to sheep red blood cell challenge1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Small-molecule immunostimulants. Synthesis and activity of 7,8-disubstituted guanosines and structurally related compounds.
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.
AID220071In 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 50:11990Journal 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.
AID142474Percent of maximum response was tested for its ability to act as B-cell mitogens (mitogenicity)1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Small-molecule immunostimulants. Synthesis and activity of 7,8-disubstituted guanosines and structurally related compounds.
AID202920Effect against semliki forest virus infection in mice at an ip dose of 200 mg/kg; 3/121990Journal 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.
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.
AID140774Augment antibody response of B cells to sheep red blood cell (SRBC) challenge (adjuvanticity)1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Small-molecule immunostimulants. Synthesis and activity of 7,8-disubstituted guanosines and structurally related compounds.
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.
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.
AID202916Effect against semliki forest virus infection in mice at an ip dose of 100 mg/kg1990Journal 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.
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.
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.
AID202918Effect against semliki forest virus infection in mice at an ip dose of 100 mg/kg; 6/121990Journal 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.
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.
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.
AID220087Percent of maximum response was tested for its ability to stimulate the natural killer response in murine in vitro cell assays1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Small-molecule immunostimulants. Synthesis and activity of 7,8-disubstituted guanosines and structurally related compounds.
AID202917Effect against semliki forest virus infection in mice at an ip dose of 200 mg/kg1990Journal 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.
AID220070In 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 100:11990Journal 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-199025 (65.79)18.7374
1990's7 (18.42)18.2507
2000's2 (5.26)29.6817
2010's2 (5.26)24.3611
2020's2 (5.26)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%
Other39 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
cytosine
[no description available]		1.9710aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		1.9610sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		1.9610aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
sym-trinitrobenzene
Trinitrobenzenes: Benzene derivatives which are substituted with three nitro groups in any position.. 1,3,5-trinitrobenzene : A trinitrobenzene in which each of the nitro groups is meta- to the other two.		2.3820trinitrobenzeneexplosive
singlet oxygen
Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.		2.2110chalcogen;
monoatomic oxygen;
nonmetal atom		macronutrient
sq-23377
Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.		1.9910cyclic ether;
enol;
polyunsaturated fatty acid;
very long-chain fatty acid		calcium ionophore;
metabolite
anticodon
Anticodon: The sequential set of three nucleotides in TRANSFER RNA that interacts with its complement in MESSENGER RNA, the CODON, during translation in the ribosome.		1.9610
muramidase
Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.		1.9710
cyclic gmp
Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.		1.96103',5'-cyclic purine nucleotide;
guanyl ribonucleotide		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
deoxyguanosine
[no description available]		1.9610purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		210guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
guanine
[no description available]		2102-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
guanosine
ribonucleoside : Any nucleoside where the sugar component is D-ribose.		4.89360guanosines;
purines D-ribonucleoside		fundamental metabolite
azaguanine
Azaguanine: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.. 8-azaguanine : A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.		210nucleobase analogue;
triazolopyrimidines		antimetabolite;
antineoplastic agent;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
8-hydroxyguanosine
8-hydroxyguanosine: immunostimulant for B lymphocytes; structure given in first source		2.3820purine nucleoside
isatoribine anhydrous
[no description available]		1.9710
loxoribine
[no description available]		1.9810
2-amino-5-iodo-6-phenyl-4-pyrimidinone
[no description available]		1.9710
bropirimine
[no description available]		1.9710pyrimidines
8-hydroxyguanine
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'. 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.		210oxopurine
8-methylguanine
8-methylguanine: structure given in first source		210
7-methyl-8-oxoguanosine
[no description available]		2.3720
8-bromo-2'-deoxyguanosine
8-bromo-2'-deoxyguanosine: structure in first source. 8-bromo-2'-deoxyguanosine : An organobromine compound comprising 2'-deoxyguanosine having a bromo substituent at position 8 of the guanine ring system.		1.9610guanosines;
organobromine compound
8-hydroxy-2'-deoxyguanosine
8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.		1.9610guanosinesbiomarker
7-methylguanosine
7-methylguanosine : A positively charged methylguanosine in which a single methyl substituent is located at position 7.		1.9610methylguanosine;
organic cation		metabolite
8-bromoguanosine
[no description available]		3.84120purine nucleoside
8-aminoguanosine
[no description available]		1.9610
nucleoside q
Nucleoside Q: A modified nucleoside which is present in the first position of the anticodon of tRNA-tyrosine, tRNA-histidine, tRNA-asparagine and tRNA-aspartic acid of many organisms. It is believed to play a role in the regulatory function of tRNA. Nucleoside Q can be further modified to nucleoside Q*, which has a mannose or galactose moiety linked to position 4 of its cyclopentenediol moiety.. queuosine : A nucleoside found in tRNA that has an additional cyclopentenyl ring added via an NH group to the methyl group of 7-methyl-7-deazaguanosine. The cyclopentenyl ring may carry other substituents.		1.96107-deazaguanine ribonucleoside
8-nitroguanosine
8-nitroguanosine: structure in first source. 8-nitroguanosine : Guanosine substituted at the purine 8-position by a nitro group.		2.1110nitroguanosine
ConditionIndicatedRelationship StrengthStudiesTrials
Germinoblastoma
[description not available]		02.3820
Infections, Togaviridae
[description not available]		01.9710
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		02.3820
Di Guglielmo Disease
[description not available]		01.9610
Leukemia, Erythroblastic, Acute
A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.		01.9610
Antibody Deficiency Syndrome
[description not available]		02.8840
Immunologic Deficiency Syndromes
Syndromes in which there is a deficiency or defect in the mechanisms of immunity, either cellular or humoral.		02.8840
Choreoathetosis Self-Mutilation Hyperuricemia Syndrome
[description not available]		0210
Idiopathic Parkinson Disease
[description not available]		0210
Lesch-Nyhan Syndrome
An inherited disorder transmitted as a sex-linked trait and caused by a deficiency of an enzyme of purine metabolism; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE. Affected individuals are normal in the first year of life and then develop psychomotor retardation, extrapyramidal movement disorders, progressive spasticity, and seizures. Self-destructive behaviors such as biting of fingers and lips are seen frequently. Intellectual impairment may also occur but is typically not severe. Elevation of uric acid in the serum leads to the development of renal calculi and gouty arthritis. (Menkes, Textbook of Child Neurology, 5th ed, pp127)		0210
Parkinson Disease
A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)		0210
Benign Neoplasms
[description not available]		01.9710
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		01.9710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		01.9710
Plasma Cell Tumor
[description not available]		01.9610
Plasmacytoma
Any discrete, presumably solitary, mass of neoplastic PLASMA CELLS either in BONE MARROW or various extramedullary sites.		01.9610
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.3720
chemdatabank.com