Page last updated: 2024-11-09

6-thioguanosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

6-thioguanosine: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2724387
CHEMBL ID283078
CHEBI ID94738
SCHEMBL ID230739
MeSH IDM0047548

Synonyms (67)

Synonym
MLS002153781 ,
smr001233165
guanosine, 6-thio-
TGR ,
6-thioguanosine
6-mercaptoguanosine
6-thioguanine ribonucleoside
85-31-4
TGS ,
nsc-29422
thioguanosine
6-thiodeoxyguanosine
(2r,3r,4s,5r)-2-(2-amino-6-sulfanyl-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
purine, 2-amino-6-mercapto-9-beta-d-ribofuranosyl
2-amino-9beta-d-ribofuranosyl-9h-purine-6-thiol
2-amino-9-beta-d-ribofuranosyl-9h-purine-6-thiol
9h-purine-6-thiol, 2-amino-9-beta-d-ribofuranosyl-
6h-purine-6-thione, 2-amino-1,9-dihydro-9-beta-d-ribofuranosyl-
2-amino-9-(beta-d-ribofuranosyl)purine-6-thiol
9h-purine-6-thiol, 2-amino-9beta-d-ribofuranosyl-
2-amino-6-mercapto-9(beta-d-ribofuranosyl)purine
einecs 201-597-2
2-amino-6-mercaptopurin-9-ylriboside
ai3-50278
6-thioguanosine (van)
BSPBIO_000413
PRESTWICK2_000347
NCGC00179568-01
BPBIO1_000455
PRESTWICK3_000347
PRESTWICK1_000347
PRESTWICK0_000347
SPBIO_002334
CHEMBL283078
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione
A841290
2-amino-6-mercaptopurine ribonucleoside; 2-amino-6-mercaptopurine riboside; 2-amino-9-(beta-d-ribofuranosyl)purine-6-thiol
HMS2096E15
unii-c558li0k8p
c558li0k8p ,
BRD-K75649340-002-02-2
HMS2232C20
2-amino-6-mercaptopurine-9-d-riboside hydrate
AKOS015904198
345909-25-3
9-.beta.-d-ribofuranosylthioguanine
thioguanosine [mi]
SCHEMBL230739
CCG-220347
2-azanyl-9-[(2r,3r,4s,5r)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]-3h-purine-6-thione
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-oxolanyl]-3h-purine-6-thione
bdbm87350
cid_2724387
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-3h-purine-6-thione
AC-24682
AKOS025401703
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1h-purine-6-thione
CHEBI:94738
mfcd00005736
HMS3713E15
Q27166529
NCGC00179568-02
BS-17652
(2r,3r,4s,5r)-2-(2-amino-6-mercapto-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
DTXSID201018977
2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-oxolanyl]-6-purinethiolate
2-amino-6-mercaptopurine-9-d-riboside

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" 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
)
0.29

Dosage Studied

ExcerptRelevanceReference
" 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
)
0.28
[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 (19)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency5.01190.631035.7641100.0000AID504339
ATAD5 protein, partialHomo sapiens (human)Potency35.48130.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency1.73580.000811.382244.6684AID686978; AID686979
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency5.62340.707912.194339.8107AID720542
67.9K proteinVaccinia virusPotency3.03000.00018.4406100.0000AID720579; AID720580
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency89.12510.707936.904389.1251AID504333
IDH1Homo sapiens (human)Potency1.45810.005210.865235.4813AID686970
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.77830.035520.977089.1251AID504332
chromobox protein homolog 1Homo sapiens (human)Potency8.91250.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency1.29950.00419.984825.9290AID504444
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency21.19230.168316.404067.0158AID720504
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency0.00710.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency0.00710.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency0.00710.15855.287912.5893AID540303
gemininHomo sapiens (human)Potency0.16360.004611.374133.4983AID624296
[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)
nuclear receptor coactivator 1 isoform 1 [Homo sapiens]Homo sapiens (human)IC50 (µMol)35.87401.15306.28039.9630AID602168
transactivating tegument protein VP16 [Human herpesvirus 1]Human alphaherpesvirus 1 (Herpes simplex virus type 1)IC50 (µMol)3.36800.94604.70169.4870AID602167
nuclear receptor coactivator 3 isoform aHomo sapiens (human)IC50 (µMol)2.54800.14764.33099.9200AID602166
[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)
PAX8Homo sapiens (human)AC501.16000.04885.435469.1700AID687027
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID584551Antibacterial activity against Bacillus anthracis Sterne 34F2 infected in mouse J774A.1 cells assessed as protection against bacteria-induced cytotoxicity using propidium iodide staining measured after 6 hrs infection2010Antimicrobial 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.
AID1918597Antiproliferative activity against human THP-1 cells with low HGPRT expression incubated for 48 hrs by CellTiter-Glo2 assay2022Journal of medicinal chemistry, 11-24, Volume: 65, Issue:22
6-Thioguanosine Monophosphate Prodrugs Display Enhanced Performance against Thiopurine-Resistant Leukemia and Breast Cancer Cells.
AID329454Inhibition of cytopathic effect in Bacillus anthracis Sterne infected mouse RAW264.7 macrophage assessed as lack of propidium iodide positive cells after 7 hrs2007The Journal of biological chemistry, Apr-20, Volume: 282, Issue:16
Identification of an in vivo inhibitor of Bacillus anthracis spore germination.
AID1918598Antiproliferative activity against human SK-BR-3 cells with low HGPRT expression incubated for 48 hrs by CellTiter-Glo2 assay2022Journal of medicinal chemistry, 11-24, Volume: 65, Issue:22
6-Thioguanosine Monophosphate Prodrugs Display Enhanced Performance against Thiopurine-Resistant Leukemia and Breast Cancer Cells.
AID1918604Effect on CCNT1 mRNA expression in HEK293T cells assessed as percentage of labeled transcripts at 100 uM incubated for 2 hrs and measured by TUC-Seq DUAL method2022Journal of medicinal chemistry, 11-24, Volume: 65, Issue:22
6-Thioguanosine Monophosphate Prodrugs Display Enhanced Performance against Thiopurine-Resistant Leukemia and Breast Cancer Cells.
AID96738Percentage of L1210 cells killed was determined in L1210 Inoculated mice at a dose of 8.1 mg/kg after a single treatment1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Synthesis and in vivo antitumor activity of 2-amino-9H-purine-6-sulfenamide, -sulfinamide, and -sulfonamide and related purine ribonucleosides.
AID1918595Antiproliferative activity against HEK293T cells with high HGPRT expression incubated for 48 hrs by CellTiter-Glo2 assay2022Journal of medicinal chemistry, 11-24, Volume: 65, Issue:22
6-Thioguanosine Monophosphate Prodrugs Display Enhanced Performance against Thiopurine-Resistant Leukemia and Breast Cancer Cells.
AID329451Inhibition of inosine and alanine-induced germination of Bacillus anthracis Sterne spore pre-incubated for 15 mins2007The Journal of biological chemistry, Apr-20, Volume: 282, Issue:16
Identification of an in vivo inhibitor of Bacillus anthracis spore germination.
AID1918605Effect on p21 mRNA expression in HEK293T cells assessed as percentage of labeled transcripts at 100 uM incubated for 2 hrs and measured by TUC-Seq DUAL method2022Journal of medicinal chemistry, 11-24, Volume: 65, Issue:22
6-Thioguanosine Monophosphate Prodrugs Display Enhanced Performance against Thiopurine-Resistant Leukemia and Breast Cancer Cells.
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.
AID100037Post inoculation lifespan was determined in L1210 Inoculated mice at a dose of 8.1 mg/Kg after a single treatment1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Synthesis and in vivo antitumor activity of 2-amino-9H-purine-6-sulfenamide, -sulfinamide, and -sulfonamide and related purine ribonucleosides.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID329452Inhibition of cytopathic effect in Bacillus anthracis Sterne infected mouse RAW264.7 macrophage at 1 uM to 2 uM after 6 hrs by propidium iodide exclusion assay2007The Journal of biological chemistry, Apr-20, Volume: 282, Issue:16
Identification of an in vivo inhibitor of Bacillus anthracis spore germination.
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.
AID1918596Antiproliferative activity against human K562 cells with low HGPRT expression incubated for 48 hrs by CellTiter-Glo2 assay2022Journal of medicinal chemistry, 11-24, Volume: 65, Issue:22
6-Thioguanosine Monophosphate Prodrugs Display Enhanced Performance against Thiopurine-Resistant Leukemia and Breast Cancer Cells.
AID584548Ratio of IC50 for inosine/L-alanine-induced Bacillus anthracis Sterne 34F2 spore germination to IC50 for Bacillus anthracis Sterne 34F2 infected in mouse J774A.1 cells assessed as protection against bacteria-induced cytotoxicity2010Antimicrobial 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.
AID93940Cytotoxicity was determined in vitro in murine leukemia L1210 Cells1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Ribose as the preferential target for the oxidized form of elliptinium acetate in ribonucleos(t)ides. Biological activities of the resulting adducts.
AID1918606Effect on ND1 mRNA expression in HEK293T cells assessed as percentage of labeled transcripts at 100 uM incubated for 2 hrs and measured by TUC-Seq DUAL method2022Journal of medicinal chemistry, 11-24, Volume: 65, Issue:22
6-Thioguanosine Monophosphate Prodrugs Display Enhanced Performance against Thiopurine-Resistant Leukemia and Breast Cancer Cells.
AID409953Inhibition of mouse liver MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID66321Inhibition Eimeria tenella growth1982Journal of medicinal chemistry, Jan, Volume: 25, Issue:1
Pyrazolo[3,4-d]pyrimidine ribonucleosides as anticoccidials. 1. Synthesis and activity of some nucleosides of purines and 4-(alkylthio)pyrazolo[3,4-d]pyrimidines.
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.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (64)

TimeframeStudies, This Drug (%)All Drugs %
pre-199015 (23.44)18.7374
1990's10 (15.63)18.2507
2000's15 (23.44)29.6817
2010's19 (29.69)24.3611
2020's5 (7.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.53

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index41.53 (24.57)
Research Supply Index4.22 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index59.70 (26.88)
Search Engine Supply Index2.01 (0.95)

This Compound (41.53)

All Compounds (24.57)

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%
Other67 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]