| Identification | Back Directory | [Name]
6-THIO-2'-DEOXYGUANOSINE | [CAS]
789-61-7 | [Synonyms]
tgdr
6-SH-dG
6-Thio-dG
NSC-71261
Aids010571
nci-c01581
Aids-010571
Thiodeoxyguanosine
6-SH-deoxyguanosine
2’-deoxythioguanosine
2’-deoxy-6-thio-guanosin
6-THIO-2'-DEOXYGUANOSINE
2'-Deoxy-6-thioguanosine
2'-Desoxy-6-thioguanosine
Thioguanine deoxyriboside
beta-2’-deoxythioguanosine
Mercaptopurine Impurity 13
Guanosine, 2'-deoxy-6-thio-
β-Thioguanine deoxyriboside
beta-thioguaninedeoxyriboside
6-Mercaptoguaninedeoxyriboside
BETA-THIOGUANIDINEDEOXYRIBOSIDE
2-AMino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-Mercaptopurine
2-AMino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-9H-purine-6(1H)-thione
2-amino-9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purine-6(1h)-thion
2-Amino-9-(2-deoxy-.beta.-D-erythropentofuranosyl)-9H-purine-6(1H)-thione | [Molecular Formula]
C10H13N5O3S | [MDL Number]
MFCD00672275 | [MOL File]
789-61-7.mol | [Molecular Weight]
283.31 |
| Chemical Properties | Back Directory | [Melting point ]
190-192 °C | [Boiling point ]
709.1±70.0 °C(Predicted) | [density ]
2.02±0.1 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), DMF (Slightly), Methanol (Slightly, Heated), Water (Very Slightly) | [form ]
Solid | [pka]
6.81±0.20(Predicted) | [color ]
Yellow to Brown |
| Hazard Information | Back Directory | [Uses]
Guanosine (G837900) derivative with cancer chemotherapeutic properties. It is involved in the inhibition of human RNase H-mediated RNA cleavage from DNA-RNA duplexes via incorporation into DNA. | [Biological Activity]
6-thio-dg is a nucleoside analogue [1], is a telomerase-mediated telomere disrupting compound [2]. it is an anti-cancer inhibitor [1]. cancer cells were very sensitive to 6-thio-dg with observed ic50 values ranging from 0.7-2.9 μm, depending on cell types [3].telomeres are found at the end of eukaryotic linear chromosomes. they are essential for genomic stability and chromosome maintenance [3].in hct116 human colon cancer cell line, treatment with 6-thio-dg made progressive telomere shortening independent of telomerase activity inhibition and induced telomere dysfunction. grn163l is a telomerase inhibitor. in hct116 cells, treatment with grn163l and 6-thio-dg together increased telomere shortening. within 1 week, 6-thio-dg killed most of hct116 cells and altered cellular morphology. normal bj fibroblast cells are telomerase silent. after 1 week, treatment with 6-thio-dg showed no effect on cell morphology. after long-term treatment with 6-thio-dg, no effect on telomere shortening was found [1].in murine mode with xenograft derived from a549 lung cancer cell line, as compared to controls, intraperitoneal injection with 2 mg/kg of 6-thio-dg every other day completely prevented progressive tumor growth. ki67 is a biomarker correlating with proliferation levels. compared to controls, 6-thio-dg decreased ki67 staining. treatment with 6-thio-dg through local injection resulted in even more dramatic decrease in the tumor growth rate compared to untreated controls [3]. | [References]
[1]. mender i, gryaznov s, dikmen zg, et al. abstract lb-125: a novel telomerase inhibitor. cancer research, 2013, 73(8 supplement): lb-125-lb-125.
[2]. mender i, gryaznov s, shay jw. a novel telomerase substrate precursor rapidly induces telomere dysfunction in telomerase positive cancer cells but not telomerase silent normal cells. oncoscience, 2015, 2(8): 693.
[3]. mender i, gryaznov s, dikmen zg, et al. induction of telomere dysfunction mediated by the telomerase substrate precursor 6-thio-2-deoxyguanosine. cancer discovery, 2015, 5(1): 82-95. |
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