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SML1296

Sigma-Aldrich

6-Thio-2′-Deoxyguanosine

≥97% (HPLC)

Synonym(s):

2′-Ddeoxy-6-thio-guanosine, 2′-Deoxy-6-thioguanosine, 2′-Deoxythioguanosine, 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 (7CI,8CI), 6-Thio-dG, NSC 71261

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O3S
CAS Number:
789-61-7
Molecular Weight:
283.31
UNSPSC Code:
12352200
PubChem Substance ID:
329825770
NACRES:
NA.77

Quality Level

100

assay

≥97% (HPLC)

form

powder

color

white to brown

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

S=C1C2=C(N([C@H]3C[C@H](O)[C@@H](CO)O3)C=N2)N=C(N)N1

InChI

1S/C10H13N5O3S/c11-10-13-8-7(9(19)14-10)12-3-15(8)6-1-4(17)5(2-16)18-6/h3-6,16-17H,1-2H2,(H3,11,13,14,19)/t4-,5-,6-/m1/s1

InChI key

SCVJRXQHFJXZFZ-HSUXUTPPSA-N

Application

6-Thio-2′-Deoxyguanosine has been used in secreted luciferase enzyme activity in tonsillar cancer cells.

Biochem/physiol Actions

6-Thio-2′-deoxyguanosine (6-thio-dG) is a nucleoside analog and telomerase substrate that is incorporated into de novo–synthesized telomeres. 6-Thio-2′-deoxyguanosine induces telomere dysfunction and rapid cell death in cancer cells, while spearing telomerase-negative cells.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Haoran Yu et al.
Virology, 521, 1-19 (2018-06-05)
Adenosine plays an important role in cell death and differentiation as well as in tumorigenesis and the intra- and extra-cellular levels range from nanomolar to millimolar levels under various physiological or pathophysiological conditions. Here we report that adenosine can activate

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