Synonym
6-thio-dG; 6thiodG; 6 thio dG; 6-Thio-2'-deoxyguanosine; Beta-TGdR; BetaTGdR; Beta TGdR; ateganosine; NSC 71261
IUPAC/Chemical Name
2-Amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
InChi Key
SCVJRXQHFJXZFZ-KVQBGUIXSA-N
InChi Code
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+/m0/s1
SMILES Code
S=C1N=C(N)NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)C3
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
283.31
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Mender I, Gryaznov S, Dikmen ZG, Wright WE, Shay JW. Induction of telomere dysfunction mediated by the telomerase substrate precursor 6-thio-2'-deoxyguanosine. Cancer Discov. 2015 Jan;5(1):82-95. doi: 10.1158/2159-8290.CD-14-0609. Epub 2014 Dec 16. PubMed PMID: 25516420; PubMed Central PMCID: PMC4293221.
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 Aug 22;2(8):693-5. eCollection 2015. PubMed PMID: 26425659; PubMed Central PMCID: PMC4580061.
3: Wellinger RJ. Turning telomerase into a Jekyll and Hyde case? Cancer Discov. 2015 Jan;5(1):19-21. doi: 10.1158/2159-8290.CD-14-1346. PubMed PMID: 25583799.
4: Sasaki S, Onizuka K, Taniguchi Y. Oligodeoxynucleotide containing s-functionalized 2'-deoxy-6-thioguanosine: facile tools for base-selective and site-specific internal modification of RNA. Curr Protoc Nucleic Acid Chem. 2012 Mar;Chapter 4:Unit 4.49.1-16. doi: 10.1002/0471142700.nc0449s48. PubMed PMID: 22395968.
5: Nishioka T, Oshiro I, Onizuka K, Taniguchi Y, Sasaki S. Efficient Thymidine-Selective DNA Interstrand Photo-activated Crosslinking by the 6-Thioguanine Connected via an Ethylene-Linker to the 2'-Deoxyribose Unit. Chem Pharm Bull (Tokyo). 2016;64(9):1315-20. doi: 10.1248/cpb.c16-00310. PubMed PMID: 27581636.
6: Jitsuzaki D, Onizuka K, Nishimoto A, Oshiro I, Taniguchi Y, Sasaki S. Remarkable acceleration of a DNA/RNA inter-strand functionality transfer reaction to modify a cytosine residue: the proximity effect via complexation with a metal cation. Nucleic Acids Res. 2014 Jul;42(13):8808-15. doi: 10.1093/nar/gku538. Epub 2014 Jun 23. PubMed PMID: 24957600; PubMed Central PMCID: PMC4117767.
7: Ping YH, Liu Y, Wang X, Neenhold HR, Rana TM. Dynamics of RNA-protein interactions in the HIV-1 Rev-RRE complex visualized by 6-thioguanosine-mediated photocrosslinking. RNA. 1997 Aug;3(8):850-60. PubMed PMID: 9257644; PubMed Central PMCID: PMC1369530.
8: Yu D, Putta MR, Bhagat L, Li Y, Zhu F, Wang D, Tang JX, Kandimalla ER, Agrawal S. Agonists of Toll-like receptor 9 containing synthetic dinucleotide motifs. J Med Chem. 2007 Dec 13;50(25):6411-8. Epub 2007 Nov 8. PubMed PMID: 17988082.
