6-Thioguanine
6-Thioguanine is a nucleotide analog of guanine that exhibits anticancer chemotherapeutic, immunosuppressive, and anti-parasitic activities. 6-Thioguanine is incorporated into DNA, altering stability of the topoisomerase II-DNA cleavage complex and increasing DNA fragmentation; these actions result in growth arrest and inhibition of proliferation across many cancer cell lines. In acute lymphoblastic leukemia (ALL) cells, 6-thioguanine increases mitochondrial dysfunction and generation of ROS, inducing a cytotoxic effect. In other in vitro models, 6-thioguanine decreases expression of TNF-related apoptosis-inducing ligand (TRAIL). Additionally, this compound inhibits growth of Toxoplasma gondii.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18834714
| Cas No. |
154-42-7 |
|---|---|
| Purity |
≥90% |
| Formula |
C5H5N5S |
| Formula Wt. |
167.19 |
| IUPAC Name |
2-amino-3,7-dihydropurine-6-thione |
| Synonym |
tioguanine, thioguanine |
| Melting Point |
>360C |
| Solubility |
Soluble in NaOH (50 mg/ml), slightly soluble in ethanol, insoluble in water |
| Appearance |
Off-white to yellow powder |
Zhang F, Fu L, Wang Y. 6-thioguanine induces mitochondrial dysfunction and oxidative DNA damage in acute lymphoblastic leukemia cells. Mol Cell Proteomics. 2013 Dec;12(12):3803-11. PMID: 24043426.
Bohon J, de los Santos CR. Effect of 6-thioguanine on the stability of duplex DNA. Nucleic Acids Res. 2005 May 19;33(9):2880-6. PMID: 15905476.
Thomas CW, Myhre GM, Tschumper R, et al. Selective inhibition of inflammatory gene expression in activated T lymphocytes: a mechanism of immune suppression by thiopurines. J Pharmacol Exp Ther. 2005 Feb;312(2):537-45. PMID: 15388785.
Pfefferkorn ER, Bzik DJ, Honsinger CP. Toxoplasma gondii: mechanism of the parasitostatic action of 6-thioxanthine. Exp Parasitol. 2001 Dec;99(4):235-43. PMID: 11888251.
Morgan CJ, Chawdry RN, Smith AR, et al. 6-Thioguanine-induced growth arrest in 6-mercaptopurine-resistant human leukemia cells. Cancer Res. 1994 Oct 15;54(20):5387-93. PMID: 7923170.
