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6-Thioguanine

Product ID T2835
Cas No. 154-42-7
Purity ≥90%
Product Unit SizeCostQuantityStock
250 mg $71.70 In stock
500 mg $114.80 In stock
1 g $179.10 In stock
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  • Description
  • Product Info
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  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

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.

Product Info

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

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

T2835 MSDS PDF

Info Sheet

T2835 Info Sheet PDF

References

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.

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