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KI12986-Mercaptopurine1 g$1360

Chemical Characteristic

Product Name6-Mercaptopurine
SynonymsPurinethol, 6-MP
CAS No.50-44-2
Molecular Weight 152.18
FormulaC5H4N4S
Chemical Name3,7-dihydropurine-6-thione
Smiles[nH]1cnc2nc[nH]c(=S)c12
Chemical Structure

Biological activities

6-Mercaptopurine is a cytotoxic drug and a purine antagonist. 6-Mercaptopurine inhibits the incorporation of both hypoxanthine and glycine into adenine nucleotides. In particular, 6-mercaptopurine inhibits the de novo biosynthesis of purines as measured by the inhibition of the incorporation of labeled formate into the combined DNA and RNA of several mouse tumors. In sensitive cells (L1210 cells), 6-mercaptopurine inhibits the conversion of inosinic acid to adenylic acid. 6-Mercaptopurine also inhibits utilization of the hypoxanthine that appears to be specific for adenine moieties. [1] 6-Mercaptopurine induces structural aberrations in addition to polyploidy or endoreduplication (P & E) of chromosomes. [2] 6-Mercaptopurine is used in the treatment of neoplastic and autoimmune diseases and in the treatment of recipients of transplanted organs. [3] 6-Mercaptopurine is effective therapy in active steroid-dependent Crohn?? disease (CD). [4] 6-Mercaptopurine is one of the most widely used medications for the treatment of childhood acute lymphoblastic leukemia. [5]

Protocols

6-Mercaptopurine is dissolved in normal saline by heating in a bath at 85 °C for 10 minutes. Stock solutions of 6-mercaptopurine are stable for months in the refrigerator. [2]

References

[1] Davidson JD, et al. Studies on the mechanism of action of 6-mercaptopurine in sensitive and resistant L1210 leukemia in vitro. Cancer Res. 1960, 20: 225-232.
[2] Nasjleti CE, et al. Chromosome damage and polyploidization induced in human peripheral leukocytes in vivo and in vitro with nitrogen mustard, 6-mercaptopurine, and A-649. Cancer Res. 1966, 26 (12): 2437-2443.
[3] Weinshilboum RM, et al. Mercaptopurine pharmacogenetics: monogenic inheritance of erythrocyte thiopurine methyltransferase activity. Am J Hum Genet. 1980, 32 (5): 651-662.
[4] Markowitz J, et al. A multicenter trial of 6-mercaptopurine and prednisone in children with newly diagnosed Crohn's disease. Gastroenterology. 2000, 119 (4): 895-902.
[5] Relling MV, et al. Mercaptopurine therapy intolerance and heterozygosity at the thiopurine S-methyltransferase gene locus. J Natl Cancer Inst. 1999, 91 (23): 2001-2008.

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