Title: Buthionine Sulfoximine
CAS Registry Number: 5072-26-4
CAS Name: 2-Amino-4-(S-butylsulfonimidoyl)butanoic acid
Additional Names: S-(3-amino-3-carboxypropyl)-S-butylsulfoximine; S-(n-butyl)homocysteine sulfoximine; BSO
Molecular Formula: C8H18N2O3S
Molecular Weight: 222.31
Percent Composition: C 43.22%, H 8.16%, N 12.60%, O 21.59%, S 14.42%
Literature References: Selective inhibitor of g-glutamyl cysteine synthetase, an enzyme in the glutathione, q.v., biosynthetic pathway. BSO-mediated depletion of intracellular glutathione has been associated with increased sensitivity of tumor cells to antineoplastic agents. Prepn: K. Hayashi, Chem. Pharm. Bull. 8, 177 (1960). Synthesis and in vitro and in vivo enzyme inhibition: O. W. Griffith, A. Meister, J. Biol. Chem. 254, 7758 (1979). Mechanism of action and metabolism in animals O. W. Griffith, ibid. 257, 13704 (1982). Chemosensitization by BSO of melphalan-resistant murine leukemia cells in vivo: S. Somfai-Relle et al., Biochem. Pharmacol. 33, 485 (1984); R. A. Kramer et al., Cancer Res. 47, 1593 (1987). Enhanced melphalan, q.v., cytotoxicity in human cancer cells in vitro: J. A. Green et al., ibid. 44, 5427 (1984); and in mice bearing human tumor xenografts: H. S. Friedman et al., J. Natl. Cancer Inst. 81, 524 (1989).
Properties: Crystals from aq ethanol, mp 214-215.5° (dec). Sol in water. Partition coefficient (octanol/water): 4.34 ±0.0004.
Melting point: mp 214-215.5° (dec)
Log P: Partition coefficient (octanol/water): 4.34 ±0.0004
Use: Biological tool for depletion of glutathione. |