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Wednesday, 11 May 2016

Buthionine Sulphoximine

Buthionine Sulphoximine

A gamma-glutamylcysteine synthetase inhibitor potentially for the treatment of solid tumors.

NSC-326231; BSO

CAS No. 5072-26-4

BUTHIONINE SULFOXIMINE; DL-Buthionine-[S,R]-sulfoximine; 5072-26-4; Buthionine sulfoxamine; Buthionine-S,R-sulfoximine; Buthione sulfoximine;

Molecular Formula:	C₈H₁₈N₂O₃S
Molecular Weight:	222.30512 g/mol

Buthionine sulfoximine (BSO) is a sulfoximine which reduces levels of glutathione and is being investigated as an adjunct withchemotherapy in the treatment of cancer.^[1] The compound inhibits gamma-glutamylcysteine synthetase, the enzyme required in the first step of glutathione synthesis. Buthionine sulfoximine may also be used to increase the sensitivity of parasites to oxidativeantiparasitic drugs.^[2]

Buthionine sulphoximine is an oncolytic agent in early clinical development at the National Cancer Institute (NCI) for the treatment of neuroblastoma in pediatric patients in combination with melphalan and bone marrow or peripheral stem cell transplantation.

DATA

1H NMR

13C NMR

Synthesis

Methionine and buthionine sulfoximines: Syntheses under mild and safe imidation/oxidation conditions
Advanced Synthesis&Catalysis (2014), 356, (10), 2209-2213

Abstract

Methionine and buthionine sulfoximines (MSO and BSO) are non-natural amino acids known to inhibit the biosynthesis of glutathione (GSH). The current syntheses of these biologically active molecules involve harsh reaction conditions and the use of hazardous reagents for the sulfur imidation. Here, improved syntheses of MSO and BSO are presented including safe and mild one-pot imidation/oxidation sequences and single-step deprotections of three different functionalities.

Methionine and Buthionine Sulfoximines: Syntheses under Mild and Safe Imidation/Oxidation Conditions

Laura Buglioni,
Vincent Bizet and
Carsten Bolm^*

DOI: 10.1002/adsc.201400354

http://onlinelibrary.wiley.com/doi/10.1002/adsc.201400354/abstract

References

Defty, CL; Marsden, JR (2012). "Melphalan in regional chemotherapy for locally recurrent metastatic melanoma.". Current topics in medicinal chemistry 12 (1): 53–60. PMID 22196271.
"Definition of buthionine sulfoximine - National Cancer Institute Drug Dictionary".

Buthionine sulfoximine
Names


IUPAC name 2-amino-4-(butylsulfonimidoyl)butanoic acid
Other names BSO
Identifiers
CAS Number	5072-26-4
ChEBI	CHEBI:28714
ChemSpider	19896
Jmol 3D model	Interactive image
MeSH	Buthionine+sulfoximine
PubChem	21157
InChI [show]
SMILES [show]
Properties
Chemical formula	C₈H₁₈N₂O₃S
Molar mass	222.305 g/mol
Density	1.29 g/mL
Melting point	215 °C (419 °F; 488 K)
Boiling point	382.3 °C (720.1 °F; 655.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).