Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione

被引：40

作者：

Alvarez-Sánchez, R

Basketter, D

Pease, C

Lepoittevin, JP ^{[1
]}

机构：

[1] Univ Strasbourg 1, CHU Strasbourg, UMR 7123, Lab Dermatochim, Strasbourg, France

[2] Unilever, SEAC, Bedford, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 02期

关键词：

D O I：

10.1016/j.bmcl.2003.11.002

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The reactivity of 4-[C-13]- and 5-[C-13]-5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) towards a model peptide and glutathione was followed by C-13 and H-1{C-13} NMR spectroscopy. Both molecules were found to react with GSH but in addition MCI was found to react with histidine and lysine to form adducts of a different nature. Reaction with histidine led to stable substitution adducts through an addition-elimination reaction at position 5 while reaction with lysine led to the formation of open adducts of the thioamide or amide type. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：365 / 368

页数：4

共 9 条

[1] Studies of chemical selectivity of hapten, reactivity, and skin sensitization potency.: 3.: Synthesis and studies on the reactivity toward model nucleophiles of the 13C-Labeled skin sensitizers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) [J].