Ab initio studies of the properties of intracellular thiols ergothioneine and ovothiol

被引:26
作者
Hand, CE [1 ]
Taylor, NJ [1 ]
Honek, JF [1 ]
机构
[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada
关键词
ergothioneine; ovothiol; ab initio; intracellular thiols; glutathione;
D O I
10.1016/j.bmcl.2005.01.014
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Intracellular naturally occurring aromatic thiols such as ergothioneine and the ovothiols have been shown to play a variety of roles in cellular function. A detailed ab initio electronic structure analysis of these thiols is reported evaluating the thermodynamics of the reactions of these intracellular thiols with alkyl thiols, HO., H2O2, ascorbate and their disulfides. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1357 / 1360
页数:4
相关论文
共 48 条
[1]   THE ANTIOXIDANT ACTION OF ERGOTHIONEINE [J].
AKANMU, D ;
CECCHINI, R ;
ARUOMA, OI ;
HALLIWELL, B .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1991, 288 (01) :10-16
[2]  
[Anonymous], 1985, OXIDATIVE STRESS
[3]  
[Anonymous], 1997, Oxidants, antioxidants, and free radicals
[4]   Ovothiol and trypanothione as antioxidants in trypanosomatids [J].
Ariyanayagam, MR ;
Fairlamb, AH .
MOLECULAR AND BIOCHEMICAL PARASITOLOGY, 2001, 115 (02) :189-198
[5]  
ASKARI A, 1962, J BIOL CHEM, V237, P1615
[6]   One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: Redox reaction involving ergothioneine and vitamin C [J].
Asmus, KD ;
Bensasson, RV ;
Bernier, JL ;
Houssin, R ;
Land, EJ .
BIOCHEMICAL JOURNAL, 1996, 315 :625-629
[7]   The exceptional glutathione peroxidase-like activity of di(3-hydroxypropyl) selenide and the unexpected role of a novel spirodioxaselenanonane intermediate in the catalytic cycle [J].
Back, TG ;
Moussa, Z ;
Parvez, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) :1268-1270
[8]   Design, synthesis and glutathione peroxidase-like properties of ovothiol-derived diselenides [J].
Bailly, F ;
Azaroual, N ;
Bernier, JL .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (21) :4623-4630
[9]   Antioxidant actions of ovothiol-derived 4-mercaptoimidazoles: glutathione peroxidase activity and protection against peroxynitrite-induced damage [J].
Bailly, F ;
Zoete, V ;
Vamecq, J ;
Catteau, JP ;
Bernier, JL .
FEBS LETTERS, 2000, 486 (01) :19-22
[10]   ERGOTHIONEINE IN CENTRAL NERVOUS-SYSTEM [J].
BRIGGS, I .
JOURNAL OF NEUROCHEMISTRY, 1972, 19 (01) :27-&