Synthesis and biological evaluation of enantiopure thionitrites: The solid-phase synthesis and nitrosation of D-glutathione as a molecular probe

被引：8
作者：
Cavero, M
Hobbs, A
Madge, D
Motherwell, WB
Selwood, D
Potier, P
机构：
[1] UCL, Christopher Ingold Labs, Dept Chem, London WC1H 0AJ, England
[2] Wolfson Inst Biomed Res, London WC1E 6AU, England
[3] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 07期
基金：
英国惠康基金;
关键词：
D O I：
10.1016/S0960-894X(00)00060-3
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The D-isomer of the naturally-occurring tripeptide glulathione (gamma-L-Glu-L-Cys-Gly, L-GSH) has been synthesised using the Fmoc solid phase peptide synthesis strategy. The D-GSH obtained has been nitrosated to give the D-isomer of the bioactive thionitrite, S-nitroso-L-glutathione. The biological activity of both enantiomers of S-nitrosoglutathione has been studied and compared to the activity of the D- and L-isomers of N-acetyl-S-nitrosopenicillamine (SNAP) and S-nitrosocysteine (CysNO). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：641 / 644
页数：4
相关论文
共 30 条
[21]   VISIBLE-LIGHT PHOTOCHEMICAL RELEASE OF NITRIC-OXIDE FROM S-NITROSOGLUTATHIONE - POTENTIAL PHOTOCHEMOTHERAPEUTIC APPLICATIONS [J].
SEXTON, DJ ;
MURUGANANDAM, A ;
MCKENNEY, DJ ;
MUTUS, B .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1994, 59 (04) :463-467
[22]   Polynitrosylated proteins: Characterization, bioactivity, and functional consequences [J].
Simon, DI ;
Mullins, ME ;
Jia, L ;
Gaston, B ;
Singel, DJ ;
Stamler, JS .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (10) :4736-4741
[23]   ON SYNTHESIS OF CYSTEINE PEPTIDES [J].
SOKOLOVSKY, M ;
WILCHEK, M ;
PATCHORNIK, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) :1202-&
[24]   S-NITROSYLATION OF PROTEINS WITH NITRIC-OXIDE - SYNTHESIS AND CHARACTERIZATION OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].
STAMLER, JS ;
SIMON, DI ;
OSBORNE, JA ;
MULLINS, ME ;
JARAKI, O ;
MICHEL, T ;
SINGEL, DJ ;
LOSCALZO, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (01) :444-448
[25]   NITRIC-OXIDE CIRCULATES IN MAMMALIAN PLASMA PRIMARILY AS AN S-NITROSO ADDUCT OF SERUM-ALBUMIN [J].
STAMLER, JS ;
JARAKI, O ;
OSBORNE, J ;
SIMON, DI ;
KEANEY, J ;
VITA, J ;
SINGEL, D ;
VALERI, CR ;
LOSCALZO, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (16) :7674-7677
[26]   BIOCHEMISTRY OF NITRIC-OXIDE AND ITS REDOX-ACTIVATED FORMS [J].
STAMLER, JS ;
SINGEL, DJ ;
LOSCALZO, J .
SCIENCE, 1992, 258 (5090) :1898-1902
[27]   L- and D-S-nitroso-beta,beta-dimethylcysteine differentially increase cGMP in cultured vascular smooth muscle cells [J].
Travis, MD ;
Stoll, LL ;
Bates, JN ;
Lewis, SJ .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1996, 318 (01) :47-53
[28]   The mechanism of nitric oxide formation from S-nitrosothiols (thionitrites) [J].
Williams, DLH .
CHEMICAL COMMUNICATIONS, 1996, (10) :1085-1091
[29]  
WILLIAMS DLH, 1996, METHOD ENZYMOL, V268, P229
[30]   Nitric oxide in biology: Its role as a ligand [J].
Williams, RJP .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :77-&
123