Synthesis and evaluation of an N-acylated photoactivatable analogue of glutathione as probe for glutathione-utilizing enzymes

被引：10

作者：

Bernardi, D ^{[1
]}

Battaglia, E ^{[1
]}

Kirsch, G ^{[1
]}

机构：

[1] Univ Metz, Lab Ingn Mol & Biochim Pharmacol, F-57078 Metz 3, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 06期

关键词：

photoaffinity labelling; inhibition; glutathione; S-transferases; benzophenone;

D O I：

10.1016/j.bmcl.2005.12.047

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The first synthesis of an N-acylated photoactivatable analogue of reduced glutathione is described. N-(4-Benzoylbenzoyl)glutathione (8) was found to be an inhibitor and a photoaffinity probe of purified rat liver glutathione S-transferases. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1601 / 1604

页数：4

共 42 条

[1] New photoactivatable analogues of glutathione disulfide [J].

Bernardi, D ;

Dicko, A ;

Kirsch, G .

SYNTHESIS-STUTTGART, 2006, (03) :509-513

[2] Peptidomimetic glutathione analogues as novel γGT stable GST inhibitors [J].

Burg, D ;

Filippov, DV ;

Hermanns, R ;

van der Marel, GA ;

van Boom, JH ;

Mulder, GJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (01) :195-205

[3]

CAVELIER F, 1990, B SOC CHIM FR, P210

[4] 3,4-EPOXYPRECOCENES AS MODELS OF CYTOTOXIC EPOXIDES - SYNTHESIS OF THE CIS ADDUCTS OCCURRING IN THE GLUTATHIONE METABOLIC PATHWAY [J].

CONCHILLO, A ;

CAMPS, F ;

MESSEGUER, A .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1728-1735

[5]

DEHALLE S, 2003, ANN NY ACAD SCI, V1010, P1

[6] Using photolabile ligands in drug discovery and development [J].

Dormán, G ;

Prestwich, GD .

TRENDS IN BIOTECHNOLOGY, 2000, 18 (02) :64-77

[7] BENZOPHENONE PHOTOPHORES IN BIOCHEMISTRY [J].

DORMAN, G ;

PRESTWICH, GD .

BIOCHEMISTRY, 1994, 33 (19) :5661-5673

[8] ROLE OF THE N-TERMINUS OF GLUTATHIONE IN THE ACTION OF YEAST GLYOXALASE-I [J].

DOUGLAS, KT ;

ALTIMARI, A ;

DSILVA, C ;

GOHEL, DI .

BIOCHEMICAL JOURNAL, 1982, 207 (02) :323-329

[9] PHOTOAFFINITY LABELS FOR ENZYMES CAPABLE OF BINDING GLUTATHIONE OR ITS DISULFIDE [J].

DSILVA, C ;

SEDDON, AP ;

DOUGLAS, KT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (12) :3029-3033

[10] Molecular design of glutathione-derived biochemical probes targeting the GS-X pump [J].

Furuta, K ;

Tomokiyo, K ;

Kuo, MT ;

Ishikawa, T ;

Suzuki, M .

TETRAHEDRON, 1999, 55 (24) :7529-7540

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