Study of a lipophilic captopril analogue binding to angiotensin I converting enzyme

被引：23

作者：

Dalkas, Georgios A. ^{[1
]}

Marchand, Damien ^{[2
]}

Galleyrand, Jean-Claude ^{[2
]}

Martinez, Jean ^{[2
]}

Spyroulias, Georgios A. ^{[1
]}

Cordopatis, Paul ^{[1
]}

Cavelier, Florine ^{[2
]}

机构：

[1] Univ Patras, Dept Pharm, GR-26504 Panepistimioupoli Rion, Greece

[2] Univ Montpellier 2, IBMM, CNRS, UM1,UM2,UMR 5247, F-34095 Montpellier, France

来源：

JOURNAL OF PEPTIDE SCIENCE | 2010年 / 16卷 / 02期

关键词：

ACE; zinc metalloenzyme; silacaptopril; docking simulations; MOLECULAR-CLONING; CRYSTAL-STRUCTURE; INHIBITORS; DESIGN; DOMAIN; SILAPROLINE; SUBSTRATE; MODEL; ACID;

D O I：

10.1002/psc.1201

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Human ACE is a central component of the renin-angiotensin system and a major therapeutic target for cardiovascular diseases. T he somatic form of the enzyme (sACE) comprises two homologous metallopeptidase domains (N and C), each bearing a zinc active site with similar but distinct substrate and inhibitor specificities. In this study, we present the biological activity of silacaptopril, a silylated analogue of captopril, and its binding affinity towards ACE. Based on the recently determined crystal structures of both the ACE domains, a series of docking calculations were carried out in order to study the structural characteristics and the binding properties of silacaptopril and its analogues with ACE. Copyright (C) 2009 European Pepticle Society and John Wiley & Sons, Ltd.

引用

页码：91 / 97

页数：7

共 34 条

[1] PKAS OF IONIZABLE GROUPS IN PROTEINS - ATOMIC DETAIL FROM A CONTINUUM ELECTROSTATIC MODEL [J].

BASHFORD, D ;

KARPLUS, M .

BIOCHEMISTRY, 1990, 29 (44) :10219-10225

[2]

CASE DAD, 2006, AMBEP 9

[3] Biological activity of silylated amino acid containing substance P analogues [J].

Cavelier, F ;

Marchand, D ;

Martinez, J ;

Sagan, S .

JOURNAL OF PEPTIDE RESEARCH, 2004, 63 (03) :290-296

[4] Influence of silaproline on peptide conformation and bioactivity [J].

Cavelier, F ;

Vivet, B ;

Martinez, J ;

Aubry, A ;

Didierjean, C ;

Vicherat, A ;

Marraud, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2917-2923

[5] Crystal structure of the N domain of human somatic angiotensin I-converting enzyme provides a structural basis for domain-specific inhibitor design [J].

Corradi, HR ;

Schwager, SLU ;

Nchinda, AT ;

Sturrock, ED ;

Acharya, KR .

JOURNAL OF MOLECULAR BIOLOGY, 2006, 357 (03) :964-974

[6] DESIGN OF POTENT COMPETITIVE INHIBITORS OF ANGIOTENSIN-CONVERTING ENZYME - CARBOXYALKANOYL AND MERCAPTOALKANOYL AMINO-ACIDS [J].

CUSHMAN, DW ;

CHEUNG, HS ;

SABO, EF ;

ONDETTI, MA .

BIOCHEMISTRY, 1977, 16 (25) :5484-5491

[7] MOLECULAR-CLONING OF HUMAN TESTICULAR ANGIOTENSIN-CONVERTING ENZYME - THE TESTIS ISOZYME IS IDENTICAL TO THE C-TERMINAL HALF OF ENDOTHELIAL ANGIOTENSIN-CONVERTING ENZYME (POLYMERASE CHAIN-REACTION ALTERNATIVE SPLICING) [J].

EHLERS, MRW ;

FOX, EA ;

STRYDOM, DJ ;

RIORDAN, JF .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (20) :7741-7745

[8] MIXED INHIBITOR PRODRUG AS A NEW APPROACH TOWARD SYSTEMICALLY ACTIVE INHIBITORS OF ENKEPHALIN-DEGRADING ENZYMES [J].

FOURNIEZALUSKI, MC ;

CORIC, P ;

TURCAUD, S ;

LUCAS, E ;

NOBLE, F ;

MALDONADO, R ;

ROQUES, BP .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (13) :2473-2481

[9] Probing the importance of spacial and conformational domains in captopril analogs for angiotensin converting enzyme activity [J].

Hanessian, S ;

Reinhold, U ;

Saulnier, M ;

Claridge, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (16) :2123-2128

[10]

HUBERT C, 1991, J BIOL CHEM, V266, P15377

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