Cation-π interactions in ligand recognition and catalysis

被引：400

作者：

Zacharias, N ^{[1
]}

Dougherty, DA ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

TRENDS IN PHARMACOLOGICAL SCIENCES | 2002年 / 23卷 / 06期

关键词：

D O I：

10.1016/S0165-6147(02)02027-8

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

The cation-pi interaction is a potent, general noncovalent binding force that is observed in a wide range of biological contexts. Here, we present an overview of well documented cases in which a cation-pi interaction makes an important contribution to small-molecule recognition at a protein binding site. From these and other studies it is clear that, in addition to the hydrophobic effect, hydrogen bonding and ion pairing, the cation-it interaction must be considered when evaluating drug-receptor interactions.

引用

页码：281 / 287

页数：7

共 77 条

[1] Detoxification of environmental mutagens and carcinogens: Structure, mechanism, and evolution of liver epoxide hydrolase [J].

Argiriadi, MA ;

Morisseau, C ;

Hammock, BD ;

Christianson, DW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (19) :10637-10642

[2] Topology of ligand binding sites on the nicotinic acetylcholine receptor [J].

Arias, HR .

BRAIN RESEARCH REVIEWS, 1997, 25 (02) :133-191

[3] Mechanisms for activation and antagonism of an AMPA-Sensitive glutamate receptor: Crystal structures of the GluR2 ligand binding core [J].

Armstrong, N ;

Gouaux, E .

NEURON, 2000, 28 (01) :165-181

[4] Opioid diketopiperazines: Synthesis and activity of a prototypic class of opioid antagonists [J].

Balboni, G ;

Guerrini, R ;

Salvadori, S ;

Tomatis, R ;

Bryant, SD ;

Bianchi, C ;

Attila, M ;

Lazarus, LH .

BIOLOGICAL CHEMISTRY, 1997, 378 (01) :19-29

[5] A model for hydride transfer in thymidylate synthase based on unnatural amino acid mutagenesis [J].

Barrett, JE ;

Lucero, CM ;

Schultz, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (34) :7965-7966

[6] Selective modification of alkylammonium ion specificity in trimethylamine dehydrogenase by the rational engineering of cation-pi bonding [J].

Basran, J ;

Mewies, M ;

Mathews, FS ;

Scrutton, NS .

BIOCHEMISTRY, 1997, 36 (08) :1989-1998

[7]

BEJC K, 2001, NATURE, V411, P269

[8] Molecular modeling of the GABA/GABAB receptor complex [J].

Bernard, P ;

Guedin, D ;

Hibert, H .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (01) :27-35

[9] Three-dimensional model of the extracellular domain of the type 4a metabotropic glutamate receptor. New insights into the activation process [J].

Bessis, AS ;

Bertrand, HO ;

Galvez, T ;

De Colle, C ;

Pin, JP ;

Acher, F .

PROTEIN SCIENCE, 2000, 9 (11) :2200-2209

[10] Tyrosine 140 of the gamma-aminobutyric acid transporter GAT-1 plays a critical role in neurotransmitter recognition [J].

Bismuth, Y ;

Kavanaugh, MP ;

Kanner, BI .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (26) :16096-16102

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