Mechanistic Studies on the Stereoselectivity of the Serotonin 5-HT1A Receptor

被引:24
作者
Yuan, Shuguang [1 ]
Peng, Qian [2 ]
Palczewski, Krzysztof [3 ]
Vogel, Horst [1 ]
Filipek, Slawomir [4 ,5 ]
机构
[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lausanne, Switzerland
[2] Univ Oxford, Dept Chem, Oxford OX1 2JD, England
[3] Case Western Reserve Univ, Sch Med, Dept Pharmacol, Cleveland, OH 44106 USA
[4] Univ Warsaw, Fac Chem & Biol, Lab Biomodeling, Warsaw, Poland
[5] Univ Warsaw, Chem Res Ctr, Warsaw, Poland
关键词
GPCRs; molecular dynamics simulations; proteins; stereoselectivity; water channels; PROTEIN-COUPLED RECEPTORS; STRUCTURAL BASIS; OPIOID RECEPTOR; SMALL MOLECULES; FORCE-FIELD; SODIUM-IONS; ACTIVATION; INSERTION; MODEL; GPCRS;
D O I
10.1002/anie.201603766
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
G-protein-coupled receptors (GPCRs) are involved in a wide range of physiological processes, and they have attracted considerable attention as important targets for developing new medicines. A central and largely unresolved question in drug discovery, which is especially relevant to GPCRs, concerns ligand selectivity: Why do certain molecules act as activators (agonists) whereas others, with nearly identical structures, act as blockers (antagonists) of GPCRs? To address this question, we employed all-atom, long-timescale molecular dynamics simulations to investigate how two diastereomers (epimers) of dihydrofuroaporphine bind to the serotonin 5-HT1A receptor and exert opposite effects. By using molecular interaction fingerprints, we discovered that the agonist could mobilize nearby amino acid residues to act as molecular switches for the formation of a continuous water channel. In contrast, the antagonist epimer remained firmly stabilized in the binding pocket.
引用
收藏
页码:8661 / 8665
页数:5
相关论文
共 36 条
[1]   Tactical Approaches to Interconverting GPCR Agonists and Antagonists [J].
Dosa, Peter I. ;
Amin, Elizabeth Ambrose .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (03) :810-840
[2]   Molecular control of δ-opioid receptor signalling [J].
Fenalti, Gustavo ;
Giguere, Patrick M. ;
Katritch, Vsevolod ;
Huang, Xi-Ping ;
Thompson, Aaron A. ;
Cherezov, Vadim ;
Roth, Bryan L. ;
Stevens, Raymond C. .
NATURE, 2014, 506 (7487) :191-196
[3]   Enantiomeric resolution of [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl](2-phenoxyethyl)amine, a potent α1 and 5-HT1A receptor ligand: an in vitro and computational study [J].
Franchini, Silvia ;
Baraldi, Annamaria ;
Sorbi, Claudia ;
Pellati, Federica ;
Cichero, Elena ;
Battisti, Umberto M. ;
Angeli, Piero ;
Cilia, Antonio ;
Brasili, Livio .
MEDCHEMCOMM, 2015, 6 (04) :677-690
[4]   Computational and Experimental Analysis of the Transmembrane Domain 4/5 Dimerization Interface of the Serotonin 5-HT1A Receptor [J].
Gorinski, Nataliya ;
Kowalsman, Noga ;
Renner, Ute ;
Wirth, Alexander ;
Reinartz, Michael T. ;
Seifert, Roland ;
Zeug, Andre ;
Ponimaskin, Evgeni ;
Niv, Masha Y. .
MOLECULAR PHARMACOLOGY, 2012, 82 (03) :448-463
[5]   Accelerated molecular dynamics simulations of ligand binding to a muscarinic G-protein-coupled receptor [J].
Kappel, Kalli ;
Miao, Yinglong ;
McCammon, J. Andrew .
QUARTERLY REVIEWS OF BIOPHYSICS, 2015, 48 (04) :479-487
[6]   Update of the CHARMM All-Atom Additive Force Field for Lipids: Validation on Six Lipid Types [J].
Klauda, Jeffery B. ;
Venable, Richard M. ;
Freites, J. Alfredo ;
O'Connor, Joseph W. ;
Tobias, Douglas J. ;
Mondragon-Ramirez, Carlos ;
Vorobyov, Igor ;
MacKerell, Alexander D., Jr. ;
Pastor, Richard W. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (23) :7830-7843
[7]  
Kräutler V, 2001, J COMPUT CHEM, V22, P501, DOI 10.1002/1096-987X(20010415)22:5<501::AID-JCC1021>3.0.CO
[8]  
2-V
[9]   Muscarinic acetylcholine receptors: novel opportunities for drug development [J].
Kruse, Andrew C. ;
Kobilka, Brian K. ;
Gautam, Dinesh ;
Sexton, Patrick M. ;
Christopoulos, Arthur ;
Wess, Juergen .
NATURE REVIEWS DRUG DISCOVERY, 2014, 13 (07) :549-560
[10]   DIRECT-ID: Automated Method to Identify and Conformational Variations Application to β2-Adrenergic GPCR [J].
Lakkaraju, Sirish Kaushik ;
Lemkul, Justin A. ;
Huang, Jing ;
MacKerell, Alexander D., Jr. .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2016, 37 (04) :416-425