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Cation−π Interactions in Ligand Recognition by Serotonergic (5-HT_(3A)) and Nicotinic Acetylcholine Receptors: The Anomalous Binding Properties of Nicotine

Beene, Darren L. and Brandt, Gabriel S. and Zhong, Wenge and Zacharias, Niki M. and Lester, Henry A. and Dougherty, Dennis A. (2002) Cation−π Interactions in Ligand Recognition by Serotonergic (5-HT_(3A)) and Nicotinic Acetylcholine Receptors: The Anomalous Binding Properties of Nicotine. Biochemistry, 41 (32). pp. 10262-10269. ISSN 0006-2960. https://resolver.caltech.edu/CaltechAUTHORS:20170125-110549324

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Abstract

A series of tryptophan analogues has been introduced into the binding site regions of two ion channels, the ligand-gated nicotinic acetylcholine and serotonin 5-HT_(3A) receptors, using unnatural amino acid mutagenesis and heterologous expression in Xenopus oocytes. A cation−π interaction between serotonin and Trp183 of the serotonin channel 5-HT3AR is identified for the first time, precisely locating the ligand-binding site of this receptor. The energetic contribution of the observed cation−π interaction between a tryptophan and the primary ammonium ion of serotonin is estimated to be approximately 4 kcal/mol, while the comparable interaction with the quaternary ammonium of acetylcholine is approximately 2 kcal/mol. The binding mode of nicotine to the nicotinic receptor of mouse muscle is examined by the same technique and found to differ significantly from that of the natural agonist, acetylcholine.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/bi020266dDOIArticle
http://pubs.acs.org/doi/abs/10.1021/bi020266dPublisherArticle
ORCID:
AuthorORCID
Lester, Henry A.0000-0002-5470-5255
Dougherty, Dennis A.0000-0003-1464-2461
Additional Information:© 2002 American Chemical Society. Received 8 April 2002. Published online 19 July 2002. Published in print 1 August 2002.
Issue or Number:32
Record Number:CaltechAUTHORS:20170125-110549324
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170125-110549324
Official Citation:Cation−π Interactions in Ligand Recognition by Serotonergic (5-HT3A) and Nicotinic Acetylcholine Receptors:  The Anomalous Binding Properties of Nicotine Darren L. Beene, Gabriel S. Brandt, Wenge Zhong, Niki M. Zacharias, Henry A. Lester, and Dennis A. Dougherty Biochemistry 2002 41 (32), 10262-10269 DOI: 10.1021/bi020266d
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:73717
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:25 Jan 2017 20:35
Last Modified:03 Oct 2019 16:30

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