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Cation-π interactions: Computational analyses of the aromatic box motif and the fluorination strategy for experimental evaluation of cys-loop receptors and related structures

Davis, Matthew R. and Dougherty, Dennis A. (2016) Cation-π interactions: Computational analyses of the aromatic box motif and the fluorination strategy for experimental evaluation of cys-loop receptors and related structures. In: 251st American Chemical Society National Meeting & Exposition, March 13-17, 2016, San Diego, CA. https://resolver.caltech.edu/CaltechAUTHORS:20160504-105529996

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Abstract

Cation-π interactions are common in biol. systems, in particular ligand- gated ion channels (LGICs). Our own studies, in addn. to more recent structural studies, have revealed the arom. box as a common motif for binding cationic ligands. With the aim of understanding the nature of the arom. box, several computational methods were evaluated for their ability to reproduce exptl. cation-π binding energies. We find the DFT method M06 with the 6-31G(d, p) basis set performs best of several methods tested. The binding of benzene to a no. of different cations (sodium, potassium, ammonium, tetramethylammonium, and guanidinium) was studied. In addn., the binding of the org. cations NH_4+ and NMe_4+ to ab initio generated arom. boxes as well as examples of arom. boxes from a no. of protein crystal structures was investigated. In addn., we have performed a study of the intrinsic distance dependence of the cation- π interaction. We find that multiple arom. residues can contribute to cation binding in a variety of LGICs including ELIC, the glycine receptor, the GABA(A) receptor, and a model of the nicotinic acetylcholine receptor. Progressive fluorination of benzene and indole was studied as well, and binding energies obtained were used to reaffirm the validity of the "fluorination strategy" to study cation-π interactions in vivo.


Item Type:Conference or Workshop Item (Paper)
Related URLs:
URLURL TypeDescription
http://www.acs.org/content/acs/en/meetings/spring-2016.htmlOrganizationConference Website
ORCID:
AuthorORCID
Davis, Matthew R.0000-0002-6374-4555
Dougherty, Dennis A.0000-0003-1464-2461
Additional Information:© 2016 American Chemical Society.
Record Number:CaltechAUTHORS:20160504-105529996
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160504-105529996
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66648
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:04 May 2016 20:19
Last Modified:03 Oct 2019 09:58

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