Cation-$\pi $ Interactions in Aromatics of Biological and Medicinal Interest: Electrostatic Potential Surfaces as a Useful Qualitative Guide

The cation-$\pi $ interaction is an important, general force for molecular recognition in biological receptors. Through the sidechains of aromatic amino acids, novel binding sites for cationic ligands such as acetylcholine can be constructed. We report here a number of calculations on prototypical c...

Full description

Saved in:
Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 1996-10, Vol.93 (20), p.10566-10571
Main Authors: Mecozzi, Sandro, West, Anthony P., Dougherty, Dennis A.
Format: Article
Language:English
Subjects:
Benzene - chemistry
Benzene Derivatives - chemistry
Binding energy
Binding sites
Cations, Monovalent
Computer Simulation
Electrical potential
Electrostatics
Furans
Gases
Histidine - chemistry
Hydrogen bonds
Indoles
Models, Molecular
Oxygen
Phenols
Phenylalanine - chemistry
Pyrroles
Sodium - chemistry
Static Electricity
Tryptophan - chemistry
Tyrosine - chemistry
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c531t-780df78c69441c8431c30b6fc5cfc2df38bd426f1e246c96037e0aa1fc66e1793
cites
container_end_page 10571
container_issue 20
container_start_page 10566
container_title Proceedings of the National Academy of Sciences - PNAS
container_volume 93
creator Mecozzi, Sandro
West, Anthony P.
Dougherty, Dennis A.
description The cation-$\pi $ interaction is an important, general force for molecular recognition in biological receptors. Through the sidechains of aromatic amino acids, novel binding sites for cationic ligands such as acetylcholine can be constructed. We report here a number of calculations on prototypical cation-$\pi $ systems, emphasizing structures of relevance to biological receptors and prototypical heterocycles of the type often of importance in medicinal chemistry. Trends in the data can be rationalized using a relatively simple model that emphasizes the electrostatic component of the cation-$\pi $ interaction. In particular, plots of the electrostatic potential surfaces of the relevant aromatics provide useful guidelines for predicting cation-$\pi $ interactions in new systems.
doi_str_mv 10.1073/pnas.93.20.10566
format article
fullrecord <record><control><sourceid>jstor_pubme</sourceid><recordid>TN_cdi_jstor_primary_40192</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><jstor_id>40192</jstor_id><sourcerecordid>40192</sourcerecordid><originalsourceid>FETCH-LOGICAL-c531t-780df78c69441c8431c30b6fc5cfc2df38bd426f1e246c96037e0aa1fc66e1793</originalsourceid><addsrcrecordid>eNp9kVFvFCEUhYnR1G313ZgYeWhMX2aFgWHA9KXdtLVJjRrtmwlhGag0LKzANPU_-KNl3HVjX0xIyOV853LhAPACozlGPXm7DirPBZm3U90x9gjMMBK4YVSgx2CGUNs3nLb0KdjP-RYhJDqO9sAe513XYj4DvxaquBiaw29rBw_hZSgmKT0dZegCPElxVQGdYbTw1EUfb5xWHqowwA9mcNqFWv1xmVzewTNvdEkxl8kEP8ViQnGV-DImq7TJUNUFr7Oxo4efR-XdRN4ZeDG6wTwDT6zy2Tzf7gfg-vzs6-J9c_Xx4nJxctXojuDS9BwNtueaCUqx5pRgTdCSWd1pq9vBEr4caMssNi1lWjBEeoOUwlYzZnAvyAE43vRdj8uVGXQdMikv18mtVPopo3LyoRLcd3kT7yThWJBqf7O1p_hjrO-WK5e18V4FE8cse05rNhhVEG1AXb8kJ2N3V2Akp_zklJ8URLZTXfOrllf_jrYzbAOr-uutPjn_qg87HP2fkPXvfTH3paIvN-htLjHtWIqwaMlv9W27Mg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>78407310</pqid></control><display><type>article</type><title>Cation-$\pi $ Interactions in Aromatics of Biological and Medicinal Interest: Electrostatic Potential Surfaces as a Useful Qualitative Guide</title><source>JSTOR Archival Journals and Primary Sources Collection</source><source>PubMed Central</source><creator>Mecozzi, Sandro ; West, Anthony P. ; Dougherty, Dennis A.</creator><creatorcontrib>Mecozzi, Sandro ; West, Anthony P. ; Dougherty, Dennis A.</creatorcontrib><description>The cation-$\pi $ interaction is an important, general force for molecular recognition in biological receptors. Through the sidechains of aromatic amino acids, novel binding sites for cationic ligands such as acetylcholine can be constructed. We report here a number of calculations on prototypical cation-$\pi $ systems, emphasizing structures of relevance to biological receptors and prototypical heterocycles of the type often of importance in medicinal chemistry. Trends in the data can be rationalized using a relatively simple model that emphasizes the electrostatic component of the cation-$\pi $ interaction. In particular, plots of the electrostatic potential surfaces of the relevant aromatics provide useful guidelines for predicting cation-$\pi $ interactions in new systems.</description><identifier>ISSN: 0027-8424</identifier><identifier>EISSN: 1091-6490</identifier><identifier>DOI: 10.1073/pnas.93.20.10566</identifier><identifier>PMID: 8855218</identifier><language>eng</language><publisher>United States: National Academy of Sciences of the United States of America</publisher><subject>Benzene - chemistry ; Benzene Derivatives - chemistry ; Binding energy ; Binding sites ; Cations, Monovalent ; Computer Simulation ; Electrical potential ; Electrostatics ; Furans ; Gases ; Histidine - chemistry ; Hydrogen bonds ; Indoles ; Models, Molecular ; Oxygen ; Phenols ; Phenylalanine - chemistry ; Pyrroles ; Sodium - chemistry ; Static Electricity ; Tryptophan - chemistry ; Tyrosine - chemistry</subject><ispartof>Proceedings of the National Academy of Sciences - PNAS, 1996-10, Vol.93 (20), p.10566-10571</ispartof><rights>Copyright 1996 National Academy of Sciences</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c531t-780df78c69441c8431c30b6fc5cfc2df38bd426f1e246c96037e0aa1fc66e1793</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://www.pnas.org/content/93/20.cover.gif</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/40192$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/40192$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793,58238,58471</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8855218$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mecozzi, Sandro</creatorcontrib><creatorcontrib>West, Anthony P.</creatorcontrib><creatorcontrib>Dougherty, Dennis A.</creatorcontrib><title>Cation-$\pi $ Interactions in Aromatics of Biological and Medicinal Interest: Electrostatic Potential Surfaces as a Useful Qualitative Guide</title><title>Proceedings of the National Academy of Sciences - PNAS</title><addtitle>Proc Natl Acad Sci U S A</addtitle><description>The cation-$\pi $ interaction is an important, general force for molecular recognition in biological receptors. Through the sidechains of aromatic amino acids, novel binding sites for cationic ligands such as acetylcholine can be constructed. We report here a number of calculations on prototypical cation-$\pi $ systems, emphasizing structures of relevance to biological receptors and prototypical heterocycles of the type often of importance in medicinal chemistry. Trends in the data can be rationalized using a relatively simple model that emphasizes the electrostatic component of the cation-$\pi $ interaction. In particular, plots of the electrostatic potential surfaces of the relevant aromatics provide useful guidelines for predicting cation-$\pi $ interactions in new systems.</description><subject>Benzene - chemistry</subject><subject>Benzene Derivatives - chemistry</subject><subject>Binding energy</subject><subject>Binding sites</subject><subject>Cations, Monovalent</subject><subject>Computer Simulation</subject><subject>Electrical potential</subject><subject>Electrostatics</subject><subject>Furans</subject><subject>Gases</subject><subject>Histidine - chemistry</subject><subject>Hydrogen bonds</subject><subject>Indoles</subject><subject>Models, Molecular</subject><subject>Oxygen</subject><subject>Phenols</subject><subject>Phenylalanine - chemistry</subject><subject>Pyrroles</subject><subject>Sodium - chemistry</subject><subject>Static Electricity</subject><subject>Tryptophan - chemistry</subject><subject>Tyrosine - chemistry</subject><issn>0027-8424</issn><issn>1091-6490</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNp9kVFvFCEUhYnR1G313ZgYeWhMX2aFgWHA9KXdtLVJjRrtmwlhGag0LKzANPU_-KNl3HVjX0xIyOV853LhAPACozlGPXm7DirPBZm3U90x9gjMMBK4YVSgx2CGUNs3nLb0KdjP-RYhJDqO9sAe513XYj4DvxaquBiaw29rBw_hZSgmKT0dZegCPElxVQGdYbTw1EUfb5xWHqowwA9mcNqFWv1xmVzewTNvdEkxl8kEP8ViQnGV-DImq7TJUNUFr7Oxo4efR-XdRN4ZeDG6wTwDT6zy2Tzf7gfg-vzs6-J9c_Xx4nJxctXojuDS9BwNtueaCUqx5pRgTdCSWd1pq9vBEr4caMssNi1lWjBEeoOUwlYzZnAvyAE43vRdj8uVGXQdMikv18mtVPopo3LyoRLcd3kT7yThWJBqf7O1p_hjrO-WK5e18V4FE8cse05rNhhVEG1AXb8kJ2N3V2Akp_zklJ8URLZTXfOrllf_jrYzbAOr-uutPjn_qg87HP2fkPXvfTH3paIvN-htLjHtWIqwaMlv9W27Mg</recordid><startdate>19961001</startdate><enddate>19961001</enddate><creator>Mecozzi, Sandro</creator><creator>West, Anthony P.</creator><creator>Dougherty, Dennis A.</creator><general>National Academy of Sciences of the United States of America</general><general>National Acad Sciences</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>19961001</creationdate><title>Cation-$\pi $ Interactions in Aromatics of Biological and Medicinal Interest: Electrostatic Potential Surfaces as a Useful Qualitative Guide</title><author>Mecozzi, Sandro ; West, Anthony P. ; Dougherty, Dennis A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c531t-780df78c69441c8431c30b6fc5cfc2df38bd426f1e246c96037e0aa1fc66e1793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Benzene - chemistry</topic><topic>Benzene Derivatives - chemistry</topic><topic>Binding energy</topic><topic>Binding sites</topic><topic>Cations, Monovalent</topic><topic>Computer Simulation</topic><topic>Electrical potential</topic><topic>Electrostatics</topic><topic>Furans</topic><topic>Gases</topic><topic>Histidine - chemistry</topic><topic>Hydrogen bonds</topic><topic>Indoles</topic><topic>Models, Molecular</topic><topic>Oxygen</topic><topic>Phenols</topic><topic>Phenylalanine - chemistry</topic><topic>Pyrroles</topic><topic>Sodium - chemistry</topic><topic>Static Electricity</topic><topic>Tryptophan - chemistry</topic><topic>Tyrosine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mecozzi, Sandro</creatorcontrib><creatorcontrib>West, Anthony P.</creatorcontrib><creatorcontrib>Dougherty, Dennis A.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mecozzi, Sandro</au><au>West, Anthony P.</au><au>Dougherty, Dennis A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cation-$\pi $ Interactions in Aromatics of Biological and Medicinal Interest: Electrostatic Potential Surfaces as a Useful Qualitative Guide</atitle><jtitle>Proceedings of the National Academy of Sciences - PNAS</jtitle><addtitle>Proc Natl Acad Sci U S A</addtitle><date>1996-10-01</date><risdate>1996</risdate><volume>93</volume><issue>20</issue><spage>10566</spage><epage>10571</epage><pages>10566-10571</pages><issn>0027-8424</issn><eissn>1091-6490</eissn><abstract>The cation-$\pi $ interaction is an important, general force for molecular recognition in biological receptors. Through the sidechains of aromatic amino acids, novel binding sites for cationic ligands such as acetylcholine can be constructed. We report here a number of calculations on prototypical cation-$\pi $ systems, emphasizing structures of relevance to biological receptors and prototypical heterocycles of the type often of importance in medicinal chemistry. Trends in the data can be rationalized using a relatively simple model that emphasizes the electrostatic component of the cation-$\pi $ interaction. In particular, plots of the electrostatic potential surfaces of the relevant aromatics provide useful guidelines for predicting cation-$\pi $ interactions in new systems.</abstract><cop>United States</cop><pub>National Academy of Sciences of the United States of America</pub><pmid>8855218</pmid><doi>10.1073/pnas.93.20.10566</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0027-8424
ispartof Proceedings of the National Academy of Sciences - PNAS, 1996-10, Vol.93 (20), p.10566-10571
issn 0027-8424
1091-6490
language eng
recordid cdi_jstor_primary_40192
source JSTOR Archival Journals and Primary Sources Collection; PubMed Central
subjects Benzene - chemistry
Benzene Derivatives - chemistry
Binding energy
Binding sites
Cations, Monovalent
Computer Simulation
Electrical potential
Electrostatics
Furans
Gases
Histidine - chemistry
Hydrogen bonds
Indoles
Models, Molecular
Oxygen
Phenols
Phenylalanine - chemistry
Pyrroles
Sodium - chemistry
Static Electricity
Tryptophan - chemistry
Tyrosine - chemistry
title Cation-$\pi $ Interactions in Aromatics of Biological and Medicinal Interest: Electrostatic Potential Surfaces as a Useful Qualitative Guide
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T17%3A59%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-jstor_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Cation-$%5Cpi%20$%20Interactions%20in%20Aromatics%20of%20Biological%20and%20Medicinal%20Interest:%20Electrostatic%20Potential%20Surfaces%20as%20a%20Useful%20Qualitative%20Guide&rft.jtitle=Proceedings%20of%20the%20National%20Academy%20of%20Sciences%20-%20PNAS&rft.au=Mecozzi,%20Sandro&rft.date=1996-10-01&rft.volume=93&rft.issue=20&rft.spage=10566&rft.epage=10571&rft.pages=10566-10571&rft.issn=0027-8424&rft.eissn=1091-6490&rft_id=info:doi/10.1073/pnas.93.20.10566&rft_dat=%3Cjstor_pubme%3E40192%3C/jstor_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c531t-780df78c69441c8431c30b6fc5cfc2df38bd426f1e246c96037e0aa1fc66e1793%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=78407310&rft_id=info:pmid/8855218&rft_jstor_id=40192&rfr_iscdi=true