The nicotinic agonist cytisine: The role of the NH···N interaction

Producción Científica

Detalles Bibliográficos
Autores: Aguado Vesperinas, Raúl, Mata López, Santiago, Sanz Novo, Miguel, Alonso Alonso, Elena Rita, León Ona, Iker, Alonso Hernández, José Luis
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Universidad de Valladolid
Repositorio:UVaDOC. Repositorio Documental de la Universidad de Valladolid
OAI Identifier:oai:uvadoc.uva.es:10324/56569
Acceso en línea:https://doi.org/10.1021/acs.jpclett.2c02021
https://uvadoc.uva.es/handle/10324/56569
Access Level:acceso abierto
Palabra clave:Agonists
Agonistas
Chemical structure
Estructura química
Molecular structure
Estructura molecular
Nicotine
Nicotina
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spelling The nicotinic agonist cytisine: The role of the NH···N interactionAguado Vesperinas, RaúlMata López, SantiagoSanz Novo, MiguelAlonso Alonso, Elena RitaLeón Ona, IkerAlonso Hernández, José LuisAgonistsAgonistasChemical structureEstructura químicaMolecular structureEstructura molecularNicotineNicotinaProducción CientíficaWe report a detailed structural study of cytisine, an alkaloid used to help with smoking cessation, looking forward to unveiling its role as a nicotinic agonist. High-resolution rotational spectroscopy has allowed us to characterize two different conformers exhibiting axial and equatorial arrangements of the piperidinic NH group. Unexpectedly, the axial form has been found as the predominant configuration, in contrast to that observed for related molecules, such as piperidine. This anomalous behavior has been justified in terms of an intramolecular NH···N hydrogen bond. Moreover, this interaction justifies the overstabilization of the axial conformer over the equatorial one and is crucial for the mechanism of action of cytisine over the nicotinic receptor, further rationalizing its behavior as a nicotinic agonist.Ministerio de Ciencia, Innovación y Universidades (project PID2019-111396GB-I00)Junta de Castilla y León (project VA244P20)European Research Council under the European Union’s Seventh Framework Programme (FP/2007- 2013)/ERC-2013-SyG (grant 610256 NANOCOSMOS)American Chemical Society2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://doi.org/10.1021/acs.jpclett.2c02021https://uvadoc.uva.es/handle/10324/56569reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolidinstname:Universidad de ValladolidIngléshttps://pubs.acs.org/doi/10.1021/acs.jpclett.2c02021info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/oai:uvadoc.uva.es:10324/565692026-06-13T12:44:47Z
dc.title.none.fl_str_mv The nicotinic agonist cytisine: The role of the NH···N interaction
title The nicotinic agonist cytisine: The role of the NH···N interaction
spellingShingle The nicotinic agonist cytisine: The role of the NH···N interaction
Aguado Vesperinas, Raúl
Agonists
Agonistas
Chemical structure
Estructura química
Molecular structure
Estructura molecular
Nicotine
Nicotina
title_short The nicotinic agonist cytisine: The role of the NH···N interaction
title_full The nicotinic agonist cytisine: The role of the NH···N interaction
title_fullStr The nicotinic agonist cytisine: The role of the NH···N interaction
title_full_unstemmed The nicotinic agonist cytisine: The role of the NH···N interaction
title_sort The nicotinic agonist cytisine: The role of the NH···N interaction
dc.creator.none.fl_str_mv Aguado Vesperinas, Raúl
Mata López, Santiago
Sanz Novo, Miguel
Alonso Alonso, Elena Rita
León Ona, Iker
Alonso Hernández, José Luis
author Aguado Vesperinas, Raúl
author_facet Aguado Vesperinas, Raúl
Mata López, Santiago
Sanz Novo, Miguel
Alonso Alonso, Elena Rita
León Ona, Iker
Alonso Hernández, José Luis
author_role author
author2 Mata López, Santiago
Sanz Novo, Miguel
Alonso Alonso, Elena Rita
León Ona, Iker
Alonso Hernández, José Luis
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Agonists
Agonistas
Chemical structure
Estructura química
Molecular structure
Estructura molecular
Nicotine
Nicotina
topic Agonists
Agonistas
Chemical structure
Estructura química
Molecular structure
Estructura molecular
Nicotine
Nicotina
description Producción Científica
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://doi.org/10.1021/acs.jpclett.2c02021
https://uvadoc.uva.es/handle/10324/56569
url https://doi.org/10.1021/acs.jpclett.2c02021
https://uvadoc.uva.es/handle/10324/56569
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://pubs.acs.org/doi/10.1021/acs.jpclett.2c02021
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolid
instname:Universidad de Valladolid
instname_str Universidad de Valladolid
reponame_str UVaDOC. Repositorio Documental de la Universidad de Valladolid
collection UVaDOC. Repositorio Documental de la Universidad de Valladolid
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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