Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments

[EN]Spectroscopic and photophysical properties of a non-steroidal anti-inflammatory drug, Nabumetone, were studied in dioxane/water mixtures, cyclodextrins (α-CD, β-CD and HP-β-CD) and besides that, for comparison, in a wide range of solvents with different polarities, viscosities and hydrogen bondi...

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Autores: Valero Juan, Margarita, Costa, Silvia M.B, Santos, M. Amélia
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2000
País:España
Institución:Universidad de Salamanca (USAL)
Repositorio:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:dnet:gredos______::26e40147562311d350115468b1f6c01f
Acceso en línea:http://hdl.handle.net/10366/171035
Access Level:acceso abierto
Palabra clave:Cyclodextrin (CD)
Nabumetone
Fluorescence spectra
Quantum yield
Lifetime
Cyclodextrins
Fluorescence
ciclodextrinas
fluorescencia
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spelling Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environmentsValero Juan, MargaritaCosta, Silvia M.BSantos, M. AméliaCyclodextrin (CD)NabumetoneFluorescence spectraQuantum yieldLifetimeCyclodextrinsFluorescenceciclodextrinasfluorescencia[EN]Spectroscopic and photophysical properties of a non-steroidal anti-inflammatory drug, Nabumetone, were studied in dioxane/water mixtures, cyclodextrins (α-CD, β-CD and HP-β-CD) and besides that, for comparison, in a wide range of solvents with different polarities, viscosities and hydrogen bonding ability. The fluorescence quantum yields (φf) and lifetimes (τf) in aqueous and in non-aqueous media, present some evidence which points to the existence of two preferred conformations in aqueous media: one with global φf=0.1–0.3 and τf2=7 ns, corresponding to the side chain completely extended and the other one, with lower global φf=0.02–0.08 and τf1=0.7–2 ns, likely associated with a folded conformation responsible for the fluorescence quenching of the naphthalene moiety by the butanone chain. The formation of one or other conformation is not much affected by the physical properties of the solvent. By contrast, the presence of water creates a very favourable environment for the formation of the folded conformation, which is essentially the only one in pure water. This behaviour is explained by a water-structure enforced hydrophobic effect and makes this drug a good water sensitive probe. Inclusion of the drug in the β-cyclodextrin emphasises the existence of two conformations, whereas in α-CD only the extended one is present, with a much higher φf=0.4 and τf=15.7 ns. Molecular mechanics (MM) and molecular orbital (MNDO) calculations also support the existence of two possible conformations in Nabumetone.Elsevier202620262000info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10366/171035reponame:GREDOS. Repositorio Institucional de la Universidad de Salamancainstname:Universidad de Salamanca (USAL)InglésAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:dnet:gredos______::26e40147562311d350115468b1f6c01f2026-06-07T06:28:51Z
dc.title.none.fl_str_mv Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
title Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
spellingShingle Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
Valero Juan, Margarita
Cyclodextrin (CD)
Nabumetone
Fluorescence spectra
Quantum yield
Lifetime
Cyclodextrins
Fluorescence
ciclodextrinas
fluorescencia
title_short Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
title_full Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
title_fullStr Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
title_full_unstemmed Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
title_sort Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
dc.creator.none.fl_str_mv Valero Juan, Margarita
Costa, Silvia M.B
Santos, M. Amélia
author Valero Juan, Margarita
author_facet Valero Juan, Margarita
Costa, Silvia M.B
Santos, M. Amélia
author_role author
author2 Costa, Silvia M.B
Santos, M. Amélia
author2_role author
author
dc.subject.none.fl_str_mv Cyclodextrin (CD)
Nabumetone
Fluorescence spectra
Quantum yield
Lifetime
Cyclodextrins
Fluorescence
ciclodextrinas
fluorescencia
topic Cyclodextrin (CD)
Nabumetone
Fluorescence spectra
Quantum yield
Lifetime
Cyclodextrins
Fluorescence
ciclodextrinas
fluorescencia
description [EN]Spectroscopic and photophysical properties of a non-steroidal anti-inflammatory drug, Nabumetone, were studied in dioxane/water mixtures, cyclodextrins (α-CD, β-CD and HP-β-CD) and besides that, for comparison, in a wide range of solvents with different polarities, viscosities and hydrogen bonding ability. The fluorescence quantum yields (φf) and lifetimes (τf) in aqueous and in non-aqueous media, present some evidence which points to the existence of two preferred conformations in aqueous media: one with global φf=0.1–0.3 and τf2=7 ns, corresponding to the side chain completely extended and the other one, with lower global φf=0.02–0.08 and τf1=0.7–2 ns, likely associated with a folded conformation responsible for the fluorescence quenching of the naphthalene moiety by the butanone chain. The formation of one or other conformation is not much affected by the physical properties of the solvent. By contrast, the presence of water creates a very favourable environment for the formation of the folded conformation, which is essentially the only one in pure water. This behaviour is explained by a water-structure enforced hydrophobic effect and makes this drug a good water sensitive probe. Inclusion of the drug in the β-cyclodextrin emphasises the existence of two conformations, whereas in α-CD only the extended one is present, with a much higher φf=0.4 and τf=15.7 ns. Molecular mechanics (MM) and molecular orbital (MNDO) calculations also support the existence of two possible conformations in Nabumetone.
publishDate 2000
dc.date.none.fl_str_mv 2000
2026
2026
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 http://hdl.handle.net/10366/171035
url http://hdl.handle.net/10366/171035
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:GREDOS. Repositorio Institucional de la Universidad de Salamanca
instname:Universidad de Salamanca (USAL)
instname_str Universidad de Salamanca (USAL)
reponame_str GREDOS. Repositorio Institucional de la Universidad de Salamanca
collection GREDOS. Repositorio Institucional de la Universidad de Salamanca
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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