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Identification of a common recognition center for a photoactive non-steroidal antiinflammatory drug in serum albumins of different species

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Identification of a common recognition center for a photoactive non-steroidal antiinflammatory drug in serum albumins of different species

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dc.contributor.author Molins-Molina, Oscar es_ES
dc.contributor.author Lence, Emilio es_ES
dc.contributor.author Limones-Herrero, Daniel es_ES
dc.contributor.author González-Bello, Concepción es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.date.accessioned 2021-01-28T04:32:05Z
dc.date.available 2021-01-28T04:32:05Z
dc.date.issued 2019-01-07 es_ES
dc.identifier.issn 2052-4110 es_ES
dc.identifier.uri http://hdl.handle.net/10251/160087
dc.description.abstract [EN] The non-steroidal anti-inflammatory drug (S)-carprofen (CPF) has been used as a photoactive probe to investigate the possible existence of a common recognition center in serum albumins (SAs) of different species. The methodology involves irradiation of the CPF/SA complexes, coupled with gel filtration chromatography or proteomic analysis of the photolysates, docking and molecular dynamics simulations. Photolysis of CPF/SA complexes at = 320 nm, and gel filtration chromatography, revealed that the protein fraction still contained the drug fluorophore, in agreement with covalent attachment of the photogenerated radical intermediate CBZ to SAs. After trypsin digestion and ESI-MS/MS, the incorporation of CBZ was detected at several positions in the different albumins. Remarkably, modifications at the IB/IIIA interface were observed in all cases (Tyr452 in HSA, RbSA and RtSA and Tyr451 in BSA, PSA and SSA). The molecular basis of this common recognition, studied by docking and molecular dynamics simulation studies on the corresponding non-covalent complexes, corroborated the experimentally observed covalent modifications. Our computational studies also revealed that the previously reported displacement of CPF by (S)-ibuprofen, a site II specific drug, would be due to an allosteric effect in site II, rather than a direct molecular displacement, as expected. es_ES
dc.description.sponsorship Financial support from the Spanish Ministry of Economy and Competiveness (CTQ2016-78875-P, SAF2016-75638-R and BES-2014-069404), Generalitat Valenciana (PROMETEO2017/075), Conselleria de Cultura, Educacion e Ordenacion Universitaria (Centro singular de investigacion de Galicia accreditation 2016-2019, ED431G/09) and the European Regional Development Fund (ERDF) is acknowledged. This work was also supported by Instituto de Salud Carlos III (ISCIII) co-funded by Fondo Europeo de Desarrollo Regional FEDER for the Thematic Networks and Co-operative Research Centres: ARADyAL (RD16/0006/0030). EL thanks the Xunta de Galicia for his postdoctoral fellowship. We are also grateful to the Centro de Supercomputacion de Galicia (CESGA) for use of the Finis Terrae II supercomputer. The proteomic analysis was performed in the proteomics facility of SCSIE University of Valencia that belongs to ProteoRed PRB2-ISCIII and is supported by grant PT13/0001, of the PE I+D+I 2013-2016, funded by ISCIII and FEDER. es_ES
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Organic Chemistry Frontiers es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Identification of a common recognition center for a photoactive non-steroidal antiinflammatory drug in serum albumins of different species es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c8qo01045e es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-75638-R/ES/DESARROLLO DE NUEVOS FARMACOS PARA EL TRATAMIENTO DE LAS INFECCIONES BACTERIANAS MULTIRESISTENTES: APROXIMACIONES QUE INCIDEN SOBRE VIABILIDAD, RESISTENCIA Y VIRULENCIA/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Xunta de Galicia//ED431G%2F09/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/ISCIII//PT13%2F0001/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//BES-2014-069404/ES/BES-2014-069404/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2016-78875-P/ES/CONTROL SUPRAMOLECULAR DE LA FOTORREACTIVIDAD EN MEDIOS MICROHETEROGENOS BASADOS EN AMINOACIDOS: GELES MOLECULARES Y PROTEINAS TRANSPORTADORAS COMO NANORREACTORES/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//RD16%2F0006%2F0030/ES/Asma, Reacciones Adversas y Alérgicas (ARADYAL)/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//PROMETEO%2F2017%2F075/ES/Reacciones fotoquímicas de biomoléculas/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Molins-Molina, O.; Lence, E.; Limones-Herrero, D.; González-Bello, C.; Miranda Alonso, MÁ.; Jiménez Molero, MC. (2019). Identification of a common recognition center for a photoactive non-steroidal antiinflammatory drug in serum albumins of different species. Organic Chemistry Frontiers. 6(1):99-109. https://doi.org/10.1039/c8qo01045e es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1039/c8qo01045e es_ES
dc.description.upvformatpinicio 99 es_ES
dc.description.upvformatpfin 109 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 6 es_ES
dc.description.issue 1 es_ES
dc.relation.pasarela S\379255 es_ES
dc.contributor.funder Xunta de Galicia es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.contributor.funder European Regional Development Fund es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
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