New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs

Detalhes bibliográficos
Autor(a) principal: Jesus, Ana R.
Data de Publicação: 2021
Outros Autores: Raposo, Luís R., Soromenho, Mário R.C., Agostinho, Daniela A. S., Esperança, José M. S. S., Baptista, Pedro V., Fernandes, Alexandra R., Reis, Patrícia M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/128324
Resumo: LA/P/0140/2020 ROTEIRO/0031/2013—PINFRA/22161/2016
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spelling New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugsBioavailabilityCytotoxicityDrug deliveryIonic liquidsOral drugsComputer Science (miscellaneous)Chemistry (miscellaneous)Mathematics(all)Physics and Astronomy (miscellaneous)LA/P/0140/2020 ROTEIRO/0031/2013—PINFRA/22161/2016In this work, we prepared new biocompatible N-alkyl cholinium-based ionic liquids to be used as cosolvents to improve the solubility of poorly water-soluble drugs, namely, sodium diclo-fenac and paracetamol. In this set of ionic liquids, we intend to understand the effect of increasing the asymmetry of the ionic liquid cation/anion by growing the length of one of the alkyl chains attached to the nitrogen center/sulfonate center on the dissolution capacity of the ionic liquid. The addition of these new ionic liquids to water increased the dissolution capacity of the drugs up to four-times that in water, and improved the pharmacodynamic properties of these drugs, especially the case of sodium diclofenac. The intermolecular interactions between the drugs and ionic liquids were investigated by NMR. Two-dimensional1H/1H nuclear overhauser effect spectroscopy (NO-ESY) revealed an interaction between sodium diclofenac and the alaninate anion from the [C2Ch]2[SucAla]. In the case of paracetamol and [C4Ch][C2SO3], it was possible to observe two inter-molecular interactions between the hydroxyl group of paracetamol and two protons from the cation [C4Ch]+. Interestingly, the ionic liquid bearing a succinyl-DL-alaninate anion, [SucAla]2−, and a N-ethyl cholinium cation, [C2Ch]+, which presented the highest ability to dissolve sodium diclofenac, showed no cytotoxicity up to 500 mM. Therefore, this ionic liquid is a potential candidate for drug delivery applications.LAQV@REQUIMTEDQ - Departamento de QuímicaUCIBIO - Applied Molecular Biosciences UnitRUNJesus, Ana R.Raposo, Luís R.Soromenho, Mário R.C.Agostinho, Daniela A. S.Esperança, José M. S. S.Baptista, Pedro V.Fernandes, Alexandra R.Reis, Patrícia M.2021-11-26T23:44:54Z2021-112021-11-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10362/128324eng2073-8994PURE: 34858293https://doi.org/10.3390/sym13112053info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-05-22T17:57:20Zoai:run.unl.pt:10362/128324Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-22T17:57:20Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
title New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
spellingShingle New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
Jesus, Ana R.
Bioavailability
Cytotoxicity
Drug delivery
Ionic liquids
Oral drugs
Computer Science (miscellaneous)
Chemistry (miscellaneous)
Mathematics(all)
Physics and Astronomy (miscellaneous)
title_short New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
title_full New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
title_fullStr New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
title_full_unstemmed New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
title_sort New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
author Jesus, Ana R.
author_facet Jesus, Ana R.
Raposo, Luís R.
Soromenho, Mário R.C.
Agostinho, Daniela A. S.
Esperança, José M. S. S.
Baptista, Pedro V.
Fernandes, Alexandra R.
Reis, Patrícia M.
author_role author
author2 Raposo, Luís R.
Soromenho, Mário R.C.
Agostinho, Daniela A. S.
Esperança, José M. S. S.
Baptista, Pedro V.
Fernandes, Alexandra R.
Reis, Patrícia M.
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
UCIBIO - Applied Molecular Biosciences Unit
RUN
dc.contributor.author.fl_str_mv Jesus, Ana R.
Raposo, Luís R.
Soromenho, Mário R.C.
Agostinho, Daniela A. S.
Esperança, José M. S. S.
Baptista, Pedro V.
Fernandes, Alexandra R.
Reis, Patrícia M.
dc.subject.por.fl_str_mv Bioavailability
Cytotoxicity
Drug delivery
Ionic liquids
Oral drugs
Computer Science (miscellaneous)
Chemistry (miscellaneous)
Mathematics(all)
Physics and Astronomy (miscellaneous)
topic Bioavailability
Cytotoxicity
Drug delivery
Ionic liquids
Oral drugs
Computer Science (miscellaneous)
Chemistry (miscellaneous)
Mathematics(all)
Physics and Astronomy (miscellaneous)
description LA/P/0140/2020 ROTEIRO/0031/2013—PINFRA/22161/2016
publishDate 2021
dc.date.none.fl_str_mv 2021-11-26T23:44:54Z
2021-11
2021-11-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/128324
url http://hdl.handle.net/10362/128324
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 2073-8994
PURE: 34858293
https://doi.org/10.3390/sym13112053
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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