New non-toxic n-alkyl cholinium-based ionic liquids as excipients to improve the solubility of poorly water-soluble drugs
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| Outros Autores: | , , , , , , |
| 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 |
| id |
RCAP_f11ea0463999537a0d49271df39dc8ad |
|---|---|
| oai_identifier_str |
oai:run.unl.pt:10362/128324 |
| network_acronym_str |
RCAP |
| network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| repository_id_str |
7160 |
| 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 |
| _version_ |
1817545831000047616 |