Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2023 |
| 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/10362/158282 |
Resumo: | Publisher Copyright: © 2023 The Author(s) |
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7160 |
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Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugsBioavailabilityCytotoxicityDicationic ionic liquidsDrug deliverySolubilityChemical Engineering (miscellaneous)Environmental Science (miscellaneous)Publisher Copyright: © 2023 The Author(s)New dicationic ionic liquids (DcILs) based on carboxylic acid-derived, N-acetyl amino acid-derived or bromide anions, and ammonium cations were synthesized and characterized. DcILs were employed as co-solvents to improve the solubility of ibuprofen and ketoprofen belonging to BCS class II. These DcILs demonstrated to be less cytotoxic towards fibroblasts L929 cells and contributed to an augment in the solubility of both drugs when compared with monocationic ionic liquids (McILs). The cytotoxic profile of some of these ILs was established, and when the linker between two ammonium cations was an ether group or a short alkyl chain an IC50 higher than 200 mM for fibroblasts L929 cells was achieved. The anion structure showed to be a key factor in the solubility of both drugs, being the family of carboxylic acid-derived, the one that presented the most significant effect, followed by N-acetyl amino acid-derived and finally bromide. The two dimensional 1H1H– NOESY NMR spectra showed the interaction between the IL and the two oral drugs, responsible for the improvement of their solubility. The lipophilicity (logP) of ibuprofen and ketoprofen reduced in the presence of these new DcILs.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNSilva, Ana B.P.Jesus, Ana R.Agostinho, Daniela A.S.Esperança, José M.S.S.Paiva, AlexandreDuarte, Ana R.C.Reis, Patrícia M.2023-09-25T22:21:11Z2023-062023-06-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article9application/pdfhttp://hdl.handle.net/10362/158282eng2772-4220PURE: 72378044https://doi.org/10.1016/j.jil.2023.100052info: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:RCAAP2024-05-22T18:14:38Zoai:run.unl.pt:10362/158282Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-22T18:14:38Repositório 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 |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs |
| title |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs |
| spellingShingle |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs Silva, Ana B.P. Bioavailability Cytotoxicity Dicationic ionic liquids Drug delivery Solubility Chemical Engineering (miscellaneous) Environmental Science (miscellaneous) |
| title_short |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs |
| title_full |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs |
| title_fullStr |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs |
| title_full_unstemmed |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs |
| title_sort |
Using dicationic ionic liquids to upgrade the cytotoxicity and solubility of poorly water-soluble drugs |
| author |
Silva, Ana B.P. |
| author_facet |
Silva, Ana B.P. Jesus, Ana R. Agostinho, Daniela A.S. Esperança, José M.S.S. Paiva, Alexandre Duarte, Ana R.C. Reis, Patrícia M. |
| author_role |
author |
| author2 |
Jesus, Ana R. Agostinho, Daniela A.S. Esperança, José M.S.S. Paiva, Alexandre Duarte, Ana R.C. Reis, Patrícia M. |
| author2_role |
author author author author author author |
| dc.contributor.none.fl_str_mv |
LAQV@REQUIMTE DQ - Departamento de Química RUN |
| dc.contributor.author.fl_str_mv |
Silva, Ana B.P. Jesus, Ana R. Agostinho, Daniela A.S. Esperança, José M.S.S. Paiva, Alexandre Duarte, Ana R.C. Reis, Patrícia M. |
| dc.subject.por.fl_str_mv |
Bioavailability Cytotoxicity Dicationic ionic liquids Drug delivery Solubility Chemical Engineering (miscellaneous) Environmental Science (miscellaneous) |
| topic |
Bioavailability Cytotoxicity Dicationic ionic liquids Drug delivery Solubility Chemical Engineering (miscellaneous) Environmental Science (miscellaneous) |
| description |
Publisher Copyright: © 2023 The Author(s) |
| publishDate |
2023 |
| dc.date.none.fl_str_mv |
2023-09-25T22:21:11Z 2023-06 2023-06-01T00:00:00Z |
| 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/10362/158282 |
| url |
http://hdl.handle.net/10362/158282 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
2772-4220 PURE: 72378044 https://doi.org/10.1016/j.jil.2023.100052 |
| dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
| eu_rights_str_mv |
openAccess |
| dc.format.none.fl_str_mv |
9 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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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mluisa.alvim@gmail.com |
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1817545957055660032 |