Cholinium-based ionic liquids with pharmaceutically active anions
Autor(a) principal: | |
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Data de Publicação: | 2014 |
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/10773/20004 |
Resumo: | Novel ionic liquids (ILs) containing cholinium as a benign cation combined with anions based on five active pharmaceutical ingredients (APIs), namely, nalidixic acid, niflumic acid, 4-amino-salicylic acid, pyrazinoic acid and picolinic acid, were prepared via a simple and sustainable two-step anion exchange reaction. The solubility of the prepared pharmaceutically active ILs (API-ILs) in both water and simulated biological fluids at 25 degrees C and 37 degrees C, as well as the solubility of the parent APIs, were measured. Further, in vitro cytotoxicity levels for both cholinium-based API-ILs and parent APIs were established using two different human cells lines, namely Caco-2 colon carcinoma cells and HepG2 hepatocellular carcinoma cells. Herein, the dual nature of ILs is exploited by combining the cheap, available and essential nutrient cholinium cation with pharmaceutically active anions, upgrading the chemical, physical and biopharmaceutical properties, particularly melting point, aqueous solubility and the potential to penetrate cell membranes of the parent APIs, without impair their cytotoxicity response which prompt opportunities for creating further advances in pharmaceutical challenges. |
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Cholinium-based ionic liquids with pharmaceutically active anionsNIFLUMIC ACIDDISSOLUTION MECHANISMNMR-SPECTROSCOPYNALIDIXIC-ACIDCELL-LINESOLUBILITYMIXTURESDRUGSPHARMACOKINETICSLIPOPHILICITYNovel ionic liquids (ILs) containing cholinium as a benign cation combined with anions based on five active pharmaceutical ingredients (APIs), namely, nalidixic acid, niflumic acid, 4-amino-salicylic acid, pyrazinoic acid and picolinic acid, were prepared via a simple and sustainable two-step anion exchange reaction. The solubility of the prepared pharmaceutically active ILs (API-ILs) in both water and simulated biological fluids at 25 degrees C and 37 degrees C, as well as the solubility of the parent APIs, were measured. Further, in vitro cytotoxicity levels for both cholinium-based API-ILs and parent APIs were established using two different human cells lines, namely Caco-2 colon carcinoma cells and HepG2 hepatocellular carcinoma cells. Herein, the dual nature of ILs is exploited by combining the cheap, available and essential nutrient cholinium cation with pharmaceutically active anions, upgrading the chemical, physical and biopharmaceutical properties, particularly melting point, aqueous solubility and the potential to penetrate cell membranes of the parent APIs, without impair their cytotoxicity response which prompt opportunities for creating further advances in pharmaceutical challenges.ROYAL SOC CHEMISTRY2017-12-07T19:32:12Z2014-01-01T00:00:00Z2014info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/20004eng2046-206910.1039/c3ra47615dAraujo, Joao M. M.Florindo, CatarinaPereiro, Ana B.Vieira, Nicole S. M.Matias, Ana A.Duarte, Catarina M. M.Rebelo, Luis P. N.Marrucho, Isabel M.info: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:RCAAP2024-02-22T11:39:05Zoai:ria.ua.pt:10773/20004Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T02:54:43.125433Repositório 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 |
Cholinium-based ionic liquids with pharmaceutically active anions |
title |
Cholinium-based ionic liquids with pharmaceutically active anions |
spellingShingle |
Cholinium-based ionic liquids with pharmaceutically active anions Araujo, Joao M. M. NIFLUMIC ACID DISSOLUTION MECHANISM NMR-SPECTROSCOPY NALIDIXIC-ACID CELL-LINE SOLUBILITY MIXTURES DRUGS PHARMACOKINETICS LIPOPHILICITY |
title_short |
Cholinium-based ionic liquids with pharmaceutically active anions |
title_full |
Cholinium-based ionic liquids with pharmaceutically active anions |
title_fullStr |
Cholinium-based ionic liquids with pharmaceutically active anions |
title_full_unstemmed |
Cholinium-based ionic liquids with pharmaceutically active anions |
title_sort |
Cholinium-based ionic liquids with pharmaceutically active anions |
author |
Araujo, Joao M. M. |
author_facet |
Araujo, Joao M. M. Florindo, Catarina Pereiro, Ana B. Vieira, Nicole S. M. Matias, Ana A. Duarte, Catarina M. M. Rebelo, Luis P. N. Marrucho, Isabel M. |
author_role |
author |
author2 |
Florindo, Catarina Pereiro, Ana B. Vieira, Nicole S. M. Matias, Ana A. Duarte, Catarina M. M. Rebelo, Luis P. N. Marrucho, Isabel M. |
author2_role |
author author author author author author author |
dc.contributor.author.fl_str_mv |
Araujo, Joao M. M. Florindo, Catarina Pereiro, Ana B. Vieira, Nicole S. M. Matias, Ana A. Duarte, Catarina M. M. Rebelo, Luis P. N. Marrucho, Isabel M. |
dc.subject.por.fl_str_mv |
NIFLUMIC ACID DISSOLUTION MECHANISM NMR-SPECTROSCOPY NALIDIXIC-ACID CELL-LINE SOLUBILITY MIXTURES DRUGS PHARMACOKINETICS LIPOPHILICITY |
topic |
NIFLUMIC ACID DISSOLUTION MECHANISM NMR-SPECTROSCOPY NALIDIXIC-ACID CELL-LINE SOLUBILITY MIXTURES DRUGS PHARMACOKINETICS LIPOPHILICITY |
description |
Novel ionic liquids (ILs) containing cholinium as a benign cation combined with anions based on five active pharmaceutical ingredients (APIs), namely, nalidixic acid, niflumic acid, 4-amino-salicylic acid, pyrazinoic acid and picolinic acid, were prepared via a simple and sustainable two-step anion exchange reaction. The solubility of the prepared pharmaceutically active ILs (API-ILs) in both water and simulated biological fluids at 25 degrees C and 37 degrees C, as well as the solubility of the parent APIs, were measured. Further, in vitro cytotoxicity levels for both cholinium-based API-ILs and parent APIs were established using two different human cells lines, namely Caco-2 colon carcinoma cells and HepG2 hepatocellular carcinoma cells. Herein, the dual nature of ILs is exploited by combining the cheap, available and essential nutrient cholinium cation with pharmaceutically active anions, upgrading the chemical, physical and biopharmaceutical properties, particularly melting point, aqueous solubility and the potential to penetrate cell membranes of the parent APIs, without impair their cytotoxicity response which prompt opportunities for creating further advances in pharmaceutical challenges. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-01-01T00:00:00Z 2014 2017-12-07T19:32:12Z |
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/10773/20004 |
url |
http://hdl.handle.net/10773/20004 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
2046-2069 10.1039/c3ra47615d |
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.publisher.none.fl_str_mv |
ROYAL SOC CHEMISTRY |
publisher.none.fl_str_mv |
ROYAL SOC CHEMISTRY |
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 |
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 |
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1799137599690899456 |