Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation

Detalhes bibliográficos
Autor(a) principal: Sintra, Tânia E.
Data de Publicação: 2021
Outros Autores: Abranches, Dinis O., Benfica, Jordana, Soares, Bruna P., Ventura, Sónia P. M., Coutinho, João A. P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/33324
Resumo: Hydrotropy is a well-established strategy to enhance the aqueous solubility of hydrophobic drugs, facilitating their formulation for oral and dermal delivery. However, most hydrotropes studied so far possess toxicity issues and are inefficient, with large amounts being needed to achieve significant solubility increases. Inspired by recent developments in the understanding of the mechanism of hydrotropy that reveal ionic liquids as powerful hydrotropes, in the present work the use of cholinium vanillate, cholinium gallate, and cholinium salicylate to enhance the aqueous solubility of two model drugs, ibuprofen and naproxen, is investigated. It is shown that cholinium vanillate and cholinium gallate are able to increase the solubility of ibuprofen up to 500-fold, while all three ionic liquids revealed solubility enhancements up to 600-fold in the case of naproxen. Remarkably, cholinium salicylate increases the solubility of ibuprofen up to 6000-fold. The results obtained reveal the exceptional hydrotropic ability of cholinium-based ionic liquids to increase the solubility of hydrophobic drugs, even at diluted concentrations (below 1 mol·kg-1), when compared with conventional hydrotropes. These results are especially relevant in the field of drug formulation due to the bio-based nature of these ionic liquids and their low toxicity profiles. Finally, the solubility mechanism in these novel hydrotropes is shown to depend on synergism between both amphiphilic ions.
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spelling Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulationHydrotropyBCS Class II drugsIonic liquidsDrug formulationBioavailabilityCholineIbuprofenNaproxenHydrotropy is a well-established strategy to enhance the aqueous solubility of hydrophobic drugs, facilitating their formulation for oral and dermal delivery. However, most hydrotropes studied so far possess toxicity issues and are inefficient, with large amounts being needed to achieve significant solubility increases. Inspired by recent developments in the understanding of the mechanism of hydrotropy that reveal ionic liquids as powerful hydrotropes, in the present work the use of cholinium vanillate, cholinium gallate, and cholinium salicylate to enhance the aqueous solubility of two model drugs, ibuprofen and naproxen, is investigated. It is shown that cholinium vanillate and cholinium gallate are able to increase the solubility of ibuprofen up to 500-fold, while all three ionic liquids revealed solubility enhancements up to 600-fold in the case of naproxen. Remarkably, cholinium salicylate increases the solubility of ibuprofen up to 6000-fold. The results obtained reveal the exceptional hydrotropic ability of cholinium-based ionic liquids to increase the solubility of hydrophobic drugs, even at diluted concentrations (below 1 mol·kg-1), when compared with conventional hydrotropes. These results are especially relevant in the field of drug formulation due to the bio-based nature of these ionic liquids and their low toxicity profiles. Finally, the solubility mechanism in these novel hydrotropes is shown to depend on synergism between both amphiphilic ions.Elsevier; International Association for Pharmaceutical Technology2021-072021-07-01T00:00:00Z2022-07-31T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttp://hdl.handle.net/10773/33324eng0939-641110.1016/j.ejpb.2021.04.013Sintra, Tânia E.Abranches, Dinis O.Benfica, JordanaSoares, Bruna P.Ventura, Sónia P. M.Coutinho, João A. P.info:eu-repo/semantics/embargoedAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-05-06T04:35:35Zoai:ria.ua.pt:10773/33324Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-06T04:35:35Repositório 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 as bioinspired hydrotropes to tackle solubility challenges in drug formulation
title Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation
spellingShingle Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation
Sintra, Tânia E.
Hydrotropy
BCS Class II drugs
Ionic liquids
Drug formulation
Bioavailability
Choline
Ibuprofen
Naproxen
title_short Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation
title_full Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation
title_fullStr Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation
title_full_unstemmed Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation
title_sort Cholinium-based ionic liquids as bioinspired hydrotropes to tackle solubility challenges in drug formulation
author Sintra, Tânia E.
author_facet Sintra, Tânia E.
Abranches, Dinis O.
Benfica, Jordana
Soares, Bruna P.
Ventura, Sónia P. M.
Coutinho, João A. P.
author_role author
author2 Abranches, Dinis O.
Benfica, Jordana
Soares, Bruna P.
Ventura, Sónia P. M.
Coutinho, João A. P.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Sintra, Tânia E.
Abranches, Dinis O.
Benfica, Jordana
Soares, Bruna P.
Ventura, Sónia P. M.
Coutinho, João A. P.
dc.subject.por.fl_str_mv Hydrotropy
BCS Class II drugs
Ionic liquids
Drug formulation
Bioavailability
Choline
Ibuprofen
Naproxen
topic Hydrotropy
BCS Class II drugs
Ionic liquids
Drug formulation
Bioavailability
Choline
Ibuprofen
Naproxen
description Hydrotropy is a well-established strategy to enhance the aqueous solubility of hydrophobic drugs, facilitating their formulation for oral and dermal delivery. However, most hydrotropes studied so far possess toxicity issues and are inefficient, with large amounts being needed to achieve significant solubility increases. Inspired by recent developments in the understanding of the mechanism of hydrotropy that reveal ionic liquids as powerful hydrotropes, in the present work the use of cholinium vanillate, cholinium gallate, and cholinium salicylate to enhance the aqueous solubility of two model drugs, ibuprofen and naproxen, is investigated. It is shown that cholinium vanillate and cholinium gallate are able to increase the solubility of ibuprofen up to 500-fold, while all three ionic liquids revealed solubility enhancements up to 600-fold in the case of naproxen. Remarkably, cholinium salicylate increases the solubility of ibuprofen up to 6000-fold. The results obtained reveal the exceptional hydrotropic ability of cholinium-based ionic liquids to increase the solubility of hydrophobic drugs, even at diluted concentrations (below 1 mol·kg-1), when compared with conventional hydrotropes. These results are especially relevant in the field of drug formulation due to the bio-based nature of these ionic liquids and their low toxicity profiles. Finally, the solubility mechanism in these novel hydrotropes is shown to depend on synergism between both amphiphilic ions.
publishDate 2021
dc.date.none.fl_str_mv 2021-07
2021-07-01T00:00:00Z
2022-07-31T00:00:00Z
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/10773/33324
url http://hdl.handle.net/10773/33324
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0939-6411
10.1016/j.ejpb.2021.04.013
dc.rights.driver.fl_str_mv info:eu-repo/semantics/embargoedAccess
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier; International Association for Pharmaceutical Technology
publisher.none.fl_str_mv Elsevier; International Association for Pharmaceutical Technology
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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