Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions

Detalhes bibliográficos
Autor(a) principal: Sales, Isabela
Data de Publicação: 2022
Outros Autores: Abranches, Dinis O., Sintra, Tânia E., Mattedi, Silvana, Freire, Mara G., Coutinho, João A.P., Pinho, Simão
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10198/27048
Resumo: Artemisinin is an antimalarial substance very sparingly soluble in water. In the attempt to identify environmental-friendly and non-toxic aqueous-based solvents to extract it from Artemisia annua L., the solubility of artemisinin in aqueous solutions of different hydrotropes was measured at 303.2 K, for hydrotrope concentrations up to 5 M. The ability of the studied hydrotropes for enhancing the artemisinin solubility increases in the following order: Na[N(CN)2] < Na[SCN] < [Chol][Van] < [Chol][Gal] < [N4,4,4,4]Cl < [Chol][Sal] < [P4,4,4,4]Cl < Na[Sal], with Na[Sal] allowing an increase in the solubility of 750 fold compared to pure water. The COSMO-RS model and experimental Kamlet-Taft solvatochromic parameters were applied to connect the solubility enhancement with solvent properties. At low hydrotrope concentration, the solubility increases with the decreasing of the difference between the Apolar Factors of the hydrotrope and artemisinin, while for higher hydrotrope concentration, the hydrogen-bond acceptor character of the hydrotrope seems to have an impact on the solubility enhancement. Even if some mechanistic understanding is still to unfold, quantitatively the empirical correlations of solubility enhancement with the hydrotrope concentration and the solvatochromic parameters show very high accuracy. In particular, 93% of the change on the artemisinin solubility enhancement could be explained using the hydrotrope concentration and two combined solvatochromic parameters (αβ and π∗2) as explaining variables.
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spelling Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutionsArtemisininIonic liquidsSaltsAqueous solubilitySolvatochromic parametersCOSMO-RSArtemisinin is an antimalarial substance very sparingly soluble in water. In the attempt to identify environmental-friendly and non-toxic aqueous-based solvents to extract it from Artemisia annua L., the solubility of artemisinin in aqueous solutions of different hydrotropes was measured at 303.2 K, for hydrotrope concentrations up to 5 M. The ability of the studied hydrotropes for enhancing the artemisinin solubility increases in the following order: Na[N(CN)2] < Na[SCN] < [Chol][Van] < [Chol][Gal] < [N4,4,4,4]Cl < [Chol][Sal] < [P4,4,4,4]Cl < Na[Sal], with Na[Sal] allowing an increase in the solubility of 750 fold compared to pure water. The COSMO-RS model and experimental Kamlet-Taft solvatochromic parameters were applied to connect the solubility enhancement with solvent properties. At low hydrotrope concentration, the solubility increases with the decreasing of the difference between the Apolar Factors of the hydrotrope and artemisinin, while for higher hydrotrope concentration, the hydrogen-bond acceptor character of the hydrotrope seems to have an impact on the solubility enhancement. Even if some mechanistic understanding is still to unfold, quantitatively the empirical correlations of solubility enhancement with the hydrotrope concentration and the solvatochromic parameters show very high accuracy. In particular, 93% of the change on the artemisinin solubility enhancement could be explained using the hydrotrope concentration and two combined solvatochromic parameters (αβ and π∗2) as explaining variables.This work was developed within the scope of the projects CICECOAveiro Institute of Materials, UIDB/50011/2020 & UIDP/50011/2020, CIMO-Mountain Research Center, UIDB/00690/2020, and Green Health (Norte-01-0145-FEDER-000042) all financed by national funds through the FCT/MEC and when appropriate co-financed by FEDER under the PT2020 and NORTE 2020 Partnership Agreement. Isabela Sales and Silvana Mattedi thanks the finantial support from CAPES and CNPq/ Brazil (CAPES: Proc. 88881.189075/2018-01 and 88887.494428/2020- 00. CNPq: Grant 303089/2019-9 and Proc.438036/2018-2).ElsevierBiblioteca Digital do IPBSales, IsabelaAbranches, Dinis O.Sintra, Tânia E.Mattedi, SilvanaFreire, Mara G.Coutinho, João A.P.Pinho, Simão2023-02-17T16:33:45Z20222022-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/27048engSales, Isabela; Abranches, Dinis. O.; Sintra, Tânia E.; Mattedi, Silvana; Freire, Mara G.; Coutinho, João A.P.; Pinho, Simão (2022). Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions. Fluid Phase Equilibria. ISSN 0378-3812. 562, p. 1-120378-381210.1016/j.fluid.2022.113556info: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:RCAAP2023-11-21T11:00:13Zoai:bibliotecadigital.ipb.pt:10198/27048Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:17:28.376994Repositório 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 Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
title Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
spellingShingle Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
Sales, Isabela
Artemisinin
Ionic liquids
Salts
Aqueous solubility
Solvatochromic parameters
COSMO-RS
title_short Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
title_full Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
title_fullStr Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
title_full_unstemmed Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
title_sort Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions
author Sales, Isabela
author_facet Sales, Isabela
Abranches, Dinis O.
Sintra, Tânia E.
Mattedi, Silvana
Freire, Mara G.
Coutinho, João A.P.
Pinho, Simão
author_role author
author2 Abranches, Dinis O.
Sintra, Tânia E.
Mattedi, Silvana
Freire, Mara G.
Coutinho, João A.P.
Pinho, Simão
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Biblioteca Digital do IPB
dc.contributor.author.fl_str_mv Sales, Isabela
Abranches, Dinis O.
Sintra, Tânia E.
Mattedi, Silvana
Freire, Mara G.
Coutinho, João A.P.
Pinho, Simão
dc.subject.por.fl_str_mv Artemisinin
Ionic liquids
Salts
Aqueous solubility
Solvatochromic parameters
COSMO-RS
topic Artemisinin
Ionic liquids
Salts
Aqueous solubility
Solvatochromic parameters
COSMO-RS
description Artemisinin is an antimalarial substance very sparingly soluble in water. In the attempt to identify environmental-friendly and non-toxic aqueous-based solvents to extract it from Artemisia annua L., the solubility of artemisinin in aqueous solutions of different hydrotropes was measured at 303.2 K, for hydrotrope concentrations up to 5 M. The ability of the studied hydrotropes for enhancing the artemisinin solubility increases in the following order: Na[N(CN)2] < Na[SCN] < [Chol][Van] < [Chol][Gal] < [N4,4,4,4]Cl < [Chol][Sal] < [P4,4,4,4]Cl < Na[Sal], with Na[Sal] allowing an increase in the solubility of 750 fold compared to pure water. The COSMO-RS model and experimental Kamlet-Taft solvatochromic parameters were applied to connect the solubility enhancement with solvent properties. At low hydrotrope concentration, the solubility increases with the decreasing of the difference between the Apolar Factors of the hydrotrope and artemisinin, while for higher hydrotrope concentration, the hydrogen-bond acceptor character of the hydrotrope seems to have an impact on the solubility enhancement. Even if some mechanistic understanding is still to unfold, quantitatively the empirical correlations of solubility enhancement with the hydrotrope concentration and the solvatochromic parameters show very high accuracy. In particular, 93% of the change on the artemisinin solubility enhancement could be explained using the hydrotrope concentration and two combined solvatochromic parameters (αβ and π∗2) as explaining variables.
publishDate 2022
dc.date.none.fl_str_mv 2022
2022-01-01T00:00:00Z
2023-02-17T16:33:45Z
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/10198/27048
url http://hdl.handle.net/10198/27048
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Sales, Isabela; Abranches, Dinis. O.; Sintra, Tânia E.; Mattedi, Silvana; Freire, Mara G.; Coutinho, João A.P.; Pinho, Simão (2022). Selection of hydrotropes for enhancing the solubility of artemisinin in aqueous solutions. Fluid Phase Equilibria. ISSN 0378-3812. 562, p. 1-12
0378-3812
10.1016/j.fluid.2022.113556
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 Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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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
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