Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids

Detalhes bibliográficos
Autor(a) principal: Sales, Isabela
Data de Publicação: 2018
Outros Autores: Abranches, Dinis O., Costa, Pedro, Sintra, Tânia E., Ventura, Sónia P.M., Mattedi, Silvana, Coutinho, João A.P., Freire, Mara G., 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/10198/24364
Resumo: Artemisinin is a sesquiterpenoid lactone peroxide, known for its potent antimalarial activity that can be extracted from Artemisia annua L. This compound is only sparingly soluble in water, making its extraction using environmental-friendly and non-toxic aqueous solvents difficult. In the attempt to overcome this limitation, hydrotropes, which are a class of compounds that can assist in increasing the solubility of hydrophobic solutes in water, were investigated in this work. In particular, the hydrotropic capability of ionic liquids (ILs) on the aqueous solubility of artemisinin was studied. The effects of IL concentration and anion nature of 1-butyl-3-methylimidazolium-based ILs on the solubility of artemisinin at 303.2 K in water were evaluated. It is here shown the excellent capacity of ILs containing thiocyanate or dicyanamide anions to enhance the solubility of artemisinin in aqueous media, with a magnitude comparable to that obtained with the best organic solvents. Furthermore, solvatochromic parameters of the ILs aqueous solutions were also measured and combined with COSMO-RS and the cooperative hydrotropy model to establish relations between the artemisinin solubility enhancement and the solvent characteristics. The solubility enhancement of artemisinin is favored by the apolarity of the medium and the lower hydrogen-bond acceptor character of the hydrotrope.
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spelling Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquidsaqueous solubilityArtemisininHydrotropyIonic liquidsSolvatochromic parametersArtemisinin is a sesquiterpenoid lactone peroxide, known for its potent antimalarial activity that can be extracted from Artemisia annua L. This compound is only sparingly soluble in water, making its extraction using environmental-friendly and non-toxic aqueous solvents difficult. In the attempt to overcome this limitation, hydrotropes, which are a class of compounds that can assist in increasing the solubility of hydrophobic solutes in water, were investigated in this work. In particular, the hydrotropic capability of ionic liquids (ILs) on the aqueous solubility of artemisinin was studied. The effects of IL concentration and anion nature of 1-butyl-3-methylimidazolium-based ILs on the solubility of artemisinin at 303.2 K in water were evaluated. It is here shown the excellent capacity of ILs containing thiocyanate or dicyanamide anions to enhance the solubility of artemisinin in aqueous media, with a magnitude comparable to that obtained with the best organic solvents. Furthermore, solvatochromic parameters of the ILs aqueous solutions were also measured and combined with COSMO-RS and the cooperative hydrotropy model to establish relations between the artemisinin solubility enhancement and the solvent characteristics. The solubility enhancement of artemisinin is favored by the apolarity of the medium and the lower hydrogen-bond acceptor character of the hydrotrope.This work was developed within the scope of the projects CICECO-Aveiro Institute of Materials, UIDB/50011/2020 & UIDP/50011/2020, CIMO-Mountain Research Center, UIDB/00690/2020, all financed by national funds through the FCT/MEC and when appropriate co-financed by FEDER under the PT2020 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).Biblioteca Digital do IPBSales, IsabelaAbranches, Dinis O.Costa, PedroSintra, Tânia E.Ventura, Sónia P.M.Mattedi, SilvanaCoutinho, João A.P.Freire, Mara G.Pinho, Simão2018-01-19T10:00:00Z20212021-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/24364engSales, Isabela; Abranches, Dinis O.; Costa, Pedro; Sintra, Tânia E.; Ventura, Sónia P.M.; Mattedi, Silvana; Coutinho, João A.P.; Freire, Mara G.; Pinho, Simão P. (2021). Enhancing Artemisinin Solubility in Aqueous Solutions: Searching for Hydrotropes based on Ionic Liquids. Fluid Phase Equilibria. ISSN 0378-3812. 534, p. 1-90378-381210.1016/j.fluid.2021.112961info: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:RCAAP2023-11-21T10:54:30Zoai:bibliotecadigital.ipb.pt:10198/24364Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:15:12.700457Repositório 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 Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
title Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
spellingShingle Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
Sales, Isabela
aqueous solubility
Artemisinin
Hydrotropy
Ionic liquids
Solvatochromic parameters
title_short Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
title_full Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
title_fullStr Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
title_full_unstemmed Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
title_sort Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
author Sales, Isabela
author_facet Sales, Isabela
Abranches, Dinis O.
Costa, Pedro
Sintra, Tânia E.
Ventura, Sónia P.M.
Mattedi, Silvana
Coutinho, João A.P.
Freire, Mara G.
Pinho, Simão
author_role author
author2 Abranches, Dinis O.
Costa, Pedro
Sintra, Tânia E.
Ventura, Sónia P.M.
Mattedi, Silvana
Coutinho, João A.P.
Freire, Mara G.
Pinho, Simão
author2_role author
author
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.
Costa, Pedro
Sintra, Tânia E.
Ventura, Sónia P.M.
Mattedi, Silvana
Coutinho, João A.P.
Freire, Mara G.
Pinho, Simão
dc.subject.por.fl_str_mv aqueous solubility
Artemisinin
Hydrotropy
Ionic liquids
Solvatochromic parameters
topic aqueous solubility
Artemisinin
Hydrotropy
Ionic liquids
Solvatochromic parameters
description Artemisinin is a sesquiterpenoid lactone peroxide, known for its potent antimalarial activity that can be extracted from Artemisia annua L. This compound is only sparingly soluble in water, making its extraction using environmental-friendly and non-toxic aqueous solvents difficult. In the attempt to overcome this limitation, hydrotropes, which are a class of compounds that can assist in increasing the solubility of hydrophobic solutes in water, were investigated in this work. In particular, the hydrotropic capability of ionic liquids (ILs) on the aqueous solubility of artemisinin was studied. The effects of IL concentration and anion nature of 1-butyl-3-methylimidazolium-based ILs on the solubility of artemisinin at 303.2 K in water were evaluated. It is here shown the excellent capacity of ILs containing thiocyanate or dicyanamide anions to enhance the solubility of artemisinin in aqueous media, with a magnitude comparable to that obtained with the best organic solvents. Furthermore, solvatochromic parameters of the ILs aqueous solutions were also measured and combined with COSMO-RS and the cooperative hydrotropy model to establish relations between the artemisinin solubility enhancement and the solvent characteristics. The solubility enhancement of artemisinin is favored by the apolarity of the medium and the lower hydrogen-bond acceptor character of the hydrotrope.
publishDate 2018
dc.date.none.fl_str_mv 2018-01-19T10:00:00Z
2021
2021-01-01T00:00:00Z
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/10198/24364
url http://hdl.handle.net/10198/24364
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Sales, Isabela; Abranches, Dinis O.; Costa, Pedro; Sintra, Tânia E.; Ventura, Sónia P.M.; Mattedi, Silvana; Coutinho, João A.P.; Freire, Mara G.; Pinho, Simão P. (2021). Enhancing Artemisinin Solubility in Aqueous Solutions: Searching for Hydrotropes based on Ionic Liquids. Fluid Phase Equilibria. ISSN 0378-3812. 534, p. 1-9
0378-3812
10.1016/j.fluid.2021.112961
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)
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