Enhancing artemisinin solubility in aqueous solutions: searching for hydrotropes based on ionic liquids
Autor(a) principal: | |
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Data de Publicação: | 2018 |
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/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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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 |
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application/pdf |
dc.source.none.fl_str_mv |
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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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