Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum

Detalhes bibliográficos
Autor(a) principal: Ferraz, Ricardo
Data de Publicação: 2022
Outros Autores: Santarém, Nuno, Santos, Andreia F. M., Jacinto, Manuel L., Cordeiro-da-Silva, Anabela, Prudêncio, Cristina, Noronha, João Paulo, Branco, Luis C., Petrovski, Zeljko
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/147036
Resumo: Funding text This research was funded by the project NORTE-01-0145-FEDER-000012, supported by Norte Portugal Regional Operational Programme (NORTE 2020), under the PORTUGAL 2020 Partnership Agreement, through the European Regional Development Fund (ERDF). This work was also supported by the Associate Laboratory for Green Chemistry LAQV financed by national funds from FCT/MCTES (UIDB/50006/2020, UIDP/50006/2020 and LA/P/0008/2020). The authors also thank Fundação para a Ciência e Tecnologia for the projects PTDC/EAM-AMB/2023/2021, PTDC/QUI-QOR/32406/2017 and PTDC/BTM-SAL/29786/2017. N.S. was supported by PTDC/SAU-PAR/31013/2017. A.F.M.S and Ž.P. also acknowledge FCT-MCTES for the PhD Grant (SFRH/BD/132551/2017) and for the Norma Transitória DL 57/2016 Program contract, respectively. The NMR spectrometers are part of The National NMR Facility, supported by FCT (ROTEIRO/0031/2013 - PINFRA/22161/2016) (co-financed by FEDER through COMPETE 2020, POCI, and PORL and FCT through PIDDAC).
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spelling Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantumactive pharmaceutical ingredientsamphotericin BLeishmania infantumleishmaniasisorganic salts and ionic liquidsFunding text This research was funded by the project NORTE-01-0145-FEDER-000012, supported by Norte Portugal Regional Operational Programme (NORTE 2020), under the PORTUGAL 2020 Partnership Agreement, through the European Regional Development Fund (ERDF). This work was also supported by the Associate Laboratory for Green Chemistry LAQV financed by national funds from FCT/MCTES (UIDB/50006/2020, UIDP/50006/2020 and LA/P/0008/2020). The authors also thank Fundação para a Ciência e Tecnologia for the projects PTDC/EAM-AMB/2023/2021, PTDC/QUI-QOR/32406/2017 and PTDC/BTM-SAL/29786/2017. N.S. was supported by PTDC/SAU-PAR/31013/2017. A.F.M.S and Ž.P. also acknowledge FCT-MCTES for the PhD Grant (SFRH/BD/132551/2017) and for the Norma Transitória DL 57/2016 Program contract, respectively. The NMR spectrometers are part of The National NMR Facility, supported by FCT (ROTEIRO/0031/2013 - PINFRA/22161/2016) (co-financed by FEDER through COMPETE 2020, POCI, and PORL and FCT through PIDDAC).Nowadays, organic salts and ionic liquids (OSILs) containing active pharmaceutical ingredients (APIs) are being explored as drug delivery systems in modern therapies (OSILs-API). In that sense, this work is focused on the development of novel OSILs-API based on amphotericin B through an innovative procedure and the evaluation of the respective biological activity against Leishmania infantum. Several ammonium, methylimidazolium, pyridinium and phosphonium organic cations combined with amphotericin B as anion were synthesized in moderate to high yields and high purities by the water-reduced buffer neutralization method. All prepared compounds were characterized to confirm the desired chemical structure and the specific optical rotation ([α]D25) was also determined. The biological assays performed on L. infantum promastigotes showed increased activity against this parasitic disease when compared with the starting chloride forms and amphotericin B alone, highlighting [P6,6,6,14][AmB] as the most promising formulation. Possible synergism in the antiprotozoal activity was also evaluated for [P6,6,6,14][AmB], since it was proven to be the compound with the highest toxicity. This work reported a simple synthetic method, which can be applied to prepare other organic salts based on molecules containing fragile chemical groups, demonstrating the potential of these OSILs-AmB as possible agents against leishmaniasis.DQ - Departamento de QuímicaLAQV@REQUIMTERUNFerraz, RicardoSantarém, NunoSantos, Andreia F. M.Jacinto, Manuel L.Cordeiro-da-Silva, AnabelaPrudêncio, CristinaNoronha, João PauloBranco, Luis C.Petrovski, Zeljko2023-01-05T22:17:13Z2022-12-192022-12-19T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article12application/pdfhttp://hdl.handle.net/10362/147036eng2079-6382PURE: 48775711https://doi.org/10.3390/antibiotics11121841info: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:RCAAP2024-03-11T05:28:01Zoai:run.unl.pt:10362/147036Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:52:45.594497Repositório 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 Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
title Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
spellingShingle Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
Ferraz, Ricardo
active pharmaceutical ingredients
amphotericin B
Leishmania infantum
leishmaniasis
organic salts and ionic liquids
title_short Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
title_full Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
title_fullStr Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
title_full_unstemmed Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
title_sort Synthesis and Biological Evaluation of Amphotericin B Formulations Based on Organic Salts and Ionic Liquids against Leishmania infantum
author Ferraz, Ricardo
author_facet Ferraz, Ricardo
Santarém, Nuno
Santos, Andreia F. M.
Jacinto, Manuel L.
Cordeiro-da-Silva, Anabela
Prudêncio, Cristina
Noronha, João Paulo
Branco, Luis C.
Petrovski, Zeljko
author_role author
author2 Santarém, Nuno
Santos, Andreia F. M.
Jacinto, Manuel L.
Cordeiro-da-Silva, Anabela
Prudêncio, Cristina
Noronha, João Paulo
Branco, Luis C.
Petrovski, Zeljko
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv DQ - Departamento de Química
LAQV@REQUIMTE
RUN
dc.contributor.author.fl_str_mv Ferraz, Ricardo
Santarém, Nuno
Santos, Andreia F. M.
Jacinto, Manuel L.
Cordeiro-da-Silva, Anabela
Prudêncio, Cristina
Noronha, João Paulo
Branco, Luis C.
Petrovski, Zeljko
dc.subject.por.fl_str_mv active pharmaceutical ingredients
amphotericin B
Leishmania infantum
leishmaniasis
organic salts and ionic liquids
topic active pharmaceutical ingredients
amphotericin B
Leishmania infantum
leishmaniasis
organic salts and ionic liquids
description Funding text This research was funded by the project NORTE-01-0145-FEDER-000012, supported by Norte Portugal Regional Operational Programme (NORTE 2020), under the PORTUGAL 2020 Partnership Agreement, through the European Regional Development Fund (ERDF). This work was also supported by the Associate Laboratory for Green Chemistry LAQV financed by national funds from FCT/MCTES (UIDB/50006/2020, UIDP/50006/2020 and LA/P/0008/2020). The authors also thank Fundação para a Ciência e Tecnologia for the projects PTDC/EAM-AMB/2023/2021, PTDC/QUI-QOR/32406/2017 and PTDC/BTM-SAL/29786/2017. N.S. was supported by PTDC/SAU-PAR/31013/2017. A.F.M.S and Ž.P. also acknowledge FCT-MCTES for the PhD Grant (SFRH/BD/132551/2017) and for the Norma Transitória DL 57/2016 Program contract, respectively. The NMR spectrometers are part of The National NMR Facility, supported by FCT (ROTEIRO/0031/2013 - PINFRA/22161/2016) (co-financed by FEDER through COMPETE 2020, POCI, and PORL and FCT through PIDDAC).
publishDate 2022
dc.date.none.fl_str_mv 2022-12-19
2022-12-19T00:00:00Z
2023-01-05T22:17:13Z
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/10362/147036
url http://hdl.handle.net/10362/147036
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 2079-6382
PURE: 48775711
https://doi.org/10.3390/antibiotics11121841
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 12
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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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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
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