Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones

Detalhes bibliográficos
Autor(a) principal: Santos, Miguel M.
Data de Publicação: 2020
Outros Autores: Alves, Celso, Silva, Joana, Florindo, Catarina, Petrovski, Zeljko, Marrucho, Isabel M., Pedrosa, Rui, Branco, Luís C.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.8/5116
Resumo: Funding: This work was supported by the Associate Laboratory for Green Chemistry LAQV and Centro de Química Estrutural, which are financed by national funds from FCT/MCTES (UIDB/50006/2020 and UID/QUI/00100/2013, respectively). The authors also thank Fundação para a Ciência e Tecnologia for the projects PTDC/QUI-OR/32406/2017, PEst-C/LA0006/2013, and ECI/BBBBQB/0230/2012, as well as one contract under Investigador FCT (L. C. Branco).
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spelling Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolonesActive pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs)AntibioticsCiprofloxacinFluoroquinolonesIonic liquidsNorfloxacinPolymorphismFunding: This work was supported by the Associate Laboratory for Green Chemistry LAQV and Centro de Química Estrutural, which are financed by national funds from FCT/MCTES (UIDB/50006/2020 and UID/QUI/00100/2013, respectively). The authors also thank Fundação para a Ciência e Tecnologia for the projects PTDC/QUI-OR/32406/2017, PEst-C/LA0006/2013, and ECI/BBBBQB/0230/2012, as well as one contract under Investigador FCT (L. C. Branco).As the development of novel antibiotics has been at a halt for several decades, chemically enhancing existing drugs is a very promising approach to drug development. Herein, we report the preparation of twelve organic salts and ionic liquids (OSILs) from ciprofloxacin and norfloxacin as anions with enhanced antimicrobial activity. Each one of the fluoroquinolones (FQs) was combined with six di erent organic hydroxide cations in 93–100% yield through a bu er-assisted neutralization methodology. Six of those were isomorphous salts while the remaining six were ionic liquids, with four of them being room temperature ionic liquids. The prepared compounds were not toxic to healthy cell lines and displayed between 47- and 1416-fold more solubility in water at 25 and 37 C than the original drugs, with the exception of the ones containing the cetylpyridinium cation. In general, the antimicrobial activity against Klebsiella pneumoniae was particularly enhanced for the ciprofloxacin-based OSILs, with up to ca. 20-fold decreases of the inhibitory concentrations in relation to the parent drug, while activity against Staphylococcus aureus and the commensal Bacillus subtilis strain was often reduced. Depending on the cation–drug combination, broad-spectrum or strain-specific antibiotic salts were achieved, potentially leading to the future development of highly bioavailable and safe antimicrobial ionic formulations.MDPIIC-OnlineSantos, Miguel M.Alves, CelsoSilva, JoanaFlorindo, CatarinaPetrovski, ZeljkoMarrucho, Isabel M.Pedrosa, RuiBranco, Luís C.2020-08-28T14:09:39Z20202020-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.8/5116engSantos, M.M.; Alves, C.; Silva, J.; Florindo, C.; Costa, A.; Petrovski, Ž.; Marrucho, I.M.; Pedrosa, R.; Branco, L.C. Antimicrobial Activities of Highly Bioavailable Organic Salts and Ionic Liquids from Fluoroquinolones. Pharmaceutics 2020, 12, 694. DOI:10.3390/pharmaceutics120806941999-492310.3390/pharmaceutics12080694info: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:RCAAP2024-01-17T15:50:39Zoai:iconline.ipleiria.pt:10400.8/5116Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:48:47.585774Repositório 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 Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
title Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
spellingShingle Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
Santos, Miguel M.
Active pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs)
Antibiotics
Ciprofloxacin
Fluoroquinolones
Ionic liquids
Norfloxacin
Polymorphism
title_short Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
title_full Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
title_fullStr Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
title_full_unstemmed Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
title_sort Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
author Santos, Miguel M.
author_facet Santos, Miguel M.
Alves, Celso
Silva, Joana
Florindo, Catarina
Petrovski, Zeljko
Marrucho, Isabel M.
Pedrosa, Rui
Branco, Luís C.
author_role author
author2 Alves, Celso
Silva, Joana
Florindo, Catarina
Petrovski, Zeljko
Marrucho, Isabel M.
Pedrosa, Rui
Branco, Luís C.
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv IC-Online
dc.contributor.author.fl_str_mv Santos, Miguel M.
Alves, Celso
Silva, Joana
Florindo, Catarina
Petrovski, Zeljko
Marrucho, Isabel M.
Pedrosa, Rui
Branco, Luís C.
dc.subject.por.fl_str_mv Active pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs)
Antibiotics
Ciprofloxacin
Fluoroquinolones
Ionic liquids
Norfloxacin
Polymorphism
topic Active pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs)
Antibiotics
Ciprofloxacin
Fluoroquinolones
Ionic liquids
Norfloxacin
Polymorphism
description Funding: This work was supported by the Associate Laboratory for Green Chemistry LAQV and Centro de Química Estrutural, which are financed by national funds from FCT/MCTES (UIDB/50006/2020 and UID/QUI/00100/2013, respectively). The authors also thank Fundação para a Ciência e Tecnologia for the projects PTDC/QUI-OR/32406/2017, PEst-C/LA0006/2013, and ECI/BBBBQB/0230/2012, as well as one contract under Investigador FCT (L. C. Branco).
publishDate 2020
dc.date.none.fl_str_mv 2020-08-28T14:09:39Z
2020
2020-01-01T00:00:00Z
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/10400.8/5116
url http://hdl.handle.net/10400.8/5116
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Santos, M.M.; Alves, C.; Silva, J.; Florindo, C.; Costa, A.; Petrovski, Ž.; Marrucho, I.M.; Pedrosa, R.; Branco, L.C. Antimicrobial Activities of Highly Bioavailable Organic Salts and Ionic Liquids from Fluoroquinolones. Pharmaceutics 2020, 12, 694. DOI:10.3390/pharmaceutics12080694
1999-4923
10.3390/pharmaceutics12080694
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 MDPI
publisher.none.fl_str_mv MDPI
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
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