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

2020Journal article Open access
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dc.contributor.authorSantos, Miguel M.
dc.contributor.authorAlves, Celso
dc.contributor.authorSilva, Joana
dc.contributor.authorFlorindo, Catarina
dc.contributor.authorPetrovski, Zeljko
dc.contributor.authorMarrucho, Isabel M.
dc.contributor.authorPedrosa, Rui
dc.contributor.authorBranco, Luís C.
dc.date.accessioned2020-08-28T14:09:39Z
dc.date.available2020-08-28T14:09:39Z
dc.date.issued2020
dc.descriptionFunding: 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).
dc.description.abstractAs 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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationSantos, 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/pharmaceutics12080694pt_PT
dc.identifier.doi10.3390/pharmaceutics12080694pt_PT
dc.identifier.issn1999-4923
dc.identifier.urihttp://hdl.handle.net/10400.8/5116
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectActive pharmaceutical ingredients as organic salts and ionic liquids (API–OSILs)pt_PT
dc.subjectAntibioticspt_PT
dc.subjectCiprofloxacinpt_PT
dc.subjectFluoroquinolonespt_PT
dc.subjectIonic liquidspt_PT
dc.subjectNorfloxacinpt_PT
dc.subjectPolymorphismpt_PT
dc.titleAntimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolonespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F00100%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FQUI-QOR%2F32406%2F2017/PT
oaire.citation.titlePharmaceuticspt_PT
oaire.citation.volume12pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream5876
oaire.fundingStream3599-PPCDT
person.familyNameAlves
person.familyNameSilva
person.familyNamePedrosa
person.givenNameCelso
person.givenNameJoana
person.givenNameRui
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person.identifier.ciencia-id3817-33DE-919E
person.identifier.orcid0000-0003-1581-2127
person.identifier.orcid0000-0003-1224-1699
person.identifier.orcid0000-0003-0970-0575
person.identifier.ridB-3366-2017
person.identifier.ridB-4815-2015
person.identifier.scopus-author-id55654969100
person.identifier.scopus-author-id56370819800
person.identifier.scopus-author-id7005010300
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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