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Novel Organic Salts Based on Mefloquine

2022-08-13Artigo científico Acesso aberto
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dc.contributor.authorSilva, Dário
dc.contributor.authorLopes, Márcio V. C.
dc.contributor.authorPetrovski, Željko
dc.contributor.authorSantos, Miguel M.
dc.contributor.authorSantos, Jussevania P.
dc.contributor.authorYamada-Ogatta, Sueli F.
dc.contributor.authorBispo, Marcelle L. F.
dc.contributor.authorde Souza, Marcus V. N.
dc.contributor.authorDuarte, Ana Rita C.
dc.contributor.authorLourenço, Maria C. S.
dc.contributor.authorGonçalves, Raoni Schroeder B.
dc.contributor.authorBranco, Luís C.
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.pblMDPI - Multidisciplinary Digital Publishing Institute
dc.date.accessioned2023-03-16T22:38:49Z
dc.date.available2023-03-16T22:38:49Z
dc.date.issued2022-08-13
dc.descriptionFunding Information: This work was supported by FCT-MCTES (PEst-C/LA0006/2013, RECI/BBBBQB/0230/2012). The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project N° 022161 (co-financed by FEDER through COMPETE 2020, POCI, PORL, and FCT through PIDDAC). Publisher Copyright: © 2022 by the authors.
dc.description.abstractThe development of novel pharmaceutical tools to efficiently tackle tuberculosis is the order of the day due to the rapid development of resistant strains of Mycobacterium tuberculosis. Herein, we report novel potential formulations of a repurposed drug, the antimalarial mefloquine (MFL), which was combined with organic anions as chemical adjuvants. Eight mefloquine organic salts were obtained by ion metathesis reaction between mefloquine hydrochloride ([MFLH][Cl]) and several organic acid sodium salts in high yields. One of the salts, mefloquine mesylate ([MFLH][MsO]), presented increased water solubility in comparison with [MFLH][Cl]. Moreover, all salts with the exception of mefloquine docusate ([MFLH][AOT]) showed improved permeability and diffusion through synthetic membranes. Finally, in vitro activity studies against Mycobacterium tuberculosis revealed that these ionic formulations exhibited up to 1.5-times lower MIC values when compared with [MFLH][Cl], particularly mefloquine camphorsulfonates ([MFLH][(1R)-CSA], [MFLH][(1S)-CSA]) and mefloquine HEPES ([MFLH][HEPES]).en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent15
dc.format.extent970884
dc.identifier.doi10.3390/molecules27165167
dc.identifier.issn1420-3049
dc.identifier.otherPURE: 56135786
dc.identifier.otherPURE UUID: 5415aae6-5387-468c-b939-a215802ac8f1
dc.identifier.otherScopus: 85136609871
dc.identifier.otherPubMed: 36014405
dc.identifier.otherPubMedCentral: PMC9412322
dc.identifier.otherWOS: 000845315900001
dc.identifier.otherORCID: /0000-0003-0800-0112/work/131002329
dc.identifier.otherORCID: /0000-0002-8104-7008/work/131002362
dc.identifier.otherORCID: /0000-0001-8973-1595/work/131002471
dc.identifier.urihttp://hdl.handle.net/10362/150735
dc.identifier.urlhttps://www.scopus.com/pages/publications/85136609871
dc.language.isoeng
dc.peerreviewedyes
dc.relationinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FQUI-QOR%2F32406%2F2017/PT
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.subjectAPI-OSILs
dc.subjectionic liquids
dc.subjectmefloquine
dc.subjectpolymorphism
dc.subjecttuberculosis
dc.subjectAnalytical Chemistry
dc.subjectChemistry (miscellaneous)
dc.subjectMolecular Medicine
dc.subjectPharmaceutical Science
dc.subjectDrug Discovery
dc.subjectPhysical and Theoretical Chemistry
dc.subjectOrganic Chemistry
dc.subjectSDG 3 - Good Health and Well-being
dc.titleNovel Organic Salts Based on Mefloquineen
dc.title.subtitleSynthesis, Solubility, Permeability, and In Vitro Activity against Mycobacterium tuberculosisen
dc.typejournal article
degois.publication.issue16
degois.publication.titleMolecules
degois.publication.volume27
dspace.entity.typePublication
oaire.awardNumberPTDC/QUI-QOR/32406/2017
oaire.awardNumberUIDB/50006/2020
oaire.awardNumberUIDP/50006/2020
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FQUI-QOR%2F32406%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
oaire.fundingStream3599-PPCDT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
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.rightsopenAccess
relation.isProjectOfPublicationabc9a315-0b2e-4296-b976-6611829dbad8
relation.isProjectOfPublicationadc84c24-ba1d-4bcd-b753-2128ce9a5faa
relation.isProjectOfPublication4d9a4d40-4803-4f3a-976b-d6eaaef42510
relation.isProjectOfPublication.latestForDiscoveryabc9a315-0b2e-4296-b976-6611829dbad8

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