Novel Organic Salts Based on Mefloquine

Detalhes bibliográficos
Autor(a) principal: Silva, Dário
Data de Publicação: 2022
Outros Autores: Lopes, Márcio V. C., Petrovski, Željko, Santos, Miguel M., Santos, Jussevania P., Yamada-Ogatta, Sueli F., Bispo, Marcelle L. F., de Souza, Marcus V. N., Duarte, Ana Rita C., Lourenço, Maria C. S., Gonçalves, Raoni Schroeder B., 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/10362/150735
Resumo: Funding 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.
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spelling Novel Organic Salts Based on MefloquineSynthesis, Solubility, Permeability, and In Vitro Activity against Mycobacterium tuberculosisAPI-OSILsionic liquidsmefloquinepolymorphismtuberculosisAnalytical ChemistryChemistry (miscellaneous)Molecular MedicinePharmaceutical ScienceDrug DiscoveryPhysical and Theoretical ChemistryOrganic ChemistrySDG 3 - Good Health and Well-beingFunding 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.The 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]).DQ - Departamento de QuímicaLAQV@REQUIMTERUNSilva, DárioLopes, Márcio V. C.Petrovski, ŽeljkoSantos, Miguel M.Santos, Jussevania P.Yamada-Ogatta, Sueli F.Bispo, Marcelle L. F.de Souza, Marcus V. N.Duarte, Ana Rita C.Lourenço, Maria C. S.Gonçalves, Raoni Schroeder B.Branco, Luís C.2023-03-16T22:38:49Z2022-08-132022-08-13T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article15application/pdfhttp://hdl.handle.net/10362/150735eng1420-3049PURE: 56135786https://doi.org/10.3390/molecules27165167info: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:RCAAP2024-03-11T05:33:05Zoai:run.unl.pt:10362/150735Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:54:17.490952Repositório 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 Novel Organic Salts Based on Mefloquine
Synthesis, Solubility, Permeability, and In Vitro Activity against Mycobacterium tuberculosis
title Novel Organic Salts Based on Mefloquine
spellingShingle Novel Organic Salts Based on Mefloquine
Silva, Dário
API-OSILs
ionic liquids
mefloquine
polymorphism
tuberculosis
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
SDG 3 - Good Health and Well-being
title_short Novel Organic Salts Based on Mefloquine
title_full Novel Organic Salts Based on Mefloquine
title_fullStr Novel Organic Salts Based on Mefloquine
title_full_unstemmed Novel Organic Salts Based on Mefloquine
title_sort Novel Organic Salts Based on Mefloquine
author Silva, Dário
author_facet Silva, Dário
Lopes, Márcio V. C.
Petrovski, Željko
Santos, Miguel M.
Santos, Jussevania P.
Yamada-Ogatta, Sueli F.
Bispo, Marcelle L. F.
de Souza, Marcus V. N.
Duarte, Ana Rita C.
Lourenço, Maria C. S.
Gonçalves, Raoni Schroeder B.
Branco, Luís C.
author_role author
author2 Lopes, Márcio V. C.
Petrovski, Željko
Santos, Miguel M.
Santos, Jussevania P.
Yamada-Ogatta, Sueli F.
Bispo, Marcelle L. F.
de Souza, Marcus V. N.
Duarte, Ana Rita C.
Lourenço, Maria C. S.
Gonçalves, Raoni Schroeder B.
Branco, Luís C.
author2_role author
author
author
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 Silva, Dário
Lopes, Márcio V. C.
Petrovski, Željko
Santos, Miguel M.
Santos, Jussevania P.
Yamada-Ogatta, Sueli F.
Bispo, Marcelle L. F.
de Souza, Marcus V. N.
Duarte, Ana Rita C.
Lourenço, Maria C. S.
Gonçalves, Raoni Schroeder B.
Branco, Luís C.
dc.subject.por.fl_str_mv API-OSILs
ionic liquids
mefloquine
polymorphism
tuberculosis
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
SDG 3 - Good Health and Well-being
topic API-OSILs
ionic liquids
mefloquine
polymorphism
tuberculosis
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
SDG 3 - Good Health and Well-being
description Funding 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.
publishDate 2022
dc.date.none.fl_str_mv 2022-08-13
2022-08-13T00:00:00Z
2023-03-16T22:38:49Z
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/10362/150735
url http://hdl.handle.net/10362/150735
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1420-3049
PURE: 56135786
https://doi.org/10.3390/molecules27165167
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 15
application/pdf
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
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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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