Novel Organic Salts Based on Mefloquine
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , , , , , , , , , |
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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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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7160 |
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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 |
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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1799138131958562816 |