Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis

A series of diverse simple C2-aryl quinolines was synthesized de novo via a straightforward synthesis based on the acid-catalyzed multicomponent imino Diels–Alder reactions. Seven selected quinolines were evaluated at different stages of Leishmania braziliensis parasite. Among them, the 6-ethyl-2-ph...

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Fecha de publicación:: 2013

Institución:: Ministerio de Ciencia Tecnología e Innovación

Repositorio:: Repositorio Institucional de Minciencias

Idioma:: eng

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spelling	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensisAceites vegetalesBiomasaChemotherapyL. braziliensisParasite bioenergeticsSterol biosynthetic pathwayC2-aryl substituted quinolinesBotánicaAceites esencialesBioquímica vegetalQuímica agrícolaLeishmaniosisMedicina tropicalA series of diverse simple C2-aryl quinolines was synthesized de novo via a straightforward synthesis based on the acid-catalyzed multicomponent imino Diels–Alder reactions. Seven selected quinolines were evaluated at different stages of Leishmania braziliensis parasite. Among them, the 6-ethyl-2-phenylquinoline 5f was able to inhibit the growth of promastigotes of this parasite without affecting the mammalian cells viability and decreasing the number of intracellular L. braziliensis amastigotes on BMDM macrophages. The mechanism of action studied for the selected compound consisted in: (1) alteration of parasite bioenergetics, by disrupting mitochondrial electrochemical potential and alkalinisation of acidocalcisomes, and (2) inhibition of ergosterol biosynthetic pathway in promastigote forms. These results validate the efficiency of quinoline molecules as leishmanicide compounds.Departamento Administrativo de Ciencia, Tecnología e Innovación [CO] Colciencias5507-543-31904Programa: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombianano2019-03-31T22:50:04Z2019-03-31T22:50:04Z2013-05-09info:eu-repo/date/embargoEnd/2024-01-31Artículo científicoinfo:eu-repo/semantics/articlehttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1pdf6 páginasapplication/pdfhttp://repositorio.colciencias.gov.co/handle/11146/34158Contiene 41 referencias bibliográficas. Véase documento adjunto10.1016/j.bmc.2013.04.063Bioorganic & Medicinal Chemistry 21 (2013) 4426–4431engPrograma: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombiana. La publicación completa está disponible en : <a href="http://repositorio.colciencias.gov.co/handle/11146/34163" target="blank">http://repositorio.colciencias.gov.co/handle/11146/34163</a>Colombiahttp://purl.org/coar/access_right/c_f1cfBompart, DazniaNúñez Durán, JorgeRodríguez, DanielKouznetsov, Vladimir V.Meléndez Gómez, Carlos M.Sojo, FelipeArvelo, FranciscoVisbal, GonzaloÁlvarez, ÁlvaroSerrano Martín, XenónGarcía Marchán, Yaeloai:repositorio.minciencias.gov.co:20.500.14143/341582023-11-29T17:42:41Z
dc.title.none.fl_str_mv	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
title	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
spellingShingle	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis Aceites vegetales Biomasa Chemotherapy L. braziliensis Parasite bioenergetics Sterol biosynthetic pathway C2-aryl substituted quinolines Botánica Aceites esenciales Bioquímica vegetal Química agrícola Leishmaniosis Medicina tropical
title_short	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
title_full	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
title_fullStr	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
title_full_unstemmed	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
title_sort	Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis
dc.subject.none.fl_str_mv	Aceites vegetales Biomasa Chemotherapy L. braziliensis Parasite bioenergetics Sterol biosynthetic pathway C2-aryl substituted quinolines Botánica Aceites esenciales Bioquímica vegetal Química agrícola Leishmaniosis Medicina tropical
topic	Aceites vegetales Biomasa Chemotherapy L. braziliensis Parasite bioenergetics Sterol biosynthetic pathway C2-aryl substituted quinolines Botánica Aceites esenciales Bioquímica vegetal Química agrícola Leishmaniosis Medicina tropical
description	A series of diverse simple C2-aryl quinolines was synthesized de novo via a straightforward synthesis based on the acid-catalyzed multicomponent imino Diels–Alder reactions. Seven selected quinolines were evaluated at different stages of Leishmania braziliensis parasite. Among them, the 6-ethyl-2-phenylquinoline 5f was able to inhibit the growth of promastigotes of this parasite without affecting the mammalian cells viability and decreasing the number of intracellular L. braziliensis amastigotes on BMDM macrophages. The mechanism of action studied for the selected compound consisted in: (1) alteration of parasite bioenergetics, by disrupting mitochondrial electrochemical potential and alkalinisation of acidocalcisomes, and (2) inhibition of ergosterol biosynthetic pathway in promastigote forms. These results validate the efficiency of quinoline molecules as leishmanicide compounds.
publishDate	2013
dc.date.none.fl_str_mv	2013-05-09 2019-03-31T22:50:04Z 2019-03-31T22:50:04Z info:eu-repo/date/embargoEnd/2024-01-31
dc.type.none.fl_str_mv	Artículo científico info:eu-repo/semantics/article
dc.type.coarversion.fl_str_mv	http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.coar.fl_str_mv	http://purl.org/coar/resource_type/c_2df8fbb1
dc.identifier.none.fl_str_mv	http://repositorio.colciencias.gov.co/handle/11146/34158 Contiene 41 referencias bibliográficas. Véase documento adjunto 10.1016/j.bmc.2013.04.063
url	http://repositorio.colciencias.gov.co/handle/11146/34158
identifier_str_mv	Contiene 41 referencias bibliográficas. Véase documento adjunto 10.1016/j.bmc.2013.04.063
dc.language.none.fl_str_mv	eng
language	eng
dc.relation.none.fl_str_mv	Programa: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombiana. La publicación completa está disponible en : <a href="http://repositorio.colciencias.gov.co/handle/11146/34163" target="blank">http://repositorio.colciencias.gov.co/handle/11146/34163</a>
dc.rights.coar.fl_str_mv	http://purl.org/coar/access_right/c_f1cf
rights_invalid_str_mv	http://purl.org/coar/access_right/c_f1cf
dc.format.none.fl_str_mv	pdf 6 páginas application/pdf
dc.coverage.none.fl_str_mv	Colombia
dc.source.none.fl_str_mv	Bioorganic & Medicinal Chemistry 21 (2013) 4426–4431
institution	Ministerio de Ciencia Tecnología e Innovación
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_	1860676507996782592

Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis

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