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dc.titleSynthesis, In Vitro Antiproliferative And Anti-mycobacterium Tuberculosis Activities Of Novel β-carboline Derivativesen
dc.contributor.authorMoreira F.M.F.pt_BR
dc.contributor.authorCroda J.pt_BR
dc.contributor.authorSarragiotto M.H.pt_BR
dc.contributor.authorFoglio M.A.pt_BR
dc.contributor.authorRuiz A.L.T.G.pt_BR
dc.contributor.authorCarvalho J.E.pt_BR
dc.contributor.authorFormagio A.S.N.pt_BR
unicamp.authorCentro Pluridisciplinar de Pesquisas Químicas Biológicas e Agrícolas, Universidade Estadual de Campinas, CP 6171, Campinas-SP, Brazilpt_BR de Ciências da Saüde and, Universidade Federal da Grande Dourados, Rodovia Dourados - Itahum, Dourados-MS, Brazilpt_BR de Ciências Agrárias, Universidade Federal da Grande Dourados, Rodovia Dourados - Itahum, Dourados-MS, Brazilpt_BR de Química, Universidade Estadual de Maringá, Avenida Colombo, 5790, Jardim Universitário, Maringá-PR, Brazilpt_BR
dc.subjectAntiproliferative Activityen
dc.subjectMycobacterium Tuberculosisen
dc.description.abstractA series of β-carboline derivatives with amino or guanidinium were synthesized and evaluated in vitro against anti-Mycobacterium tuberculosis and for antiproliferative activities against nine human cancer cell lines. The compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline (24.9 μg mL-1) and 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline (26.9 μg mL-1) were the most active against M. Tuberculosis (MTB). Compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline and 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline, which had the same substituted groups, inhibited the growth of all human tumor cell lines with growth inhibitory activity (GI50) values from 1.37 to 9.20 mmol L-1. Also in this series, compounds 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline demonstrated significant activity against NCI/ADR cells. Among compounds with a terminal guanidine group, compounds 1-(4-hydroxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (27.8 μg mL-1) and 1-(3-nitrophenyl)-3-carboxamide(ethyl) guanidine β-carboline (37.4 μg mL-1) demonstrated the greatest activity against MTB. Additionally, compounds 1-(4-methoxyphenyl)-3-carboxamide(ethyl)guanidine β-carboline (GI50 = 0.45 mmol L-1) effectively inhibited growth and was highly selective against NCI/ADR. The in silico study revealed that 1-(4-hydroxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(ethylamine) β-carboline, 1-(4-hydroxyphenyl)-3-carboxamide(propylamine) β-carboline, 1-(4-methoxyphenyl)-3-carboxamide(propylamine) β-carboline and 1-(3-nitrophenyl)-3-carboxamide(propylamine) β-carboline compounds follow the rules established by Lipinski, suggesting that this compound has no problems with oral bioavailability. © 2016 Sociedade Brasileira de Química.en
dc.relation.ispartofJournal of the Brazilian Chemical Societypt_BR
dc.publisherSociedade Brasileira de Quimicapt_BR
dc.identifier.citationJournal Of The Brazilian Chemical Society. Sociedade Brasileira De Quimica, v. 27, n. 8, p. 1398 - 1405, 2016.pt_BR
dc.description.sponsorshipCAPES, Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorpt_BR
dc.description.sponsorshipCNPq, Conselho Nacional de Desenvolvimento Científico e Tecnológicopt_BR
dc.description.sponsorship1Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)pt_BR
dc.description.sponsorship1Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
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