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dc.contributor.CRUESPUNIVERSIDADE DE ESTADUAL DE CAMPINASpt_BR
dc.typeArtigopt_BR
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
unicamp.author.externalFaculdade de Ciências da Saüde and, Universidade Federal da Grande Dourados, Rodovia Dourados - Itahum, Dourados-MS, Brazilpt_BR
unicamp.author.externalFaculdade de Ciências Agrárias, Universidade Federal da Grande Dourados, Rodovia Dourados - Itahum, Dourados-MS, Brazilpt_BR
unicamp.author.externalDepartamento de Química, Universidade Estadual de Maringá, Avenida Colombo, 5790, Jardim Universitário, Maringá-PR, Brazilpt_BR
dc.subjectAntiproliferative Activityen
dc.subjectMycobacterium Tuberculosisen
dc.subjectSynthesisen
dc.subjectβ-carbolineen
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.date.issued2016pt_BR
dc.identifier.citationJournal Of The Brazilian Chemical Society. Sociedade Brasileira De Quimica, v. 27, n. 8, p. 1398 - 1405, 2016.pt_BR
dc.language.isoEnglishpt_BR
dc.description.volume27pt_BR
dc.description.issuenumber8pt_BR
dc.description.firstpage1398pt_BR
dc.description.lastpage1405pt_BR
dc.rightsabertopt_BR
dc.sourceScopuspt_BR
dc.identifier.issn0103-5053pt_BR
dc.identifier.doi10.5935/0103-5053.20160062pt_BR
dc.identifier.urlhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-84982706049&doi=10.5935%2f0103-5053.20160062&partnerID=40&md5=6d6b695f5e9728963e92af08fbdef5dfpt_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
dc.date.available2017-08-17T19:17:56Z-
dc.date.accessioned2017-08-17T19:17:56Z-
dc.description.provenanceMade available in DSpace on 2017-08-17T19:17:56Z (GMT). No. of bitstreams: 1 2-s2.0-84982706049.pdf: 299943 bytes, checksum: 093b5a1419a032c999596331db3659f0 (MD5) Previous issue date: 2016en
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/324233-
dc.identifier.idScopus2-s2.0-84982706049pt_BR
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