Synthesis And Evaluation Of Novel Hybrids Beta-carboline-4-thiazolidinones As Potential Antitumor And Antiviral Agents

dc.creatorBarbosa
dc.creatorValeria Aquilino; Barea
dc.creatorPaula; Mazia
dc.creatorRenata Sespede; Ueda-Nakamura
dc.creatorTania; da Costa
dc.creatorWillian Ferreira; Foglio
dc.creatorMary Ann; Goes Ruiz
dc.creatorAna Lucia T.; de Carvalho
dc.creatorJoao Ernesto; Vendramini-Costa
dc.creatorDebora Barbosa; Nakamura
dc.creatorCelso Vataru; Sarragiotto
dc.creatorMaria Helena
dc.date2016
dc.datenov
dc.date2017-11-13T13:55:24Z
dc.date2017-11-13T13:55:24Z
dc.date.accessioned2018-03-29T06:08:53Z
dc.date.available2018-03-29T06:08:53Z
dc.identifierEuropean Journal Of Medicinal Chemistry . Elsevier France-editions Scientifiques Medicales Elsevier, v. 124, p. 1093 - 1104, 2016.
dc.identifier0223-5234
dc.identifier1768-3254
dc.identifierWOS:000388544600086
dc.identifier10.1016/j.ejmech.2016.10.018
dc.identifierhttp://www-sciencedirect-com.ez88.periodicos.capes.gov.br/science/article/pii/S0223523416308807?via%3Dihub
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/329640
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1366665
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionA series of novel hybrids beta-carboline-4-thiazolidinones were synthesized and evaluated for their in vitro antitumor activity against human cancer cell lines and for antiviral activity towards Herpes simplex virus type-1 (HSV-1). From the N'-(2-ylidene-4-thiazolidinone)-beta-carboline-3-carbohydrazide series (9-11), compounds 9c and 11d were the most active, showing growth inhibition 50% (GI(50)) values less than 5 mu M for all cell lines tested. Compound 9c, bearing the 4-dimethylaminophenyl group at C-1 of beta-carboline was selected for further investigation concerning cell death and cell cycle profile, focusing on the human renal adenocarcinoma cell line 786-0. Treatments with 25 mu M of compound 9c induced cell death after 15 h of treatment, characterized by phosphatidylserine exposure and loss of membrane integrity. Moreover, treatment with 12.5 mu M promoted a sub-G1 arrest, which indicates cell death. Derivatives of the N-(2-substituted-aryl-4-thiazolidinone)-beta-carboline-3-carboxamide series (18-23) showed a potent activity and high selectivity for glioma (U251) and ovarian (OVCAR-3) cancer cell lines. Also, some beta-carboline-4-thiazolidinone hybrids showed potent antiviral activity against Herpes simplex virus type-1. The N-(2-substituted-aryl-4-thiazolidinone)-carboxamide moiety in 18, 19 and 22 confer a potent anti-HSV-1 activity for these derivatives, which presented EC50 values of 0.80, 2.15 and 2.02 mu M, respectively. The assay results showed that the nature of 4-thiazolidinone moiety and of the substituent attached at the 3- and 1- position of beta-carboline nucleus influenced the antitumor and antiviral activities. (C) 2016 Elsevier Masson SAS. All rights reserved.
dc.description124
dc.description1093
dc.description1104
dc.descriptionFundacao Araucaria (Brazil, PR) [23.444-FA]
dc.descriptionFundacao de Amparo a Pesquisa de Sao Paulo (FAPESP) [2015/08338-6]
dc.descriptionCAPES
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.languageEnglish
dc.publisherElsevier France-Editions Scientifiques Medicales Elsevier
dc.publisherParis
dc.relationEuropean Journal of Medicinal Chemistry
dc.rightsfechado
dc.sourceWOS
dc.subjectBeta-carboline
dc.subject4-thiazolidinone
dc.subjectAntitumor
dc.subjectAntiviral
dc.titleSynthesis And Evaluation Of Novel Hybrids Beta-carboline-4-thiazolidinones As Potential Antitumor And Antiviral Agents
dc.typeArtículos de revistas


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