Design And Synthesis Of N-acylated Aza-goniothalamin Derivatives And Evaluation Of Their In Vitro And In Vivo Antitumor Activity

dc.creatorBarcelos R.C.
dc.creatorPastre J.C.
dc.creatorVendramini-Costa D.B.
dc.creatorCaixeta V.
dc.creatorLongato G.B.
dc.creatorMonteiro P.A.
dc.creatorDe Carvalho J.E.
dc.creatorPilli R.A.
dc.date2014
dc.date2015-06-25T17:54:33Z
dc.date2015-11-26T14:35:01Z
dc.date2015-06-25T17:54:33Z
dc.date2015-11-26T14:35:01Z
dc.date.accessioned2018-03-28T21:38:26Z
dc.date.available2018-03-28T21:38:26Z
dc.identifier
dc.identifierChemmedchem. John Wiley And Sons Ltd, v. 9, n. 12, p. 2725 - 2743, 2014.
dc.identifier18607179
dc.identifier10.1002/cmdc.201402292
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84913545729&partnerID=40&md5=4fff8e2c48b17994898070aaf1f07648
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/86712
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/86712
dc.identifier2-s2.0-84913545729
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1248261
dc.descriptionHerein we describe the synthesis of a focused library of compounds based on the structure of goniothalamin (1) and the evaluation of the potential antitumor activity of the compounds. N-Acylation of aza-goniothalamin (2) restored the in vitro antiproliferative activity of this family of compounds. 1- (E)-But-2-enoyl-6-styryl-5,6-dihydropyridin-2(1H)-one (18) displayed enhanced antiproliferative activity. Both goniothalamin (1) and derivative 18 led to reactive oxygen species generation in PC-3 cells, which was probably a signal for caspase-dependent apoptosis. Treatment with derivative 18 promoted Annexin V/7-aminoactinomycin D double staining, which indicated apoptosis, and also led to G2/M cell-cycle arrest. In vivo studies in Ehrlich ascitic and solid tumor models confirmed the antitumor activity of goniothalamin (1), without signs of toxicity. However, derivative 18 exhibited an unexpectedly lower in vivo antitumor activity, despite the treatments being administered at the same site of inoculation. Contrary to its in vitro profile, aza-goniothalamin (2) inhibited Ehrlich tumor growth, both on the ascitic and solid forms. Our findings highlight the importance of in vivo studies in the search for new candidates for cancer treatment.
dc.description9
dc.description12
dc.description2725
dc.description2743
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dc.languageen
dc.publisherJohn Wiley and Sons Ltd
dc.relationChemMedChem
dc.rightsfechado
dc.sourceScopus
dc.titleDesign And Synthesis Of N-acylated Aza-goniothalamin Derivatives And Evaluation Of Their In Vitro And In Vivo Antitumor Activity
dc.typeArtículos de revistas


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