Docking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues

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dc.contributorSistema FMUSP-HC: Faculdade de Medicina da Universidade de São Paulo (FMUSP) e Hospital das Clínicas da FMUSP
dc.contributor.authorAMARAL, Daniel Nascimento do
dc.contributor.authorCAVALCANTI, Bruno C.
dc.contributor.authorBEZERRA, Daniel P.
dc.contributor.authorFERREIRA, Paulo Michel P.
dc.contributor.authorCASTRO, Rosane de Paula
dc.contributor.authorSABINO, Jose Ricardo
dc.contributor.authorMACHADO, Camila Maria Longo
dc.contributor.authorCHAMMAS, Roger
dc.contributor.authorPESSOA, Claudia
dc.contributor.authorSANT'ANNA, Carlos M. R.
dc.contributor.authorBARREIRO, Eliezer J.
dc.contributor.authorLIMA, Lidia Moreira
dc.date.accessioned2014-09-30T14:39:17Z
dc.date.available2014-09-30T14:39:17Z
dc.date.issued2014
dc.description.abstractCancer is the second most common cause of death in the USA. Among the known classes of anticancer agents, the microtubule-targeted antimitotic drugs are considered to be one of the most important. They are usually classified into microtubule-destabilizing (e. g., Vinca alkaloids) and microtubule-stabilizing (e. g., paclitaxel) agents. Combretastatin A4 (CA-4), which is a natural stilbene isolated from Combretum caffrum, is a microtubule-destabilizing agent that binds to the colchicine domain on beta-tubulin and exhibits a lower toxicity profile than paclitaxel or the Vinca alkaloids. In this paper, we describe the docking study, synthesis, antiproliferative activity and selectivity index of the N-acylhydrazone derivatives (5a-r) designed as CA-4 analogues. The essential structural requirements for molecular recognition by the colchicine binding site of beta-tubulin were recognized, and several compounds with moderate to high antiproliferative potency (IC50 values <= 18 mu M and >= 4 nM) were identified. Among these active compounds, LASSBio-1586 (5b) emerged as a simple antitumor drug candidate, which is capable of inhibiting microtubule polymerization and possesses a broad in vitro and in vivo antiproliferative profile, as well as a better selectivity index than the prototype CA-4, indicating improved selective cytotoxicity toward cancer cells.
dc.description.indexMEDLINE
dc.description.sponsorshipCNPq
dc.description.sponsorshipFAPERJ
dc.description.sponsorshipINCT-INOFAR [573.564/2008-6, E-26/170.020/2008]
dc.identifier.citationPLOS ONE, v.9, n.3, article ID e85380, 16p, 2014
dc.identifier.doi10.1371/journal.pone.0085380
dc.identifier.issn1932-6203
dc.identifier.urihttps://observatorio.fm.usp.br/handle/OPI/7453
dc.language.isoeng
dc.publisherPUBLIC LIBRARY SCIENCE
dc.relation.ispartofPlos One
dc.rightsopenAccess
dc.rights.holderCopyright PUBLIC LIBRARY SCIENCE
dc.subject.otherhollow-fiber assay
dc.subject.otherin-vivo
dc.subject.otherbinding-affinity
dc.subject.otheranticancer drugs
dc.subject.otherbeta-tubulin
dc.subject.othermodel
dc.subject.othermicrotubules
dc.subject.otherdynamics
dc.subject.othertarget
dc.subject.othergrowth
dc.subject.wosMultidisciplinary Sciences
dc.titleDocking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues
dc.typearticle
dc.type.categoryoriginal article
dc.type.versionpublishedVersion
dspace.entity.typePublication
hcfmusp.author.externalAMARAL, Daniel Nascimento do:Univ Fed Rio de Janeiro, Inst Nacl Ciencia & Tecnol Farmacos & Medicamento, Lab Avaliacao & Sintese Subst Bioat LASSBio, Rio De Janeiro, Brazil; Univ Fed Rio de Janeiro, Inst Quim, Programa Posgrad Quim, Rio De Janeiro, Brazil
hcfmusp.author.externalCAVALCANTI, Bruno C.:Univ Fed Ceara, Fac Med, Dept Fisiol & Farmacol, Fortaleza, Ceara, Brazil
hcfmusp.author.externalBEZERRA, Daniel P.:Univ Fed Ceara, Fac Med, Dept Fisiol & Farmacol, Fortaleza, Ceara, Brazil
hcfmusp.author.externalFERREIRA, Paulo Michel P.:Univ Fed Piaui, Dept Ciencias Biol, Picos, Brazil
hcfmusp.author.externalCASTRO, Rosane de Paula:Univ Fed Goias, Inst Fis, Goiania, Go, Brazil
hcfmusp.author.externalSABINO, Jose Ricardo:Univ Fed Goias, Inst Fis, Goiania, Go, Brazil
hcfmusp.author.externalPESSOA, Claudia:Univ Fed Ceara, Fac Med, Dept Fisiol & Farmacol, Fortaleza, Ceara, Brazil
hcfmusp.author.externalSANT'ANNA, Carlos M. R.:Univ Fed Rural Rio de Janeiro, Dept Quim, Seropedica, Brazil
hcfmusp.author.externalBARREIRO, Eliezer J.:Univ Fed Rio de Janeiro, Inst Nacl Ciencia & Tecnol Farmacos & Medicamento, Lab Avaliacao & Sintese Subst Bioat LASSBio, Rio De Janeiro, Brazil; Univ Fed Rio de Janeiro, Inst Quim, Programa Posgrad Quim, Rio De Janeiro, Brazil
hcfmusp.author.externalLIMA, Lidia Moreira:Univ Fed Rio de Janeiro, Inst Nacl Ciencia & Tecnol Farmacos & Medicamento, Lab Avaliacao & Sintese Subst Bioat LASSBio, Rio De Janeiro, Brazil; Univ Fed Rio de Janeiro, Inst Quim, Programa Posgrad Quim, Rio De Janeiro, Brazil
hcfmusp.citation.scopus56
hcfmusp.contributor.author-fmusphcCAMILA MARIA LONGO MACHADO
hcfmusp.contributor.author-fmusphcROGER CHAMMAS
hcfmusp.description.articlenumbere85380
hcfmusp.description.issue3
hcfmusp.description.volume9
hcfmusp.origemWOS
hcfmusp.origem.pubmed24614859
hcfmusp.origem.scopus2-s2.0-84897559253
hcfmusp.origem.wosWOS:000332839300002
hcfmusp.publisher.citySAN FRANCISCO
hcfmusp.publisher.countryUSA
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hcfmusp.remissive.sponsorshipCNPq
hcfmusp.remissive.sponsorshipFAPERJ
hcfmusp.remissive.sponsorshipINCTs
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