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

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dc.contributor Sistema FMUSP-HC: Faculdade de Medicina da Universidade de São Paulo (FMUSP) e Hospital das Clínicas da FMUSP
dc.contributor.author AMARAL, Daniel Nascimento do
CAVALCANTI, Bruno C.
BEZERRA, Daniel P.
FERREIRA, Paulo Michel P.
CASTRO, Rosane de Paula
SABINO, Jose Ricardo
MACHADO, Camila Maria Longo FMUSP-HC
CHAMMAS, Roger FMUSP-HC
PESSOA, Claudia
SANT'ANNA, Carlos M. R.
BARREIRO, Eliezer J.
LIMA, Lidia Moreira
dc.date.issued 2014
dc.identifier.citation PLOS ONE, v.9, n.3, article ID e85380, 16p, 2014
dc.identifier.issn 1932-6203
dc.identifier.uri http://observatorio.fm.usp.br/handle/OPI/7453
dc.description.abstract Cancer 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.sponsorship · CNPq
· FAPERJ
· INCT-INOFAR [573.564/2008-6, E-26/170.020/2008]
dc.language.iso eng
dc.publisher PUBLIC LIBRARY SCIENCE
dc.relation.ispartof Plos One
dc.rights openAccess
dc.subject.other hollow-fiber assay; in-vivo; binding-affinity; anticancer drugs; beta-tubulin; model; microtubules; dynamics; target; growth
dc.title Docking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues
dc.type article
dc.rights.holder Copyright PUBLIC LIBRARY SCIENCE
dc.description.group LIM/43
dc.description.group LIM/24
dc.identifier.doi 10.1371/journal.pone.0085380
dc.identifier.pmid 24614859
dc.type.category original article
dc.type.version publishedVersion
hcfmusp.author MACHADO, Camila Maria Longo:HC:LIM/43
hcfmusp.author CHAMMAS, Roger:FM:MDR
hcfmusp.author.external · AMARAL, 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
· CAVALCANTI, Bruno C.:Univ Fed Ceara, Fac Med, Dept Fisiol & Farmacol, Fortaleza, Ceara, Brazil
· BEZERRA, Daniel P.:Univ Fed Ceara, Fac Med, Dept Fisiol & Farmacol, Fortaleza, Ceara, Brazil
· FERREIRA, Paulo Michel P.:Univ Fed Piaui, Dept Ciencias Biol, Picos, Brazil
· CASTRO, Rosane de Paula:Univ Fed Goias, Inst Fis, Goiania, Go, Brazil
· SABINO, Jose Ricardo:Univ Fed Goias, Inst Fis, Goiania, Go, Brazil
· PESSOA, Claudia:Univ Fed Ceara, Fac Med, Dept Fisiol & Farmacol, Fortaleza, Ceara, Brazil
· SANT'ANNA, Carlos M. R.:Univ Fed Rural Rio de Janeiro, Dept Quim, Seropedica, Brazil
· BARREIRO, 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
· LIMA, 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.origem.id 2-s2.0-84897559253
hcfmusp.origem.id WOS:000332839300002
hcfmusp.publisher.city SAN FRANCISCO
hcfmusp.publisher.country USA
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dc.description.index MEDLINE
hcfmusp.citation.scopus 30
hcfmusp.citation.wos 22
hcfmusp.affiliation.country Brasil


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