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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Synthesis of methoxylated goniothalamin, aza-goniothalamin and gamma-pyrones and their in vitro evaluation against human cancer cells

Texto completo
Autor(es):
Barcelos, Rosimeire Coura [1] ; Pastre, Julio Cezar [1] ; Caixeta, Vanessa [1] ; Vendramini-Costa, Debora Barbosa [2, 3] ; de Carvalho, Joao Ernesto [2, 3] ; Pilli, Ronaldo Aloise [1, 2]
Número total de Autores: 6
Afiliação do(s) autor(es):
[1] Univ Estadual Campinas, Inst Quim, Dept Quim Organ, BR-13083970 Campinas, SP - Brazil
[2] Univ Estadual Campinas, Inst Biol, Programa Posgrad Biol Celular & Estrutural, BR-13083970 Campinas, SP - Brazil
[3] Univ Estadual Campinas, Div Farmacol & Toxicol, Ctr Pluridisciplinar Pesquisas Quim Biol & Agr CP, BR-13083970 Campinas, SP - Brazil
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: Bioorganic & Medicinal Chemistry; v. 20, n. 11, p. 3635-3651, JUN 1 2012.
Citações Web of Science: 26
Resumo

The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved. (AU)

Processo FAPESP: 09/51602-5 - Biologia química: novos alvos moleculares naturais e sintéticos contra o câncer, estudos estruturais, avaliação biológica e modo de ação
Beneficiário:Ronaldo Aloise Pilli
Linha de fomento: Auxílio à Pesquisa - Temático
Processo FAPESP: 10/16990-1 - Síntese e avaliação da atividade citotóxica de gama-diidropironas: análogos de goniotalamina e de abyssinona II
Beneficiário:Júlio Cezar Pastre
Linha de fomento: Bolsas no Brasil - Pós-Doutorado