Understanding the cytotoxic effects of new isovanillin derivatives through phospholipid Langmuir monolayers

Autor(es)

de Carvalho, Ana C. ^[1] ; Girola, Natalia ^[2] ; de Figueiredo, Carlos R. ^[2] ; Machado, Andre C. ^[1] ; de Medeiros, Livia S. ^[1] ; Guadagnin, Rafael C. ^[1] ; Caseli, Luciano ^[1] ; Veiga, Thiago A. M. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Paulo, Dept Chem, Diadema, SP - Brazil

^[2] Univ Fed Sao Paulo, Dept Microbiol Immunol & Parasitol, Expt Oncol Unit UNONEX, Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: BIOORGANIC CHEMISTRY; v. 83, p. 205-213, MAR 2019.
• Citações Web of Science: 0

Resumo

Twenty-one isovanillin derivatives were prepared in order to evaluate their cytotoxic properties against the cancer cell lines B16F10-Nex2, HL-60, MCF-7, A2058 and HeLa. Among them, seven derivatives exhibited cytotoxic activity. We observed that for obtaining smaller IC50, values and for increasing the index of selectivity, two structural features are very important when compared with isovanillin (1); a hydroxymethyl group at C-1 and the replacement of the hydroxyl group at C-3 by different alkyl groups. As the lipophilicity of the compounds was changed, we decided to investigate the interaction of the cytotoxic isovallinin derivatives on cell membrane models through Langmuir monolayers by employing the lipids DPPC (1,2-diplamitoyl-sn-glycero-3-phosphocoline) and DPPS (1,2-diplamitoyl-sn-glycero-3-phosphoserine). The structural changes on the scaffold of the compounds modulated the interaction with the phospholipids at the air-water interface. These results were very important to understand the biophysical aspects related to the interaction of the cytotoxic compounds with the cancer cell membranes. (AU)

• Processo FAPESP: 10/51313-0 - Obtenção de substâncias fitotóxicas de espécies vegetais presentes em solos minerais da Mina do Sossego - PA com ação fitoremediadoras e controle ambiental
• Beneficiário: Thiago André Moura Veiga
• Modalidade de apoio: Auxílio à Pesquisa - Parceria para Inovação Tecnológica - PITE