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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
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]
Total Authors: 8
Affiliation:
[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
Total Affiliations: 2
Document type: Journal article
Source: BIOORGANIC CHEMISTRY; v. 83, p. 205-213, MAR 2019.
Web of Science Citations: 0
Abstract

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)