Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol

Autor(es)

da Silva, Flavia T. ^[1] ; Gomes, Kaio S. ^[2] ; Machado, Fabricio C. ^[3] ; Loureiro, Leticia L. ^[3] ; Travassos, Luiz R. ^[3] ; Martins, Tereza S. ^[1] ; Lago, Joao Henrique G. ^[2] ; Camilo, Fernanda F. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Paulo, Dept Quim, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP - Brazil

^[2] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210580 Santo Andre, SP - Brazil

^[3] Univ Fed Sao Paulo, Dept Microbiol Imunol & Parasitol, Unidade Oncol Expt, BR-04021001 Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Brazilian Chemical Society; v. 32, n. 5, p. 1002-1008, MAY 2021.
• Citações Web of Science: 0

Resumo

Electrochemical procedures have emerged as a powerful tool for the synthesis of complex organic molecules including transformation of natural products. In this study, the electrosynthesis of biseugenol in MeOH afforded one new oxidized derivative, which was characterized as methoxyl-oxo-biseugenol (MOB) by nuclear magnetic resonance (NMR) and electrospray ionization-high resolution mass spectrometry (ESI-HRMS) analysis. Since biseugenol was previously described as a cytotoxic natural product, MOB was also tested against tumoral cells B16F10-Nex2 (murine metastatic melanoma) and SKMEL-25 (human metastatic melanoma) as well as against non-tumoral cells MØ Raw 264.7 (murine macrophage immortalized) and HUVEC (human umbilical endothelium). As results, MOB showed inhibitory concentration that affects 50% of cells (IC50) values of 9.5 ± 1.6 mg mL-1(B16F10Nex2), 13.2 ± 2.5 mg mL-1 (SKMEL-25), 19.9 ± 3.5 mg mL-1 (MØ Raw 264.7) and 36.3 ± 7.4 mg mL-1 (HUVEC). Therefore, selectivity index (SI) values of MOB to tumoral cells B16F10Nex2 and SKMEL-25 were calculated as 2.1 and 2.8, respectively, higher than biseugenol (1.4 and 1.7, respectively). Based on these results, the superior cytotoxic activity of MOB in comparison to biseugenol could be associated, at least in part, to the presence of a non-aromatic ring and a conjugated carbonyl system instead of a phenol moiety. (AU)

• Processo FAPESP: 18/20826-4 - Preparação e avaliação de propriedades de nanopartículas suportadas em filmes de celulose não modificada
• Beneficiário: Fernanda Ferraz Camilo
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 18/07885-1 - Biomoléculas oriundas de espécies vegetais de áreas remanescentes da Mata Atlântica e do Cerrado para tratamento de doenças tropicais negligenciadas - aspectos químicos e farmacológicos
• Beneficiário: João Henrique Ghilardi Lago
• Modalidade de apoio: Auxílio à Pesquisa - Programa BIOTA - Regular