New Chalcone Ester Derivatives as Potential Cytotoxic Agents.

Autor: da Silva RB; Department of Chemistry, Universidade Federal do Espírito Santo (UFES), Avenida Fernando Ferrari 514, 29075-910, Vitória - ES, Brazil., Borlot JRPO; Graduate Program on Chemistry, Universidade Federal do Espírito Santo (UFES), Avenida Fernando Ferrari 514, 29075-910, Vitória - ES, Brazil., Rosa Santos C; Graduate Program on Chemistry, Universidade Federal do Espírito Santo (UFES), Avenida Fernando Ferrari 514, 29075-910, Vitória - ES, Brazil., Rodrigues E Oliveira L; Department of Chemistry and Environmental Sciences, Institute of Biosciences, Humanities and Exact Sciences, Universidade Estadual Paulista (UNESP), 15054-000, São José do Rio Preto - SP, Brazil., de Almeida LC; Department of Pharmacology, Institute of Biomedical Sciences, Universidade de São Paulo (USP), 05508-900, São Paulo - SP, Brazil., Veras Costa-Lotufo L; Department of Pharmacology, Institute of Biomedical Sciences, Universidade de São Paulo (USP), 05508-900, São Paulo - SP, Brazil., Octávio Regasini L; Department of Chemistry and Environmental Sciences, Institute of Biosciences, Humanities and Exact Sciences, Universidade Estadual Paulista (UNESP), 15054-000, São José do Rio Preto - SP, Brazil., Rezende Kitagawa R; Graduate Program on Chemistry, Universidade Federal do Espírito Santo (UFES), Avenida Fernando Ferrari 514, 29075-910, Vitória - ES, Brazil., de Medeiros EF; Department of Chemistry, Universidade Federal do Espírito Santo (UFES), Avenida Fernando Ferrari 514, 29075-910, Vitória - ES, Brazil., de Souza Borges W; Graduate Program on Chemistry, Universidade Federal do Espírito Santo (UFES), Avenida Fernando Ferrari 514, 29075-910, Vitória - ES, Brazil.
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2024 Nov; Vol. 21 (11), pp. e202400799. Date of Electronic Publication: 2024 Oct 03.
DOI: 10.1002/cbdv.202400799
Abstrakt: Chalcones are a group of molecules with recognized biological potential against many diseases, including cancer. Thus, studies on this structure and derivatives have become an attractive chemical strategy to optimize their observed biological activities. One of the synthetic routes used to obtain chalcone derivatives is esterification using either commercial acid chlorides or carboxylic acids. This work focuses on preparing chalcone derivatives and investigating their biological potential against cancer cells. Compound 3'-hydroxychalcone (1) was synthetized by Claisen-Schmidt condensation followed by esterification of the 3'-OH, resulting in eight compounds named 1a-b and 2a-f. All structures were confirmed by 1 H and 13 C NMR and FT-IR, and cytotoxicity was evaluated in the HCT 116 (colon adenocarcinoma), MCF-7 (breast adenocarcinoma), and CCD-18Co (nontumoral colon fibroblasts) cell lines. Chalcone derivatives were generally more active toward the colon cancer cell line, and 1a and 2b were selected for IC 50 determination, presenting IC 50 values of approximately 10 μM in HCT 116 cells and above 20 μM in both MCF7 and CDC-18-Co cells, suggesting moderate selectivity. Additionally, we tested compounds 1a and 2b in combination with doxorubicin, but they did not act synergistically with this anthracycline. In conclusion, considering these compounds obtained by the esterification reaction, 1a and 2d showed better results against cytotoxic cells.
(© 2024 Wiley-VHCA AG, Zurich, Switzerland.)
Databáze: MEDLINE
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