2-Acetyl-5,8-dihydro-6-(4-methyl-3-pentenyl)-1,4- naphthohydroquinone-Derived Chalcones as Potential Anticancer Agents

Maldonado, Javier; Oliva, Alfonso; Molinari, Aurora; Acevedo, Waldo

Keywords: antiproliferative activity, molecular docking, chalcone-1,4-naphthoquinone/benzohydroquinone


Based on previous results with benzoindazolequinone (BIZQ) and 3-methylnaphtho [2,3- d]isoxazole-4,9-quinone (NIQ) derivatives, a novel series of chalcone-1,4-naphthoquinone/benzohy- droquinone (CNQ and CBHQ) compounds were synthesized from 2-acetyl-5,8-dihydro-6-(4-methyl- 3-pentenyl)-1,4-naphthohydroquinone. Their structures were elucidated via spectroscopy. These hybrids were assessed in vivo for their antiproliferative activity on MCF-7 breast adenocarcinoma and HT-29 colorectal carcinoma cells, revealing cytotoxicity with IC50 values between 6.0 and 110.5 µM. CBHQ hybrids 5e and 5f displayed enhanced cytotoxicity against both cell lines, whereas CNQ hybrids 6a–c and 6e exhibited higher cytotoxic activity against MCF-7 cells. Docking studies showed strong binding energies (∆Gbin) of CNQs to kinase proteins involved in carcinogenic pathways. Furthermore, our in silico analysis of drug absorption, distribution, metabolism, and excretion (ADME) properties suggests their potential as candidates for cancer pre-clinical assays.

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Título de la Revista: MOLECULES
Volumen: 28
Número: 7172
Editorial: MDPI
Fecha de publicación: 2023
Página de inicio: 1
Página final: 28
URL: https://doi.org/10.3390/molecules28207172