New anthraquinone drugs and their anticancer activities: Cytotoxicity, DFT, docking and ADMET properties

Abstract

Amino-anthraquinone derivatives are the most important polycyclic compounds from an occupational health perspective. Among compounds with a cyclic structure, amino anthracene is given high attention because of its carcinogenic potential. The stringent precautions required to handle carcinogens apply to many drugs. Here we synthesize new anthraquinone derivatives with important yield. Characterized with NMR and mass spectroscopy analysis. Then, we evaluate their efficiency against prostate cancer in the PC-3 cell line. From the result, the dialkylated amino-anthraquinone derivatives B and the monoalkylated product with pyrazole exhibited high cytotoxicity potency (IC50 = 0.452 and 0.476 µM for B and D, respectively). From the theoretical study using Molecular Docking, we find the same order of efficiency obtained experimentally by cytotoxicity study. Then, the pharmacokinetic results show that the synthetic drugs used in this study respect the Lipinski, Ghose, Egan, and Veber roles. In addition to this, the density functional theory was used in conjunction with the Gaussian 16 simulation package at the B3LYP/6-311G** level of theory in order to locate the most chemically active compound among the amino-anthraquinone derivatives.