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Pentafluorophenyl substitution of natural di(indol-3-yl)methane strongly enhances growth inhibition and apoptosis induction in various cancer cell lines.
Chemistry & Biodiversity 2019 Februrary 5
Di(indol-3-yl)methane (DIM, 1) is a known weakly antitumoral compound formed by digestion of indole-3-carbinol, an ingredient of various Brassica vegetables. Out of a series of nine fluoroaryl derivatives of 1, three pentafluorophenyl derivatives 2c, 2h and 2i were identified that exhibited a two to five times greater anti-proliferative effect and an increased apoptosis induction when compared with 1 in the following carcinoma cell lines: BxPC-3 pancreas, LNCaP prostate, C4-2B prostate, PC3 prostate and the triple-negative MDA-MB-231 breast carcinoma. Compound 2h was particularly efficacious against androgen-refractory C4-2B prostate cancer cells (IC50 = 6.4 µM) and 2i against androgen-responsive LNCaP cells (IC50 = 6.2 µM). In addition, 2c and 2h exhibited distinct activity in three cancer cell lines resistant to 1.
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