| Summary: | A series of latonduine derivatives, namely 11-nitro-indolo[2,3-<i>d</i>]benzazepine-7-(1-amino-hydantoin) (<b>B</b>), triazole-fused indolo[2,3-<i>d</i>]benzazepine-based Schiff bases <b>HL<sup>1</sup></b> and <b>HL<sup>2</sup></b> and metal complexes [M(<i>p</i>-cymene)(HL<sup>1</sup>)Cl]Cl, where M = Ru (<b>1</b>), Os (<b>2</b>), and [Cu(HL<sup>2</sup>)Cl<sub>2</sub>] (<b>3</b>) were synthesized and characterized by spectroscopic techniques (UV–vis, <sup>1</sup>H, <sup>13</sup>C, <sup>15</sup>N–<sup>1</sup>H HSQC NMR) and ESI mass spectrometry. The molecular structures of <b>B</b> and <b>HL<sup>1</sup></b> were confirmed by single-crystal X-ray diffraction, while that of <b>3</b> by electron diffraction of nanometer size crystalline sample. Molecular docking calculations of species <b>B</b> in the binding pocket of PIM-1 enzyme revealed that the 1-amino-hydantoin moiety is not involved in any hydrogen-bonding interactions, even though a good accommodation of the host molecule in the ATP binding pocket of the enzyme was found. The antiproliferative activity of organic compounds <b>B</b>, <b>HL<sup>1</sup></b> and <b>HL<sup>2</sup></b>, as well as complexes <b>1</b>–<b>3</b> was investigated in lung adenocarcinoma A549, colon adenocarcinoma LS-174 and triple-negative breast adenocarcinoma MDA-MB-231 cells and normal human lung fibroblast cells MRC-5 by MTT assays; then, the results are discussed.
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