24588-83-8Relevant academic research and scientific papers
Synthesis, X-ray crystal structure, DNA/protein binding and cytotoxicity studies of five α-aminophosphonate N-derivatives
Wang, Qingming,Yang, Lei,Ding, Hui,Chen, Xuanrong,Wang, Hua,Tang, Xinhui
, p. 132 - 139 (2016/11/11)
Five new α-aminophosphonates are synthesized and characterized by EA, FT-IR, 1H NMR, 13C NMR, 31P NMR, ESI-MS and X-ray crystallography. The X-ray analyses reveal that the crystal structures of 1–5 are monoclinic or triclinic system with the space group P 21/c, P ? 1, P ? 1, P2(1)/c and P ? 1, respectively. All P atoms of 1–5 have tetrahedral geometries involving two O-ethyl groups, one Cα atom, and a double bond O atom. The binding interaction of five new α-aminophosphonate N-derivatives (1–5) with calf thymus(CT)-DNA have been investigated by UV–visible and fluorescence emission spectrometry. The apparent binding constant (Kapp) values follows the order: 1 (3.38 × 105 M?1) > 2 (3.04 × 105 M?1) > 4 (2.52 × 105 M?1) > 5 (2.32 × 105 M?1) > 3 (2.10 × 105 M?1), suggesting moderate intercalative binding mode between the compounds and DNA. In addition, fluorescence spectrometry of bovine serum albumin (BSA) with the compounds 1–5 showed that the quenching mechanism might be a static quenching procedure. For the compounds 1–5, the number of binding sites were about one for BSA and the binding constants follow the order: 1 (2.72 × 104 M?1) > 2 (2.27 × 104 M?1) > 4 (2.08 × 104 M?1) > 5 (1.79 × 104 M?1) > 3 (1.17 × 104 M?1). Moreover, the DNA cleavage abilities of 1 exhibit remarkable changes and the in vitro cytotoxicity of 1 on tumor cells lines (MCF-7, HepG2 and HT29) have been examined by MTT and shown antitumor effect on the tested cells.
