Ruthenium-Nitrosyl Complexes with Glycine, L-Alanine, L-Valine, L-Proline, D-Proline, L-Serine, L-Threonine and L-Tyrosine: Synthesis, X-ray Diffraction Structures, Spectroscopic and Electrochemical Properties and Antiproliferative Activity

摘要

The reactions of [Ru(NO)Cl5]2− with glycine (Gly), L-\ud16 alanine (L-Ala), L-valine (L-Val), L-proline (L-Pro), D-proline (D-Pro),\ud17 L-serine (L-Ser), L-threonine (L-Thr), and L-tyrosine (L-Tyr) in n-\ud18 butanol or n-propanol afforded eight novel complexes (1−8) of the\ud19 general formula [RuCl3(AA−H)(NO)]−, where AA = Gly, L-Ala, L-\ud20 Val, L-Pro, D-Pro, L-Ser, L-Thr, and L-Tyr, respectively. The\ud21 compounds were characterized by elemental analysis, electrospray\ud22 ionization mass spectrometry (ESI-MS), 1H NMR, UV−visible and\ud23 ATR IR spectroscopy, cyclic voltammetry, and X-ray crystallography.\ud24 X-ray crystallography studies have revealed that in all cases the same\ud25 isomer type (from three theoretically possible) was isolated, namely\ud26 mer(Cl),trans(NO,O)-[RuCl3(AA−H)(NO)], as was also recently\ud27 reported for osmium analogues with Gly, L-Pro, and D-Pro (see Z. Anorg. Allg. Chem. 2013, 639, 1590−1597). Compounds 1, 4,\ud28 5, and 8 were investigated by ESI-MS with regard to their stability in aqueous solution and reactivity toward sodium ascorbate. In\ud29 addition, cell culture experiments in three human cancer cell lines, namely, A549 (nonsmall cell lung carcinoma), CH1 (ovarian\ud30 carcinoma), and SW480 (colon carcinoma), were performed, and the results are discussed in conjunction with the lipophilicity of\ud31 compounds.