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

Rathgeb, Anna and Böhm, Andreas and Novak, Maria S. and Gavriluta, Anatolie and Dömötör, Orsolya and Enyedy, Éva Anna and Tommasino, Jean Bernard (2014) 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. INORGANIC CHEMISTRY, 53 (5). pp. 2718-2729. ISSN 0020-1669

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Abstract

The reactions of [Ru(NO)Cl5]2− with glycine (Gly), L- 16 alanine (L-Ala), L-valine (L-Val), L-proline (L-Pro), D-proline (D-Pro), 17 L-serine (L-Ser), L-threonine (L-Thr), and L-tyrosine (L-Tyr) in n- 18 butanol or n-propanol afforded eight novel complexes (1−8) of the 19 general formula [RuCl3(AA−H)(NO)]−, where AA = Gly, L-Ala, L- 20 Val, L-Pro, D-Pro, L-Ser, L-Thr, and L-Tyr, respectively. The 21 compounds were characterized by elemental analysis, electrospray 22 ionization mass spectrometry (ESI-MS), 1H NMR, UV−visible and 23 ATR IR spectroscopy, cyclic voltammetry, and X-ray crystallography. 24 X-ray crystallography studies have revealed that in all cases the same 25 isomer type (from three theoretically possible) was isolated, namely 26 mer(Cl),trans(NO,O)-[RuCl3(AA−H)(NO)], as was also recently 27 reported for osmium analogues with Gly, L-Pro, and D-Pro (see Z. Anorg. Allg. Chem. 2013, 639, 1590−1597). Compounds 1, 4, 28 5, and 8 were investigated by ESI-MS with regard to their stability in aqueous solution and reactivity toward sodium ascorbate. In 29 addition, cell culture experiments in three human cancer cell lines, namely, A549 (nonsmall cell lung carcinoma), CH1 (ovarian 30 carcinoma), and SW480 (colon carcinoma), were performed, and the results are discussed in conjunction with the lipophilicity of 31 compounds.

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