Institute of Parasitology, Vetsuisse Faculty, University of Berne, Länggass-Strasse 122, CH-3012 Berne, Switzerland.
J Med Chem. 2012 May 10;55(9):4178-88. doi: 10.1021/jm300291a. Epub 2012 Apr 20.
Two series of η(6)-areneruthenium(II) phosphite complexes were prepared, characterized, and evaluated in vitro for their toxic potential against Echinococcus multilocularis metacestodes. Neutral complexes of general formula [(η(6)-p-cymene)RuCl(2){P(OR)(3)}] (R = Et, (i)Pr, Ph) with two easily exchangable chloride ligands showed only minor toxicity, whereas the substitution of these moieties against a β-diketonate (2,2,6,6-tetramethylheptanedionate) ligand led to hydrolytically stable complex salts of type [(η(6)-p-cymene)Ru(β-diketonate){P(OR)(3)}][BF(4)] (R = Et, (i)Pr, Ph) with comparable in vitro toxicity (50% PGI release at c = 1.4 - 4.7 μM) to the reference drug nitazoxanide (50% PGI release at c = 1.2 μM). In addition, the latter complexes were highly toxic against rat hepatoma cells (IC(50) = 0.40-2.0 μM) and less toxic against human foreskin fibroblasts (IC(50) = 1.1-2.9 μM) and Vero cells (IC(50) = 1.2-8.9 μM). The measured cytotoxicities against mammalian cells are, to the best of our knowledge, among the highest ever observed for ruthenium-based complexes. In conclusion, complex salts of type [(η(6)-p-cymene)Ru(β-diketonate){P(OR)(3)}][BF(4)] might be interesting candidates for further development toward anthelmintic drugs and/or highly cytotoxic metal compounds.
两种系列的η(6)-芳基钌(II)亚磷酸酯配合物被制备、表征,并在体外评估其对多房棘球蚴包虫的潜在毒性。具有两个易交换的氯离子配体的中性配合物,通式为[(η(6)-p-枯烯)RuCl2{P(OR)3}](R=Et,(i)Pr,Ph),显示出较小的毒性,而这些部分被β-二酮(2,2,6,6-四甲基庚二酮)配体取代后,导致水解稳定的配合盐,类型为[(η(6)-p-枯烯)Ru(β-二酮){P(OR)3}][BF4](R=Et,(i)Pr,Ph),与参考药物硝唑尼特具有相当的体外毒性(c=1.4-4.7 μM 时 50%PGI 释放)。此外,这些配合物对大鼠肝癌细胞具有高度毒性(IC50=0.40-2.0 μM),对人包皮成纤维细胞(IC50=1.1-2.9 μM)和 Vero 细胞(IC50=1.2-8.9 μM)的毒性较低。据我们所知,针对哺乳动物细胞的测量细胞毒性是迄今观察到的钌基配合物中最高的之一。总之,[(η(6)-p-枯烯)Ru(β-二酮){P(OR)3}][BF4]配合盐可能是进一步开发驱虫药和/或高细胞毒性金属化合物的有前途的候选物。