Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, Serbia.
Innovative Centre Faculty of Chemistry Belgrade, University of Belgrade, Studentski trg 12-16, Serbia.
J Inorg Biochem. 2020 Sep;210:111164. doi: 10.1016/j.jinorgbio.2020.111164. Epub 2020 Jun 26.
Three new ruthenium(II)-arene complexes, [Ru(η-p-cymene)(L)Cl] (C1) where L is N-((4 methoxyphenyl)carbamothioyl)benzamide; [Ru(η-p-cymene)(L)Cl] (C2) where L is 4-(3-benzoylthioureido)benzoic acid and [Ru(η-p-cymene)(L)Cl] (C3) where L is methyl 4-(3- benzoylthioureido)benzoate have been synthetized, characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performed using H and C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Ray diffraction analysis. X-Ray diffraction analysis of C1 showed typical expected "piano-stool" geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, in herein described complex, upon coordination the four-membered ring was formed, instead of six-membered chelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma (HeLa) cell line and IC values ranged from 29.68 to 52.36 μM and the complexes were more active than related ligands (except in case of C2 where it is found that IC value is close to IC value of related ligand). Complex [Ru(η-p-cymene)(L)Cl] (C1) expressed the highest cytotoxic activity with IC value of 29.7 μM. Complexes and ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans. Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well. Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans to over 1000 μg/ml for several bacterial species.
三种新型钌(II)-芳烃配合物,[Ru(η-p-cymene)(L)Cl](C1),其中 L 为 N-((4-甲氧基苯基)氨甲酰基)苯甲酰胺;[Ru(η-p-cymene)(L)Cl](C2),其中 L 为 4-(3-苯甲酰基硫脲基)苯甲酸和[Ru(η-p-cymene)(L)Cl](C3),其中 L 为 4-(3-苯甲酰基硫脲基)苯甲酸甲酯已被合成、表征,并评估了它们的抗菌和抗癌活性。采用 H 和 C NMR、IR 光谱、质谱、电导率测量和 X 射线衍射分析对其进行了表征。C1 的 X 射线衍射分析表明,具有典型的预期“钢琴凳”几何形状,其中配体通过苯甲酰基硫脲衍生物的氮和硫原子与钌配位。有趣的是,在所描述的配合物中,在配位时形成了四元环,而不是常见的六元螯合配体。在人宫颈腺癌(HeLa)细胞系中测定细胞毒性活性,IC 值范围为 29.68 至 52.36 μM,且这些配合物比相关配体更具活性(除了 C2 外,其 IC 值接近相关配体的 IC 值)。配合物[Ru(η-p-cymene)(L)Cl](C1)具有最高的细胞毒性活性,IC 值为 29.7 μM。这些配合物和配体被测试了对九种革兰氏阳性和革兰氏阴性细菌以及一种酵母-白色念珠菌的活性。临床念珠菌株也包括在测试过程中。复合物对白色念珠菌的最小抑菌浓度值为 62.5 μg/ml,而对几种细菌的最小抑菌浓度值则超过 1000 μg/ml。