Abstract

New gold(I) phosphine thiolate complexes [(Ph₃P)Au(SLⁿ)] I–V with Schiff bases LⁿSH containing redox-active catechol, phenol, or quinone methide moieties were synthesized and characterized. The molecular structure of compound I in the crystalline state was established by X-ray diffraction (CCDC no. 2237815). The electrochemical behavior of compounds I–V was studieв by cyclic voltammetry. The proposed electrooxidation mechanism of the complexes involves the Au–S bond cleavage, the disulfide formation, as well as the oxidation of the redox active group of the ligand. In the cathode region, complexes I–III tend to form relatively stable monoanionic species. The radical scavenging activity of complexes decreases in comparison to free ligands in the reactions with synthetic radicals and the CUPRAC test. Compounds I, II, IV, and V have no clear-cut effect on the promoted DNA damage; however, they show antioxidant action in the non-enzymatic lipid peroxidation of rat liver homogenate. Compounds I–V demonstrate a weak antibacterial activity against Staphylococcus aureus strains. The gold(I) complexes cytotoxicity was studied against A-549, MCF-7, and HTC-116 cancer cell lines using MTT assay. The test compounds are characterized by higher selectivity to certain types of cells than the sulfur-containing Schiff bases. The presence of quinone methide moiety in the ligand in case of V significantly increases the cytotoxicity against all of the cell lines.

中文翻译：

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三苯基膦硫醇金 (I) 与氧化还原活性席夫碱的配合物：合成、电化学性质和生物活性

摘要

合成并表征了新的硫醇金 (I) 膦配合物 [(Ph ₃ P)Au(SL ⁿ )] I – V与席夫碱 L ^{n SH，其中含有氧化还原活性儿茶酚、苯酚或醌甲基化物部分。}通过X射线衍射(CCDC no.2237815)建立了结晶状态的化合物I的分子结构。通过循环伏安法研究了化合物I – V的电化学行为。所提出的配合物电氧化机制涉及Au-S键断裂、二硫键形成以及配体氧化还原活性基团的氧化。在阴极区域，配合物I –III倾向于形成相对稳定的单阴离子物质。在与合成自由基的反应和 CUPRAC 测试中，与游离配体相比，配合物的自由基清除活性降低。化合物I、II、IV和V对促进的DNA损伤没有明显的作用；然而，它们在大鼠肝匀浆的非酶促脂质过氧化中显示出抗氧化作用。化合物I - V对金黄色葡萄球菌菌株表现出弱抗菌活性。使用 MTT 测定研究金 (I) 复合物对 A-549、MCF-7 和 HTC-116 癌细胞系的细胞毒性。测试化合物的特点是对某些类型的细胞比含硫希夫碱具有更高的选择性。在V的情况下，配体中醌甲基化物部分的存在显着增加了针对所有细胞系的细胞毒性。