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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Heterometallic platinum(ii) compounds with β-aminoethylferrocenes: Synthesis, electrochemical behaviour and anticancer activity
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Heterometallic platinum(ii) compounds with β-aminoethylferrocenes: Synthesis, electrochemical behaviour and anticancer activity

机译:具有β-氨基乙基二茂铁的杂金属铂(ii)化合物:合成,电化学行为和抗癌活性

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摘要

A new family of heterometallic compounds 3-6 containing ferrocenyl and platinum(ii) centers has been synthesized by reaction of 1-β- aminoethylferrocene (1) and 1,1′-bis(β-aminoethyl)ferrocene (2) with Pt(ii) precursors. Using K _2[PtCl _4] as the Pt(ii) source, the cis-square-planar neutral compounds [Fe{η ~5-C _5H _4(CH _2) _2NH _2} _2PtCl _2] (3) and [{Fe(η ~5-C _5H _4(CH _2) _2NH _2)(η ~5-C _5H _5)} _2PtCl _2] (5) were obtained. Reaction of cis-[PtCl _2(dmso) _2] with 1 and 2 resulted in the displacement of dmso and chloride ligands from the platinum coordination sphere, affording the cationic and neutral compounds [Fe{η ~5- C _5H _4(CH _2) _2NH _2} _2Pt(dmso)Cl]Cl (4) and [Fe(η ~5-C _5H _4(CH _2) _2NH _2)(η ~5-C _5H _5)Pt(dmso)Cl _2] (6). Compounds 3-6 were thoroughly characterized using multinuclear (~1H, ~(13)C, ~(195)Pt) NMR, IR spectroscopy, ESI mass spectrometry and elemental analysis. Single-crystal X-ray analysis of heterometallic 6 confirmed the cis geometry of the molecule and revealed that the platinum atom is held in a perfect square-planar geometry. The electrochemical behaviour of the heterometallic compounds 3-6, which has been examined by cyclic (CV) and square wave (SWV) voltammetries in dichloromethane and dmso solution, is characterized by the reversible one-electron oxidation of the ferrocene moieties. The results of the biological activity studies revealed that the organometallic complex 5 is active against all cell lines with GI _(50) values in the range 1.7-2.3 μM. When compared to the standard anticancer drug cisplatin, heterotrimetallic 5, possessing two aminoethylferrocenyl units coordinated to the Pt(ii) center, showed a greater activity profile in the colon cancer cell line. Cell cycle studies revealed that the new mixed compound exhibits a mechanism of action different to cisplatin.
机译:通过1-β-氨基乙基二茂铁(1)和1,1'-双(β-氨基乙基)二茂铁(2)与Pt(1)反应合成了一个新的含二茂铁基和铂(ii)中心的杂金属化合物3-6族。 ii)前体。使用K _2 [PtCl _4]作为Pt(ii)源,顺式-方形平面中性化合物[Fe {η〜5-C _5H _4(CH _2)_2NH _2} _2PtCl _2](3)和[{Fe得到(η〜5-C _5H _4(CH _2)_2NH _2)(η〜5-C _5H _5)} _2PtCl _2](5)。顺式-[PtCl _2(dmso)_2]与1和2的反应导致dmso和氯化物配体从铂配位球中置换,得到阳离子和中性化合物[Fe {η〜5- C _5H _4(CH _2) )_2NH _2} _2Pt(dmso)Cl] Cl(4)和[Fe(η〜5-C _5H _4(CH _2)_2NH _2)(η〜5-C _5H _5)Pt(dmso)Cl _2](6 )。使用多核(〜1H,〜(13)C,〜(195)Pt)NMR,IR光谱,ESI质谱和元素分析对化合物3-6进行了全面表征。异金属6的单晶X射线分析证实了分子的顺式几何结构,并揭示了铂原子保持在理想的方形平面几何结构中。异金属化合物3-6的电化学行为已通过在二氯甲烷和dmso溶液中的循环(CV)和方波(SWV)伏安法进行了研究,其特征在于二茂铁部分可逆的单电子氧化。生物活性研究的结果表明,有机金属配合物5对GI_(50)值在1.7-2.3μM范围内的所有细胞系均具有活性。与标准抗癌药顺铂相比,具有两个与Pt(ii)中心配位的氨基乙基二茂铁基单元的异三金属5在结肠癌细胞系中显示出更大的活性。细胞周期研究表明,新的混合化合物表现出不同于顺铂的作用机理。

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