Synthesis, structure, electrochemistry, and cytotoxic properties of ferrocenyl ester derivatives.
Synthesis, structure, electrochemistry, and cytotoxic properties of ferrocenyl ester derivatives.
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DOI：
10.1155/2009/420784
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
Meléndez E
中科院分区：
文献类型：
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作者：
Gao LM;Hernández R;Matta J;Meléndez E
合成了一系列具有不同亲油性的二茂铁酯配合物，并用光谱和分析方法对其结构进行了表征。报道了Fe(C5H4CO2CH3)2、Fe(CpCOOCH3)(CpCOOCH2CH3)和Fe(CpCOOCH2CH3)2的合成。用X射线单晶衍射法测定了Fe(C5H4CO2CH3)2的固态结构。Fe(C5H4CO2CH3)2的环戊二烯基环实际上呈遮蔽构象，侧基并不完全相反。循环伏安表征表明，由于侧基对环戊二烯配体的电吸附作用，官能化的二茂铁在电位EPA处的氧化程度高于二茂铁。采用四甲基偶氮唑盐生物活性测定法测定了Fe(C5H4CO2CH2CH2)2、Fe(C5H4CO2CH2CH=CH2)2、Fe(C5H4CO2CH3)2、Fe(CpCOOCH3)(CpCOOCH2CH3)和Fe(CpCOOCH2CH3)2对结肠癌HT-29和乳腺癌MCF-7细胞株的细胞毒作用，并与二茂铁和二茂铁进行了比较。Fe(C5H4CO2CH2CH=CH2)2对HT-29细胞的IC50值最高，为180(10)μM，对MCF-7细胞的IC50值为190(30)μM，其细胞毒性与二茂铁相似。细胞毒性数据表明，随着官能化二茂铁亲脂性的增加，其细胞毒性提高，接近二茂铁的细胞毒性。
A series of ferrocenyl ester complexes, varying the lipophilic character of the pendant groups, was prepared and characterized by spectroscopic and analytical methods. The syntheses of Fe(C5H4CO2CH3)2, Fe(CpCOOCH3) (CpCOO CH2CH3), and Fe(CpCOOCH2CH3)2 are reported. The solid-state structure of Fe(C5H4CO2CH3)2 has been determined by X-ray crystallography. Fe(C5H4CO2CH3)2 has the cyclopentadienyl rings virtually in an eclipsed conformation with the pendant groups not completely opposite to each other. Cyclic voltammetry characterization showed that the functionalized ferrocenes oxidize at potentials, Epa, higher than ferrocene as a result of the electro withdrawing effect of the pendant groups on the cyclopentadienyl ligand. The cytotoxicities of Fe(C5H4CO2CH2CH2OH)2, Fe(C5H4CO2CH2CH=CH2)2, Fe(C5H4CO2CH3)2, Fe(CpCOOCH3)(CpCOOCH2CH3), and Fe(CpCOOCH2CH3)2 in colon cancer HT-29 and breast cancer MCF-7 cell lines were measured by the MTT biological viability assay and compared to ferrocene and ferrocenium. Fe(C5H4CO2CH2CH=CH2)2 showed the best IC50 values, 180(10) μM for HT-29 and 190(30) μM for MCF-7 cell lines, with cytotoxicities similar to ferrocenium. The cytotoxic data suggest that as we increase the lipophilic character of the functionalized ferrocene, the cytotoxicity improves approaching to the cytotoxic activity of ferrocenium.