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本文引用的文献

1
The Conformations of 17β-Estradiol (E2) and 17α-Estradiol as Determined by Solution NMR.通过溶液核磁共振确定的17β-雌二醇（E2）和17α-雌二醇的构象
Tetrahedron Lett. 2010 Jul 7;51(27):3465-3469. doi: 10.1016/j.tetlet.2010.04.077.
2
AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading.AutoDock Vina：通过新的评分函数、高效优化和多线程改进对接的速度和准确性。
J Comput Chem. 2010 Jan 30;31(2):455-61. doi: 10.1002/jcc.21334.
3
Synthesis, structure, electrochemistry, and cytotoxic properties of ferrocenyl ester derivatives.二茂铁基酯衍生物的合成、结构、电化学及细胞毒性性质
Met Based Drugs. 2009;2009:420784. doi: 10.1155/2009/420784. Epub 2009 Mar 24.
4
Recent applications of chiral ferrocene ligands in asymmetric catalysis.手性二茂铁配体在不对称催化中的最新应用。
Angew Chem Int Ed Engl. 2006 Nov 27;45(46):7674-715. doi: 10.1002/anie.200602482.
5
Metal complex SERMs (selective oestrogen receptor modulators). The influence of different metal units on breast cancer cell antiproliferative effects.金属络合物选择性雌激素受体调节剂（SERMs）。不同金属单元对乳腺癌细胞抗增殖作用的影响。
Dalton Trans. 2006 Jan 28(4):529-41. doi: 10.1039/b509984f. Epub 2005 Sep 27.
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Vitamin D and prevention of colorectal cancer.维生素D与结直肠癌的预防
J Steroid Biochem Mol Biol. 2005 Oct;97(1-2):179-94. doi: 10.1016/j.jsbmb.2005.06.018. Epub 2005 Oct 19.
7
Modification of the estrogenic properties of diphenols by the incorporation of ferrocene. Generation of antiproliferative effects in vitro.通过引入二茂铁对双酚雌激素特性的修饰。体外产生抗增殖作用。
J Med Chem. 2005 Jun 16;48(12):3937-40. doi: 10.1021/jm050251o.
8
Bioorganometallic chemistry of ferrocene.二茂铁的生物有机金属化学
Chem Rev. 2004 Dec;104(12):5931-85. doi: 10.1021/cr0101510.
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The first organometallic selective estrogen receptor modulators (SERMs) and their relevance to breast cancer.
Curr Med Chem. 2004 Sep;11(18):2505-17. doi: 10.2174/0929867043364487.
10
The syntheses and catalytic applications of unsymmetrical ferrocene ligands.不对称二茂铁配体的合成及其催化应用
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具有雌激素和维生素 D2 的向量化二茂铁：合成、细胞毒性活性和对接研究。

Vectorized ferrocenes with estrogens and vitamin D2: synthesis, cytotoxic activity and docking studies.

机构信息

University of Puerto Rico, Department of Chemistry, PO Box 9019, Mayaguez, PR 00681.

出版信息

Dalton Trans. 2011 Oct 7;40(37):9557-65. doi: 10.1039/c1dt10995b. Epub 2011 Aug 18.

DOI:10.1039/c1dt10995b
PMID:21850331
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4461443/
Abstract

Three ferrocene complexes vectorized with estrogens and vitamin D(2) were synthesized and fully characterized by spectroscopic, electrochemical and computational methods. The synthesis of these esters was accomplished by reacting ferrocenoyl chloride with the corresponding ROH groups (R = ergocalciferol, estradiol, estrone). The cytotoxicity of these complexes in HT-29 colon cancer and MCF-7 breast cancer cell lines was investigated in vitro. Only ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate showed good cytotoxic activity in both cell lines, exceeding those of ferrocenium and ferrocene. In MCF-7, ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate exhibited remarkable IC(50), in the low micromolar range. This may be attributed to the presence of the estradiol vector. Docking studies between alpha-estrogen receptor ligand binding site and ferrocenoyl 17β-hydroxy-estra-1,3,5(10)-trien-3-olate revealed some key hydrophobic interactions that might explain the cytotoxic activity of this ester.

摘要

三种雌激素和维生素 D（2）标记的二茂铁配合物已被合成，并通过光谱、电化学和计算方法进行了全面表征。这些酯的合成是通过使二茂铁酰氯与相应的 ROH 基团（R = 麦角钙化醇、雌二醇、雌酮）反应来完成的。这些配合物在 HT-29 结肠癌细胞系和 MCF-7 乳腺癌细胞系中的细胞毒性在体外进行了研究。只有二茂铁酰基 17β-羟基-雌-1,3,5(10)-三烯-3-醇酯在两种细胞系中均显示出良好的细胞毒性活性，超过了 ferrocenium 和 ferrocene。在 MCF-7 中，二茂铁酰基 17β-羟基-雌-1,3,5(10)-三烯-3-醇酯的 IC（50）值在低微摩尔范围内显著降低。这可能归因于雌二醇载体的存在。与α-雌激素受体配体结合位点之间的对接研究表明，ferrocenoyl 17β-羟基-雌-1,3,5(10)-三烯-3-醇酯存在一些关键的疏水相互作用，这可能解释了这种酯的细胞毒性活性。