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A family of manganese complexes containing heterocyclic-based ligands with cytotoxic properties
Journal of Inorganic Biochemistry ( IF 3.8 ) Pub Date : 2018-02-10 , DOI: 10.1016/j.jinorgbio.2018.01.021
Jessica Castro , Ester Manrique , Marlon Bravo , Maria Vilanova , Antoni Benito , Xavier Fontrodona , Montserrat Rodríguez , Isabel Romero

We describe the synthesis of three new manganese (II) complexes containing the bidentate ligands 2-(1-methyl-3-pyrazolyl)pyridine (pypz-Me) and ethyl 2-(3-(pyridine-2-yl)-1H–pyrazol-1-yl)acetate (pypz-CH2COOEt), with formula [MnX2(pypz-Me)2] (X = Cl 1, CF3SO3 2) and [Mn(CF3SO3)2(pypz-CH2COOEt)2] 3. Complexes 13 have been characterized through analytical, spectroscopic and electrochemical techniques, as well as by monocrystal X-ray diffraction analysis. The complexes show a six-coordinated Mn(II) ion though different stereoisomers have been isolated for the three compounds. Complexes 13, together with the previously described compounds [MnCl2(pypz-H)2] 4, [Mn(CF3SO3)2(pypz-H)2] 5, [Mn(NO3)2(pypz-H)2] 6, [MnCl2(H2O)2(pypz-H)2] 7 (pypz-H = 2-(3-pyrazolyl)pyridine) and ([Mn(CF3SO3)2((−)-L)2] 8, ((−)-L = (−)-pinene[5,6]bipyridine), were tested in vitro for cytotoxic activity against NCI-H460 and OVCAR-8 cancer cell lines. The geometry of a specific compound does not seem to influence its activity in a significant extent. However, among the tested compounds those that display hydrophobic substituents on the pyrazole ring and triflate ions as labile ligands show the best antiproliferative properties. Specifically, compound 8 containing the pinene-bipyridine ligand presents an antiproliferative activity similar to that of cisplatin and higher than that of carboplatin, and displays selectivity for tumour cells. Its antiproliferative effect is due to the generation of ROS species that allow the compound to interact with DNA.



中文翻译:

含杂环配体的锰配合物,具有细胞毒性

我们描述了三种新的锰(II)配合物的合成,这些配合物包含双齿配体2-(1-甲基-3-吡唑基)吡啶(pypz-Me)和乙基2-(3-(吡啶-2-基)-1H–吡唑-1-基)乙酸乙酯(pypz-CH 2 COOEt烷基),具有式[MNX 2(pypz-ME)2 ](X =氯- 1,CF 3 SO 3 - 2)和[锰(CF 3 SO 32(pypz-CH 2 COOEt )2 ] 3。配合1 - 3通过分析,光谱学和电化学技术以及单晶X射线衍射分析来表征。尽管已为三种化合物分离出不同的立体异构体,但该络合物显示出六配位的Mn(II)离子。配合物1 - 3,与之前描述的化合物一起[的MnCl 2(pypz-H)2 ] 4,[锰(CF 3 SO 32(pypz-H)2 ] 5,[锰(NO 32(pypz -H)2 ] 6,[MnCl 2(H 2 O)2(pypz-H)2 ] 7(pypz-H = 2-(3-吡唑基)吡啶)和([Mn(CF 3 SO 32((-)-L)2 ] 8,((-)-L =(-)-pinene [5,6] bipyridine)在体外测试对NCI-H460和OVCAR-8癌细胞系的细胞毒活性,特定化合物的几何形状似乎在很大程度上不会影响其活性然而,在所测试的化合物中,那些在吡唑环和三氟甲磺酸酯离子上表现出疏水取代基的化合物作为不稳定的配体表现出最佳的抗增殖性能,具体而言,化合物8含有pin烯-联吡啶配体的化合物具有与顺铂相似的抗增殖活性,并且比卡铂具有更高的抗增殖活性,并显示出对肿瘤细胞的选择性。它的抗增殖作用是由于产生了使化合物与DNA相互作用的ROS物种。

更新日期:2018-02-10
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