Zinc, copper and nickel derivatives of 2-[2-bromoethyliminomethyl]phenol as topoisomerase inhibitors exhibiting anti-proliferative and anti-metastatic properties

Lee Sze Koon; Tan Kong Wai; Ng Seik Weng

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Zinc, copper and nickel derivatives of 2-[2-bromoethyliminomethyl]phenol as topoisomerase inhibitors exhibiting anti-proliferative and anti-metastatic properties

机译：2- [2-溴乙基亚氨基甲基]苯酚的锌，铜和镍衍生物作为拓扑异构酶抑制剂，具有抗增殖和抗转移的特性

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Three transition metal derivatives of (2-[2-bromoethyliminomethyl] phenol), M[OC6H4CH=NCH2CH2Br](2) (M is zinc, copper and nickel) along with Ni[OC6H4CH=NCH2CH2](2)(H2O)(4)center dot 2Br, were found to inhibit topoisomerase I (topo I) activity, induce DNA cleavage and bind to calf thymus DNA. The compounds were found to be cytotoxic when tested against cancer cell lines (A2780, MCF-7, HT29, HepG2, A549, PC3, LNCaP), and were anti-invasive against PC3. The inhibitory strength of the metal complexes was higher than that of the organic compound. The neutral metal complexes were synthesized by the reaction of the metal acetates with the Schiff base ligand whereas the bromide salt was obtained upon recrystallization of the nickel derivative from water. In the crystal structure of this salt, the cyclized Schiff base ligand binds to the nickel atom through its nitrogen donor, the metal atom showing an all-trans octahedral geometry. The metal atom in Cu[OC6H4CH=NCH2CH2Br](2) exists in a square-planar environment.

机译：（2- [2-溴乙基亚氨基甲基]苯酚的三种过渡金属衍生物，M [OC6H4CH = NCH2CH2Br]（2）（M为锌，铜和镍）以及Ni [OC6H4CH = NCH2CH2]（2）（H2O）（4中心点2Br被发现抑制拓扑异构酶I（拓扑I）的活性，诱导DNA裂解并与小牛胸腺DNA结合。测试该化合物对癌细胞系（A2780，MCF-7，HT29，HepG2，A549，PC3，LNCaP）具有细胞毒性，并且对PC3具有抗侵袭性。金属配合物的抑制强度高于有机化合物的抑制强度。中性金属配合物是通过金属乙酸盐与席夫碱配体的反应合成的，而溴化物盐是在镍衍生物从水中重结晶后获得的。在这种盐的晶体结构中，环化的席夫碱配体通过其氮供体与镍原子键合，金属原子呈现全反八面体几何形状。 Cu [OC6H4CH = NCH2CH2Br]（2）中的金属原子存在于正方形平面环境中。

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《RSC Advances》 |2014年第104期|共13页
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Lee Sze Koon; Tan Kong Wai; Ng Seik Weng;
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1. Zinc, copper and nickel derivatives of 2-[2-bromoethyliminomethyl]phenol as topoisomerase inhibitors exhibiting anti-proliferative and anti-metastatic properties [J] . Lee Sze Koon, Tan Kong Wai, Ng Seik Weng RSC Advances . 2014,第104期

机译：2- [2-溴乙基亚氨基甲基]苯酚的锌，铜和镍衍生物作为拓扑异构酶抑制剂，具有抗增殖和抗转移的特性
2. Ligating properties of tridentate Schiff base ligands, 2-[[(2-pyridinylmethyl)imino]methyl] phenol (HSALIMP) and 2-[[[2-(2-pyridinyl)ethyl]imino]methyl]phenol (HSALIEP) with zinc(II), cadmium(II), nickel(II) and manganese(III) ions. X-ray crystal str [J] . Tandon SS., Thompson LK., Chander S. Inorganica Chimica Acta . 2000,第0期

机译：三齿席夫碱配体，2-[[[（2-吡啶基甲基）亚氨基]甲基]苯酚（HSALIMP）和2-[[[[2-（2-吡啶基乙基）亚氨基]甲基]苯酚（HSALIEP）与锌的连接特性（II），镉（II），镍（II）和锰（III）离子。 X射线晶体
3. Synthesis and characterization of manganese (II),cobalt(II),nickel(II),copper(II) and zinc(II) complexes with 2-[2'-hydroxy salicylidene 5'-(4"-phenyl,2"-thiazolylazo)]benzoic acid and 2-[2'-hydroxy salicylidene 5'-(4"-phenyl,2"-thiazolylazo)]phenol [J] . P P Hankare, S S Chavan Indian Journal of Chemistry, Section A. Inorganic, Physical, Theoretical & Analytical . 2003,第3期

机译：锰（II），钴（II），镍（II），铜（II）和锌（II）与2- [2'-羟基水杨叉5'-（4“-苯基，2”-噻唑基）和苯甲酸2- [2'-羟基水杨基5'-（4“-苯基，2”-噻唑基）
4. Synthesis and spectroscopic properties of 2-(7-Fluoro-1H-imidazo4,5-bphenazin-2-yl)-phenol Derivatives [C] . Lei Yingjie, Ouyang Jie, Ding Mei International Conference on Advanced Engineering Materials and Technology . 2011

机译：2-（7-氟-1H-咪唑4,5-B苯中素-2-基）-phenol衍生物的合成和光谱性质
5. I. Complexation of iron(II), cobalt(II), nickel(II) and copper(II) by hexadentate tripodal aminopyridyl chelators II. Binding preferences for zinc(II) relative to nickel(II) and copper(II) in novel tetradentate aminopyridyl chelators [D] . Childers, Matthew Lloyd 2007

机译：一，铁（Ⅱ），钴（Ⅱ），镍（Ⅱ）和铜（Ⅱ）与六齿三脚架氨基吡啶基螯合剂的络合作用。新型四齿氨基吡啶基螯合剂中锌（II）相对于镍（II）和铜（II）的结合偏好
6. Nickel(II) Copper(II) and Zinc(II) Complexes of 9-2- (Phosphonomethoxy)ethyl-8-azaadenine (98aPMEA)the 8-Aza Derivative of the Antiviral Nucleotide Analogue 9-2-(Phosphonomethoxy)ethyl adenine (PMEA). Quantification of Four Isomeric Species in Aqueous Solution [O] . Raquel B. Gómez-Coca, Antonín Holý, Rosario A. Vilaplana, 2004

机译：9- 2-（Phosphoomethoxymethoxy）ethyl -8-azaadenine（98aPMEA）的镍（II）铜（II）和锌（II）配合物抗病毒核苷酸类似物9- 2-（膦甲氧基）乙基腺嘌呤（PMEA）的8-氮杂衍生物。水溶液中四种异构体的定量
7. Nickel(II), Copper(II) and Zinc(II) Complexes of 9-[2- (Phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA), the 8-Aza Derivative of the Antiviral Nucleotide Analogue 9-[2-(Phosphonomethoxy)ethyl] adenine (PMEA). Quantification of Four Isomeric Species in Aqueous Solution [O] . Gómez-Coca, Raquel B., Holý, Antonín, Vilaplana, Rosario A., 2004

机译：9- [2-（Phosphoomethoxymethoxy）ethyl] -8-azaadenine（9,8aPMEA）的镍（II），铜（II）和锌（II）配合物，抗病毒核苷酸类似物9- [2-（膦甲氧基）乙基]腺嘌呤（PMEA）的8-氮杂衍生物。水溶液中四种异构体的定量
8. Synthesis and Properties of Homonuclear Dimetallic Nickel(II), Copper(II) and Zinc(II) Complexes of p-Xylenediyl and 2-Butynediyl-Bridged Dicyclenes. [R] . Crane, C. G., Burrows, C. J. 1993

机译：对二甲苯二基和2-丁二基桥连二环的双核二聚镍（II），铜（II）和锌（II）配合物的合成和性质。

Zinc, copper and nickel derivatives of 2-[2-bromoethyliminomethyl]phenol as topoisomerase inhibitors exhibiting anti-proliferative and anti-metastatic properties

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