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Oxidovanadium(V) complexes of aroylhydrazones incorporating heterocycles: synthesis, characterization and study of DNA binding, photoinduced DNA cleavage and cytotoxic activities

机译:含杂环的芳酰hydr的氧化钒(V)配合物:DNA结合,光致DNA裂解和细胞毒性活性的合成,表征和研究

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Four neutral oxidovanadium(V) complexes VO2L1 (1), VO2L2 (2), VOL3(OEt) (3) and VOL4(OEt)EtOH (4) [where HL1 = 2-thiophenoylhydrazone of 2-acetylpyridine, HL2 = 2-amino benzoylhydrazone of 2-benzoyl pyridine, H2L3 = isonicotinoylhydrazone of 2-hydroxy acetophenone, H2L4 = 2-furoylhydrazone of 2-hydroxy-1-napthaldehyde] with a hydrazone scaffold containing either furan, thiophene and pyridine residues have been synthesised. All complexes were thoroughly characterized by various spectroscopic (IR, UV-Vis, NMR and ESI-MS) and single crystal X-ray diffraction techniques. Crystallography establishes five-coordinate geometries, distorted toward square pyramidal for each of 1 and 2, based on a tridentate-O,N,N coordinating anion and two oxido-O atoms. The dianion in 3 is tetradentate, coordinating one V atom as for 1 and 2, and bridging another via the pyridyl-N atom, and the N2O4 octahedral coordination geometry is completed by oxido- and ethanolate-O atoms. The result of the V-N bridging is a helical coordination polymer. An NO5 octahedral geometry is found in 4 defined by a tridentate-O,N,O anion, as well as oxido-, ethanolate- and ethanol-O atoms. Biological studies reveal that 1-4 have DNA binding propensity and show these to interact with CT-DNA through the minor groove binding mode, with binding constants ranging from 10(3) to 10(5) M-1. All complexes show good photo-induced cleavage of pUC19 supercoiled plasmid DNA with 3 showing the highest photo-induced DNA cleavage activity of similar to 65%. Additionally, 1-4 are cytotoxic against the human cervical cancer cell line (HeLa) with IC50 values ranging from 10 to 20 mu M.
机译:四种中性氧化钒(V)络合物VO2L1(1),VO2L2(2),VOL3(OEt)(3)和VOL4(OEt)EtOH(4)[其中HL1 = 2-乙酰基吡啶的2-噻吩酰hydr,HL2 = 2-氨基合成了带有含呋喃,噻吩和吡啶残基的骨架的2-苯甲酰吡啶的苯甲酰,、 H2L3 = 2-羟基苯乙酮的异烟酰yl,H2L4 = 2-羟基-1-萘乙醛的2-呋喃hydr。所有配合物均通过各种光谱(红外,紫外-可见,NMR和ESI-MS)和单晶X射线衍射技术进行了全面表征。晶体学基于三齿-O,N,N配位阴离子和两个氧-O原子,建立了五坐标的几何形状,对于1和2中的每一个,都向方形锥体变形。 3中的二价阴离子是四齿的,与1和2配位一个V原子,并通过吡啶基-N原子桥连另一个,N2O4八面体的配位几何结构是由氧-和乙醇-O原子完成的。 V-N桥接的结果是螺旋配位聚合物。发现NO5八面体的几何形状由4个三齿-O,N,O阴离子以及氧化,乙醇化和乙醇-O原子定义。生物学研究表明1-4具有DNA结合倾向,并显示它们通过小沟结合模式与CT-DNA相互作用,结合常数范围为10(3)至10(5)M-1。所有复合物均显示出pUC19超螺旋质粒DNA的良好光诱导裂解性,其中3个显示出最高的光诱导DNA裂解活性,接近65%。此外,1-4对人宫颈癌细胞系(HeLa)具有细胞毒性,IC50值介于10至20μM之间。

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