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Charge-assisted hydrogen bond and nitrile⋯nitrile interaction directed supramolecular associations in Cu(II) and Mn(II) coordination complexes: anticancer, hematotoxicity and theoretical studies
New Journal of Chemistry ( IF 3.3 ) Pub Date : 2020/03/05 , DOI: 10.1039/d0nj00075b
Pranay Sharma 1, 2, 3, 4 , Anshuman Gogoi 1, 2, 3, 4 , Akalesh K. Verma 2, 3, 4, 5, 6 , Antonio Frontera 7, 8, 9, 10 , Manjit K. Bhattacharyya 1, 2, 3, 4
Affiliation  

Two new coordination complexes of Cu(II) and Mn(II), viz., [Cu(bpy)(H2O)4]SO4·2H2O (1) and [Mn(4-CNpy)2(H2O)3SO4]·H2O (2) (bpy = 2,2′-bipyridine, 4-CNpy = 4-cyanopyridine), have been synthesized and characterized by using single crystal X-ray diffraction, elemental analysis, FT-IR spectroscopy, electronic spectroscopic techniques and TGA. The crystal structure of 1 uncovers the formation of sulfate–water assemblies involving lattice and coordinated water molecules, while complex 2 reveals the presence of unconventional weak T-shaped CN⋯CN contacts in the layered architecture. We have analysed the unconventional interesting interactions using DFT calculations, molecular electrostatic potential (MEP), the NCI plot and QTAIM computational tools. The interaction energies of the two H-bonded dimers in 1 are very large because of the coulombic attraction between the dicationic H-bonded donor and the dianionic acceptor. It is interesting to observe that despite the energy of the H-bonds being very small compared to the total dimerization energy, the final geometry of the assembly in 1 is due to the charge assisted directional H-bonds instead of the non-directional ion-pair interactions. The DFT study reveals that the T-shaped CN⋯CN interaction in 2 is very weak, in good agreement with the small MEP energy at the nitrile carbon atom. Anticancer studies of the compounds have been carried out using Dalton's lymphoma cell line using MTT and apoptosis assay. The results of compound 1 and 2 mediated cell cytotoxicity on the DL cancer cell line showed a significant concentration-dependent reduction in cell viability, while negligible cytotoxicity was observed in normal (PBMC) cells. The docking simulation results also confirm the interaction of the complexes with the active sites of amino acids of the target proteins. Furthermore, pharmacophore models (2D and 3D) for the compounds were mapped to the H-bond donor, positive ionisable area and hydrophobic features that are important for establishing biological activities. No hematotoxicity was recorded for the compounds after treatment in normal mice.

中文翻译:

Cu(II)和Mn(II)配位化合物中的电荷辅助氢键和腈腈相互作用指导超分子缔合:抗癌,血液毒性和理论研究

Cu(II)和Mn(II)的两个新的配位络合物,[Cu(bpy)(H 2 O)4 ] SO 4 ·2H 2 O(1)和[Mn(4-CNpy)2(H 2 O)3 SO 4 ]·H 2 O(2)(bpy = 2,2'-联吡啶(4-CNpy = 4-氰基吡啶)已通过使用单晶X射线衍射,元素分析,FT-IR光谱,电子光谱技术和TGA进行了表征。1的晶体结构揭示了涉及晶格和配位水分子的硫酸盐-水组件的形成,而复合物2则揭示了分层结构中存在非常规的弱T形CN⋯CN接触。我们使用DFT计算,分子静电势(MEP),NCI图和QTAIM计算工具分析了非常规有趣的相互作用。在两个H键合的二聚体的相互作用能1是因为双阳离子氢键供体和双阴离子受体之间的库仑引力的非常大。有趣的是,尽管氢键的能量与总二聚能相比非常小,但组件的最终几何形状为1这是由于电荷辅助的方向性H键而不是非方向性离子对相互作用引起的。该DFT的研究显示,在所述T形CN CN⋯相互作用2非常弱,在腈碳原子与小MEP能量吻合。已经使用道尔顿氏淋巴瘤细胞系通过MTT和凋亡测定法对化合物进行了抗癌研究。化合物12的结果介导的DL癌细胞系的细胞毒性表现出显着的浓度依赖性降低其细胞活力,而在正常(PBMC)细胞中观察到的细胞毒性可忽略不计。对接模拟结果还证实了复合物与靶蛋白氨基酸活性位点的相互作用。此外,将化合物的药效团模型(2D和3D)映射到H键供体,可电离的正面积和疏水性特征,这些特征对于建立生物活性至关重要。在正常小鼠中治疗后,未记录化合物的血液毒性。
更新日期:2020-04-06
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