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Water-soluble Cu(II)-complexes of Schiff base amino acid derivatives as biological reagents and sufficient catalysts for oxidation reactions
Journal of the Taiwan Institute of Chemical Engineers ( IF 5.5 ) Pub Date : 2020-08-22 , DOI: 10.1016/j.jtice.2020.08.010
Ahmad D.M. Mohamad , Eman R. El-Shrkawy , Maryam F.I. Al-Hussein , Mohamed Shaker S. Adam

Two novel water-soluble Cu(II) complexes (Cu-PSA and Cu-PSL) are synthesized from easily accessible Schiff base amino acid ligands (HPSA and HPS), as sodium sulfonate salts, obtained from D,L-phenylalanine and D,L-leucine, respectively. Their chemical composition is confirmed using various spectroscopic analyses (NMR, UV–vis, IR and mass spectroscopies, CHN micro-analyses, conductivities, TGA, and magnetism). The effect of sodium sulfonate group (Na+ SO3 group) on the chemical behavior of both Cu-PSA and Cu-PSL complexes is studied catalytically and biologically. Catalytically, Cu-PSA and Cu-PSL exhibit high reactivity in the (ep)oxidation of 1,2-cyclooctene and benzyl alcohol in polar reaction media, (acetonitrile or water) at 80°C, under homogeneous reaction condition. Biologically, the Cu-complexes and their ligands (HPSA and HPS) are tested for antimicrobial activity against some pathogens strains. Both Cu-complexes reveal higher performance than their corresponding ligands. Cu-PSA and Cu-PSL complexes are also examined for ctDNA-interaction, which studied using various techniques including spectroscopy, viscosity and gel-electrophoresis. Despite, their low lipophilicity due to the sodium sulfonate group (salting group), they show potentially high electrostatic interaction with ctDNA. The binding potential of these compounds is also investigated by molecular docking showing the role of the central metal ion (Cu2+) and the salting group in the ctDNA interaction. For anticancer reactivity, both ligands (HPSA, HPSL), and their complexes (Cu-PSA or Cu-PSL) are examined against hepatocellular carcinoma (HepG2) cell line, breast carcinoma (MCF7) cell line and colon carcinoma (HCT-116) cell line. The obtained results are encouraging and after optimization the Cu-complexes could be potentially anticancer drug candidates.



中文翻译:

席夫碱氨基酸衍生物的水溶性铜(Ⅱ)配合物作为生物试剂和足够的氧化反应催化剂

两种新颖的水溶性Cu(II)配合物(Cu-PSA和Cu-PSL)由易于获得的席夫碱氨基酸配体(HPSA和HPS)合成为磺酸钠盐,得自D,L-苯丙氨酸和D, L-亮氨酸分别。通过各种光谱分析(NMR,UV-vis,IR和质谱,CHN微量分析,电导率,TGA和磁性)可以确认其化学成分。磺酸钠组的效果(钠+ SO 3 -基团)在两个铜PSA和Cu-PSL络合物的化学行为被催化和生物研究。在极性反应介质(乙腈或水)中,Cu-PSA和Cu-PSL在1,2-环辛烯和苄醇的(环)氧化反应中显示出高反应活性°C,在均匀反应条件下。在生物学上,测试了铜配合物及其配体(HPSA和HPS)对某些病原体菌株的抗菌活性。两种铜配合物均比其相应的配体具有更高的性能。还检查了Cu-PSA和Cu-PSL复合物的ct DNA相互作用,已使用包括光谱学,粘度和凝胶电泳在内的各种技术进行了研究。尽管由于磺酸钠基团(盐基)的亲油性低,它们显示出与ct DNA潜在的高静电相互作用。还通过分子对接研究了这些化合物的结合势,结果显示了中心金属离子(Cu 2+)和盐基在ct中的作用。DNA相互作用。对于抗癌反应性,针对肝细胞癌(HepG2)细胞系,乳腺癌(MCF7)细胞系和结肠癌(HCT-116),检查了两个配体(HPSA,HPSL)及其复合物(Cu-PSA或Cu-PSL)。细胞系。获得的结果令人鼓舞,并且在优化后,铜配合物可能是潜在的抗癌药物候选物。

更新日期:2020-10-04
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