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设计、表征、致畸性测试、抗菌、抗真菌和几种高自旋 Fe(II)席夫碱氨基酸配合物与 DNA 的相互作用。

Design, characterization, teratogenicity testing, antibacterial, antifungal and DNA interaction of few high spin Fe(II) Schiff base amino acid complexes.

机构信息

Chemistry Department, Faculty of Science, Sohag University, Sohag 82534, Egypt.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2013 Jul;111:266-76. doi: 10.1016/j.saa.2013.03.061. Epub 2013 Apr 4.

Abstract

In this study, new Fe(II) Schiff base amino acid chelates derived from the condensation of o-hydroxynaphthaldehyde with L-alanine, L-phenylalanine, L-aspartic acid, L-histidine and L-arginine were synthesized and characterized via elemental, thermogravimetric analysis, molar conductance, IR, electronic, mass spectra and magnetic moment measurements. The stoichiometry and the stability constants of the complexes were determined spectrophotometrically. Correlation of all spectroscopic data suggested that Schiff bases ligands exhibited tridentate with ONO sites coordinating to the metal ions via protonated phenolic-OH, azomethine-N and carboxylate-O with the general formulae [Fe(HL)2]·nH2O. But in case of L-histidine, the ligand acts as tetradentate via deprotonated phenolic-OH, azomethine-N, carboxylate-O and N-imidazole ring ([FeL(H2O)2]·2H2O), where HL=mono anion and L=dianion of the ligand. The structure of the prepared complexes is suggested to be octahedral. The prepared complexes were tested for their teratogenicity on chick embryos and found to be safe until a concentration of 100 μg/egg with full embryos formation. Moreover, the interaction between CT-DNA and the investigated complexes were followed by spectrophotometric and viscosity measurements. It was found that, the prepared complexes bind to DNA via classical intercalative mode and showed a different DNA activity with the sequence: nhi>nari>nali>nasi>nphali. Furthermore, the free ligands and their complexes are screened for their in vitro antibacterial and antifungal activity against three types of bacteria, Escherichia coli, Pseudomonas aeruginosa and Bacillus cereus and three types of anti fungal cultures, Penicillium purpurogenium, Aspergillus flavus and Trichotheium rosium in order to assess their antimicrobial potential. The results show that the metal complexes are more reactive with respect to their corresponding Schiff base amino acid ligands.

摘要

在这项研究中,我们合成并通过元素分析、热重分析、摩尔电导率、红外光谱、电子光谱、质谱和磁矩测量对邻羟基萘醛与 L-丙氨酸、L-苯丙氨酸、L-天冬氨酸、L-组氨酸和 L-精氨酸缩合得到的新型 Fe(II)Schiff 碱氨基酸配合物进行了表征。通过分光光度法确定了配合物的化学计量和稳定常数。所有光谱数据的相关性表明,Schiff 碱配体表现出三齿配位,通过质子化的酚-OH、亚胺-N 和羧酸盐-O 与金属离子配位,配位数为 ON0,其通用化学式为[Fe(HL)2]·nH2O。但在 L-组氨酸的情况下,配体通过去质子化的酚-OH、亚胺-N、羧酸盐-O 和 N-咪唑环以四齿配位([FeL(H2O)2]·2H2O),其中 HL 为配体的单核阴离子,L 为配体的二价阴离子。推测所制备的配合物的结构为八面体。我们测试了这些配合物对鸡胚的致畸性,发现直到浓度达到 100μg/卵时仍具有完全胚胎形成能力,且是安全的。此外,我们通过分光光度法和粘度测量研究了配合物与 CT-DNA 的相互作用。结果表明,所制备的配合物通过经典的嵌入模式与 DNA 结合,并表现出不同的 DNA 活性,其序列为: nhi>nari>nali>nasi>nphali。此外,我们还对游离配体及其配合物进行了体外抗菌和抗真菌活性测试,以评估它们的抗菌潜力,实验针对三种细菌(大肠杆菌、铜绿假单胞菌和蜡样芽孢杆菌)和三种抗真菌培养物(紫色青霉、黄曲霉和罗斯青霉)进行了测试。结果表明,金属配合物相对于其相应的 Schiff 碱氨基酸配体具有更高的反应活性。

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