含酚衍生物的偶氮席夫碱衍生的铜（II）和锌（II）金属配合物的合成、表征、计算及染色行为

Synthesis, characterization, computational and dyeing behavior of Cu(II) and Zn(II) metal complexes derived from azo-Schiff bases containing phenol derivatives.

作者信息

Elbadawy Hemmat A, Eldissouky Ali, El-Apasery Morsy Ahmed, Elsayed Doaa S, Alaswad Entesar A

机构信息

Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt.

Dyeing, Printing and Textile Auxiliaries Department, Textile Research and Technology Institute, National Research Centre, Giza, Egypt.

出版信息

BMC Chem. 2025 Jul 10;19(1):207. doi: 10.1186/s13065-025-01571-6.

DOI:10.1186/s13065-025-01571-6

PMID:40640886

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12243252/

Abstract

UNLABELLED

This study discusses the synthesis, characterization, and applications of two novel azo-Schiff bases, HL and HL, derived from HL, 4-((3-formyl-4-hydroxyphenyl)diazenyl)benzenesulfonamide with -aminophenol and -amino-thiophenol, respectively, and their Cu(II) and Zn(II) complexes. Stability, dyeing, biological activity, and computational investigations with experimental data are examined. HL, HL and their metal complexes were fully characterized utilizing different physicochemical techniques, such as UV-Vis, FTIR, mass spectra, thermal analysis (TGA, DTG and DTA), as well as EPR, molar conductivity measurements for metal complexes. The experimental findings showed that the metals were ligated to the azo-Schiff bases, HL and HL via the azomethine-N and phenolic-O or thiolato-S, respectively. The properties of the compounds as polyester fabric dyes were examined. They were evaluated for color fastness to washing, rubbing, and perspiration using ISO 105-C02:1989, X12:1987, and E04:1989. The colored materials’ superior intra-fiber diffusion inside the substrate may explain their exceptional washing and rubbing and perspiration fastness. In vitro antimicrobial efficiency of all products was explored against a panel of pathogenic bacteria, including Gram-positive bacteria and , Gram-negative bacteria and , and pathogenic fungi and , compared to Gentamycin and Ketoconazole as standards. Additionally, the cytotoxicity of developed compounds in one human cell line, lung carcinoma (A-549), was examined, demonstrating how chelation and molecular structure can affect anticancer activity. Compared to Ascorbic acid, their antioxidant activities were evaluated, and their ability to reduce DPPH radical was affected by molecular composition and structure. For free ligands, HL > HL > HL decreased power. For metal complexes, [Cu(L)₂]0.5 H₂O was more potent than [Zn(L)₂].2H₂O, but [Zn(L)₂].2H₂O >[Cu(L)₂]0.3 H₂O, as antioxidant. The applied computational studies and molecular docking on the proposed structures of the complexes were in good agreement with the experimental results.

SUPPLEMENTARY INFORMATION

The online version contains supplementary material available at 10.1186/s13065-025-01571-6.

摘要

未标注

本研究讨论了两种新型偶氮席夫碱HL和HL'的合成、表征及应用。HL由4 - ((3 - 甲酰基 - 4 - 羟基苯基)重氮基)苯磺酰胺分别与对氨基酚和对氨基苯硫酚衍生而来，还研究了它们的铜(II)和锌(II)配合物。结合实验数据对稳定性、染色性能、生物活性及进行了计算研究。利用不同的物理化学技术对HL、HL'及其金属配合物进行了全面表征，如紫外 - 可见光谱、傅里叶变换红外光谱、质谱、热分析（热重分析、微商热重分析和差示热分析），以及电子顺磁共振、金属配合物的摩尔电导率测量。实验结果表明，金属分别通过甲亚胺 - N和酚羟基 - O或硫醇基 - S与偶氮席夫碱HL和HL'配位。研究了这些化合物作为聚酯织物染料的性能。按照ISO 105 - C02:1989、X12:1987和E04:1989标准对它们的耐洗色牢度、耐摩擦色牢度和耐汗渍色牢度进行了评估。有色材料在底物内优异的纤维内扩散可能解释了它们出色的耐洗、耐摩擦和耐汗渍色牢度。以庆大霉素和酮康唑为标准，研究了所有产品对一组病原菌的体外抗菌效率，包括革兰氏阳性菌和、革兰氏阴性菌和以及致病真菌和。此外，还检测了所开发化合物在一种人类细胞系肺癌（A - 549）中的细胞毒性，证明了螯合作用和分子结构如何影响抗癌活性。与抗坏血酸相比，评估了它们的抗氧化活性，其还原二苯代苦味酰基自由基的能力受分子组成和结构的影响。对于游离配体，HL > HL' > HL的能力依次降低。对于金属配合物，作为抗氧化剂，[Cu(L)₂]·0.5H₂O比[Zn(L)₂]·2H₂O更有效，但[Zn(L)₂]·2H₂O > [Cu(L)₂]·0.3H₂O。对配合物的拟议结构进行的计算研究和分子对接与实验结果吻合良好。