Investigation of biological activity of oxindole semicarbazones based copper (II) complexes: Synthesis, antimicrobial activities and molecular modelling

IF 2.4 3区化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR

Polyhedron Pub Date : 2024-08-30 DOI:10.1016/j.poly.2024.117208

Irtiqa Ashraf Mir , Qurat Ul Ain , Iqubal Singh , Rannan Carmieli , Rekha Sharma

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Abstract

Copper (II) acetate reacted with 2-oxindole semicarbazone (2-Hoxsc, H¹L), 3-methyl 2-oxindole semicarbazone (3-MeHoxsc, H²L) and 6-Chloro-2-oxindole semicarbazone (6-ClHoxsc, H³L) in 1:2 (M:L) molar ratio to form complexes of general formula, [Cu(L₂)] (¹L, 1; ²L 2; ³L 3. Stoichiometric ratio of complexes was established using UV–Vis spectroscopy. All the complexes were characterised by the CHN analysis, IR, ESR spectroscopy and Mass spectrometry. From the ESR spectrum, g values obtained (g_‖ = 2.20; g_⊥ = 2.05) for complex 2 confirms axial symmetry for this complex, whereas a broad isotropic signal in 1 and 3 (g_iso = 2.060, 1; 2.057, 3) indicates extensive exchange coupling. All the synthesized compounds (ligands and complexes) complexes were examined for their anti-tubercular activity against M. tuberculosis H37RV strain. Compounds were also tested for their anti-bacterial (B. subtilis, K. pneumonia) and antifungal (C. auris, C. albicans) activities. Biological investigations revealed that the antimicrobial activities (anti-TB, antibacterial and antifungal) of ligands get improved on complexation with Cu (II) due to formation of chelate ring, which can make the ligand a more powerful biological agent. Complex 3 has shown excellent anti-TB (MIC = 1.6 g/ml) and antibacterial (ZOI = 26 mm at 5 mg/mL) activities. Strong binding of complex 3 was observed (K_b = 24.22 × 10⁵ M⁻¹) with Human Serum Albumin (HSA) using fluorescence spectroscopy. Molecular modelling of complex 3 was also done with the active site of amino acid of M. tuberculosis enoyl reductase. The minimal binding energy of −10.1 kcal/mol indicated significant intermolecular interaction between M. tuberculosis enoyl reductase and complex 3 and is in well agreement with experimental data.

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基于铜 (II) 复合物的吲哚半咔唑酮生物活性研究：合成、抗菌活性和分子建模

醋酸铜（II）与 2-氧化吲哚缩氨基脲（2-Hoxsc，H1L）、3-甲基 2-氧化吲哚缩氨基脲（3-MeHoxsc，H2L）和 6-氯-2-氧化吲哚缩氨基脲（6-ClHoxsc，H3L）以 1:2 的摩尔比（M:L）反应生成通式为 [Cu(L2)] （1L，1；2L 2；3L 3）的配合物。利用紫外可见光谱确定了配合物的化学计量比。所有配合物均通过氯化萘分析、红外光谱、电子能谱和质谱进行了表征。从 ESR 光谱上看，络合物 2 的 g 值（g‖= 2.20；g⊥= 2.05）证实了该络合物的轴对称性，而 1 和 3 中的宽同向信号（giso = 2.060，1；2.057，3）表明存在广泛的交换偶联。对所有合成的化合物（配体和复合物）复合物进行了抗结核 M. tuberculosis H37RV 菌株的抗结核活性检测。此外，还检测了化合物的抗细菌（枯草杆菌、肺炎双球菌）和抗真菌（白色念珠菌、白色念珠菌）活性。生物学研究表明，配体与铜（II）络合后，由于形成了螯合环，配体的抗菌活性（抗结核、抗菌和抗真菌）得到了提高，从而使配体成为更强的生物制剂。络合物 3 显示出卓越的抗结核（MIC = 1.6 g/ml）和抗菌（5 mg/mL 时 ZOI = 26 mm）活性。利用荧光光谱法观察到复合物 3 与人血清白蛋白（HSA）有很强的结合力（Kb = 24.22 × 105 M-1）。还将复合物 3 与结核杆菌烯酰还原酶的氨基酸活性位点进行了分子建模。最低结合能为 -10.1 kcal/mol，表明结核杆菌烯酰还原酶与复合物 3 之间存在明显的分子间相互作用，与实验数据十分吻合。

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来源期刊

Polyhedron 化学-晶体学

CiteScore

4.90

自引率

7.70%

发文量

515

审稿时长

2 months

期刊介绍： Polyhedron publishes original, fundamental, experimental and theoretical work of the highest quality in all the major areas of inorganic chemistry. This includes synthetic chemistry, coordination chemistry, organometallic chemistry, bioinorganic chemistry, and solid-state and materials chemistry. Papers should be significant pieces of work, and all new compounds must be appropriately characterized. The inclusion of single-crystal X-ray structural data is strongly encouraged, but papers reporting only the X-ray structure determination of a single compound will usually not be considered. Papers on solid-state or materials chemistry will be expected to have a significant molecular chemistry component (such as the synthesis and characterization of the molecular precursors and/or a systematic study of the use of different precursors or reaction conditions) or demonstrate a cutting-edge application (for example inorganic materials for energy applications). Papers dealing only with stability constants are not considered.