The structural characterization and biological activity of sulfamethoxazolyl-azo-p-cresol, its copper(ii ) complex and their theoretical studies
| Autor: | Chittaranjan Sinha, Nayim Sepay, Dipankar Das, Suvroma Gupta, Suman Roy, Elena López-Torres, Sudipa Mondal, Paramita Dutta, Nilima Sahu |
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| Rok vydání: | 2016 |
| Předmět: |
biology
010405 organic chemistry Hydrogen bond Stereochemistry Supramolecular chemistry chemistry.chemical_element Active site DHPS Aromaticity General Chemistry 010402 general chemistry 01 natural sciences Copper Catalysis 0104 chemical sciences Crystallography chemistry Octahedron Materials Chemistry biology.protein Chelation |
| Zdroj: | New Journal of Chemistry. 40:5019-5031 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/c5nj02983j |
| Popis: | (E)-4-((2-Hydroxy-5-methylphenyl)diazenyl)-N-(5-methylisoxazole-3-yl)benzene sulfonamide (SMX-NN-C6H3(p-Me)-OH, 1) and its Cu(II) complex, [Cu(SMX-NN-C6H3(p-Me)-O)2]n (2), have been characterized by spectroscopic data and single crystal X-ray diffraction studies. The supramolecular 1D chain of 1 is constituted by inter- and intra-molecular hydrogen bonds and also by π⋯π interactions of aromatic rings. Complex 2 has a tetragonally distorted octahedral structure in which ligand 1 serves as an N,O chelator and forms a planar Cu(N,O)2 motif; two axial positions are occupied by the oxazolyl-N of neighbouring units and a 3D structure is formed. The biological activities of these compounds have been evaluated against Gram positive (B. subtilis; IC50: 105 μg ml−1 (1) and 105 μg ml−1 (2)) and Gram negative bacteria (E. coli; IC50: 66.36 μg ml−1 (1) and 62.2 μg ml−1 (2)) and the complexes exhibit better efficiency. Interactions of DNA with 1 and 2 have been examined and the binding constants are Kb(1), 5.920 × 104 M−1 and Kb(2), 4.445 × 104 M−1. The in silico test is used to predict the most favoured binding mode of 1 and 2 with the active site residues of DHPS (dihydropteroate synthetase) of E. coli and of DNA. The Cu(II) complex (2) binds more efficiently (CDOCKER energy, 2, −61.35 a.u.) in the DHPS cavity than ligand 1 (CDOCKER energy, 1, −43.90 a.u.). The electronic structures and spectral properties of 1 and 2 have been investigated by DFT and TD-DFT computation of optimized geometries of the compounds. |
| Databáze: | OpenAIRE |
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