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Antibacterial activities of sulfamethoxazolyl-azo-phenols and their Cu(II) complexes along with molecular docking properties

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Abstract

Sulfamethoxazolyl-azo-phenols [SMX–N=N–C6H2(R)(R/)–OH] (1a, 2a) and their Cu(II) complexes, [Cu(SMX–N=N–C6H2(R)(R/)–O)2] (1b, 2b) (R = p-OMe, R/ = H, 1a/1b; R = p-Cl, R/ = m-CH3, 2a/2b) show antibacterial sensitivity against Gram-positive bacteria, B. subtillis; IC50: 281.47 ± 1.84 μM (1a), 126.39 ± 1.66 μM (1b), and 279.94 ± 3.15 μM (2a), 123.62 ± 1.27 μM(2b), and Gram-negative bacteria, E. coli; IC50: 204.66 ± 3.31 μM (1a) and 89.05 ± 1.48 μM (1b), 223.13 ± 2.71 μM (2a), and 98.26 ± 1.59 μM (2b). Interaction of DNA with free ligand (1a and 2a) is insignificant, while the complexes (1b and 2b) interact strongly and the binding constants are K b, 8.413 × 104 M−1 (1b) and 6.56 × 105 M−1 (2b). Optimized structures of the compounds are docked with protein structure of DHPS (E. coli) to propose the most favoured binding mode of the drugs in the active site. The in silico test of the compound helps to understand drug metabolism, drug–protein interactions, and toxicity (ADMET).

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Abbreviations

ADMET:

Absorption, distribution, metabolism, and excretion-toxicity in pharmacokinetics

ATCC:

American-type culture collection

B3LYP:

Becke, three-parameter, Lee–Yang–Parr

CAMD:

Computer-aided molecular design

DFT:

Density functional theory

DHPS:

Dihydropteroate synthase

PDB:

Protein data bank

SMX:

Sulfamethoxazole

TD DFT:

Time-dependent density functional theory

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Acknowledgements

Financial support from West Bengal Department of Science and Technology (228/1(10)/(Sanc.)/ST/P/S&T/9G-16/2012), Kolkata and University Grants Commission (F.42-333/2013(SR)), New Delhi is gratefully acknowledged. Miss. Ananya Das Mahapatra, NICED, Kolkata, is thankfully acknowledged for help.

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Authors and Affiliations

  1. Department of Chemistry, Jadavpur University, Kolkata, West Bengal, 700032, India

    Nilima Sahu, Sudipa Mondal, Nayim Sepay & Chittaranjan Sinha

  2. Department of Biotechnology, Haldia Institute of Technology, Purba Medinipur, Haldia, West Bengal, 721657, India

    Suvroma Gupta

  3. Departamento de Química Inorgánica, Universidad Autónoma de Madrid, c/Francisco Tomás y Valiente, 7, Cantoblanco, 28049, Madrid, Spain

    Elena Torres-Lopez

  4. Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan

    Shinnosuke Tanaka & Takashiro Akitsu

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  1. Nilima Sahu
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Correspondence to Chittaranjan Sinha.

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Sahu, N., Mondal, S., Sepay, N. et al. Antibacterial activities of sulfamethoxazolyl-azo-phenols and their Cu(II) complexes along with molecular docking properties. J Biol Inorg Chem 22, 833–850 (2017). https://doi.org/10.1007/s00775-017-1461-4

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  • DOI: https://doi.org/10.1007/s00775-017-1461-4

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