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Synthesis, spectral and extended spectrum beta-lactamase studies of transition metal tetraaza macrocyclic complexes

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Abstract

Urinary tract infections commonly occur in humans due to microbial pathogens invading the urinary tract, which can bring about a range of clinical symptoms and potentially fatal sequelae. The present study is aimed at addressing the development of a new antimicrobial agent against extended spectrum beta lactamase (ESBL) producing E. coli bacteria. We have synthesised some biologically potent (NNNN) donor macrocycles (L 1  = dibenzo[f,n]dipyrido[3,4-b:4′,3′-j][1,4,9,12]tetraazacyclohexadecine-6,11,18,23(5H,12H, 7H, 24H)-tetraone, and L 2  = 6,12,19,25-tetraoxo-4,6,11,12,16,18,23,24-octahydrotetrabenzo [b,g,k,p][1,5,10,14]tetra azacyclooctadecine-2,13-dicarboxylic acid) and their Ti and Zr metal complexes in alcoholic media using microwave protocol. Macrocyclic ligands were synthesised by incorporating of 3,5-diaminobenzoic acid, phthalic acid and 3,4-diaminopyridine in 1:1:1 molar ratio. The macrocyclic ligands and their metal complexes have been characterised by elemental analysis, conductance measurement, magnetic measurement and their structure configurations have been determined by various spectroscopic (FTIR, 1H/13C NMR, UV–Vis, LC–MS mass, XRD and TGA) techniques. [ZrL2Cl2]Cl2 metal complex shows excellent antibacterial activity against ESBLs. A zone of inhibition and minimum inhibitory concentration was determined by McFarland and the dilution method, respectively. The spectral studies confirm the binding sites of the nitrogen atom of the macrocycles. An octahedral geometry has been assigned to the metal complexes based on the findings.

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Acknowledgements

We are thankful to Professor Aditya Shastri Vice-Chancellor of Banasthali University, Rajasthan, for kindly extending the facilities of “Banasthali Centre of Education” for research in basic sciences sanctioned under CURIE programme of the Department of Science and Technology, New Delhi, and Sandeep K. Shrivastava, Centre for Innovation, Research & Development (CIRD), Dr B. Lal Clinical Laboratory Pvt. Ltd. Jaipur, India, for helping us in biological analysis.

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Authors and Affiliations

  1. Department of Chemistry, Banasthali University, Banasthali, 304022, India

    Dinesh Kumar & Nutan Sharma

  2. Department of Chemistry, American College of Dubai, 36778, Dubai, UAE

    Manjula Nair

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  1. Dinesh Kumar
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  2. Nutan Sharma
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  3. Manjula Nair
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Corresponding author

Correspondence to Dinesh Kumar.

Electronic supplementary material

Below is the link to the electronic supplementary material. Electronic supplementary information (ESI): FTIR spectra of ligand L2 and its complex [ZrL2Cl2]Cl2, 1H NMR spectra of ligand L2 and complex [ZrL2Cl2]Cl2, 13C NMR spectra of ligand L2, and complex [ZrL2Cl2]Cl2, LC–MS mass spectra of ligand L2 and complex [ZrL2Cl2]Cl2, the molecular fragmentation patterns for ligand L2, TGA graph of complex [ZrL2Cl2]Cl2, UV–Vis spectra of ligand L2 and complex [ZrL2Cl2]Cl2, X-ray powder diffraction data of L2 and complex [Zr(L2)Cl2]Cl2, % Inhibition for the ligand L2 and its complex [ZrL2Cl2]Cl2, the growth curve of the complex with negative control, table of Physical properties, molar conductance (Λm), and elemental analysis data of the ligands and their metal complexes, table of IR spectral data (cm−1) of the ligands and their corresponding tetraaza macrocyclic complexes, and table of XRD data of complex of [Zr(L2)Cl2]Cl2

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Kumar, D., Sharma, N. & Nair, M. Synthesis, spectral and extended spectrum beta-lactamase studies of transition metal tetraaza macrocyclic complexes. J Biol Inorg Chem 22, 535–543 (2017). https://doi.org/10.1007/s00775-017-1440-9

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  • DOI: https://doi.org/10.1007/s00775-017-1440-9

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