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Synthesis, theoretical studies, antibacterial, and antibiofilm activities of novel azo-azomethine chelates against the pathogenic bacterium Proteus mirabilis

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Abstract

2-((1-(4-((2,4,6-trioxohexahydropyrimidin-5-yl)diazenyl) phenyl) ethylidene) amino) benzoic acid (H3L), and its V(IV), Co(II), Ni(II), Cu(II), Pd(II) and Ag(I) chelates were synthesized. They were defined using multiple spectral and analytical techniques. With the exception of Ag(I) chelate, all chelates possessed non-electrolytic character. Square pyramidal shape was proposed for V(IV) chelate and Square planar for the other chelates. The analysis of functional group bands of H3L and its coordination compounds alludes that H3L chelated as neutral tetradentate via nitrogen atoms of azo and azomethine groups, oxygen atom of carbonyl of barbituric acid and OH of the carboxylic group. TG/DTG predicted the thermal behaviors of all compounds. The antibacterial activity of H3L and its coordination compounds was conducted against Proteus mirabilis at concentrations of 250, 500, and 1000 µg/mL. Ag(I) at 1000 µg/mL, showed the most inhibiting potency against P. mirabilis and registered zone of inhibition of 28.33 ± 0.84 mm and highest biofilm inhibition of 70.31%. At 50 Gy of gamma irradiation, the reducing effect of Ag(I) chelate was improved. The protein interruption of P. mirabilis was greatly interrupted by increasing the concentration of the chaletes. Also, Ag(I) showed the highest cytotoxicity with IC50 value of 11.5 µg/ mL. The novelty of this study is the synthesis of a new azo-Schiff base and this is almost the first publication of the effect of azo-Schiff ligands against that bacterial strain P. mirabilis.

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Acknowledgements

The authors thank the Chemistry Department, Faculty of Science, Menoufia University and National Center for Radiation Research and Technology, Egyptian Atomic Energy Authority (EAEA) for the possibility to use their equipment, facilities and gamma irradiation.

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  1. Chemistry Department, Faculty of Science, Menoufia University, Shebeen El-Kom, Egypt

    Fatma I. Abouzayed, Shimaa G. Hussien & Saeyda A. Abouel-Enein

  2. Drug Radiation Research Department, National Center for Radiation Research and Technology (NCRRT), Egyptian Atomic Energy Authority, Cairo, Egypt

    Rasha Mohammad Fathy & Gharieb S. El-Sayyad

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S. A. Abouel-Enein, F. I. Abouzayed, and R. M. Fathy designed the skeleton of the work. F. I. Abouzayed, S. G. Hussien, R. M. Fathy, and G. S. El-Sayyad performed the methodology. All authors shared in writing and revising the manuscript. All authors contributed to the manuscript and approved the submission.

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Abouzayed, F.I., Fathy, R.M., Hussien, S.G. et al. Synthesis, theoretical studies, antibacterial, and antibiofilm activities of novel azo-azomethine chelates against the pathogenic bacterium Proteus mirabilis. Biometals (2024). https://doi.org/10.1007/s10534-024-00608-y

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