New Metronidazole Derivative and Some of its Complexes with Antibiofilm Study
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Abstract
Synthesis of a new ligand, namely [bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl) hydrogen borate] (BIB), utilizing the reaction of metronidazole with boric acid in a (2:1) mole ratio The metal complexes were synthesized utilizing the reaction of (NiCl2.6H2O and CuCl2 .2H2O) with (BIB) ligand in a 2:1 (L:M) mole ratio. All synthesized compounds were characterized utilizing spectroscopic techniques such as infrared (FTIR), nuclear magnetic resonance of protons(1H NMR), ultra violet and visible radiation (UV-Vis), thermal analysis (TG), atomic absorption (A.A.S.), micro elemental analysis (C.H.N.S.), melting point (m.p.), magnetic susceptibility, molar conductivity, and chloride content measurements. All complexes were paramagnetic and electrolyte, and the suggested geometries were the tetrahedral of nickel and the distorted octahedral of copper complexes. Against the Gram-negative bacterium Pseudomonas auroginosa (G-), all synthesized compounds were evaluated as anti-biofilm agents. Strikingly, the copper (II) complexes tested exhibit significant activity against biofilms and were better at removing biofilms than metronidazole (an antibiotic that is currently used to treat infections), ligand (BIB), and nickel (II) complexes.
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Çelik, A. ; Aras Ateş, N., The frequency of sister chromatid exchanges in cultured human peripheral blood lymphocyte treated with metronidazole in vitro. Drug and Chemical toxicology, 2006, 29(1),85-94. DOI: https://doi.org/10.1080/01480540500408663
Kapoor, V.K.; Chadha, R.; Venisetty, P.K. ; Prasanth, S., Medicinal significance of nitroimidazoles—some recent advances, Journal of Scientific& Industrial Research, 2003, 62, 659-665.
Ali, A.E.; Elasala, G.S. ; Ibrahim, R.S., Synthesis, characterization, spectral, thermal analysis and biological activity studies of metronidazole complexes. Journal of Molecular Structure, 2019, 1176, 673-684.
Radko, L., Stypuła-Trębas, S., Posyniak, A., Żyro, D. ; Ochocki, J., Silver (I) complexes of the pharmaceutical agents metronidazole and 4-hydroxymethylpyridine: comparison of cytotoxic profile for potential clinical application. Molecules, 2019, 24(10), 1949.
Siddappa, K.; Mallikarjun, M.; Reddy, P.T. ; Tambe, M., Spectrophotometric determination of metronidazole through Schiff's base system using vanillin and PDAB reagents in pharmaceutical preparations. Eclética Química, 2008, 33, 41-46 . DOI: https://doi.org/10.1590/S0100-46702008000400005
Pal, R., Boric acid in organic synthesis: scope ; recent developments. ARKIVOC: Online Journal of Organic Chemistry, 2018, 462, 1-26. DOI: https://doi.org/10.24820/ark.5550190.p010.462
Gujral, S.S., UV-Visible spectral analysis of boric acid in different solvents: a case study. International Journal of Pharmaceutical Sciences and Research, 2015, 6(2), 830.
Hemmati, F.; Salehi, R.;Ghotaslou, R.; Kafil, H.S.; Hasani, A.; Gholizadeh, P.;Rezaee, M.A., The assessment of antibiofilm activity of chitosan-zinc oxide-gentamicin nanocomposite on Pseudomonas aeruginosa and Staphylococcus aureus. International Journal of Biological Macromolecules, 2020, 163, 2248-2258.
Ogwuegbu Martin, O.C.; Kenechukwu, E.C.; Stanley, O.C.; Patricia, E.N. ; Ebere, E.C., Stoichiometric Determination of Fe (II), Ni (II) and Cu (II) Complexes of Metronidazole. International Journal of Chemical Science,2019,3(1), 25-29 .
Ramukutty, S. ; Ramachandran, E., Crystal growth by solvent evaporation and characterization of metronidazole. Journal of crystal growth, 2012, 351(1), 47-50. DOI: https://doi.org/10.1016/j.jcrysgro.2012.04.017
Al-Azzawi, A.M. ; Huseeni, M.D.,Design and synthesis of novel homo and copolymerization based on 4-(N-maleimidylmethylbenzylidene)-4'-(N-citraconamic acid)-1, 1'-biphenyl. Egyptian Journal of Chemistry, 2022, 65(1), 159-166.
Hasan, N.A. ; Baqer, S.R., Preparation, Characterization, Theoretical and Biological Study of new Complexes with mannich base, 2chloro–N-5-(Piperidin-1-ylmethylthio)-1, 3, 4-Thiadiazol-2-yl) acetamide. Ibn AL-Haitham Journal For Pure and Applied Sciences, 2023, 36(1), 260-271.
Obaleye, J.A. ; Lawal, A., Synthesis, characterization and antifungal studies of some metronidazole complexes, 2007, JASEM , 11(4), 15 -18.
Gao, S.; Liu, Y.; Feng, S. ; Lu, Z., Synthesis of borosiloxane/ polybenzoxazine hybrids as highly efficient and environmentally friendly flame retardant materials. Journal of Polymer Science Part A: Polymer Chemistry, 2017, 55(14), 2390-2396. DOI: https://doi.org/10.1002/pola.28628
Jiang, N.; Zhou, Z.; Xu, W.; Ma, H. ;Ren, F., Preparation of heat resistant boron-containing phenyl silicone oil and its initial degradation mechanism in air. Materials Research Express, 2021, 8(6), 065304.
Waszczykowska, A.; Żyro, D.; Jurowski, P. ; Ochocki, J., Effect of treatment with silver (I) complex of metronidazole on ocular rosacea: Design and formulation of new silver drug with potent antimicrobial activity. Journal of Trace Elements in Medicine and Biology, 2020, 61, 126531.
Kalinowska-Lis, U.; Felczak, A.; Chęcińska, L.; Zawadzka, K.; Patyna, E.; Lisowska, K. ; Ochocki, J., Synthesis, characterization and antimicrobial activity of water-soluble silver (I) complexes of metronidazole drug and selected counter-ions. Dalton Transactions, 2015, 44(17), 8178-8189. DOI: https://doi.org/10.1039/C5DT00403A
Khaleel, A.M.N. ; Jaafar, M.I., Synthesis and characterization of boron and 2-aminophenol Schiff base ligands with their Cu (II) and Pt (IV) complexes and evaluation as antimicrobial agents. Oriental Journal of Chemistry, 2017, 33(5), 2394-2404. DOI: https://doi.org/10.13005/ojc/330532
Eugene-Osoikhia, T.T., Synthesis, Characterisation and antimicrobial studies of Metal (II) Complexes of Ofloxacin and Metronidazole. ChemSearch Journal, 2020, 11(1), 74-82 .
Al-Jebouri, G.S. ; NOORIKHALEEL, A.M., synthesis of New Boron Compounds with Amoxicillin and Some of Its Metal Complexes with Use Them in Antibacterial, Assessment of Hepatoprotictive and Kidneyactivity, Anticancer and Antioxidant Applications. SYNTHESIS, 2019, 12(3).
Abdul-Ghani, A.J. ; Khaleel, A., Synthesis and characterization of new schiff bases derived from N (1)-substituted isatin with dithiooxamide and their co (II), Ni (II), Cu (II), Pd (II), and Pt (IV) complexes. Bioinorganic Chemistry and Applications, 2009,2009, 1-12. DOI: https://doi.org/10.1155/2009/413175
Jassim, S.A. ; Khaleel, A.M.N., Characterization And Synthesis Of New Schiff Base Compound From Levofloxacin And L-Cysteine With Its Cu (Ii) And Pt (Iv) Complexes And Estimation Antibacterial And Antifungal Activities. Biochemical and cellular archives, 2021, 21, 2187-2195.
Ali, I., Wani, W.A. ; Saleem, K., Empirical formulae to molecular structures of metal complexes by molar conductance. Synthesis and reactivity in inorganic, metal-organic, and nano-metal chemistry, 2013, 43(9), 1162-1170. DOI: https://doi.org/10.1080/15533174.2012.756898
Hussein, N.A. and Abbas, A.K. Synthesis, spectroscopic characterization and thermal study of some transition metal complexes derived from caffeine azo ligand with some of their applications. Eurasian Chem Commun, 2022,4(1), 67-93.
Brady, R.A., Leid, J.G., Calhoun, J.H., Costerton, J.W. ; Shirtliff, M.E., Osteomyelitis and the role of biofilms in chronic infection. FEMS Immunology & Medical Microbiology, 2008,52(1), 13-22 . DOI: https://doi.org/10.1111/j.1574-695X.2007.00357.x
Beenken, K.E., Mrak, L.N., Griffin, L.M., Zielinska, A.K., Shaw, L.N., Rice, K.C., Horswill, A.R., Bayles, K.W. ; Smeltzer, M.S., Epistatic relationships between sarA and agr in Staphylococcus aureus biofilm formation. PloS one, 2010,5(5), 10790 . DOI: https://doi.org/10.1371/journal.pone.0010790
Mahdi, L.H.; Jabbar, H.S. ; Auda, I.G., Antibacterial immunomodulatory and antibiofilm triple effect of Salivaricin LHM against Pseudomonas aeruginosa urinary tract infection model. International journal of biological macromolecules,2019,134, 1132-1144 .
Tawfeeq, H.K.; Hamid, M. ;Fahad Al-Mathkhury, H.J., The Prevalence of Pseudomonas aeruginosa among Baghdad Hospitalised Patients. Medico-Legal Update, 2021, 21(2).
Radojević, I.; Vasić, S.; Čomić, L.; Trifunović, S.;Mijajlović, M.; Nikolić, M. ; Radić, G., Antibacterial and antibiofilm screening of new platinum (IV) complexes with some s-alkyl derivatives of thiosalicylic acid. Kragujevac Journal of Science,2017,(39),137-143. DOI: https://doi.org/10.5937/KgJSci1739137R
Al-Mathkhury, H.J.F.; Al-Dhamin, A.S. ; Al-Taie, K.L., Antibacterial and antibiofilm activity of flaxseed oil. Iraqi Journal of Science,2016,1086-1095.
Abid, N.; Hamad, E.; Ibrahim, M. ;Abid, H., Antibacterial and antibiofilm activities of taxifolin against vancomycin-resistant S. aureus (VRSA). Baghdad Journal of Biochemistry and Applied Biological Sciences,2022,3(04),262-272.
Ali, R.; Shanan, Z.J.; Saleh, G.M. ; Abass, Q., Green synthesis and the study of some physical properties of MgO nanoparticles and their antibacterial activity. Iraqi Journal of Science,2020, 266-276. DOI: https://doi.org/10.24996/ijs.2020.61.2.9
Pahonțu, E.; Ilieș, D.C.; Shova, S.; Oprean, C.; Păunescu, V.; Olaru, O.T.; Rădulescu, F.Ș.; Gulea, A.; Roșu, T. ; Drăgănescu, D.Synthesis, characterization, antimicrobial and antiproliferative activity evaluation of Cu (II), Co (II), Zn (II), Ni (II) and Pt (II) complexes with isoniazid-derived compound. Molecules,2017,22(4), 650. DOI: https://doi.org/10.3390/molecules22040650
Al-Ammash, M.S.J., Study the effect of alcoholic extract of Nigella sativa seeds on Trichomomas vaginalis in vitro. Ibn AL-Haitham Journal For Pure and Applied Science, 2017,30(3),10-18. DOI: https://doi.org/10.30526/30.3.1596