Mixed Ligand Complexes of Ni2+, Cu2+ and Zn2+ Ions Containing N-(4-methoxybenzylidene)isonicotinohydrazone Schiff Base and 1,10-Phenanthroline : Synthesis, Characterization, Antimicrobial and Antioxidant Properties
Md. Ashrafuzzaman
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
Farzana Khanm Camellia
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
Md. Delwar Hossain
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
Md. Golam Mostafiz Shovon
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
Hafizur Rahman
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
Md. Tanvir Hossain
Department of Chemistry, Pabna University of Science and Technology, Pabna, Bangladesh.
Md. Hafijur Rahman
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
Md. Kudrat-E-Zahan
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
Md. Masuqul Haque *
Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh.
*Author to whom correspondence should be addressed.
Abstract
N-(4-methoxybenzylidene) isonicotinohydrazone (L1) Schiff base ligand was prepared by the condensation reaction of isonicotinic acid hydrazide (INH) and 4-methoxybenzaldehyde. A series of metal complexes of Ni2+, Cu2+ and Zn2+ ions was synthesized with Schiff base ligand (primary ligand, L1) and 1, 10-phenanthroline (L2) as a secondary ligand in stoichiometry ratio (1:1:1). Moreover, the synthesized ligand and its complexes have been characterized by analytical and physical properties, conductivity, magnetic susceptibility measurements, FTIR-spectra, and UV-Visible spectra. Conductivity measurements indicated that all complexes were 1:2 electrolytic in nature. IR spectra recommended that the oxygen of the carbonyl group (=CO) and nitrogen of the azomethine group (-C=N) were coordinated with metal ions. The confirmation of a square planar structure for Ni2+ and Cu2+ complexes, as well as a tetrahedral structure for the Zn2+ ion complex, was supported by their respective magnetic moment values and UV-Visible spectra. The antimicrobial activity of the metal complexes formed by L1 and L2 was evaluated against Escherichia coli and Pseudomonas sp. The metal complexes formed by the combination of L1 and L2 were subjected to testing against Escherichia coli and Pseudomonas sp. The Zn(II) complex exhibited superior antibacterial activity compared to the reference drug Kanamycin-30 against both bacterial strains in the tested compounds. In addition, the synthesised metal complexes demonstrated a comparatively moderate level of antioxidant activity when compared to the Schiff base. The Cu2+-complex exhibited the highest level of activity, while the Zn2+ -complex demonstrated the lowest antioxidant activity, which was comparable to that of BHT.
Keywords: Schiff base, transition metals, antibacterial, antioxidant, DPPH
How to Cite
Downloads
References
Thorat BR, Kamat P, Khandekar D, Lele S, Mustapha M, Sawant S, Jadhav R, Kolekar S, Yamgar R, Atram RG. Synthesis and Fluorescence study of Novel Schiff Bases of Isoniazide. J. Chem. Pharm. Res. 2011;3(6):1109-1117.
Gadada N, Reinout M, Amorn P, “Synthesis and Antimicrobial Activity of New Schiff Base Compounds Containing 2-Hydroxy-4-pentadecylbenzaldehyde Moiety”. Advan. Chem. 2014;1-9.
Omoruyi GI, Eric CH. Spectroscopy, Crystal and Molecular Structures of New 4-Acylpyrazolone Dinitrophenylhydrazones. Crystals. 2016; 6:127.
Ndahi NP, Nasiru YP. Complexes of cobalt(II), nickel(II) and zinc(II) with schiff bases derived from 4-anisaldehyde. Inter. J. Pharma. Sci. Res. 2012;3(12):5116-5120.
Shubhangi NK, Harjeet DJ. Synthesis, Characterization, and Antimicrobial Studies of N, O Donor Schiff Base Polymeric Complexes. J. Chem. 2013;1-5.
Riyadh MA, Enaam IY, Mohamad JAJ. Co(II) and Cd(II) Complexes Derived from Heterocyclic Schiff-Bases: Synthesis, Structural Characterisation, and Biological Activity. The Sci. World J. 2013;1-7
Gupta B, Fahmi N, Co(II) and Ni(II) Complexes with Schiff Base Ligands: Synthesis, Characterization, and Biological Activity. Russian J. Gen. Chem. 2016;86(5):1182–1190.
Ashok NP,Uttam MY, Pratik AD, Pravin US. Synthesis of some Novel Halogenated Platinum (II) Complexes of Active Schiff’s Base Ligand Derived from 5-Bromo Isatin and Evaluation of their Antibacterial Activity. World Sci. News. 2015;10:32-43.
Rosenberg B, Vancamp L, Krigas T, “Inhibition of Cell Division in Escherichia coli by Electrolysis Products from a Platinum Electrode. Nature. 1965;205: 698-699.
Ashok NP, Uttam MY, Pratik AD, Pravin US. Synthesis and Antimicrobial Activities of Novel Palladium (II) Complexes of Active Schiff’s Base Ligand Derived from 5-Bromo Isatin. Inter. Letters Chem. Phy. Astro. 2015;52:22-27.
Lucica VA, Angela K, Cristian A, Adina MM. Synthesis and characterization of new complexes of some divalent transition metals with 2-acetyl-pyridyl-isonicotinoylhydrazone. J. Therm. Anal.Calorim. 2012;107:573–584.
Rafeye R, Anita A. Synthesis and Characterization of New Schiff Bases of Ethylenediamine and Benzaldehyde Derivatives, Along with Their Iron Complexes. J. Appli. Chem. Res. 2015; 9(2):59-65.
Obasuyi EI, Iyekowa O. Synthesis, Characterization and Antimicrobial of Schfiff Base from 5-Bromo –Salicylaldehyde and P-Toluidine. J. Appl. Sci. Environ. Manage. 2018;22(11):1733–1736.
Koteswara RV, Subba RS, Satheesh KB, Reddi MNK, Naga RC, Ghosh SK. Synthesis of Schiff's bases in aqueous medium: a green alternative approach with effective mass yield and high reaction rates”. Green Chem. Let. Rev. 2010;3(3):217-223.
Haythem AS, Eman AAS, Ibrahim MM, Amal GAB, Mohammad SM. Synthesis, characterization and biological activity of Schiff bases derived from metronidazole. Med. Chem. Res. 2012:21:2969–2974.
Violet DV, Daniel PT, Renganathan R, Elsa F, Detlef WB. Novel Bioactive Co(II), Cu(II), Ni(II) and Zn(II) Complexes with Schiff Base Ligand Derived from Histidine and 1,3-Indandione: Synthesis, Structural Elucidation, Biological Investigation and Docking Analysis J. Fluoresc; 2016.
Laila HAR, Rafat MEK, Lobna AEN, Ahmed MAD. DNA binding ability mode, spectroscopic studies, hydrophobicity, and in vitro antibacterial evaluation of some new Fe(II) complexes bearing ONO donors amino acid Schiff bases. Arabian J. Chem; 2013.
Prashanthi YK, Kiranmai, Ira, Sathish KK, Vijay KC, Shivaraj. Spectroscopic characterization and biological activity of mixed ligand complexes of Ni(II) with 1,10 Phenanthroline and Heterocyclic Schiff Bases. Bioinorg. Chem. Appli. 2012; 1-9.
Chaviara AT, Cox PJ, Repana KH, Papi RM, Papazisis KT, Zambouli D, Kortsaris AH, Kyriakidis DA, Bolos CA. Copper(II) Schiff base coordination compounds of dien with heterocyclic aldehydes and 2-amino-5-methyl-thiazole: synthesis, characterization, antiproliferative and antibacterial studies. Crystal structure of CudienOOCl2”. J. Inorg. Biochem. 2004; 98:1271.
Ciller JA, Seoane C, Soto JL, Yruretagoyena B. Synthesis of heterocyclic compounds. LI. Schiff bases of ethyl 2-aminofurancarboxylates”. J. Heterocycl. Chem. 1986;23:1583.
Omyma AMA. Palladium(II) and zinc(II) complexes of neutral [N2O2] donor Schiff bases derived from furfuraldehyde: Synthesis, characterization, fluorescence and corrosion inhibitors of ligands. Spectrochimica Acta Part A: Molec. Biomolec. Spect. 2014;132:52-60.
Anoop KP, Abhishek B, Vikas B, Apoorva D. Structural, electronic, and vibrational properties of isoniazid and its derivative N-Cyclopentylidenepyridine-4-carbohydrazide: A quantum chemical study. J. Theoret. Chem. 2014;1-15.
Garner RN, Pierce CG, Reed CR, Brennessel WW. Photoinitiated Treatment of Mycobacterium using Ru(II) Isoniazid Complexes”. norganicaChimi. Acta; 2017. DOI: 10.1016/j.ica.2017.02.031
Zubatyuk RI, Kucherenko LI, Mazur IA, Khromyleva OV, Shishkin O V. A theoretical structural study of isoniazid complexes with thiotriazoline. Chem. Hetero. Comp. 2014;50(3):476-482.
Guilian L, Jingrui Z, Yi J, Li-li Z, Haican L, Machao L, Xiuqin Z, Kanglin W. Cross-resistance of isoniazid, para-aminosalicylic acid and pasiniazid against isoniazid-resistant Mycobacterium tuberculosis isolates in China. J. Glob. Antimicr. Resis. 2020;20:275–281.
Imran A, Waseem AW, Kishwar S. Empirical formulae to molecular structures of metal complexes by molar conductance. Syn. React. Inorg. Metal-Org., Nano-Metal Chem.,T.F. G. 2013; 43(9):1162-1170
Mariana LD, Angela K, Nicoale S, Adin MM. Transition metal M(II) complexes with isonicotinic acid 2-(9-anthrylmethylene)-hydrazide. J. Serb. Chem. Soc. 2010;75:1515.
Raman N, Dhaveethu RJ, Sakthivel A. Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies. J. Chem. Sci. 2007;119(40):303–310.
Sulekh C, Lokesh KG, Deepali J, “Spectroscopic studies on Mn(II), Co(II), Ni(II), and Cu(II) complexes with N-donor tetradentate (N4) macrocyclic ligand derived from ethylcinnamate moiety. Spectrochimi. Acta Part A. 2004;60: 2411–2417.
Mitu L, Mohamed N, Iqbal S, Raman N, Muhammad I, Sharma SK. Template synthesis, characterization and biological activity of Cu(II), Ni(II), Co(II), Zn(II) Complexes with Isonicotinoylhydra. E-J. Chem. 2010;7(1):227-233
Farhana A, Sadia AD, Saddam H, Shaheen S, Kudrat EZ. Synthesis, spectral and thermal characterization of selected metal complexes containing schiff base ligands with antimicrobial activities. Asian J. Chem. Sci. 2018;4(3): 1-19.
Saud IAR, Mohammad S, Ambreen A, Yusuf AKM, Abdul L. Synthesis, spectroscopic characterization and biological activities of N4O2 Schiff base ligand and its metal complexes of Co(II), Ni(II), Cu(II) and Zn(II). Spectromica. Acta Part A. 2012;93:86-94.
Arun V, Sridevi N, Robinson PP, Manju S, Yusuff KKM, Ni(II) and Ru(II) Schiff base complexes as catalysts for the reduction of benzene. J. Mol. Catal. A : Chem. 2009;304:191-198.
Kirza A, Mitu L, Stanica N. Complex combinations of transition metals d with the isonicotinoylhydrazone ligand -2-hidroxi-1-naftaldehid. Rev. Chim. Bucharest. 2005;2:137
Riyadh MA, Enaam IY, Mohamad JAJ. Co(II) and Cd(II) Complexes Derived from Heterocyclic Schiff-Bases: Synthesis, Structural Characterisation, and Biological Activity. The Sci. World J. 2013;1-6.
Kehinde OO, Joseph AA, Cyril EE, Olayinka OA, Akinlolu K, Tadigoppula N. (E)-N'-(2, 4-dihydroxybenzylidene)nicotinohydrazide and its Metal Complexes: Synthesis, Characterisation and Antitubercular Activity. Pak. j. sci. ind. res. Ser. A: phys. sci. 2016;59(2):63-75.
Kehinde OO, Joseph AA, Cyril OEE, Tolutope OS, Akinlolu K, Micheal AM, Tadigoppula N. Transition Metal Complexes of (E)-N’-(4 cyanobenzylidene) nicotinohydrazide): Synthesis, Structural and Anti-Mycobacterial Activity Study. J. Appli. Sci. 2015;15(10):1210-1222.
Kehinde OO, Micheal AM, Raju KVSN , Tadigoppula N. Structural and in vitro anti-tubercular activity study of (E)-N’-(2,6-dihydroxybenzylidene)nicotinohydrazide and some transition metal complexes. J. Iran Chem. Soc. 2015;12:815–829.
Gehad GM, Omar MM, Amr AI. Biological activity studies on metal complexes of novel tridentate Schiff base ligand. Spectroscopic and thermal characterization. European J. Medi. Chem. 2009;44:4801–4812.
Lawal M, Obaleye JA, Bamigboye MO, Nnabuike GG, Ayinla SO, Rajee AO, Babamale HF, Ajibola AA. Mixed metal complexes of isoniazid and ascorbic acid: Chelation, characterization and antimicrobial activities. Nigerian J. Chem. Res. 2017;22(1).
Latifa MA, Tania Tofaza BM, Chakia HM, Tariqul Islama, Saddam Hossaina, Kudrat-E-Zahan. Synthesis, characterization, and biological activity of the schiff base and Its Ni(II), Cu(II), and Zn(II) Complexes Derived from 4-(Dimethylamino)benzaldehyde and S-Benzyldithiocarbazate. Russian Journal of General Chemistry. 2019;89(6):1197-1201.
Rehab KAS, Ahmed TN, Eman MA. Synthesis, characterization and antimicrobial evaluation of mixed ligand complexes of Manganese(II), cobalt(II), copper(II), nickel(II) and Mercury(ii) with 1,10 phenanthroline and a Bidentate schiff base”. Eur. Chem. Bull. 2016;5(8): 335-338.
Kechukwu PE, Peter AA. Synthesis, characterization and biological studies of Metal(II)Complexes of (3E)-3-[(2-{(E)-[1-(2,4 Dihydroxyphenyl)ethylidene]amino}ethyl)imino]-1-phenylbutan-1-one Schiff Base”. Molecules. 2015;20:9788-9802 DOI:10.3390/molecules20069788.
Saddam HM, Shaheed ASME, Haque MM, Ranjan KM, Zakaria CM, Kudrat EZM. Synthesis and Characterization of Cu(II) and Co(II) complexes containing Schiff base ligands towards potential biological application”. J. Chem. Bio. Phy. Sci. Sec. A. 2018;8(4):654-668.
Gondia NK, Priya J, Sharma SK. Synthesis and physico-chemical characterization of a Schiff base and its zinc complex. Res. Chem. Intermed. 2017;43:1165–11783.
Kismat AE, Saddam HM, Nur ABM, Zahid AASM, Ranjan KM, Mannan MA, Zakaria CM, Kudrat EZM. Synthesis, spectral and thermal characterization on bioactive complexes of Mg(II), Zn(II), Sn(II), VO(II) and Bi(III) Ions Containing Schiff Base Ligand. J. Chem. Bio. Phy. Sci. 2019;9(4): 201-218.
Patel MN, Pansuriya PB, Parmar PA, Gandhi DS. Synthesis, characterization, and thermal and biocidal aspects of drug-based metal complexes. Pharma. Chem. J. 2008;42(12):687-692.
Kadtala V, Nirmala G, Sreenu D, Kumar K, Krishnan R, Shivaraj. Crystal structure, DNA interactions, antioxidant and antitumor activity of thermally stable Cu(II), Ni(II) and Co(III) complexes of an N,O donor Schiff base ligand. Poly. 2019:171:86–97
Sumalatha V, Aveli R, Narendrula V, Nirmala G, Sreenu D, Shivaraj. Synthesis, characterization, DNA binding propensity, nuclease efficacy, antioxidant and antimicrobial activities of Cu(II), Co(II) and Ni(II) complexes derived from 4-(trifluoromethoxy)aniline Schiff bases”. Chem. Data Collect. 2019;20: 1-12.
Nighat N, Irshad A, Nizam D, Amjad W, Sadeeq U-R, Abdul S, Farhan K, Sher K, Simon P, Kamal U. Synthesis, characterization and antioxidant activity of Nickel(II) Schiff Base Complexes Derived from 4-(Dimethylamino)benzaldehyde. J. Chem. Soc. Pak. Chem. Soc. Pak. 2020;42(2):238-242.
Kadtala V, Nirmala G, Sreenu D, Kumar K, Krishnan R, Shivaraj. Crystal structure, DNA interactions, antioxidant and antitumor activity of thermally stable Cu(II), Ni(II) and Co(III) complexes of an N,O donor Schiff base ligand. Poly. 2019; 171:86–97.
Saif M, Hoda FES, Mahmoud MM, Mohamed FE, Nabeel AI, Fouad R. Synthesis, characterization, and antioxidant/cytotoxic activity of new chromone Schiff base nanocomplexes of Zn(II), Cu(II), Ni(II) and Co(II). J. Molec. Struct; 2016. DOI:10.1016/j.molstruc.2016.03.060.