SYNTHESIS, SPECTRAL CHARACTERIZATION AND BIOPOTENTIAL SIGNIFICANCE OF Co(II) AND Ni(II) COMPLEXES WITH BIOLOGICALLY ACTIVE LIGANDS
Abstract
New Cobalt(II) and Nickel(II) metal complexes of 2-aminothiazole (ATZ) and benzoate ion (BEN) ligands were synthesized under microwave irradiation. The empirical formulae and the structure of the complexes have been deduced from CHN analysis, electrical conductance, magnetic moment, electronic (DRS method), Infra Red spectra, TGA analysis, cyclic voltammetry and powder-XRD techniques. The low electrical conductance values indicate that the complexes are non-electrolyte (1:0) type. The electronic spectra and the magnetic moment indicate the structures of the complexes are found to be octahedral geometry. Infra Red spectra illustrate that 2-aminothiazole and benzoate ion is bonded to the metal ion in a monodentate approach. The antifungal activities of ligands and their cobalt(II) and nickel(II) metal complexes were studied aligned with the few microorganisms by agar - well diffusion method at 100,200 and 400 conc. µg/ml concentration. The prepared cobalt(II) and nickel(II) metal complexes show prospective action against the tested fungi as compared to free 2-aminothiazole ligand. The free radical scavenging action of the prepared complexes and the ligand has been resolute by measuring their interface with the stable free radical DPPH. The complexes have larger antioxidant activity as compared to the free ligand. DNA-binding properties have been calculated by fluorescence-emissions method. The obtained results suggest that the complexes powerfully bind to DNA because of metal complexes are well-known to speed up the drug action and the capability of healing agent which can repeatedly be enhanced leading coordination with a metal ion.
Keywords:
2-aminothiazole, benzoate ion, antifungal, antioxidant, DNA-binding property.DOI
https://doi.org/10.25004/IJPSDR.2020.120104References
Das D, Sikdar P, Bairagi M. Recent developments of 2-aminothiazoles in medicinal chemistry. European journal of medicinal chemistry. 2016;109:89-98.
Ibatullin UG, Petrushina TF, Leitis LY, Minibaev IZ, Logvin BO. Synthesis and transformations of 4-substituted 2-aminothiazoles. Chemistry of Heterocyclic Compounds. 1993;29(5):612-615.
Singh K, Singh S, Taylor JA. Monoazo disperse dyes—Part 1: Synthesis, spectroscopic studies and technical evaluation of monoazo disperse dyes derived from 2-aminothiazoles. Dyes and Pigments. 2002;54(3):189-200.
Geronikaki A, Vicini P, Dabarakis N, Lagunin A, Poroikov V, Dearden J, Modarresi H, Hewitt M, Theophilidis G. Evaluation of the local anaesthetic activity of 3-aminobenzo [d] isothiazole derivatives using the rat sciatic nerve model. European journal of medicinal chemistry. 2009;44(2):473-481.
Papadopoulou C, Geronikaki A, Hadjipavlou-Litina D. Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine. Il Farmaco. 2005;60(11-12):969-973.
Kreutzberger A, Tantawy A. Antibacterial agents. 7. Aminomethinylation of guanidino heterocycles. Archiv der Pharmazie. 1981; 314(11):968-969.
Khalifa ME, Gobouri AA. Biological screening and assessment of certain substituted monoazo heterocycles containing sulphur and/or nitrogen and their seleno like moieties. Polish Journal of Chemical Technology. 2017;19(4):28-35.
Khalifa ME, Metwally MA, Abdel-Latif E, Amer FA. Synthesis of some new 5-arylazothiazole derivatives as disperse dyes for dyeing polyester fibers. Int. J. Text. Sci. 2012;1(6):62-68.
Metwally M, Khalifa M, Attia E, Amer F. New arylhydrazonothiazolidin-5-one disperse dyes for dyeing polyester fibers. Polish Journal of Chemical Technology. 2010;12(1):1-6.
Metwally MA, Abdel-Lat if E, Amer FA. New 4-arylazo-2-(substituted)-3-phenyl-1, 3-thiazolidin-5-ones as disperse dyes part 1. J. Text. Assoc. 2001;63:155-159.
Metwally MA, Abdel-Latif E, Amer FA. New 4-arylazo-2-bromo-2-(α-bromosubstituted)-3-phenyl-1, 3-thiazolidin-5-ones dyes for dyeing polyester fabrics part 2. J. Text. Assoc. Nov-Dec. 2002; 149-54.
Metwally M, Khalifa M, Attia E, Amer F. New arylhydrazonothiazolidin-5-one disperse dyes for dyeing polyester fibers. Polish Journal of Chemical Technology. 2010;12(1):1-6.
Metwally MA, Abdel-Latif E, Amer FA, Kaupp G. Synthesis of new 5-thiazolyl azo-disperse dyes for dyeing polyester fabrics. Dyes and Pigments. 2004;60(3):249-264.
Metwally MA, Abdel-Latif E, Khalil AM, Amer FA, Kaupp G. New azodisperse dyes with thiazole ring for dyeing polyester fabrics. Dyes and Pigments. 2004; 62(2): 181-195.
Khalifa ME, Abdel‐Latif E, Gobouri AA. Disperse Dyes Based on 5‐Arylazo‐thiazol‐2‐ylcarbamoyl‐thiophenes: Synthesis, Antimicrobial Activity and Their Application on Polyester. Journal of Heterocyclic Chemistry. 2015;52(3):674-680.
Yüce AO, Mert BD, Kardaş G, Yazıcı B. Electrochemical and quantum chemical studies of 2-amino-4-methyl-thiazole as corrosion inhibitor for mild steel in HCl solution. Corrosion Science. 2014;83:310-316.
Khaled KF, Amin MA. Corrosion monitoring of mild steel in sulphuric acid solutions in presence of some thiazole derivatives–molecular dynamics, chemical and electrochemical studies. Corrosion Science. 2009;51(9):1964-1975.
Al-Hajjar FH, Al-Kharafi FM. 2-amino-thiazole and 2-amino-4, 6-dimethylpyrimidine as corrosion inhibitors for copper. Corrosion science. 1988;28(2):163-171.
Pourjavid MR, Razavi T. 2-Amino-4-(4-aminophenyl) thiazole application as an ionophore in the construction of a Lu (III) selective membrane sensor. Chinese Chemical Letters. 2012;23(3):343-346.
Joshi KC, Pathak VN, Arya P. Synthesis of Some New Fluorine Containing 2-(N-Arylamino)/2-methyl-4-aryl Thiazoles and Their Bactericidal Activity. Agricultural and Biological Chemistry. 1979;43(2):199-201.
Rajapandiyan K, Shanthi S, Vidya S. assessment of microbial quality in marketed herbal drugs sold in trichy city. International Journal of Pharmaceutical, Chemical and Biological Sciences. 2013;3(3).
Govindharaju R, Balasubramaniyan S, Palanivelan L, Marlin Risana M, Mukil Meenakshi V. Synthesis, characterization and binding properties towards CT-DNA of mixed-ligand Cu(II) complex with 2-aminobenzonitrle and octanoate ion. Int J Pharm Sci and Res 2019;10(11):5137-5145.
Govindharaju R, Durairaj P, Maruthavanan T, Marlin Risana M, Ramachandramoorthy T. Synthesis, Spectral Characterization and Pharmacological Significance of Cr(III) and Mn(II) Complexes with Schiff Base and Thiocyanate Ion as Ligands. Int. J. Pharm. Sci. Drug Res. 2019;11(5):174-180.
Muruganantham N, Govindharaju R and Anitha P: An investigation of the DNA binding properties of Mn2+, Co2+ and Ni2+ complexes with 2-aminobenzonitrile and octanoate ion as ligands. Int J Pharm Sci and Res. 2019;10(12):5606-5611.
Govindharaju R, Balasubramaniyan S, Rajasekar K, Ramachandramoorthy T. Preparation, Spectroscopic Characterization and Biological Activities of Co (II) and Ni (II) Complexes with 2-Aminobenzonitrile and Octanoate Ligands. International Journal of Pharma Research and Review. 2014;3(10):8-13.
Govindharaju R, Balasubramaniyan S, Palanivelan L, Marlin Risana M, Mukil Meenakshi V. Synthesis, characterization and binding properties towards CT-DNA of mixed-ligand Cu(II) complex with 2-aminobenzonitrle and octanoate ion. Int J Pharm Sci and Res 2019;10(11):5137-5145.
Pachori K, Malik S, Wankhede S. Synthesis, Characterization and Antimicrobial studies of Transition metal Complexes of Co(II) and Ni(II) derived from Cefadroxil. Res. J. Chem. Sci. 2014;4(2):75-80.
Patel MN, Patel VJ. Studies on novel coordination polymers of a tetradentate ligand with some transition metal ions. Synthesis and Reactivity in Inorganic and Metal-organic Chemistry. 1989;19(2):137-155.
Shriodkar SG, Mane PS, Chondhekar TK. Synthesis and fungitoxic studies of Mn (II), Co (II), Ni (II) and Cu (II) with some heterocyclic Schiff base ligands. Indian Journal of Chemistry A. 2001;40:1114-1117.
Mohamed GG, Sharaby CM. Metal complexes of Schiff base derived from sulphametrole and o-vanilin: synthesis, spectral, thermal characterization and biological activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2007;66(4-5):949-958.
Shriodkar SG, Mane PS, Chondhekar TK. Synthesis and fungitoxic studies of Mn (II), Co (II), Ni (II) and Cu (II) with some heterocyclic Schiff base ligands. Indian Journal of Chemistry A. 2001;40:1114-1117.
Kavitha N, Lakshmi PA. Synthesis, characterization and thermogravimetric analysis of Co (II), Ni (II), Cu (II) and Zn (II) complexes supported by ONNO tetradentate Schiff base ligand derived from hydrazino benzoxazine. Journal of Saudi Chemical Society. 2017;21:S457-466.
Govindharaju R, Balasubramaniyan S, Rajasekar K, Ramachandramoorthy T. Preparation, Spectroscopic Characterization and Biological Activities of Co (II) and Ni (II) Complexes with 2-Aminobenzonitrile and Octanoate Ligands. International Journal of Pharma Research and Review. 2014;3(10):8-13.
Raman N, Johnson Raja S, Joseph J, Dhaveethu Raja J. Synthesis, spectral characterization and DNA cleavage study of heterocyclic Schiff base metal complexes. Journal of the Chilean Chemical Society. 2007;52(2):1138-1141.
Rajasekar M, Sreedaran S, Prabu R, Narayanan V, Jegadeesh R, Raaman N, Kalilur Rahiman A. Synthesis, characterization, and antimicrobial activities of nickel (II) and copper (II) Schiff-base complexes. Journal of Coordination Chemistry. 2010;63(1):136-146.
Al-Sabaawi SA. Synthesis and Characterization of some Mononuclear Mn (II), Fe (II), Co (II), Ni (II), Cu (II) and Zn (II) Complexes containing Bis-(2-thiophenelidene) thiosemicarbazone ligand. College Of Basic Education Researches Journal. 2012;11(3):765-776.
Palanivelan L , Balasubramaniyan S , Govindharaju R, Ramachandramoorthy T. An eco-friendly synthesis, spectral characterization and biological significance of Ni(II) complex with 2, 4-Thiazolidinedione and Benzoate ion as ligands. International Journal of Advanced Scientific Research and Management. 2018;3(12):66-70.
Palanivelan L, Balasubramaniyan S, Rajasekar K, Govindharaju R, Ramachandramoorthy T. Microwave assisted synthesis, Spectral characterization and Biological activities of Cu (II) complex with 2, 4-thiazolidinedione and benzoate ion as ligands. Journal of Applied Chemistry. 2018;11(7):20-24.
Kulkarni AD, Patil SA, Badami PS. Electrochemical properties of some transition metal complexes: synthesis, characterization and in-vitro antimicrobial studies of Co (II), Ni (II), Cu (II), Mn (II) and Fe (III) complexes. International Journal of Electrochemical Science. 2009;4(5):717-729.
Singh DP, Kumar R, Tyagi P. Template synthesis, spectroscopic studies and biological screening of macrocyclic complexes derived from thiocarbohydrazide and benzil. Transition metal chemistry. 2006; 31(7): 970-973.
Govindharaju R, Muruganantham N, Balasubramaniyan S, Palanivelan L, Jayalakshmi B, Rajalakshmi K, Ramachandramoorthy T. Synthesis, Spectral Characterization and Biological Evaluation of Cr(III) Complex with Mixed N,N and O-donor Ligands. Int. J. Pharm. Investigation. 2019;9(4):158-163.
Turkoglu O, Soylak M, Belenli I. Electrical conductivity of chloro (phenyl) glyoxime and its Co (II), Ni (II) and Cu (II) complexes. Collection of Czechoslovak chemical communications. 2003;68(7):1233-1242.
Justin Dhanaraj C, Sivasankaran Nair M. Synthesis, characterization, and antimicrobial studies of some Schiff-base metal (II) complexes. Journal of Coordination Chemistry. 2009;62(24):4018-4028.
Dhanaraj CJ, Nair MS. Synthesis and characterization of metal (II) complexes of poly (3-nitrobenzylidene-1-naphthylamine-co-succinic anhydride). European Polymer Journal. 2009;45(2):565-72.
Ahmad R, Ali AM, Israf DA, Ismail NH, Shaari K, Lajis NH. Antioxidant, radical-scavenging, anti-inflammatory, cytotoxic and antibacterial activities of methanolic extracts of some Hedyotis species. Life Sciences. 2005;76(17):1953-1964.
Turkoglu O, Soylak M, Belenli I. Electrical conductivity of chloro (phenyl) glyoxime and its Co(II), Ni(II) and Cu(II) complexes. Collection of Czechoslovak chemical communications. 2003;68(7):1233-1242.
Howe-Grant M, Wu KC, Bauer WR, Lippard SJ. Binding of platinum and palladium metallointercalation reagents and antitumor drugs to closed and open DNAs. Biochemistry. 1976;15(19):4339-4346.
Gao E, Zhu M, Yin H, Liu L, Wu Q, Sun Y. Synthesis, characterization, interaction with DNA and cytotoxicity in vitro of dinuclear Pd(II) and Pt(II) complexes dibridged by 2, 2′-azanediyldibenzoic acid. Journal of inorganic biochemistry. 2008;102(10):1958-1964.
Dey S, Sarkar S, Paul H, Zangrando E, Chattopadhyay P. Copper(II) complex with tridentate N donor ligand: synthesis, crystal structure, reactivity and DNA binding study. Polyhedron. 2010;29(6):1583-1587.
Wu H, Jia F, Kou F, Liu B, Yuan J, Bai Y. A Schiff base ligand N-(2-hydroxylacetophenone)-3-oxapentane-1, 5-diamine and its nickel(II) complex: synthesis, crystal structure, antioxidation, and DNA-binding properties. Transition Metal Chemistry. 2011;36(8):847-853.
Stang PJ, Olenyuk B. Self-assembly, symmetry, and molecular architecture: Coordination as the motif in the rational design of supramolecular metallacyclic polygons and polyhedra. Accounts of chemical research. 1997;30(12): 502-518.
Yuan L, Lu XH, Xiao X, Zhai T, Dai J, Zhang F, Hu B, Wang X, Gong L, Chen J, Hu C. Flexible solid-state supercapacitors based on carbon nanoparticles/MnO2 nanorods hybrid structure. ACS nano. 2011;6(1):656-661.
Muruganantham N, Govindharaju R and Anitha P: An investigation of the DNA binding properties of Mn2+, Co2+ and Ni2+ complexes with 2-aminobenzonitrile and octanoate ion as ligands. Int J Pharm Sci and Res. 2019;10(12):5606-5611.
Boerner LJ, Zaleski JM. Metal complex–DNA interactions: from transcription inhibition to photoactivated cleavage. Current opinion in chemical biology. 2005;9(2):135-144.
Published

