SYNTHESIS, CHARACTERIZATION, DNA CLEAVAGE AND ANTIMICROBIAL ACTIVITIES OF SCHIFF BASE LIGAND DERIVED FROM 5-CHLORO-3-PHENYL-1H-INDOLE-2-CARBOXYHYDRAZIDE AND O-VANILLIN AND ITS METAL (II) COMPLEXES
Abstract
Objective: The main objective of the present work was to synthesize a new Schiff base ligand 5-chloro-N'-(2-hydroxy-3-methoxybenzylidene)-3-phenyl-1H-indole-2-carbohydrazide and its Cu (II), Co (II), Ni (II) and Zn (II) complexes and study their biological activity.
Methods: The compounds are characterized by elemental analysis and various physicochemical techniques like IR, 1H NMR, ESI-mass, UV-Visible, TGA analyzes and molar conductance data. All the compounds were screened for their antibacterial and antifungal activity by MIC method. Further, antioxidant activity was performed by using 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and DNA cleavage activity by Agarose Gel Electrophoresis (AGE) method.
Results: Spectral investigations suggested octahedral coordination geometrical arrangement for all the metal (II) complexes, having 1:2 stoichiometric ratio of the type [M(L)2]. The antimicrobial activity results revealed that the metal complexes were found to be more active than the free ligand. Furthermore, the DNA cleavage activity of the compounds on plasmid DNA pBR322 molecule showed moderate activity.
Conclusion: The newly synthesized ligand acts as ONO donor tridentate chelate and coordinated through an oxygen atom of carbonyl function, azomethine nitrogen and phenolic oxygen atom to the Cu, Co, Ni and Zn metal ions and form octahedral geometrical arrangement. All the complexes are found to be non-electrolytic in nature. Further, all the newly prepared compounds showed moderate biological activity.
Keywords: Indole, o-Vanillin, Transition metal complexes, Powder XRD, ESR, DNA cleavage Antimicrobial, AntioxidantÂ
Downloads
References
Singh K, Barwa MS, Tyagi P. Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with bidentate schiff bases derived by heterocyclic ketone. Eur J Med Chem 2006;41:147-53.
Bakir M, Green O, Mulder WH. Synthesis, characterization and molecular sensing behavior of [ZnCl 2 (η 3-N, N, O-dpkbh)](dpkbh= di-2-pyridyl ketone benzoyl hydrazone). J Mol Struct 2008;873:17-28.
Nagesh GY, Mruthyunjayaswamy BHM. Synthesis, characterization and biological relevance of some metal (II) complexes with oxygen, nitrogen, and oxygen (ONO) donor schiff base ligand derived from thiazole and 2-hydroxy-1-naphthaldehyde. J Mol Struct 2015;1085:198-206.
Guo Z, Sadler PJ. Medicinal inorganic chemistry. Adv Inorg Chem 2000;49:183-306.
Arion VB, Reisner E, Fremuth M, Jakupec MA, Keppler BK, Kukushkin VY, et al. Synthesis, X-ray diffraction structures, spectroscopic properties, and in vitro antitumor activity of isomeric (1H-1,2,4-Triazole)Ru(III) complexes. Inorg Chem 2003;42:6024-31.
Nagesh GY, Mahendra RK, Mruthyunjayaswamy BHM. Synthesis, characterization, thermal study and biological evaluation of Cu(II), Co(II), Ni(II) and Zn(II) complexes of Schiff base ligand containing thiazole moiety. J Mol Struct 2015;1079:423-32.
Kozlyuk N, Lopez T, Roth P, Acquaye JH. Synthesis and the characterization of Schiff-base copper complexes: reactivity with DNA, 4-NPP, and BNPP. Inorg Chim Acta 2015;428:176-84.
Vijesh AM, Isloor AM, Shetty P, Shetty P, Sudarshan S, Fun HK. New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents. Eur J Med Chem 2013;62:410-5.
Keypour H, Khanmohammadi H, Wainwright, and KP, Taylor MR. Synthesis, crystal structure, NMR and ab initio molecular orbital studies of some magnesium(II) macrocyclic Schiff-base complexes, with two 2-aminoethyl pendant arms. Inorg Chim Acta 2004;357:1283-91.
Bagihalli GB, Avaji PG, Patil SA, Badamiet PS. Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur J Med Chem 2008;43:2639-49.
Bedfort RB, Bruce DW, Frost RM, Goodby JW, Hirdb M. Iron (III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens. Chem Commun 2004;24:2822-3.
Bryliakov KP, Talsi EP, Evgenii P. Evidence for the formation of an iodosylbenzene (salen) active iron intermediate in a (salen)iron (III)-catalyzed asymmetric sulfide oxidation. Angew Chem Int Ed 2004;43:5228-30.
Gulcan M, Sonmez M. Synthesis and characterization of Cu(II), Ni(II), Co(II), Mn(II) and Cd(II) transition metal complexes of tridentate Schiff base derived from O-vanillin and N-aminopyrimidine-2-thione. Phosphorus Sulfur Silicon Relat Elem 2011;186:1962-71.
Queffelec C, Bailly F, Mbemba G, Mouscadet JF, Hayes S, Debyser Z, et al. Synthesis and antiviral properties of some polyphenols related to Salvia genus. Bioorg Med Chem Lett 2008;18:4736-40.
Lirdprapamongkol K, Kramb JP, Suthiphongchai T, Surarit R, Srisomsap C, Dannhardt G, et al. Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo. J Agric Food Chem 2009;57:3055-63.
Xuan TD, Toyama T, Fukuta M, Khanh TD, Tawata S. Chemical interaction in the invasiveness of cogongrass (Imperatacylindrica (L.) Beauv.). J Agric Food Chem 2009;57:9448-53.
Tabassum S, Amir S, Arjmand F, Pettinari C, Marchetti F, Masciocchi N, et al. Mixed-ligand Cu(II)–vanillin Schiff base complexes; effect of co-ligands on their DNA binding, DNA cleavage, SOD mimetic and anticancer activity. Eur J Med Chem 2013;60:216-32.
Nagesh GY, Mahadev DU, Mruthyunjayaswamy BHM. Mononuclear metal (II) Schiff base complexes derived from thiazole and o-vanillin moieties: synthesis, characterization, thermal behavior and biological evaluation. Int J Pharm Sci Rev Res 2015;31:190-7.
Mendham J, Denney RC, Barnes JD, Thomas MJK. Vogel’s quantitative chemical analysis. 6nd ed. Prentice Hall London; 2000.
Hiremath SP, Mruthyunjayaswamy BHM, Purohit MG. Synthesis of substituted 2-aminoindolees and 2-(2‟-Phenyl-1‟, 3‟, 4‟-oxadiazolyl) amino indoles. Indian J Chem 1978;16B:789-92.
Sadana AK, Miraza Y, Aneja KR, Prakash O. Hypervalent iodine mediated synthesis of 1-aryl/hetryl-1,2,4-triazolo[4,3-a] pyridines and 1-aryl/hetryl 5-methyl-1,2,4-triazolo[4,3-a]quinolines as antibacterial agents. Eur J Med Chem 2003;38:533-6.
Sambrook J, Fritsch EF, Maniatis T. Molecular cloning: a laboratory manual. 2nd ed. Cold Spring Harbor Laboratory, Cold Spring Harbor (NY); 1989.
Singh RP, Murthy KNC, Jayaprakasha GK. Studies on the antioxidant activity of pomegranate (Punica granatum) peel and seed extracts using in vitro models. J Agric Food Chem 2002;50:81-6.
Geary WJ. The use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord Chem Rev 1971;7:81-122.
Roy S, Mandal TN, Das K, Butcher RJ, Rheingold AL, Kar SK. Syntheses, characterization, and X-ray crystal structures of two cis-di oxovanadium (V) complexes of pyrazole-derived, Schiff-base ligands. J Coord Chem 2010;63:2146-57.
Chandra S, Gupta LK. Electronic, EPR, Magnetic and mass spectral studies of mono and homo binuclear Co(II) and Cu(II) complexes with a novel macrocyclic ligand. Spectrochim Acta Part A 2005;62:1102-6.
Dholakiya PP, Patel MN. Synthesis, spectroscopic studies, and antimicrobial activity of Mn(II), Co(II), Ni(II), Cu(II), And Cd(II) complexes with bidentate schiff bases and 2,2′-Bipyridylamine. Synth React Inorg Met–Org Chem 2002;32:753-62.
Koji A, Kanako M, Ohba M, Okawa H. Site specificity of metal ions in heteronuclear complexes derived from an End-Off†compartmental ligand. Inorg Chem 2002;41:4461-7.
Rai RA. Metal complexes of 5-(o)hydroxyphenyl-1,3,4-oxadiazole-2-thione. J Inorg Nucl Chem 1980;42:450-3.
Underhill AE, Billing DE. Calculations of the racah parameter b for nickel (II) and cobalt (II) compounds. Nature 1966;210:834-5.
Satyanarayana DN. Electronic absorption spectroscopy and related technique, University Press: India Limited, (New Delhi); 2001.
Singh DP, Kumar R, Malik V, Tyagi P. Synthesis and characterization of complexes of Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) with macrocycle 3,4,11,12-tetraoxo-1,2,5,6,9,10,13,14-octaazacyclo-hexadeca-6,8,14,16-tetraene and their biological screening. Transition Met Chem 2007;32:1051-5.
Baranwal BP, Gupta T. Synthesis and physicochemical studies on iron (II, III, III) and cobalt (II) thiocarboxylates. Synth React Inorg Met-Org Chem 2004:34:1737-54.
Rao TR, Archana P. Synthesis and spectral studies on 3d metal complexes of mesogenic Schiff base ligands. Part 1. Complexes of Nâ€(4â€Butylphenyl) salicyl aldimine. Synth React Inorg Met-Org Chem 2005;35:299-304.
Balasubramanian S, Krishnan CN. Synthesis and characterization of five-coordinate macrocyclic complexes of nickel(II) and copper(II). Polyhedron 1986;5:669-75.
Thaker BT, Tandel PK, Patel AS, Vyas CJ, Jesani MS, Patel DM. Synthesis and mesomorphic characterization of Cu(II), Ni(II) and Pd(II) complex with azomethine and chalcone as a bridging group. Indian J Chem 205;44A:265-70.
Kilveson D. Publications of daniel kivelson. J Phys Chem B 1997;101:8631-4.
Hathaway BJ, Billing DE. The electronic properties and stereochemistry of mononuclear complexes of the copper (II) ion. Coord Chem Rev 1970;5:143-207.
Mruthyunjayaswamy BHM, Nagesh GY, Ramesh M, Priyanka B, Heena B. Synthesis, characterization and antioxidant activity of Schiff base ligand and its metal complexes containing thiazole moiety. Der Pharm Chem 2015;7:556-62.
Chohan ZH, Arif M, Akhtar MA, Supuran CT. Metal-based antibacterial and antifungal agents: synthesis, characterization, and in vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds. Bioinorg Chem Appl 2006:1-13. doi.org/10.1155/ BCA/ 2006/83131. [Article in Press]
Yernale NG, Mruthyunjayaswamy BHM. Synthesis, Characterization, Antimicrobial, DNA Cleavage, and in vitro cytotoxic studies of some metal complexes of schiff base ligand derived from thiazole and quinoline moiety. Bioinorg Chem Appl 2014;314963:1-17.
Thimmaiah KN, Lioyd WD, Chandrappa GT. Stereochemistry and fungitoxicity of complexes of p-anisaldehyde thiosemicarbazone with Mn(II), Fe(II), Co(II) and Ni(II). Inorg Chem Acta 1985;106:81-5.
El-Wahab ZHA, Mashaly MM, Salman AA, El-Shetary BA, Faheim AA. Co(II), Ce(III) and UO2(VI) bis-salicylate thiosemicarbazide complexes: binary and ternary complexes, thermal studies and antimicrobial activity. Spectrochim Acta A 2004;60:2861-73.
Mahendra Raj K, Vivekanand B, Nagesh GY, Mruthyunjayaswamy BHM. Synthesis, spectroscopic characterization, electrochemistry and biological evaluation of some binuclear transition metal complexes of bicompartmental ONO donor ligands containing benzo[b]thiophene moiety. J Mol Struct 2014;1059:280-93.
Yernale NG, Mruthyunjayaswamy BHM. Metal (II) Complexes of ONO donor Schiff base ligand as a new class of bioactive compounds containing indole core: Synthesis and characterization. Int J Pharm Pharm Sci 2016;8:197-204.