METAL (II) COMPLEXES OF ONO DONOR SCHIFF BASE LIGAND AS A NEW CLASS OF BIOACTIVE COMPOUNDS CONTAINING INDOLE CORE: SYNTHESIS AND CHARACTERIZATION
Keywords:
Indole, 2-hydroxy-1-napthaldehyde, Transition metal complexes, Antimicrobial, DNA cleavage, Powder XRD, ESR, Thermal analysisAbstract
Objective: The present communication deals with the synthesis and characterization of biologically active Cu (II), Co (II), Ni (II) and Zn (II) complexes of ONO donor Schiff base ligand derived from the condensation of 5-methyl-3-phenyl-1H-indole-2-carbohydrazide with 2-hydroxy-1-napthaldehyde.
Methods: The chemical structures of the Schiff base ligand and its metal complexes were elucidated by elemental analysis and various physicochemical techniques like IR, 1H NMR, ESI mass, double beam UV-visible spectra, ESR, thermal analysis, powder XRD, conductometric and magnetic susceptibility measurements. Newly synthesized compounds were screened for their antibacterial and antifungal activities.
Results: Spectral investigations suggested octahedral coordination geometrical arrangement for Cu (II), Co (II) and Ni (II) complexes, having 1:2 stoichiometric ratio of the type [M(L)2] whereas the tetrahedral coordination geometric arrangement of Zn(II) complex, with 1:1 stoichiometric ratio of the type [Zn(L)Cl]. The antimicrobial activity results revealed that the metal complexes were found to be more active than the free ligand. Furthermore, the DNA cleavage activity was also studied using plasmid DNA pBR322 as a target molecule, and the compounds showed moderate activity.
Conclusion: A new Cu (II), Co (II), Ni (II) and Zn (II) complexes were prepared with tridentate ONO donor novel Schiff base ligand (L) and characterized by various physicochemical techniques and all the complexes are found to be non-electrolytic in nature. In addition, all the newly prepared compounds are found to be biologically active.
Â
Downloads
References
Thompson KH, Orvig C. Metal complexes in medicinal chemistry: new vistas and challenges in drug design. Dalton Trans 2006;6:761-4.
Timerbaev AR, Hartinger CG, Aleksenko SS, Keppler BK. Interactions of antitumor metallodrugs with serum proteins: advances in characterization using modern analytical methodology. Chem Rev 2006;106:2224-48.
Ming LJ. Structure and function of metallo antibioticsâ€. Med Res Rev 2003;23:697-762.
Refat MS, El-Sayed MY, Adam AMA. Cu(II), Co(II) and Ni(II) complexes of new schiff base ligand: synthesis, thermal and spectroscopic characterizations. J Mol Struct 2013;1038:62-72.
Nejo AA, Kolawole GA, Nejo AO. Synthesis, characterization, antibacterial, and thermal studies of unsymmetrical Schiff-base complexes of cobalt(II). J Coord Chem 2010;63:4398-410.
Osredkar J, Sustar N. Copper and Zinc, Biological role and significance of Copper/Zinc Imbalance. J Clin Toxicol 2011;S3:1.
Sheikh J, Juneja H, Ingle V, Ali P, Hadda TB. Synthesis and in vitro biology of Co (II), Ni (II), Cu (II) and Zinc (II) complexes of functionalized beta-diketone bearing energy buried potential antibacterial and antiviral O, O pharmacophore sites. J Saudi Chem Soc 2011;17:269-76.
Al-Quawasmeh RA, Huesca M, Nedunuri V, Peralta R, Wright J, Lee Y, et al. Potent antimicrobial activity of 3-(4, 5-diaryl-1H-imidazol-2-yl)-1H-indole derivatives against methicillin-resistant Staphylococcus aureus. Bioorg Med Chem Lett 2010;20:3518-20.
Mascal M, Modes KV, Durmus A. Concise photochemical synthesis of the antimalarial indole alkaloid decursivine. Angew Chem Int Ed Engl 2011;50:4445-6.
Mandour AH, El-Sawy ER, Shaker KH, Mustafa MA. Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of 1,8-dihydro-1-ary1-8-alkyl pyrazolo(3,4-b) indoles. Acta Pharm 2010;60:73-8.
Narayana B, Ashalatha BV, Vijayaraj KK, Fernandes J, Sarojini BK. Synthesis of some new biologically active 1,3,4-oxadiazolyl nitro indoles and a modified Fischer indole synthesis of ethyl nitro indole-2-carboxylates. Bioorg Med Chem 2005;13:4638-44.
Ty N, Dupeyre G, Chabot GG, Seguin J, Tillequin F, Scherman D, et al. Synthesis and biological evaluation of new disubstituted analogs of 6-methoxy-3-(3',4',5'-trimethoxybenzoyl)-1H-indole (BPR0L075), as potential antivascular agents. Bioorg Med Chem 2008;16:7494-503.
Zandt MCV, Jones ML, Gunn DE, Geraci LS, Jones JH, Sawicki DR, et al. Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for the treatment of chronic diabetic complications. J Med Chem 2005;48:3141-52.
Sechi M, Derudas M, Dallocchio R, Dessi A, Bacchi A, Sannia L, et al. Design and synthesis of novel indole beta-diketo acid derivatives as HIV-1 integrase inhibitors. J Med Chem 2004;47:5298-310.
Chinni SR, Li Y, Upadhyay S, Koppolu PK, Sarkar FH. Indole-3-carbinol (I3C) induced cell growth inhibition, G1 cell cycle arrest and apoptosis in prostate cancer cells. Oncogene 2001;20:2927-36.
Merwade AY, Rajur SB, Basanagoudar LD. Synthesis and antiallergic activities of 10-substituted-4-chloro-12-methyl(or phenyl)-1,2-dihydroquinoxalino[1,2-a] indoles. Indian J Chem 1990;29B:1113-7.
Fernandez AE, Monge VA. Spanish Patent 400,436†chemical abstract. Spanish Patent Trademark Office 1975;83:114205.
Sinnur KH, Siddappa S, Hiremath SP, Purohit MG. Synthesis of substituted 2-(1 ', 3', 4'-oxadiazol-2'yl) indoles. Indian J Chem 1986;25B:716-29.
Jeewoth T, Wah HLK, Bhowon MG, Ghoorohoo D, Babooram K. Synthesis and anti-bacterial/catalytic properties of Schiff bases and Schiff base metal complexes derived from 2,3-diaminopyridine. Synth React Inorg Met-Org Nano-Met Chem 2000;30:1023-38.
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 2014:1-17. doi: 10.1155/2014/314963. [Article in Press]
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.
Nagesh GY, Mahendra Raj K, 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.
Nagesh GY, Mahadev UD, Mruthyunjayaswamy BHM. Mononuclear metal (II) schiff base complexes derived from thiazole and O-Vanillin moieties: synthesis, Characterization, Thermal behaviour 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) aminoindoles. Indian J Chem 1978;16B:789-92.
Sadana AK, Mirza 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.
Roy S, Mandal TN, Das K, Butcher RJ, Rheingold AL, Kar SK. Syntheses, characterization, and X-ray crystal structures of two cis-dioxovanadium (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.
Liu H, Wang H, Gao F, Niu D, Lu Z. Self-assembly of copper (II) complexes with substituted aryl hydrazones and monodentate Nheterocycles: synthesis, structure, and properties. J Coord Chem 2007;60:2671-8.
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.
Bayoumi HA, Alaghaz AMA, Aljahdali MS. Cu(II), Ni(II), Co(II) and Cr(III) Complexes with N2O2-Chelating schiff's base ligand incorporating azo and sulfonamide moieties: spectroscopic, electrochemical behavior and thermal decomposition studies. Int J Electrochem Sci 2013;8:9399-413.
Satyanarayana DN. Electronic Absorption Spectroscopy and Related Techniques, 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. Ind 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.
Fouda MFR, Abd-el-zaher MM, Shadofa M, El Saied FA, Ayad MI, El-Tabl AS. Synthesis and characterization of transition metal complexes of N′-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methylene]thiophene-2-carbohydrazide. Trans Met Chem 2008;219:219-28.
Abdallah SM, Zayed MA, Mohamad GG. Synthesis and spectroscopic characterization of new tetradentate schiff base and its coordination compounds of NOON donor atoms and their antibacterial and antifungal activity. Arab J Chem 2010;3:103-13.
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;2006:1-13.
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.
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.
Meyer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, McLaughlin JL. Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med 1982;45:31-4.
Petering DH, Sigel H. Carcinostatic copper complexes, in Metal Ions in Biological Systems†Marcel Dekker (NY); 1980.