Antimicrobial and DNA-Cleavage Studies of 22-Membered N₄ Tetraaza Macrocyclic Triazoles: Template Synthesis and Physicochemical Characterization

REFERENCES

• Champness , N. R. , Frampton , C. S. , Reid , G. and Tocher , D. A. 1994 . Mixed phospha-thia macrocyclic chemistry: synthesis and characterisation of [M(Ph2[14]aneP2S2)]2+,M = Pd, Pt and [RhCl2(Ph2[14]aneP2S2)]+. single crystal structures of [Pt(Ph2[14]aneP2S2)](PF6)2.MeNO2 and trans-[RhCl2(Ph2[14]aneP2S2)]PF6. (Ph2[14]aneP2S2 = 1,5-diphenyl-1,5-diphospha-8,12-dithiacyclotetradecane) . J. Chem. Soc., Dalton. Trans. , 20 : 3031 – 3038 .
   Google Scholar
• Fraustoda Silva , J. J.R. and Williams , R. J.P. 1991 . The Biological Chemistry of the Elements , Oxford : Clarendon Press .
   Google Scholar
• Vallarino , L. M.J. 1991 . Handbook on the Physics and Chemistry of Rare Earths , Edited by: Gschneidner , K. A. Jr. and Eyring , L. 191 – 285 . Amsterdam : Elsevier .
   Google Scholar
• Hernandez-Molina , R. and Mederos , A. 2004 . Comprehensive Coordination Chemistry II , Edited by: McCleverty , J. A. and Meyer , T. J. 12 – 28 . Amsterdam : Elsevier .
   Google Scholar
• Gerbeleu , N. V. , Arion , V. B. and Burges , J. 1999 . Template Synthesis of Macrocyclic Compounds , Weinheim : Wiely-VCH .
   Google Scholar
• Parker , D. , Dickins , R. S. , Purschmann , H. , Crossland , C. and Howard , J. A.K. 2002 . Being excited by lanthanide coordination complexes: aqua species, chirality, excited-state chemistry, and exchange dynamics . Chem. Rev. , 102 : 1977 – 2010 .
   PubMed Web of Science ®Google Scholar
• Toth , E. L. and Helm , A. E. 2004 . “ Merbach ” . In Comprehensive Coordination Chemistry II , Edited by: McCleverty , J. A. and Meyer , T. J. 35 – 49 . Amsterdam : Elsevier .
   Google Scholar
• Woods , M. , Kovacs , Z. , Zhang , S. and Sherry , A. D. 2003 . Towards the rational design of magnetic resonance imaging contrast agents: isolation of the two coordination isomers of lanthanide DOTA-type complexes . Angew. Chem. Int. Ed. , 42 : 5889 – 5892 .
   PubMed Web of Science ®Google Scholar
• Keire , D. A. , Jang , Y. H. , Li , L. , Dasgupta , S. , Goddard , W. A. III and Shively , J. E. 2001 . Chelators for radioimmunotherapy: I. NMR and ab initio calculation studies on 1,4,7,10-tetra(carboxyethyl)-1,4,7,10-tetraazacyclododecane (DO4Pr) and 1,4,7-Tris(carboxymethyl)-10-(carboxyethyl)-1,4,7,10-tetraazacyclododecane (DO3A1Pr) . Inorg. Chem. , 40 : 4310 – 4318 .
   PubMed Web of Science ®Google Scholar
• Williams , L. A.D. , Howell , R. C. , Young , R. and Kahwa , I. A. 2001 . Neuropharmological actions of some binuclear lanthanide(III) complexes . Comp. Biochem. Physiol. C , 128 : 119 – 125 .
   PubMed Web of Science ®Google Scholar
• Woods , M. , Kovacs , Z. and Sherry , A. D. 2002 . Targeted complexes of lanthanide(III) ions as Therapeutic and diagnostic pharmaceuticals . J. Supramolecular Chem. , 2 : 1 – 15 .
   Google Scholar
• Keypour , H. , Khanmohammadi , H. , Wainwright , K. P. and Taylor , M. R. 2004 . Syntheis, 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. , 357 : 1283 – 1291 .
   Web of Science ®Google Scholar
• Ma , W. , Tian , Y. , Zhang , S. , Wu , J. , Fun , H. and Chantrapromma , S. 2006 . Synthesis and characterization of 1,8-bis(ferrocenylmethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclote tradecane, a macrocyclic ligand and its complexes . Transition Met. Chem. , 31 : 97 – 102 .
   Web of Science ®Google Scholar
• Muller , J. G. , Chen , X. , Dadiz , A. C. , Rokita , S. E. and Burrows , C. J. 1993 . Macrocyclic nickel complexes in DNA recognition and oxidation . Pure. Appl. Chem. , 65 : 545 – 550 .
   Web of Science ®Google Scholar
• Liu , J. , Lu , T. B. , Deng , H. , Ji , L. N. , Qu , L. H. and Zhou , H. 2003 . Synthesis, DNA-binding and cleavage studies of macrocyclic copper(II) complexes . Transition Met. Chem. , 28 : 116 – 121 .
   Web of Science ®Google Scholar
• Kong , D. and Xie , Y. 2002 . Synthesis, structural characterization of tetraazamacrocyclic ligand, five coordinated zinc(II)complex . Inorg. Chim. Acta. , 338 : 142 – 147 .
   Web of Science ®Google Scholar
• Seto , J. , Tamura , S. , Asai , N. , Kishii , N. , Kijima , Y. and Matsuzawa , N. 1996 . Macrocyclic functional dyes: applications to optical disk media, photochemical hole burning and nonlinear optics . Pure. Appl. Chem. , 68 : 1429 – 1434 .
   Web of Science ®Google Scholar
• Chaudhary , A. , Bansal , N. , Gajraj , A. and Singh , R. V. 2003 . Antifertility, antibacterial, antifungal and percent disease incidence aspects of macrocyclic complexes of manganese(II) . J. Inorg. Biochem. , 96 : 393 – 400 .
   PubMed Web of Science ®Google Scholar
• Singh , R. V. and Chaudhary , A. 2004 . Biologically relevant tetraaza macrocyclic complexes of manganese: Synthetic, spectral, antimicrobial, antifertility and anti-inflammatory approach . J. Inorg. Biochem. , 98 : 1712 – 1721 .
   PubMed Web of Science ®Google Scholar
• Avagi , P. G. and Patil , S. A. 2008 . Synthesis, spectral, thermal, solid state d.c. electrical conductivity, fluorescence and biological studies of lanthanum(III) and thorium(IV) complexes of 24-membered macrocyclic triazoles . J. Coord. Chem. , 61 : 2570 – 2583 .
   Google Scholar
• Vogel , AIA. 1962 . A Text Book of Quantitative Inorganic Analyses , 3rd ed. , London : ELBS Longman's Green and Co. Ltd. .
   Google Scholar
• Avagi , P. G. and Patil , S. A. 2009 . Synthesis, spectral characterization and microbiological studies of Co(II), Ni(II) and Cu(II) complexes with some novel 20-membered macrocyclic hydrazino-1,2,4-triazole Schiff bases . J. Enz. Inhib. Med. Chem. , 24 : 140 – 150 .
   PubMedGoogle Scholar
• Patil , S. A. , Kamble , U. V. and Badami , P. S. 2009 . Template synthesis, characterization, in vitro antimicrobial, and DNA cleavage studies of Co(II), Ni(II), Cu(II), and Zn(II) complexes with 15-membered N2O2 diazadioxa macrocycles . Main Group Chem. , 8 : 189 – 206 .
   Web of Science ®Google Scholar
• Shakir , M. , Kumar , O. and Varkey , S. P. 1992 . 3-mercapto-1,2-propanediol and its 1-methoxy and 1-ethoxy derivatives, HSCH2CH(OH)CH2OR′ (R′ = H, CH3, C2H5), as uninegative bidentate bridging ligands: Synthesis and characterization of dimeric complexes with cobalt, copper and silver . Polyhedron , 11 : 2831 – 2836 .
   Web of Science ®Google Scholar
• Rana , V. B. , Singh , P. , Singh , D. P. and Teotia , M. P. 1982 . Trivalent chromium, manganese, iron and cobalt chelates of a tetradentate N6 macrocyclic ligand . Transition Met. Chem. , 7 : 174 – 177 .
   Web of Science ®Google Scholar
• Shakir , M. , Varkey , S. P. , Firdaus , F. and Hameed , P. S. 1994 . Template synthesis of iron(II), cobalt(II), copper(II) and zinc(II) complexes of diamidediimine macrocycles . Polyhedron , 15 : 2319 – 2325 .
   Google Scholar
• Lever , A. B.P. 1984 . Inorganic Electronic Spectroscopy , Amsterdam : Elsevier .
   Google Scholar
• Chandra , S. and Gupta , S. 2005 . Copper(II) complexes with twelve to fourteenmembered ring macrocyclic ligands . J. Ind. Chem. Soc. , 82 : 1087 – 1090 .
   Web of Science ®Google Scholar
• Shakir , M. , Chishti , H. T.N. and Chingasubam , P. 2006 . Metal ion-directed synthesis of 16-membered tetraazamacrocyclic complexes and their physico-chemical studies . Spectrochim Acta , 64 ( A ) : 512 – 517 .
   PubMedGoogle Scholar
• Bard , A.-J. and Izatt , L.-R. 2001 . Electrochemical Methods Fundamentals and Applications , 2nd ed. , New York : Wiley .
   Google Scholar
• Sadana , A. K. , Miraza , Y. , Aneja , K. R. and Prakash , O. 2003 . 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. , 38 : 533 – 536 .
   PubMed Web of Science ®Google Scholar
• Greenwood , D. , Snack , R. and Peurtherer , J. 1997 . Medical Microbiology: A Guide to Microbial Infections: Pathogensis, Immunity, Laboratory Diagnosis and Control , 15th ed. , Edinburgh, , UK : Churchill Livingstone .
   Google Scholar
• Efthimiadou , E. K. , Thomadaki , H. , Sanakis , Y. , Raptopoulou , C. P. , Katsaros , N. , Scorilas , A. , Karaliota , A. and Psomas , G. 2007 . Structure and biological properties of the copper(II) complex with the quinolone antibacterial drug N-propyl-norfloxacin and 2,2′-bipyridine . J. Inrg. Biochem. , 101 : 64 – 73 .
   PubMed Web of Science ®Google Scholar
• Chohan , Z. H. , Supuran , C. T. and Scozzafava , A. 2004 . Metalloantibiotics: Synthesis and antibacterial activity of cobalt(II), copper(II), nickel(II) and zinc(II) complexes of kefzol . J. Enz. Inhib. Med. Chem. , 19 : 79 – 84 .
   PubMed Web of Science ®Google Scholar
• Chohan , Z. H. and Praveen , M. 2001 . Synthesis, characterization, coordination and antibacterial properties of novel asymmetric 1,1′-disubstituted ferrocene-derived Schiff-base ligands and their Co(II), Cu(II) Ni(II) and Zn(II) complexes . Appl. Organomet. Chem. , 15 : 617 – 625 .
   Web of Science ®Google Scholar
• Chohan , Z. H. , Pervez , H. , Rauf , A. , Khan , K. M. and Supuran , C. T. 2004 . Isatin-derived antibacterial and antifungal compounds and their transition metal complexes . J. Enz. Inhib. Med. Chem. , 19 : 417 – 423 .
   PubMed Web of Science ®Google Scholar
• Chohan , Z. H. , Supuran , C. T. and Scozzafava , A. 2005 . Metal binding and antibacterial activity of ciprofloxacin complexes . J. Enz. Inhib. Med. Chem. , 20 : 303 – 305 .
   PubMed Web of Science ®Google Scholar
• Chohan , Z. H. , Scozzafava , A. and Supuran , C. T. 2002 . Unsymmetrical 1,1′-disubstituted ferrocenes: synthesis of Co(II), Cu(II), Ni(II) and Zn(II) chelates of ferrocenyl-1-thiadiazolo-1′-tetrazole, -1-thiadiazolo-1′-triazole and -1-tetrazolo-1′-triazole with antimicrobial properties . J. Enz. Inhib. Med. Chem. , 17 : 261 – 266 .
   PubMed Web of Science ®Google Scholar
• Chohan , Z. H. , Hassan , M. U. , Khan , K. M. and Supuran , C. T. 2005 . In-vitro antibacterial, antifungal and cytotoxic properties of sulfonamide-derived Schiff's bases and their metal complexes . J. Enz. Inhib. Med. Chem. , 20 : 183 – 188 .
   PubMed Web of Science ®Google Scholar
• Sigman , D. S. , Graham , D. R. , Aurora , V. and Stern , A. M. 1979 . Oxygen-dependent cleavage of DNA by the 1,10-phenanthroline.cuprous complex. Inhibition of escherichia coli DNA polymerase . J. Biol. Chem. , 254 : 122 – 169 .
   Google Scholar
• Umezawa , H. 1976 . Structure and action of bleomycin . Prog. Biochem. Pharmacol. , 11 : 18 – 27 .
   PubMedGoogle Scholar
• Burger , R. M. 1998 . Cleavage of nucleic acids by bleomycin . Chem. Rev. , 98 : 1153 – 1169 .
   PubMed Web of Science ®Google Scholar