Synthesis, Crystal Structure, Stacking Effect and Antibacterial Studies of a Novel Quaternary Copper (II) Complex with Quinolone

The structural properties of a new copper (II) complex [Cu2(cip)2(bpy)2(pip)]·6H2O (bpy=2,2’-bipyridyl, cip=1-cyclopropyl-6-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, pip= piperazinyl anion), obtained during the synthesis of the copper complex with ciprofloxacin (cpf), has been investigated. The complex crystallizes in the triclinic system, space group P-1. The cell dimensions are: a=6.874(2) Å, b= 10.761(3) Å, c= 17.969(5) Å, α=80.071(6)°, β= 85.253(6)°, γ=79.109(6)°,V=1284.5(6) Å3, and Z=2. The Cu (II) ion displays a five-coordinate square pyramidal coordination with two nitrogen donors from bpy, the 4-keto and 3-carboxylate oxygen donors of cip, and the third nitrogen atom of the pip anion occupying the fifth site. There is a stack effect between cip ring and bpy ring from another molecule, where the stacking distance is about 3.5 Å. The results of elemental analysis and FT-IR measurement are also included. Both ligand and complex were assayed against gram-positive and gram-negative bacteria by the doubling dilutions method. The complex shows the same minimal inhibitory concentration (MIC) against S. Aureus and E. Coli bacteria as the corresponding ligand.

[1]  Wangjun Guo Synthesis, electron paramagnetic resonance properties and antibacterial studies of copper (II) complex containing norfloxacin. , 2003 .

[2]  Longwei Zhu,et al.  SYNTHESIS AND CRYSTAL STRUCTURE OF A NEW COPPER(II) COMPLEX CONTAINING FLUOROQUINOLONE , 2002 .

[3]  M. Villa,et al.  Complexes of Ni(II) and Cu(II) with ofloxacin. Crystal structure of a new Cu(II) ofloxacin complex. , 2001, Journal of inorganic biochemistry.

[4]  N. Barba-Behrens,et al.  Coordination chemistry of some biologically active ligands , 2000 .

[5]  P. Bukovec,et al.  Antibacterial tests of bismuth(III)-quinolone (ciprofloxacin, cf) compounds against Helicobacter pylori and some other bacteria. Crystal structure of (cfH2)2[Bi2Cl10].4H2O. , 1998, Journal of inorganic biochemistry.

[6]  I. Turel,et al.  Crystal structure and characterization of the bismuth(III) compound with quinolone family member (ciprofloxacin). Antibacterial study , 1997 .

[7]  T. Hambley,et al.  Copper(II) complexes of the fluoroquinolone antimicrobial ciprofloxacin. Synthesis, X-ray structural characterization, and potentiometric study. , 1996, Journal of inorganic biochemistry.

[8]  T. Hambley,et al.  Synthesis and X-ray structural characterization of an iron(III) complex of the fluoroquinolone antimicrobial ciprofloxacin, [Fe(CIP)(NTA)]3·5H2O (NTANitrilotriacetato) , 1995 .

[9]  E. Cantón,et al.  Synthesis, characterization, and crystal structure of [Cu(cinoxacinate)2].2H2O complex: a square-planar CuO4 chromophore. Antibacterial studies. , 1995, Journal of inorganic biochemistry.

[10]  L. Martínez-Aguilera,et al.  Some mixed-ligand complexes of copper(II) with drugs of the quinolone family and (NN) donors. Crystal structure of [Cu(phen)(Cnx)(H2O)]NO3 · H2O , 1993 .

[11]  T J O'Donnell,et al.  Mechanism of inhibition of DNA gyrase by quinolone antibacterials: a cooperative drug--DNA binding model. , 1989, Biochemistry.

[12]  Joseph L. Walter,et al.  The Infrared Spectra of Complex Molecules , 1982 .

[13]  S. Neidle Topics in Nucleic Acid Structure , 1981 .

[14]  D. H. Brown,et al.  Antiinflammatory effects of some copper complexes. , 1980, Journal of medicinal chemistry.

[15]  J. Sorenson COPPER CHELATES AS POSSIBLE ACTIVE FORMS OF THE ANTIARTHRITIC AGENTS , 1976 .

[16]  J. Sorenson Copper chelates as possible active forms of the antiarthritic agents. , 1976, Journal of medicinal chemistry.

[17]  A. Chakravorty,et al.  Some mixed-ligand complexes of copper(II) , 1973 .

[18]  L. J. Bellamy The infra-red spectra of complex molecules , 1962 .

[19]  G. D. Rieck,et al.  International tables for X-ray crystallography , 1962 .

[20]  P. P. Ewald,et al.  International Tables for X-Ray Crystallography , 1953, Nature.