Copper(II) complexes of hydroxyflavone derivatives as potential bioactive molecule to combat antioxidants: synthesis, characterization and pharmacological activities

A variety of novel copper complexes were synthesized and characterized of the formulae [Cu(L1)(OAc)], [CuL2(H2O)], [CuL3(H2O)], [CuL4(OAc)], [CuL5(H2O)] [CuL6], [CuL7], [CuL8](OAc) and [CuL9], where L1L9 represents Schiff base ligands [derived by the condensation of 5-hydroxyflavone with 4-aminoantipyrine (L1), o-aminophenol (L2), o-aminobenzoic acid (L3), o-aminothiazole (L4), thiosemicarbazide (L5), 4-aminoantipyrine-o-aminophenol (L6), 4-aminoantipyrine-o-aminobenzoic acid (L7), 4-aminoantipyrine-o-aminothiazole(L8) and 4-aminoantipyrine-thiosemicarbazide (L9)]. The spectral and magnetic results of the Cu(II) complexes exhibit square planar geometry. The DNA binding properties of copper complexes were studied by using electronic absorption spectra, viscosity and thermal denaturation experiments. The results show that the complexes were interacting with calf thymus (CT DNA). The in vitro antimicrobial activities of the investigated compounds were tested against the bacterial species and fungal species. Superoxide dismutase and antioxidant activities of the copper complexes have also been studied. Copyright © 2011 John Wiley & Sons, Ltd.

[1]  D. N. Dhar,et al.  Applications of metal complexes of Schiff bases-A review , 2009 .

[2]  J. Anacona,et al.  Synthesis, crystal structure and superoxide dismutase activity of [pyrrolidinium][Co(sulfathiazole)3(pyrrolidine)] , 2009 .

[3]  P. Chattopadhyay,et al.  Copper(II) complexes of tridentate SNO ligands: synthesis, characterization and crystal structure , 2009 .

[4]  R. Villalonga,et al.  Antioxidative properties of copper(II) complexes , 2009 .

[5]  Bao-dui Wang,et al.  Synthesis, characterization, antioxidant activity and DNA-binding studies of two rare earth(III) complexes with naringenin-2-hydroxy benzoyl hydrazone ligand. , 2008, European journal of medicinal chemistry.

[6]  H. Bhojya Naik,et al.  Binding and photocleavage of DNA by mixed ligand Co(III) and Ni(II) complexes of thiophene[2, 3-b] quinoline and phenanthrolie/bipyridine , 2008, BioMetals.

[7]  M. Kurtoglu,et al.  A new vic-dioxime ligand containing two azo substituents and its mononuclear nickel(II), cobalt(II), and copper(II) complexes; synthesis, characterization, spectroscopic and biological studies , 2008 .

[8]  S. Upreti,et al.  Schiff bases functionalized with PPh2 and SPh groups and their Ni(II) and Pd(II) complexes : Synthesis, crystal structures and applications of a Pd complex for Suzuki-Miyaura Coupling , 2008 .

[9]  S. Chaudhuri,et al.  Catalytic efficacy of Schiff-base copper(II) complexes: Synthesis, X-ray structure and olefin oxidation , 2008 .

[10]  S. Djebbar,et al.  Synthesis, characterization and antifungal activity of a series of manganese(II) and copper(II) complexes with ligands derived from reduced N,N'-O-phenylenebis(salicylideneimine). , 2008, Journal of inorganic biochemistry.

[11]  Kalv I. Hemanth Kumar,et al.  A novel one-pot oxidative cyclization of 2′-amino and 2′-hydroxychalcones employing FeCl3·6H2O–methanol. Synthesis of 4-alkoxy-2-aryl-quinolines and flavones , 2007 .

[12]  A. Aswar,et al.  Synthesis, characterization, electrical and biological studies on some bivalent metal complexes , 2007 .

[13]  Mohsen S. Asker,et al.  Synthesis, characterization and biological activity of some platinum(II) complexes with Schiff bases derived from salicylaldehyde, 2-furaldehyde and phenylenediamine. , 2007, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[14]  P. S. Subramanian,et al.  Synthesis, spectral characterization and structural investigation on some 4-aminoantipyrine containing Schiff base Cu(II) complexes and their molecular association , 2007 .

[15]  K. Reddy,et al.  Synthesis, characterization, DNA interaction and cleavage activity of new mixed ligand copper(II) complexes with heterocyclic bases , 2007 .

[16]  Wenjie Mei,et al.  Photoinduced cleavage and DNA-binding of the Ruthenium(II) polypyridyl complex [Ru(phen)2(ipbd)](ClO4)2 , 2007 .

[17]  J. Nitschke Construction, substitution, and sorting of metallo-organic structures via subcomponent self-assembly. , 2007, Accounts of chemical research.

[18]  Yong-mei Wang,et al.  Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine-derived schiff bases. , 2006, Journal of inorganic biochemistry.

[19]  F. Karatas,et al.  Antioxidant, pro‐oxidant effect of the thiosemicarbazone derivative Schiff base (4‐(1‐phenylmethylcyclobutane‐3‐yl)‐2‐(2‐hydroxybenzylidenehydrazino) thiazole) and its metal complexes on rats , 2006, Cell biochemistry and function.

[20]  P. Bednarski,et al.  Synthesis, crystal structure and biological activities of copper(II) complexes with chelating bidentate 2-substituted benzimidazole ligands. , 2006, Journal of inorganic biochemistry.

[21]  L. Ji,et al.  Synthesis, characterization and DNA-binding of novel chiral complexes Δ- and Λ-[Ru(bpy)2L]2+ (L = o-mopip and p-mopip) , 2006 .

[22]  Guanghua Zhao,et al.  Synthesis, characterization and biological activity of lanthanum(III) complexes containing 2-methylene-1,10-phenanthroline units bridged by aliphatic diamines. , 2006, Journal of inorganic biochemistry.

[23]  A. Stefankiewicz,et al.  Self‐Assembly and Characterization of Grid‐Type Copper(I), Silver(I), and Zinc(II) Complexes , 2005 .

[24]  Kim R Dunbar,et al.  Interactions of metal-metal-bonded antitumor active complexes with DNA fragments and DNA. , 2005, Accounts of chemical research.

[25]  S. Chandra,et al.  EPR, mass, IR, electronic, and magnetic studies on copper(II) complexes of semicarbazones and thiosemicarbazones. , 2005, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[26]  R. Gust,et al.  Development of cobalt(3,4-diarylsalen) complexes as tumor therapeutics. , 2004, Journal of medicinal chemistry.

[27]  A. Castiñeiras,et al.  Magnetic, spectroscopic, structural and biological properties of mixed-ligand complexes of copper(II) with N, N, N', N , N -pentamethyldiethylenetriamine and polypyridine ligands , 2004 .

[28]  T. Lu,et al.  Interaction of macrocyclic copper(II) complexes with calf thymus DNA: effects of the side chains of the ligands on the DNA-binding behaviors , 2003 .

[29]  P. Weinberger,et al.  Synthesis and thermal studies on iron(III) complexes of 4-N-(4′-antipyrylmethylidene)aminoantipyrine with varying counter ions , 2003 .

[30]  W. Kaminsky,et al.  Structural and spectral studies of di-2-pyridyl ketone 3-piperidyl- and 3-hexamethyleneiminylthiosemicarbazone and their cobalt(II), nickel(II) and copper(II) complexes , 2002 .

[31]  S. Dhar,et al.  Effect of steric encumbrance of tris(3-phenylpyrazolyl)borate on the structure and properties of ternary copper(II) complexes having N,N-donor heterocyclic bases. , 2002, Inorganic chemistry.

[32]  R. Patel,et al.  E.s.r., visible and SOD studies of imidazolate bridged Cu(2)(II,II), Cu(II)Zn(II) and Cu(II)Ni(II) complexes with pentamethyldiethylenetriamine as capping ligand: a plausible model for superoxide dismutase. , 2002, Journal of inorganic biochemistry.

[33]  O. Nusetti,et al.  Crystal Structure and Superoxide Dismutase Activity of [Cu(Imidazole)2(Quinoline)Cl2]·0.5[Cu(Imidazole)4Cl2] , 2002 .

[34]  M. Moawad,et al.  Synthesis, characterization and antimicrobial activity of cobalt(II), nickel(II)and copper(II) complexes with new asymmetrical Schiff base ligands derived from 7-formyanil-substituted diamine-sulphoxine and acetylacetone , 2001 .

[35]  D. West,et al.  Structural and spectral studies of di-2-pyridyl ketone N(4)-methyl- and N(4)-dimethylthiosemicarbazone and their metal complexes , 2001 .

[36]  P. Viswanathamurthi,et al.  Ruthenium(II) complexes containing bidentate Schiff bases and their antifungal activity , 2001 .

[37]  Shoichiro Yamada,et al.  Advancement in stereochemical aspects of Schiff base metal complexes , 1999 .

[38]  S. Lippard,et al.  Structure, Recognition, and Processing of Cisplatin-DNA Adducts. , 1999, Chemical reviews.

[39]  D. Odom,et al.  Recognition and reaction of metallointercalators with DNA. , 1999, Chemical reviews.

[40]  K. Jeyasubramanian,et al.  Spectral and redox models for blue copper proteins: copper(II) complexes of β-diketonimines from a Knoevenagel condensate , 1998 .

[41]  T. Tullius,et al.  Oxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar Moiety. , 1998, Chemical reviews.

[42]  B. Armitage Photocleavage of Nucleic Acids. , 1998, Chemical reviews.

[43]  P. Yang,et al.  Diorganotin(IV) antitumor agent. (C2H5)2SnCl2 (phen)/nucleotides aqueous and solid-state coordination chemistry and its DNA binding studies. , 1996, Journal of inorganic biochemistry.

[44]  H. Wakita,et al.  Preparation of 14-, 18-, and 22-Membered Tetraaza Macrocycles and Their Complexing Ability for Copper(II) and Nickel(II) Ions , 1990 .

[45]  Y. Anjaneyulu,et al.  Preparation, Characterization and Antimicrobial Activity Studies on Some Ternary Complexes of Cu(II) with Acetylacetone and Various Salicylic Acids , 1986 .

[46]  C. Winterbourn Hydroxyl radical production in body fluids. Roles of metal ions, ascorbate and superoxide. , 1981, The Biochemical journal.

[47]  M. Waring Structural and conformational studies on quinoxaline antibiotics in relation to the molecular basis of their interaction with DNA , 1977 .

[48]  W. Geary The use of conductivity measurements in organic solvents for the characterisation of coordination compounds , 1971 .

[49]  J. Looker,et al.  A high‐yield modification of the baker‐venkataraman rearrangement. Application to the synthesis of 5‐hydroxyflavone and 6,8‐dichloro‐5‐hydroxyflavone , 1964 .