DNA Binding and Oxidative Cleavage Activity of Ternary (α-Lipoic Acid) Copper(II) Complex of Heterocyclic Base

REFERENCES

• (a) Sigman , D. S. , Mazumder , A. and Perrin , D. M. 1993 . Chemical nucleases . Chem. Rev. , 93 : 2295 – 2316 .
   Web of Science ®Google Scholar
• Meunier , B. 1992 . metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage . Chem. Rev. , 92 : 1411 – 1456 .
   Web of Science ®Google Scholar
• Erkkila , K. E. , Odom , D. T. and Barton , J. K. 1999 . Recognition and reaction of metallointercalators with DNA . Chem. Rev. , 99 : 2777 – 2795 .
   PubMed Web of Science ®Google Scholar
• Lahiri , D. , Majumdar , R. , Patra , A. K. and Chakravarty , A. R. 2010 . Anaerobic DNA cleavage in red light by dicopper (II) complexes on disulphide bond activation . J. Chem. Sci. , 122 : 321 – 333 .
   Web of Science ®Google Scholar
• Dong , X. , Wang , X. , Lin , M. , Sun , H. , Yang , X. and Guo , Z. 2010 . Promotive effect of the platinum moiety on the DNA cleavage activity of copper-based artificial nucleases . Inorg. Chem. , 49 : 2541 – 2549 .
   PubMed Web of Science ®Google Scholar
• Ramakrishnan , S. , Rajendiran , V. , Palaniandavar , M. , Periasamy , V. S. , Srinag , B. S. , Krishnamurthy , H. and Akbarsha , M. A. 2008 . Induction of cell death by ternary copper (II) complexes of L-tyrosine and diimines: Role of coligands on DNA binding and cleavage and anticancer activity . Inorg. Chem. , 48 : 1309 – 1322 .
   Web of Science ®Google Scholar
• Belousoff , M J. , Tjioe , L. , Graham , B. and Spiccia , L. 2008 . Synthesis, x-ray crystal structures and phosphate ester cleavage properties of bis(2-pyridylmethyl)amine copper (II) complexes with guanidinium pendant groups . Inorg. Chem. , 47 : 8641 – 8651 .
   PubMed Web of Science ®Google Scholar
• Robertazzi , A. V. , Vargiu , A. , Magistrato , P. , Ruggerone , P. , De Hoog , P. and Reedijk , J. 2009 . J. Phys. Chem. B , 113 : 10881 – 10890 .
   PubMed Web of Science ®Google Scholar
• Maheswari , P. U. , Van derSter , M. , Smulders , S. , Barends , S. , van Wezel , G. P. , Massera , C. , Roy , S. , Dulk , D. H. , Gamez , P. and Reedijk , J. 2008 . Structure, cytotoxicity and DNA-cleavage properties of the complexx [CuII(pbt)Br2] . Inorg. Chem. , 47 : 3719 – 3724 .
   PubMed Web of Science ®Google Scholar
• Lahiri , D. , Bhowmick , T. , Pathak , B. , Shameema , O. , Patra , A. K. and Ramakumar , S. 2009 . Chakravarty, A.R. Anaerobic photocleavage of dna in red light by dicopper (II) complexes of 3,3′-dithiodipropionic acid . Inorg. Chem. , 48 : 339 – 349 .
   PubMed Web of Science ®Google Scholar
• Barve , A. , Kumbhar , A. , Bhat , M. , Joshi , B. , Butcher , R. , Sonawane , U. and Joshi , R. 2009 . Mixed-ligand copper (II) maltolate complexes: synthesis, characterization, DNA binding and cleavage and cytotoxicity . Inorg. Chem. , 48 : 9120 – 9132 .
   PubMed Web of Science ®Google Scholar
• (a) Bhat , S. S. , Kumbhar , A. A. , Heptullah , H. , Khan , A. A. , Gobre , V. V. , Gejji , S. P. and Puranik , V. G. 2011 . Synthesis, electronic structure, DNA and protein binding, DNA cleavage and anticancer activity of fluorophore-labeled copper (II) complexes . Inorg. Chem. , 50 : 545
   PubMed Web of Science ®Google Scholar
• Arbuse , A. , Font , M. , Martínez , M. A. , Fontrodona , X. , Prieto , M. J. , Moreno , V. , Sala , X. and Llobet , A. 2009 . DNA-cleavage induced by new macrocyclic schiff base dinuclear Cu(I) complexes containing pyridyl pendant arms . Inorg. Chem. , 48 : 11098 – 11107 .
   PubMed Web of Science ®Google Scholar
• (a) Biewenga , G. Ph. , Haenen , G. R.M.M. and Bast , A. 1997 . “ An overview of Lipoate Chemistry ” . In Lipoic Acid in Health & Disease , Edited by: Fuchs , J. , Packer , L. and Zimmer , G . 1 – 32 . New York : Marcel Dekker .
   Google Scholar
• Raddatz , G. and Bisswanger , H. 1997 . Receptor site and stereospecifity of dihydrolipoamide dehydrogenase for R- and S-lipoamide: a molecular modeling study . J. Biotech. , 58 : 89 – 100 .
   PubMed Web of Science ®Google Scholar
• (a) Caroli , J. , Thölen , H. , Hecht , Y. , Rautureau , M. , Bognel , J. C. and Lauga , J. 1966 . Acute atrophy of the liver due to viral hepatitis treated by coenzyme A, alpha-lipoic acid, D.P.N and cocarboxylase . Rev. Med. Chir. Mal. Foie , 41 : 7 – 18 .
   PubMedGoogle Scholar
• Boysen , K. H. 1967 . Experiences with the preparation thioctacid on a psychiatric ward . Med Welt , 7 : 395 – 400 .
   PubMedGoogle Scholar
• Shie , C. S. 1965 . Studies on the antidotal effects of lipoic acid against potassium antimony tartrate . Yao Xue Bao , 12 : 249 – 253 .
   PubMedGoogle Scholar
• De Benedictis , G. and Cascudi , G. 1959 . Experimental research on a possible preventive action of thioctic acid (in acute mercuric chloride poisoning). IV . G. Clin. Med. , 40 : 1159 – 1167 .
   PubMedGoogle Scholar
• Cutolo , E. and Reduzzi , F. 1956 . Protective action of thioctic acid in potassium cyanide poisoning . Experientia , 12 : 214 – 215 .
   PubMedGoogle Scholar
• Sabat , M. and Sigel , H. 1996 . Metal ions in Biological Systems , Vol. 32 , 521 New York, and Basel : Marcel Dekker .
   Google Scholar
• Dhar , S. , Reddy , P. A.N. , Nethaji , M. , Mahadevan , S. , Saha , M. K. and Chakravarty , A. R. 2002 . 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 . Inorg. Chem. , 41 : 3469 – 3476 .
   PubMed Web of Science ®Google Scholar
• (a) Patra , A. K. , Dhar , S. , Nethaji , M. and Chakravarty , A. R. 2003 . Visible light-induced nuclease activity of a ternary mono-phenanthroline copper (II) complex containing L-methionine as a photosensitizer . Chem. Commun. , : 1562 – 156315 .
   PubMed Web of Science ®Google Scholar
• Patra , A. K. , Dhar , S. and Chakravarty , A. R. 2005 . Red-light photosensitized cleavage of DNA by (L-lysine)(phenanthroline base) copper (II) complexes . Dalton Trans. , : 2798 – 2804 .
   PubMed Web of Science ®Google Scholar
• Patra , A. K. , Nethaji , M. and Chakravarty , A. R. 2007 . Synthesis, crystal structure, DNA binding and photo-induced DNA cleavage activity of (S-methyl-L-cysteine) copper (II) complexes of heterocyclic bases . J. Inorg. Biochem. , 101 : 233 – 244 .
   PubMed Web of Science ®Google Scholar
• Perrin , D. D. , Armarego , W. L.F. and Perrin , D. R. 1980 . Purification of Laboratory Chemicals , Oxford , , England : Pergamon Press .
   Google Scholar
• (a) Venkatraman , R. , Zubkowski , J. D. and Valente , E. J. 1999 . Aqua(1, 10-phenanthroline)(L-prolinato)copper (II) nitrate monohydrate . Acta Cryst. C , 55 : 1241 – 124317 .
   Google Scholar
• Sgarabotto , P. , Bisceglie , F. , Pelosia , G. and Rahman , L. A. 1999 . Synthesis, X-ray crystal structures and characterization of copper (II)-2, 2′-bipyridyl derivatives of (4-amino)-hippuric acid and of l-proline . Polyhedron , 18 : 2505 – 2510 .
   Web of Science ®Google Scholar
• (a) LePecq , J. B. and Paoletti , C. 1967 . A fluorescent complex between ethidium bromide and nucleic acids. Physical-chemical characterization . J. Mol. Biol. , 27 : 87 – 106 .
   PubMed Web of Science ®Google Scholar
• Neidle , S. 2001 . DNA minor-groove recognition by small molecules . Nat. Prod. Rep. , 18 : 291 – 309 .
   PubMed Web of Science ®Google Scholar
• Bernadou , J. , Pratviel , G. , Bennis , F. , Girardet , M. and Meunier , B. 1989 . Potassium monopersulfate and a water-soluble manganese porphyrin complex, [Mn(TMPyP)](OAc)5, as an efficient reagent for the oxidative cleavage of DNA . Biochemistry , 28 : 7268 – 7275 .
   PubMed Web of Science ®Google Scholar
• Deacon , G. B. and Phillips , R. J. 1980 . Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination . Coord. Chem. Rev. , 33 : 227 – 250 .
   Web of Science ®Google Scholar
• Waring , M. J. 1965 . Complex formation between ethidium bromide and nucleic acids . J. Mol. Biol. , 13 : 269 – 82 .
   PubMed Web of Science ®Google Scholar
• Lee , M. , Rhodes , A. L. , Wyatt; Forrow , S. and Hartley , J. A. 1993 . GC base sequence recognition by oligoimidazolecarboxamide and C-terminus-modified analogs of distamycin deduced from circular dichroism, proton nuclear magnetic resonance and methidium propyl ethylene diamine tetraacetate-iron(II) footprinting studies . Biochemistry , 32 : 4237 – 4245 .
   PubMed Web of Science ®Google Scholar
• (a) Hirohama , T. , Kuranuki , Y. , Ebina , E. , Sugizaki , T. , Arii , H. , Chikira , M. , Selvi , P. T. and Palaniandavar , M. 2005 . Copper (II) complexes of 1,10-phenanthroline-derived ligands: studies on DNA binding properties and nuclease activity . J. Inorg. Biochem. , 99 : 1205 – 1219 .
   PubMed Web of Science ®Google Scholar
• Satyanarayana , S. , Dabrowiak , J. C. and Chaires , J. B. 1992 . Neither delta- nor lambda-tris(phenanthroline) ruthenium(II) binds to DNA by classical intercalation . Biochemistry , 31 : 9319 – 9324 .
   PubMed Web of Science ®Google Scholar
• Bailly , C. and Chaires , J. B. 1998 . Sequence-specific DNA minor groove binders. Design and synthesis of netropsin and distamycin analogues . Bioconjugate Chem. , 9 : 513 – 538 .
   PubMed Web of Science ®Google Scholar
• (a) Coll , C. A. , Frederick , M. , Wang , A. H. and Rich , A. 1987 . A bifurcated hydrogen-bonded conformation in the d(AT) base pairs of the DNA dodecamer d(CGCAAATTTGCG) and its complex with distamycin . Proc. Natl. Acad. Sci. USA , 84 : 8385 – 8389 .
   PubMed Web of Science ®Google Scholar
• Seog , K. K. and Norden , B. 1993 . Methyl green. A DNA major-groove binding drug . FEBS Lett. , 315 : 61 – 64 .
   PubMed Web of Science ®Google Scholar
• Shim , Y.-H. , Arimondo , P. B. , Laigle , A. , Garbesi , A. and Lavielle , S. 2004 . Relative DNA binding affinity of helix 3 homeodomain analogues, major groove binders, can be rapidly screened by displacement of prebound ethidium bromide. A comparative study . Org. Biomol. Chem. , 2 : 915 – 921 .
   PubMed Web of Science ®Google Scholar
• Aruoma , O. I. , Halliwell , B. and Dizdaroglu , M. 1989 . Iron ion-dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/xanthine oxidase . J. Bio. Chem. , 264 : 13024 – 13028 .
   PubMed Web of Science ®Google Scholar
• Klein , S. M. , Cohen , G. and Cederbaum , A. I. 1981 . Production of formaldehyde during metabolism of dimethyl sulfoxide by hydroxyl radical-generating systems . Biochemistry , 20 : 6006 – 6012 .
   PubMed Web of Science ®Google Scholar
• Zelenko , O. , Gallagher , J. and Sigman , D. S. 1997 . Scission of DNA with Bis(1,10-phenanthroline)copper without intramolecular hydrogen migration . Angew. Chem., Int. Ed. , 36 : 2776 – 2778 .
   Web of Science ®Google Scholar
• Sigman , D. S. 1990 . Chemical nucleases . Biochemistry , 29 : 9097 – 9105 .
   PubMed Web of Science ®Google Scholar