Evaluation of a new copper(II)-curcumin complex as superoxide dismutase mimic and its free radical reactions

Free Radical Biology and Medicine

Volumn 39, Issue 6, 2005, Pages 811-822

  Barik, Atanu ^a   Mishra, Beena ^a   Shen, Liang ^b   Mohan, Hari ^a   Kadam, R M ^a   Dutta, S ^c   Zhang, Hong Yu ^b   Priyadarsini, K Indira ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

^b SHANDONG UNIVERSITY OF TECHNOLOGY   (China)

^c WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antioxidant; Cu(II) curcumin complex; Curcumin; Density functional theory; Free radicals; SOD mimics; Superoxide radicals

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ACETIC ACID; ANTIOXIDANT; AZIDE; COPPER COMPLEX; CURCUMIN; DIMETHYL SULFOXIDE; FREE RADICAL; LIPID; PHENOL DERIVATIVE; SUPEROXIDE; SUPEROXIDE DISMUTASE; XANTHINE; XANTHINE OXIDASE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE; ENZYME ACTIVITY; ENZYME ASSAY; FINITE ELEMENT ANALYSIS; INFRARED SPECTROSCOPY; LIPID PEROXIDATION; MASS SPECTROMETRY; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PULSE RADIOLYSIS; QUANTUM CHEMISTRY; STOICHIOMETRY; ULTRAVIOLET SPECTROSCOPY;

ANTIOXIDANTS; CARBON; CATALYSIS; COPPER; CURCUMIN; DIMETHYL SULFOXIDE; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; LIPID PEROXIDATION; LIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICELLES; MODELS, CHEMICAL; OCTOXYNOL; OXYGEN; PROTEIN BINDING; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, INFRARED; SUPEROXIDE DISMUTASE; SUPEROXIDES; TEMPERATURE; ULTRAVIOLET RAYS; XANTHINE; XANTHINE OXIDASE;

CURCUMA LONGA;

EID: 23744497715     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2005.05.005     Document Type: Article

References (67)

1. Turrens J.F., Mitochondrial source of reactive oxygen species under pathologic conditions. www.antioxidant.com.ar/12/Art165.htm
2. I. Fridovich Superoxide radical and superoxide dismutase Acc. Chem. Res. 5 1972 321 322
3. B. Halliwell, and J.M.C. Gutteridge Free Radicals in Biology and Medicine second ed. 1989 Clarendon Oxford
4. J.M. McCord, and I. Fridovich Superoxide dismutase: an enzymatic function for erythrocupreil (hemocuprein) J. Biol. Chem. 244 1969 6049 6055
5. G. Czapski, and S. Goldstein Requirements for SOD mimics operating in vitro to work also in vivo Free. Radic. Res. Comm. 12-13 1991 167 171
6. B.A. Omar, S.C. Flores, and J.M. McCord Superoxide dismutase: pharmacological developments and applications Adv. Pharmacol. 23 1992 109 161
7. J.M. Matés Effects of antioxidant enzymes in the molecular control of reactive oxygen species toxicology Toxicology 153 2000 83 104
8. K.M. Faulkner, R.D. Stevens, and I. Fridovich Characterization of Mn(III) complexes of linear and cyclic desferrioxamins as mimics of superoxide dismutase activity Arch. Biochem. Biophys. 310 2 1994 341 346
9. M. Casolaro, M. Chelli, M. Ginanneschi, F. Lachi, L. Messori, M. Muniz-Miranda, A.M. Papini, T. Kowalik-Jansowska, and H. Kozlowski Spectroscopic and potentiometric study of the SOD mimic system copper(II)/ acetyl-L-histidylglycine J. Inorg. Biochem. 89 2002 181 190
10. Y. Tian, Y. Fang, C. Sun, W. Shen, Q. Luo, and M. Shen Effects of copper coordinate complexes on the scavenging of reactive oxygen species Biochem. Biophys. Res. Commun. 191 1993 646 653
11. I. Batinic-Haberle, S.I. Liochev, I. Spasojevic, and I.A. Fridovich Potent superoxide dismutase mimic: manganese β-octabromo-meso-tetrakis-(N- methylpyridinium-4-yl) porphyrin Arch. Biochem. Biophys. 343 1997 225 233
12. K. Jitsukawa, M. Harata, H. Arii, H. Sakurai, and H. Masuda SOD activities of the copper complexes with tripodal polypyridylamine ligands having a hydrogen bonding site Inorg. Chim. Acta 324 2001 108 116
13. R.H. Weis, D.J. Fretland, D.A. Baron, U.S. Ryan, and D.P. Riley Manganese based superoxide dismutase mimetics inhibit neutrophil infiltration in vivo J. Biol. Chem. 271 42 1996 26149 26156
14. Z. Durackova, A.M. Mendiola, T.M. Sevilla, and A. Valent Thiohydrazone copper (II) complexes, the relationship between redox properties and superoxide dismutase mimetic activity Bioelectrochem. Bioenerget. 48 1999 109 116
15. M. Kodera, Y. Tachi, S. Hirota, K. Katayama, H. Shimakoshi, K. Kano, K. Fujisawa, Y. Moro-oka, Y. Naruta, and T. Kitagawa Superoxodicopper (II) complex oxidatively generated by reaction of Di-μ-hydroxodicopper (II) complex with hydrogen peroxide Chem. Lett. 1998 389 390
16. D.P. Riley Functional mimics of superoxide dismutase enzymes as therapeutic agents Chem. Rev. 99 1999 2573 2587
17. J.S. Valentine, and A.B. Curtis A convenient preparation of solution of superoxide and the reaction of superoxide anion with a copper (II) complex J. Am. Chem. Soc. 97 1975 224 226
18. B.B. Aggarwal, A. Kumar, and A.C. Bharti Anticancer potential of curcumin: preclinical and clinical studies Anticancer Res. 23 2003 363 398
19. J.K. Lip, and S.Y. Lin-Shiau Mechanism of cancer chemoprevention by curcumin Proc. Natl. Sci. Commun. 25 BOC (B) 2001 59 66
20. R. Motterlini, R. Foresti, R. Bassi, and C.J. Green Curcumin, an antioxidant and anti-inflammatory agents, induce heme oxygenase-1 and protects endothelial cells against oxidative stress Free Radic. Biol. Med. 28 2000 1303 1312
21. B. Mishra, K.I. Priyadarsini, M.K. Bhide, R.M. Kadam, and H. Mohan Reaction of superoxide radicals with curcumin: probable mechanisms by optical spectroscopy and EPR Free Radic. Res. 38 2004 355 362
22. K.I. Priyadarsini Free radical reactions of curcumin in membrane models Free Radic. Biol. Med. 23 6 1997 838 843
23. A.L. Cheng, C.H. Hsu, J.K. Lin, M.M. Hsu, Y.F. Ho, T.S. Shen, J.Y. Ko, J.T. Lin, B.R. Lin, M.S. Wu, H.S. Yu, S.H. Jee, G.S. Chen, T.M. Chen, C.A. Chen, M.K. Lai, Y.S. Pu, M.H. Pan, Y.J. Wang, C.C. Tsai, and C.Y. Hsieh Phase I clinical trials of curcumin: a chemopreventive agent in patients with high risk or pre-malignant lesions Anticancer Res. 21 4B 2001 2895 2900
24. L. Baum, and A. Ng Curcumin interaction with copper and iron suggest one possible mechanism of action in Alzheimer's disease animals models J. Alzh. Dis. 6 4 2004 367 377
25. J.P. Annaraj, K.M. Ponvel, P. Athappan, and S. Srinivasan Synthesis, spectra and redox behavior of copper (II) complexes of curcumin diketimines as models for copper protein Transition Metal Chem. 29 2004 722 727
26. O. Vajragupta, P. Boonchoong, and L.J. Berliner Manganese complexes of curcumin analogues: evaluation of hydroxyl radical scavenging ability, superoxide dismutase activity and stability towards hydrolysis Free Radic. Res. 38 2004 303 314
27. O. Vajragupta, P. Boonchoong, H. Watanabe, M. Tohda, N. Kummasud, and Y. Sumanont Manganese complexes of curcumin and its derivatives: evaluation for the radical scavenging ability and neuroprotective activity Free Radic. Biol. Med. 23 2003 838 843
28. Y. Sumanont, Y. Murakami, M. Tohda, O. Vajragupta, K. Matsumoto, and H. Watanabe Evaluation of the nitric oxide radical scavenging activity of manganese complexes of curcumin and its derivative Biol. Pharm. Bull. 27 2004 170 173
29. S. Dutta, A. Murugkar, and N. Gandhe Padhye. Enhanced antioxidant activities of curcumin metal conjugates Metal Based Drugs 8 2001 183 187
30. M. Borsari, E. Ferrari, R. Grandi, and M. Saladini Curcuminoids as potential new iron chelating agents: spectroscopic, polarographic and potentiometric study on their Fe(III)-complexing ability Inorg. Chim. Acta 328 2002 61 68
31. H.F. Ji, and H.Y. Zhang A new strategy to combat Alzheimer's disease. Combining radical scavenging potential with metal-protein-attenuating ability in one molecule Biorg. Med. Chem. Lett. 15 2005 21 24
32. D.T. Sawyer, and J.S. Valentine How super is superoxide? Acc. Chem. Res. 14 1981 393 400
33. S.S. Kumar, K.I. Priyadarsini, and K.B. Sainis Free radical scavenging activity of vanillin using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical Redox Rep. 7 1 2002 35 40
34. M. Wang, Y. Jin, and C.T. Ho Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2′-diphenyl-1-picryl hydrazyl radical J. Agric. Food. Chem. 47 1999 3974 3977
35. M.A.N. Razvi, T. Jayasekharan, S. Tauro, H.S. Mishra, and S.K. Mahajan Development and performance testing of a matrix assisted laser desorption ionization time-of-flight mass spectrometer 10th ISMAS Work Shop on Mass Spectrometry 2002 Bhubaneshwar India 256
36. P.C. Rakshit Physical Chemistry fifth ed. 1993 Sarat Book House Calcutta, India
37. J. Robak, and R.J. Gryglewski Flavonoids are scavengers of superoxide anions Biochem. Pharmacol. 37 5 1988 837 841
38. B. Mishra, K.I. Priyadarsini, M. Sudheer Kumar, M.K. Unnikrishnan, and H. Mohan Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol Bioorg. Med. Chem. 11 2003 2677 2685
39. B.N. Pandey, and K.P. Mishra Radiation induced oxidative damage modification by cholesterol in liposomal membrane Radiat. Phys. Chem. 54 1999 481 489
40. J.W.T. Spinks, and R.J. Woods An introduction to radiation chemistry third ed. 1990 Wiley Interscience New York 95 101
41. N. Sreejayan, M.N.A. Rao, K.I. Priyadarsini, and T.P.A. Devasagayam Inhibition of radiation induced lipid peroxidation by curcumin Int. J Pharmacol. 151 1997 127 130
42. S.M. Khopde, K.I. Priyadarsini, S.N. Guha, J.C. Satav, P. Venkatesan, and M.N.A. Rao Inhibition of radiation-induced lipid peroxidation by tetrahydrocurcumin: possible mechanisms by pulse radiolysis Biosci. Biotechnol. Biochem. 64 3 2000 503 509
43. S.N. Guha, P.N. Moorthy, K. Kishore, D.B. Naik, and K.N. Rao One electron reduction of thionine studied by pulse radiolysis Proc. Indian Acad. Sci. (Chem. Sci.) 99 1987 261 271
44. E.M. Fielden J.H. Baxendale R.D. Busi The study of Fast Processes and Transient Species by Electron Pulse Radiolysis 1984 Reidel London 59
45. G.V. Buxton, C.L. Greenstock, W.P. Helman, and A.B. Ross Critical review of rate constants for reaction of hydrated electron, hydrogen atoms and hydroxyl radicals in aqueous solution J. Phys. Chem. Ref. Data 17 1988 513 886
46. P. Neta, and R.E. Huie Rate constants for reaction of inorganic radicals in aqueous solutions J. Phys. Chem. Ref. Data. 17 1988 1027 1284
47. P. Wardman Reduction potentials of one-electron couples involving free radical in aqueous solutions J. Phys. Chem. Ref. Data 18 1989 1673 1755
48. P. Hohenberg, and W. Kohn In homogeneous electron gas Phys. Rev. 136 1964 B864 B871
49. W. Kohn, and L.J. Sham Self-consistent equations including exchange and correlation effects Phys. Rev. 140 1965 A1133 A1138
50. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation energy formula into a functional of the electron density Phys. Rev. B 37 1988 785 789
51. A.D. Becke A new mixing of Hartree-Fock and local density-functional theories J. Chem. Phys. 98 1993 1372 1377
52. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields J. Phys. Chem. 98 1994 11623 11627
53. H.F. Ji, and H.Y. Zhang A theoretical study on Cu(II)-binding modes and antioxidant activity of mammalian normal prion protein Chem. Res. Toxicol. 17 2004 471 475
54. R.E. Stratmann, G.E. Scuseria, and M.J. Frisch An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules J. Chem. Phys. 109 1998 8218 8224
55. S. Miertus, E. Scrocco, and J. Tomasi Electrostatic interaction of a solute with a continuum. A direct utilization of ab-initio molecular potentials for the prevision of solvent effects Chem. Phys. 55 1981 117 129
56. S. Miertus, and J. Tomasi Approximate evaluations of the electrostatic free energy and internal energy changes in solution processes Chem. Phys. 65 1982 239 241
57. M. Cossi, V. Barone, and J. Cammi Ab initio study of solvated molecules: a new implementation of the polarizable continuum model Chem. Phys. Lett. 255 1996 327 335
58. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03 2003 Gaussian Inc.
59. G.B. Deacon, and R.J. Phillips Relationships between the carbon-oxygen stretching frequencies of carbaxylato complexes and the type of carboxylate coordination Coord. Chem. Rev. 33 1980 227 250
60. K. Nakamoto Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, Applications in Coord. Organometallic and Bioinorganic Chem 1997 Wiley New York
61. B. Bleaney, and K.D. Bowers Anomalous paramagnetism of copper acetate Proc. R. Soc. 214 1952 451 465
62. H. Abe, and J. Shimada Paramagnetic resonance in copper acetate monohydrate J. Phys. Soc. Jpn. 12 11 1957 1255 1258
63. N. DennisChasteen, and R. LinnBelford Triplet state of a binuclear copper dl- tartarate and electron paramagnetic resonance spectra of copper tartarate Inorg. Chem. 9 1 1970 169 177
64. 2O: isolated ions and exchange-coupled pairs Phys. Rev. 150 1 1966 226 234
65. K.I. Priyadarsini, D.K. Maity, G.H. Naik, Kumar M. Sudheer, M.K. Unnikrishnan, J.G. Satav, and H. Mohan Role of phenolic O-H and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin Free Radic. Biol. Med. 35 5 2003 475 484
66. Y.M. Sun, H.Y. Zhang, D.Z. Chen, and C.B. Liu Theoretical elucidation on the antioxidant mechanism of curcumin: a DFT study Org. Lett. 4 17 2002 2909 2911
67. H.-Y. Zhang Structure-activity relationships and rational design strategies for radical- scavenging antioxidants Curr. Comput.-Aided Drug Design 1 2005 257 273