Evaluation of a new copper(II)-curcumin complex as superoxide dismutase mimic and its free radical reactions.
A mononuclear (1:1) copper complex of curcumin, a phytochemical from turmeric, was synthesized and examined for its superoxide dismutase (SOD) activity. The complex was characterized by elemental analysis, IR, NMR, UV-VIS, EPR, mass spectroscopic methods and TG-DTA, from which it was found that a copper atom is coordinated through the keto-enol group of curcumin along with one acetate group and one water molecule. Cyclic voltammetric studies of the complex showed a reversible Cu(2+)/Cu(+) couple with a potential of 0.402 V vs NHE. The Cu(II)-curcumin complex is soluble in lipids and DMSO, and insoluble in water. It scavenges superoxide radicals with a rate constant of 1.97 x 10(5) M(-1) s(-1) in DMSO determined by stopped-flow spectrometer. Subsequent to the reaction with superoxide radicals, the complex was found to be regenerated completely, indicating catalytic activity in neutralizing superoxide radicals. Complete regeneration of the complex was observed, even when the stoichiometry of superoxide radicals was 10 times more than that of the complex. This was further confirmed by EPR monitoring of superoxide radicals. The SOD mimicking activity of the complex was determined by xanthine/xanthine oxidase assay, from which it has been found that 5 microg of the complex is equivalent to 1 unit of SOD. The complex inhibits radiation-induced lipid peroxidation and shows radical-scavenging ability. It reacts with DPPH radicals with rate constant 10 times less than that of curcumin. Pulse radiolysis-induced one-electron oxidation of the complex by azide radicals in TX-100 micellar solutions produced strongly absorbing ( approximately 500 nm) phenoxyl radicals, indicating that the phenolic moiety of curcumin remained intact on complexation with copper. The results confirm that the new Cu(II)-curcumin complex possesses SOD activity, free radical neutralizing ability, and antioxidant potential. Quantum chemical calculations with density functional theory have been performed to support the experimental observations.
Barik
Atanu
A
Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India.
Mishra
Beena
B
Shen
Liang
L
Mohan
Hari
H
Kadam
R M
RM
Dutta
S
S
Zhang
Hong-Yu
HY
Priyadarsini
K Indira
KI
D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003474:Curcumin / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals; D015227:Lipid Peroxidation; D008055:Lipids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008823:Micelles; D008956:Models, Chemical; D017830:Octoxynol / Q000494:pharmacology; D010100:Oxygen / Q000737:chemistry / Q000378:metabolism; D011485:Protein Binding; D013053:Spectrophotometry; D013055:Spectrophotometry, Infrared; D013482:Superoxide Dismutase / Q000378:metabolism*; D013481:Superoxides / Q000737:chemistry; D013696:Temperature; D014466:Ultraviolet Rays; D019820:Xanthine / Q000737:chemistry; D014969:Xanthine Oxidase / Q000378:metabolism
D000975:Antioxidants; D005609:Free Radicals; D008055:Lipids; D008823:Micelles; D013481:Superoxides; D019820:Xanthine; D002244:Carbon; D003300:Copper; D017830:Octoxynol; D013482:Superoxide Dismutase; D014969:Xanthine Oxidase; D003474:Curcumin; D010100:Oxygen; D004121:Dimethyl Sulfoxide