Differential antioxidant/pro-oxidant activity of dimethoxycurcumin, a synthetic analogue of curcumin

Free Radical Research

Volumn 45, Issue 8, 2011, Pages 959-965

  Kunwar, Amit ^a   Barik, Atanu ^a   Sandur, Santosh K ^a   Priyadarsini, Indira K ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Antioxidant; Curcumin; Dimethoxycurcumin; Pro oxidant; ROS

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIOXIDANT; CURCUMIN; DIMETHOXYCURCUMIN; GENOMIC DNA; HYDROXIDE; PEROXY RADICAL; PHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; CELLULAR DISTRIBUTION; CHEMICAL REACTION; CONFERENCE PAPER; CYTOTOXICITY; DRUG DNA BINDING; FLUORESCENCE; HUMAN; LYMPHOCYTE; METHYLATION; NONHUMAN; NUCLEAR LOCALIZATION SIGNAL; TUMOR CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CURCUMIN; DRUG EVALUATION, PRECLINICAL; HUMANS; LYMPHOCYTES; OXIDATION-REDUCTION; SPLEEN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79960091795     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715762.2011.571681     Document Type: Conference Paper

References (47)

1. Aggarwal BB, Harikumar KB. Potential therapeutic effects of curcumin, the anti-infl ammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. Int J Biochem Cell Biol 2009; 41:40-59.
2. Aggarwal BB, Sundaram C, Malani N, Ichikawa H. Curcumin: the Indian solid gold. In: The molecular targets and therapeutic uses of curcumin in health and disease. New York: Springer; 2007. p 1-76.
3. Anand P, Thomas SG, Kunnumakkara AB, Sundaram C, Harikumar KB, Sung B, Tharakan ST, Misra K, Priyadarsini KI, Rajasekharan KN, Aggarwal BB. Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature. Biochem Pharmacol 2008;76:1590-1611.
4. Zhang Q, Zhong Y, Yan LN, Sun X, Gong T, Zhang ZR. Synthesis and preliminary evaluation of curcumin analogues as cytotoxic agents. Bioorg Med Chem Lett 2011;21: 1010-1014.
5. Ohtsu H, Xiao Z, Ishida J, Nagai M, Wang H-K, Itokawa H, Su C-Y, Shih C, Chiang T, Chang E, Lee Y, Tsai M-Y, Chang C, Lee K-H. Antitumor agents. 217. Curcumin analogues as novel androgen receptor antagonists with potential as anti-prostate cancer agents. J Med Chem 2002;4: 5037-5042. (Pubitemid 35278699)
6. Yodkeeree S, Chaiwangyen W, Garbisa S, Limtrakul P. Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the downregulation of MMPs and uPA. J Nutr Biochem 2009;20: 87-95.
7. Boonrao M, Yodkeeree S, Ampasavate C, Anuchapreeda S, Limtrakul P. The inhibitory effect of turmeric curcuminoids on matrix metalloproteinase-3 secretion in human invasive breast carcinoma cells. Arch Pharm Res 2010;33:989-998.
8. Sandur SK, Pandey MK, Sung B, Ahn KS, Murakami A, Sethi G, Limtrakul P, Badmaev V, Aggarwal BB. Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-infl ammatory and anti-proliferative responses through a ROS-independent mechanism. Carcinogenesis 2007;28:1765-1773. (Pubitemid 47289040)
9. Jeong GS, Oh GS, Pae HO, Jeong SO, Kim YC, Shin MK, Seo BY, Han SY, Lee HS, Jeong JG, Koh JS, Chung HT. Comparative effects of curcuminoids on endothelial heme oxygenase-1 expression: ortho-methoxy groups are essential to enhance heme oxygenase activity and protection. Exp Mol Med 2006;38:393-400. (Pubitemid 44390517)
10. Tamvakopoulos C, Dimas K, Sofi anos ZD, Hatziantoniou S, Han Z, Liu ZL, Wyche JH, Pantazis P. Metabolism and anticancer activity of the curcumin analogue, dimethoxycurcumin. Clin Cancer Res 2007;13:1269-1277. (Pubitemid 46424068)
11. Lee JW, Hong HM, Kwon DD, Pae HO, Jeong HJ. Dimethoxycurcumin, a structural analogue of curcumin, induces apoptosis in human renal carcinoma caki cells through the production of reactive oxygen species, the release of cytochrome C, and the activation of caspase-3. Korean J Urol 2010;51:870-878.
12. Halliwell B, Gutteridge JMC. Free radicals in biology and medicine. 2 nd ed. Oxford: Clarendon; 1989.
13. Priyadarsini KI, Maity DK, Naik GH, Kumar MS, Unnikrishnan MK, Satav JG, Mohan H. Role of phenolic O-H and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Radic Biol Med 2003;35:475-484. (Pubitemid 37289157)
14. Priyadarsini KI. Free radical reactions of curcumin in membrane models. Free Radic Biol Med 1997;23:838-843.
15. Singh U, Barik A, Singh BG, Priyadarsini KI. Reactions of reactive oxygen species (ROS) with curcumin analogues: structure-activity relationship. Free Radic Res 2011;45: 317-325.
16. Mishra B, Priyadarsini KI, Bhide MK, Kadam RM, Mohan H. Reactions of superoxide radicals with curcumin: probable mechanisms by optical spectroscopy and EPR. Free Radic Res 2004;38:355-362. (Pubitemid 38455859)
17. Chattopadhyay I, Biswas K, Bandyopadhyay U, Banerjee RK. Turmeric and curcumin: biological actions and medicinal applications. Curr Sci 2004;87:44-53. (Pubitemid 39403908)
18. Jayaprakasha GK, Jaganmohan Rao L, Sakariah KK. Antioxidant activities of curcumin, demethoxycurcumin and bisdemethoxycurcumin. Food Chem 2006;98:720-724.
19. Strimpakos A, Sharma RA. Curcumin: preventive and therapeutic properties in laboratory studies and clinical trials. Antiox Redox Signal 2008;10:511-549.
20. Kunwar A, Sandur SK, Krishna M, Priyadarsini KI. Curcumin mediates time and concentration dependent regulation of redox homeostasis leading to cytotoxicity in macrophage cells. Eur J Pharmacol 2009;611:8-16.
21. Banerjee A, Kunwar A, Mishra B, Priyadarsini KI. Concentration dependent antioxidant/pro-oxidant activity of curcumin studies from AAPH induced hemolysis of RBCs. Chem Biol Interact 2008;174:134-139.
22. Somparn P, Phisalaphong C, Nakornchai S, Unchern S, Morales NP. Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives. Biol Pharm Bull 2007;30:74-78. (Pubitemid 46066323)
23. Ramsewak RS, DeWitt DL, Nair MG. Cytotoxicity, antioxidant and anti-infl ammatory activities of curcumins I-III from Curcuma longa. Phytomedicine 2000;7:303-308. (Pubitemid 30618495)
24. Toda S, Ohnishi M, Kimura M, Nakashima K. Action of curcuminoids on the hemolysis and lipid peroxidation of mouse erythrocytes induced by hydrogen peroxide. J Ethnopharmacol 1988;23:105-108.
25. Sreejayan N, Rao MNA. Curcuminoids as potent inhibitors of lipid peroxidation. J Pharm Pharmacol 1994;46: 1013-1016.
26. Jeong GS, Oh GS, Pae HO, Jeong SO, Kim YC, Shin MK. Comparative effects of curcuminoids on endothelial heme oxygenase-1 expression: ortho-methoxy groups are essential to enhance heme oxygenase activity and protection. Exp Mol Med 2006;38:393-400.
27. Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R. Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett 1995;94:79-83.
28. Okada K, Wangpoengtrakul C, Tanaka T, Toyokuni S, Uchida K, Osawa T. Curcumin and especially tetrahydrocurcumin ameliorate oxidative stress-induced renal injury in mice. J Nutr 2001;131:2090-2095. (Pubitemid 32720635)
29. Khopde SM, Priyadarsini KI, Venkatesan P, Rao MNA. Free radical scavenging ability and antioxidant effi ciency of curcumin and its substituted analogue. Biophys Chem 1999;80: 85-91.
30. Chen WF, Deng SL, Zhou B, Yang L, Liu ZL. Curcumin and its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups. Free Radic Biol Med 2006;40:526-535. (Pubitemid 43139688)
31. Jeong SO, Oh GS, Ha HY, Soon Koo B, Sung Kim H, Kim YC, Kim EC, Lee KM, Chung HT, Pae HO. Dimethoxycurcumin, a synthetic curcumin analogue, induces heme oxygenase-1 expression through Nrf2 activation in RAW264.7 macrophages. J Clin Biochem Nutr 2009;44: 79-84.
32. Pae HO, Jeong SO, Kim HS, Kim SH, Song YS, Kim SK, Chai KY, Chung HT. Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NFkappaB activation in RAW264.7 macrophages activated with LPS. Mol Nutr Food Res 2008;52:1082-1091.
33. Hatcher H, Planalp R, Cho J, Torti FM, Torti SV. Curcumin: from ancient medicine to current clinical trials. Cell Mol Life Sci 2008;65:1631-1652.
34. Fang J, Lu J, Holmgren A. Thioredoxin reductase is irreversibly modifi ed by curcumin: a novel molecular mechanism for its anticancer activity. J Biol Chem 2005;280: 25284-25290. (Pubitemid 40934623)
35. Hail N, Jr. Mitochondrial reactive oxygen species affect sensitivity to curcumin-induced apoptosis. Free Radic Biol Med 2008;44:1382-1393.
36. Syng-Ai C, Kumari AL, Khar A. Effect of curcumin on normal and tumor cells: role of glutathione and bcl-2. Mol Cancer Ther 2004;3:1101-1108. (Pubitemid 39295007)
37. Lin SS, Huang HP, Yang JS, Wu JY, Hsia TC, Lin CC, Lin CW, Kuo CL, Gibson Wood W, Chung JG. DNA damage and endoplasmic reticulum stress mediated curcumin-induced cell cycle arrest and apoptosis in human lung carcinoma A-549 cells through the activation caspases cascadeand mitochondrial-dependent pathway. Cancer Lett 2008; 272: 77-90.
38. Everett PC, Meyers JA, Makkinje A, Rabbi M, Lerner A. Preclinical assessment of curcumin as a potential therapy for B-CLL. Am J Hematol 2007;82:23-30. (Pubitemid 46033388)
39. Ramachandran C, You W. Differential sensitivity of human mammary epithelial and breast carcinoma cell lines to curcumin. Breast Cancer Res Treat 1999;54:269-278. (Pubitemid 29322350)
40. Hsu Y-C, Weng H-C, Lin S, Chien YW. Curcuminoids - cellular uptake by human primary colon cancer cells as quantitated by a sensitive HPLC assay and its relation with the inhibition of proliferation and apoptosis. J Agric Food Chem 2007;55:8213-8222.
41. Kunwar A, Barik A, Mishra B, Rathinasamy K, Pandey R, Priyadarsini KI. Quantitative cellular uptake, localization and cytotoxicity of curcumin in normal and tumor cells. Biochim Biophys Acta 2008;1780:673-679.
42. Kunwar A, Barik A, Pandey R, Priyadarsini KI. Transport of liposomal and albumin loaded curcumin to living cells: an absorption and fl uorescence spectroscopic study. Biochim Biophys Acta 2006;1760:1513-1520. (Pubitemid 44428033)
43. Kunwar A, Simon E, Singh U, Chittela RK, Sharma D, Sandur SK, Priyadarsini KI. Interaction of a curcumin analogue dimethoxycurcumin with DNA. Chem Biol Drug Des 2011;77:281-287.
44. Priyadarsini KI. Photophysics, photochemistry and photobiology of curcumin: studies from organic solutions, biomimetics and living cells. J Photochem Photobiol C: Photochem Rev 2009;10:81-95.
45. Nafi si S, Adelzadeh M, Norouzi Z, Sarbolouki MN. Curcumin binding to DNA and RNA. DNA Cell Biol 2009; 28:201-208.
46. Zsila F, Bikadi Z, Simonyi M. Circular dichroism spectroscopic studies reveal pH dependent binding of curcumin in the minor groove of natural and synthetic nucleic acids. Org Biomol Chem 2004 ;2:2902-2910.
47. Senthil K, Sarojini R. Curcumin-DNA interaction studied by fourier transform infrared spectroscopy. Int J Biotech Biochem Report 2009. Available online at: http://www.thefreelibrary. com/-a0215925286, accessed date 28 December 2010 .