DNa breakage induced by piceatannol and copper(II): Mechanism and anticancer properties

Oncology Letters

Volumn 3, Issue 5, 2012, Pages 1087-1094

  Li, Zhensheng ^a   Yang, Xiaozhan ^a,b   Dong, Shiwu ^a   Li, Xiaohui ^a  

^a THIRD MILITARY MEDICAL UNIVERSITY   (China)

^b CHONGQING UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Anticancer; Copper; Piceatannol; Polyphenols; Pro oxidant

Indexed keywords

CUPRIC ION; DNA; HYDROXYL RADICAL; PICEATANNOL; REACTIVE OXYGEN METABOLITE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CONTROLLED STUDY; DNA CLEAVAGE; DNA DAMAGE; DNA STRAND BREAKAGE; DRUG MECHANISM; ELECTRON TRANSPORT; FLUORESCENCE SPECTROSCOPY; GEL ELECTROPHORESIS; INFRARED SPECTROSCOPY; ULTRAVIOLET SPECTROSCOPY;

EID: 84863281269     PISSN: 17921074     EISSN: 17921082     Source Type: Journal    
DOI: 10.3892/ol.2012.597     Document Type: Article

References (42)

1. Galati G and O'Brien PJ: Potential toxicity of flavonoids and other dietary phenolics: significance for their chemopreventive and anticancer properties. Free Radic Biol Med 37: 287-303, 2004.
2. Bhat SH, Azmi AS and Hadi SM: Prooxidant DNA breakage induced by caffeic acid in human peripheral lymphocytes: involvement of endogenous copper and a putative mechanism for anticancer properties. Toxicol Appl Pharmacol 218: 249-255, 2007.
3. Ahmad A, Syed FA, Singh S and Hadi SM: Prooxidant activity of resveratrol in the presence of copper ions: mutagenicity in plasmid DNA. Toxicol Lett 15: 1-12, 2005.
4. Jung YJ and Surh YJ: Oxidative DNA damage and cytotoxicity induced by copper-stimulated redox cycling of salsolinol, a neurotoxic tetrahydroisoquinoline alkaloid. Free Radic Biol Med 30: 1407-1417, 2001.
5. Fukuhara K, Nagakawa M, Nakanishi I, Ohkubo K, Imai K, Urano S, Fukuzumi S, Ozawa T, Ikota N, Mochizuki M, Miyata N and Okuda H: Structural basis for DNA-cleaving activity of resveratrol in the presence of Cu(II). Bioorg Med Chem 14: 1437-1443, 2006.
6. Fukuhara K and Miyata N: Resveratrol as a new type of DNA-cleaving agent. Bioorg Med Chem Lett 8: 3187-3192, 1998.
7. Azmi AS, Bhat SH, Hanif S and Hadi SM: Plant polyphenols mobilize endogenous copper in human peripheral lymphocytes leading to oxidative DNA breakage: A putative mechanism for anticancer properties. FEBS Letters 580: 533-538, 2006.
8. Ebara M, Fukuda H, Hatano R, Saisho H, Nagato Y, Suzuki K, Nakajima K, Yukawa M, Kondo F, Nakayama A and Sakurai H: Relationship between copper, zinc and metallothionein in hepatocellular carcinoma and its surrounding liver parenchyma. J Hepatol 33: 415-422, 2000.
9. Hadi SM, Asad SF, Singh S and Ahmad A: Putative mechanism for anticancer and apoptosis-inducing properties of plant-derived polyphenolic compounds. IUBMB Life 50: 167-171, 2000.
10. Dipak KD and Nilanjana M: Resveratrol in cardioprotection: a therapeutic promise of alternative medicine. Mol Interv 6: 36-47, 2006.
11. Meherzia M, Ferid L, Salem E, Mohamed A and Ezzedine A: Strong cardioprotective effect of resveratrol, a red wine polyphenol, on isolated rat hearts after ischemia/reperfusion injury. Arch Biochem Biophys 457: 1-6, 2007.
12. Shyamal KG and Dipak KD: Resveratrol and chemoprevention. Cancer Letters 284: 1-6, 2009.
13. Athar M, Back JH, Tang XW, Kim KH, Kopelovich L, Bickers DR and Kim AL: Resveratrol: A review of preclinical studies for human cancer prevention. Toxicol Appl Pharmacol 224: 274-283, 2007.
14. Asensi M, Medina I, Ortega A, Corretera J, Carmen-Bano M, Obrador E and Estrela MJ: Inhibition of cancer growth by resveratrol is related to its low bioavailability. Free Radic Biol Med 33: 387-398, 2002.
15. Marier JF, Vachon P, Gritsas A, Zhang J, Moreau JP and Ducharme MP: Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model. J Pharmacol Exp Ther 302: 369-373, 2002.
16. Yu C, Shin YG, Kosmeder JW, Pezzuto JM and Van Breemen RB: Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate. Rapid Commun Mass Spectrom 17: 307-313, 2003.
17. Ferrigni NR, McLaughlin JL, Powell RG and Smith CR: Use of potato disc and brine shrimp bioassays to detect activity and isolate piceatannol as the antileukemic principle from the seeds of Euphorbia lagascae. J Nat Prod 47: 347-352, 1984.
18. Cantos E, Espin JC, Fernandez MJ, Oliva J and Tomas-Barberan FA: Postharvest UV-C-irradiated grapes as a potential source for producing stilbene-enriched red wines. J Agric Food Chem 51: 1208-1214, 2003.
19. Ku KL, Chang PS, Cheng YC and Lien CY: Production of stilbenoids from the callus of Arachis hypogaea: a novel source of the anticancer compound piceatannol. J Agric Food Chem 53: 3877-3881, 2005.
20. Matsuda H, Tomohiro N, Hiraba K, Harima S, Ko S, Matsuo K, Yoshikawa M and Kubo M: Study on anti-Oketsu activity of rhubarb II. Anti-allergic effects of stilbene components from Rhei undulati Rhizoma (dried rhizome of Rheum undulatum cultivated in Korea). Biol Pharm Bull 24: 264-267, 2001.
21. Rimando AM, Kalt W, Magee JB, Dewey J and Ballington JR: Resveratrol, pterostilbene, and piceatannol in vaccinium berries. J Agric Food Chem 52: 4713-4719, 2004.
22. Kim YH, Kwon HS, Kim DH, Cho HJ, Lee HS, Jun JG, Park JHY and Kim JK: Piceatannol, a stilbene present in grapes, attenuates dextran sulfate sodium-induced colitis. Int Immunopharmacol 8: 1695-1702, 2008.
23. Jin CY, Moonb DO, Lee KJ, Kim MO, Lee JD, Choi YH, Park YM and Kimb GY: Piceatannol attenuates lipopolysaccharide-induced NF-κB activation and NF-κB-related proinflammatory mediators in BV2 microglia. Pharmacol Res 54: 461-467, 2006.
24. Kuo PL and Hsu YL: The grape and wine constituent piceatannol inhibits proliferation of human bladder cancer cells via blocking cell cycle progression and inducing Fas/membrane bound Fas ligand-mediated apoptotic pathway. Mol Nutr Food Res 52: 408-418, 2008.
25. Kim YH, Park C, Lee JO, Kim GY, Lee WH, Choi YH and Ryu CH: Induction of apoptosis by piceatannol in human leukemic U937 cells through down-regulation of Bcl-2 and activation of caspases. Oncol Rep 19: 961-967, 2008.
26. Potter GA, Patterson LH, Wanogho E, Perry PJ, Butler PC, Ijaz T, Ruparelia KC, Lamb JH, Farmer PB, Stanley LA and Burke MD: The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br J Cancer 86: 774-778, 2002.
27. Piver B, Fer M, Vitrac X, Merillon JM, Dreano Y, Berthou F and Lucas D: Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem Pharmacol 68: 773-782, 2004.
28. Ovesná Z, Kozics K, Bader Y, Saiko P, Handler N, Erker T and Szekeres T: Antioxidant activity of resveratrol, piceatannol and 3,3',4,4',5,5'-hexahydroxy-trans-stilbene in three leukemia cell lines. Oncol Rep 16: 617-624, 2006.
29. Viola G, Acqua FD, Gabellini N, Moro S, Vedaldi D and Ihmels H: Indolo[2,3-b]-quinolizinium bromide: an efficient intercalator with DNA-photodamaging properties. Chembiochem 3: 550-558, 2002.
30. Cholody WM, Kosakowska-Cholody T, Hollingshead MG, Hariprakasha HK and Michejda CJ: A new synthetic agent with potent but selective cytotoxic activity against cancer. J Med Chem 48: 4474-4481, 2005.
31. Hotzel C, Marotto A and Pindur U: New propylamine oligopyrrole carboxamides linked to a heterocyclic or anthraquinone system: synthesis, DNA binding, topoisomerase I inhibition and cytotoxicity. Eur J Med Chem, 38: 189-197, 2003.
32. Rittich B, Španová A, Falk M, Beneš MJ and Hrubý M: Cleavage of double stranded plasmid DNA by lanthanide complexes. J Chromatogr B 800: 169-173, 2004.
33. Ahmad A, Asad SF, Singh S and Hadi SM: DNA breakage by resveratrol and Cu(II): reaction mechanism and bacteriophage inactivation. Cancer Lett 154: 29-37, 2000.
34. Selvakumar B, Rajendiran V, Uma Maheswari P, Stoeckli-Evans H and Palaniandavar M: Structures, spectra, and DNA-binding properties of mixed ligand copper(II) complexes of iminodiacetic acid: The novel role of diimine co-ligands on DNA conformation and hydrolytic and oxidative double strand DNA cleavage. J Inorg Biochem 100: 316-330, 2006.
35. Zheng LF, Wei QY, Cai YJ, Fang JG, Zhou B, Yang L and Liu ZL: DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu (II) ions: mechanism and structure-activity relationship. Free Radic Biol Med 41: 1807-1816, 2006.
36. Tu C, Wu XF, Liu Q, Wang XY, Xu Q and Guo ZJ: Crystal structure, DNA-binding ability and cytotoxic activity of platinum(II)2,2'-dipyridylamine complexes. Inorg Chim Acta 357: 95-102, 2004.
37. Samuni AM, Chuang EY, Krishna MC, Stein W, DeGraff W, Russo A and Mitchell JB: Semiquinone radical intermediate in catecholic estrogen-mediated cytotoxic and mutagenesis: chemoprevention strategies with antioxidants. Proc Natl Acad Sci USA 100: 5390-5395, 2003.
38. Haque ME, Asanuma M, Higashi Y, Miyazaki I, Tanaka KI and Ogawa N: Apoptosis-inducing neurotoxicity of dopamine and its metabolites via reactive quinone generation in neuroblastoma cells. Biochim Biophys Acta 1619: 39-52, 2003.
39. Azmi AS, Bhat SH and Hadi SM: Resveratrol-Cu(II) induced DNA breakage in human peripheral lymphocytes: Implications for anticancer properties. FEBS Lett 579: 3131-3135, 2005.
40. Paola S and Riccardo G: Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. J Nutr Biochem 16: 449-466, 2005.
41. Yoshino M, Haneda M, Naruse M, Htay HH, Tsubouchi R, Qiao SL, Li WH, Murakami K and Yakochi T: Prooxidant activity of curcumin; copper-dependant formation of 8-hydroxy-20-deoxyguanosine in DNA and induction of apoptotic cell death. Toxicol In Vitro 16: 783-788, 2004.
42. Braña MF and Ramos A: Naphthalimides as anti-cancer agents: synthesis and biological activity. Curr Med Chem Anticancer Agents 1: 237-255, 2001.