Ortho-dihydroxychalcones as cupric ion-dependent prooxidants: Activity and mechanisms

Food Chemistry

Volumn 141, Issue 2, 2013, Pages 1259-1266

  Wang, Qi ^a   Qian, Yi Ping ^a   Dai, Fang ^a   Lu, Dong Liang ^a   Yan, Wen Jing ^a   Chen, Yang ^b   Zhou, Bo ^a  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Apoptosis; Copper; DNA damage; Hydroxychalcone; Mechanism; Prooxidant; Reactive oxygen species

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; CELL DEATH; CHEMICAL BONDS; COPPER; DNA; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; MECHANISMS;

CHEMICAL MECHANISM; DNA CLEAVING ACTIVITY; DNA DAMAGES; ELECTRON TRANSFER; HYDROXYCHALCONE; LOW CONCENTRATIONS; PROOXIDANT; REACTIVE OXYGEN SPECIES;

IONS;

3',4' DIHYDROXYCHALCONE; 3,4 DIHYDROXYCHALCONE; 3,4,3',4' TETRAHYDROXYCHALCONE; ANTIOXIDANT; CHALCONE DERIVATIVE; CUPRIC ION; PLASMID DNA; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CELL STRAIN HEPG2; CELL VIABILITY; CONTROLLED STUDY; COVALENT BOND; DNA DAMAGE; DNA STRAND BREAKAGE; ELECTRON TRANSPORT; HUMAN; HUMAN CELL; OXIDATION; OXIDATION REDUCTION POTENTIAL; PH; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET SPECTROSCOPY;

EID: 84878384095     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.04.022     Document Type: Article

References (46)

1. Alexandre, J., Hu, Y., Lu, W., Pelicano, H., & Huang, P. (2007). Novel action of paclitaxel against cancer cells: bystander effect mediated by reactive oxy (Pubitemid 46762129)
2. Antosiewicz, J., Ziolkowski, W., Kar, S., Powolny, A. A., & Singh, S. V. (2008). Role of reactive oxygen intermediates in cellular responses to dietary cancer chemopreventive agents. Planta Medica, 74, 1570-1579.
3. Chen, Q., Espey, M. G., Sun, A. Y., Lee, J.-H., Krishna, M. C., Shacter, E., et al. (2007). Ascorbate in pharmacologic concentrations selectively generates ascorbate radical and hydrogen peroxide in extracellular fluid in vivo. Proceedings of the National Academy of Sciences of the United States of America, 104, 8749-8754. (Pubitemid 47175383)
4. Chen, Q., Espey, M. G., Sun, A. Y., Pooput, C., Kirk, K. L., Krishna, M. C., et al. (2008). Pharmacologic doses of ascorbate act as a prooxidant and decrease growth of aggressive tumor xenografts in mice. Proceedings of the National Academy of Sciences of the United States of America, 105, 11105-11109.
5. D'Autréaux, B., & Toledano, M. B. (2007). ROS as signalling molecules: mechanisms that generate specificity in ROS homeostasis. Nature Reviews Molecular Cell Biology, 8, 813-824. (Pubitemid 47462134)
6. 13C NMR spectroscopic analyses. Phytochemistry, 59, 429-433. (Pubitemid 34202562)
7. Dickinson, B. C., & Chang, C. J. (2011). Chemistry and biology of reactive oxygen species in signaling or stress responses. Nature Chemical Biology, 7, 504-511.
8. II ions: mechanism, structure-activity relationship, and biological implications. Chemistry-A European Journal, 15, 12889-12899.
9. Gupte, A., & Mumper, R. J. (2009). Elevated copper and oxidative stress in cancer cells as a target for cancer treatment. Cancer Treatment Reviews, 35, 32-46.
10. Hadi, S. M., Bhat, S. H., Azmi, A. S., Hanif, S., Shamim, U., & Ullah, M. F. (2007). Oxidative breakage of cellular DNA by plant polyphenols: a putative mechanism for anticancer properties. Seminars in Cancer Biology, 17, 370-376. (Pubitemid 47369169)
11. Hail, N., Jr., Cortes, M., Drake, E. N., & Spallholz, J. E. (2008). Cancer chemoprevention: a radical perspective. Free Radical Biology & Medicine, 45, 97-110.
12. Hajji, H. E., Nkhili, E., Tomao, V., & Dangles, O. (2006). Interactions of quercetin with iron and copper ions: complexation and autoxidation. Free Radical Research, 40, 303-320. (Pubitemid 43245446)
13. Hayakawa, F., Kimura, T., Hoshino, N., & Ando, T. (1999). DNA cleavage activities of (-)-epigallocatechin, (-)-epicatechin, (+)-catechin, and (-)-epigallocatechin gallate with various kind of metal ions. Bioscience, Biotechnology, and Biochemistry, 63, 1654-1656. (Pubitemid 129555166)
14. Hider, R. C., Liu, Z. D., & Khodr, H. H. (2001). Metal chelation of polyphenols. Methods in Enzymology, 335, 190-203. (Pubitemid 32507238)
15. Jamier, V., Ba, L. A., & Jacob, C. (2010). Selenium-and tellurium-containing multifunctional redox agents as biochemical redox modulators with selective cytotoxicity. Chemistry-A European Journal, 16, 10920-10928.
16. Jing, Y., Dai, J., Chalmers-Redman, R. M., Tatton, W. G., & Waxman, S. (1999). Arsenic trioxide selectively induces acute promyelocytic leukemia cell apoptosis via a hydrogen peroxide-dependent pathway. Blood, 94, 2102-2111. (Pubitemid 29430427)
17. Khan, M. M. T., & Martell, A. E. (1967). Metal ion and metal chelate catalyzed oxidation of ascorbic acid by molecular oxygen. I. Cupric and ferric ion catalyzed oxidation. Journal of the American Chemical Society, 89, 4176-4185.
18. Klinke, P., & Gibian, H. (1961). Über Chalkone. Chemische Berichte, 94, 26-38.
19. Li, A. S.-H., Bandy, B., Tsang, S.-S., & Davison, A. J. (2000). DNA-breaking versus DNA protecting activity of four phenolic compounds in vitro. Free Radical Research, 33, 551-566. (Pubitemid 32103697)
20. II ions and the stilbene-chroman hybrid with a catechol moiety synergistically induced DNA damage, and cell cycle arrest and apoptosis of HepG2 cells: an interesting acid/base-promoted prooxidant reaction. Chemistry-A European Journal, 18, 11100-11106.
21. Litwinienko, G., & Ingold, K. U. (2007). Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Accounts of Chemical Research, 40, 222-230.
22. Lou, J. R., Zhang, X.-X., Zheng, J., & Ding, W.-Q. (2010). Transient metals enhance cytotoxicity of curcumin: potential involvement of the NF-κB and mTOR signaling pathways. Anticancer Research, 30, 3249-3255.
23. Martín-Cordero, C., León-González, A. J., Calderón-Montaño, J. M., Burgos-Morón, E., & López-Lázaro, M. (2012). Pro-oxidant natural products as anticancer agents. Current Drug Targets, 13, 1006-1028.
24. Mira, L., Fernandez, M. T., Santos, M., Rocha, R., Floréncio, M. H., & Jennings, K. R. (2002). Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity. Free Radical Research, 36, 1199-1208. (Pubitemid 35230240)
25. Mochizuki, M., Yamazaki, S., Kano, K., & Ikeda, T. (2002). Kinetic analysis and mechanistic aspects of autoxidation of catechins. Biochimica et Biophysica Acta, 1569, 35-44. (Pubitemid 34165555)
26. Muir, S. R., Collins, G. J., Robinson, S., Hughes, S., Bovy, A., & Ric De Vos, C. H. (2001). Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols. Nature Biotechnology, 19, 470-474. (Pubitemid 32428292)
27. Oldoni, T. L. C., Cabral, I. S. R., Regitano d'Arce, M. A. B., Rosalen, P. L., Ikegaki, M., Nascimento, A. M., et al. (2011). Isolation and analysis of bioactive isoflavonoids and chalcone from a new type of Brazilian propolis. Separation and Purification Technology, 77, 208-213.
28. Perron, N. R., García, C. R., Pinzón, J. R., Chaur, M. N., & Brumaghim, J. L. (2011). Antioxidant and prooxidant effects of polyphenol compounds on coppermediated DNA damage. Journal of Inorganic Biochemistry, 105, 745-753.
29. Policastro, L. L., Ibañez, I. L., Notcovich, C., Duran, H. A., & Podhajcer, O. L. (2012). The tumor microenvironment: characterization, redox considerations, and novel approaches for reactive oxygen species-targeted gene therapy. Antioxidants & Redox Signaling. http://dx.doi.org/10.1089/ars. 2011.4367.
30. Prasad, N. R., Jeyanthimala, K., & Ramachandran, S. (2009). Caffeic acid modulates ultraviolet radiation-B induced oxidative damage in human blood lymphocytes. Journal of Photochemistry and Photobiology B: Biology, 95, 196-203.
31. Qian, Y.-P., Shang, Y.-J., Teng, Q.-F., Chang, J., Fan, G.-J., Wei, X., et al. (2011). Hydroxychalcones as potent antioxidants: structure-activity relationship analysis and mechanism considerations. Food Chemistry, 126, 241-248.
32. Quideau, S., Deffieux, D., Douat-Casassus, C., & Pouységu, L. (2011). Plant polyphenols: chemical properties, biological activities, and synthesis. Angewandte Chemie International Edition, 50, 586-621.
33. Samuni, A. M., Chuang, E. Y., Krishna, M. C., Stein, W., DeGraff, W., Russo, A., et al. (2003). Semiquinone radical intermediate in catecholic estrogen-mediated cytotoxicity and mutagenesis: chemoprevention strategies with antioxidants. Proceedings of the National Academy of Sciences of the United States of America, 100, 5390-5395. (Pubitemid 36542715)
34. Satoh, K., Takada, M., Kadofuku, T., & Sakagami, H. (1997). Copper, but not iron, enhances apoptosis-inducing activity of antioxidants. Anticancer Research, 17, 2487-2490. (Pubitemid 27352641)
35. Simizu, S., Umezawa, K., & Imoto, M. (1998). Requirement of caspase-3(-like) protease-mediated hydrogen peroxide production for apoptosis induced by various anticancer drugs. The Journal of Biological Chemistry, 273, 26900-26907. (Pubitemid 28471710)
36. Singh, N. P., McCoy, M. T., Tice, R. R., & Schneider, E. L. (1988). A simple technique for quantitation of low levels of DNA damage in individual cells. Experimental Cell Research, 175, 184-191.
37. Tamboli, V. F., Re, N., Coletti, C., Defant, A., Mancini, I., & Tosia, P. (2012). A joint experimental and theoretical investigation on the oxidative coupling of resveratrol induced by copper and iron ions. International Journal of Mass Spectrometry, 319-320, 55-63.
38. Tatsumi, H., Nakase, H., Kano, K., & Ikeda, T. (1998). Mechanistic study of the autoxidation of reduced flavin and quinone compounds. Journal of Electroanalytical Chemistry, 443, 236-242. (Pubitemid 128391927)
39. Trachootham, D., Alexandre, J., & Huang, P. (2009). Targeting cancer cells by ROS mediated mechanisms: a radical therapeutic approach? Nature Reviews Drug Discovery, 8, 579-591.
40. Ullah, M. F., Shamim, U., Hanif, S., Azmi, A. S., & Hadi, S. M. (2009). Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A. Molecular Nutrition & Food Research, 53, 1376-1385.
41. Winterbourn, C. C. (2008). Reconciling the chemistry and biology of reactive oxygen species. Nature Chemical Biology, 4, 278-286. (Pubitemid 351550893)
42. Wondrak, G. T. (2009). Redox-directed cancer therapeutics: molecular mechanisms and opportunities. Antioxidants & Redox Signaling, 11, 3013-3069.
43. Yamamoto, T., Yoshimura, M., Yamaguchi, F., Kouchi, T., Tsuji, R., Saito, M., et al. (2004). Anti-allergic activity of naringenin chalcone from a tomato skin extract. Bioscience Biotechnology Biochemistry, 68, 1706-1711. (Pubitemid 39260301)
44. Yang, J., Liu, G.-Y., Lu, D.-L., Dai, F., Qian, Y.-P., Jin, X.-L., et al. (2010). Hybridincreased radical-scavenging activity of resveratrol derivatives by incorporating a chroman moiety of vitamin E. Chemistry-A European Journal, 16, 12808-12813.
45. Yu, H.-N., Yin, J.-J., & Shen, S.-R. (2004). Growth inhibition of prostate cancer cells by epigallocatechin gallate in the presence of Cu2+. Journal of Agricultural and Food Chemistry, 52, 462-466.
46. Zheng, L.-F., Wei, Q.-Y., Cai, Y.-J., Fang, J.-G., Zhou, B., Yang, L., et al. (2006). DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu(II) ions: mechanism and structure-activity relationship. Free Radical Biology & Medicine, 41, 1807-1816. (Pubitemid 44839142)