Cu 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

Volumn 18, Issue 35, 2012, Pages 11100-11106

  Liu, Guo Yun ^a   Yang, Jie ^a   Dai, Fang ^a   Yan, Wen Jing ^a   Wang, Qi ^a   Li, Xiu Zhuang ^a   Ding, De Jun ^a   Cao, Xiao Yan ^a   Zhou, Bo ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

antitumor agents; apoptosis; DNA damage; prooxidants; reactive oxygen species

Indexed keywords

ANTI-TUMOR AGENTS; BASE SOLUTION; CELL-CYCLE ARREST; CHEMICAL MECHANISM; DNA DAMAGES; GENERATION METHOD; HEPG2 CELLS; PLASMID DNA; POLYPHENOLIC COMPOUND; PRO-OXIDANT SYSTEMS; PRO-OXIDANTS; PROOXIDANT; REACTIVE OXYGEN SPECIES; SPECTRAL CHANGE;

DNA; OXYGEN; PHENOLS; REACTION INTERMEDIATES; SPECTROSCOPY;

CELL DEATH;

ANTINEOPLASTIC AGENT; CATECHOL; CATECHOL DERIVATIVE; CHROMAN DERIVATIVE; COPPER; DNA; OXIDIZING AGENT; REACTIVE OXYGEN METABOLITE; STILBENE DERIVATIVE;

APOPTOSIS; ARTICLE; CELL CYCLE CHECKPOINT; CELL STRAIN HEPG2; CHEMISTRY; DISORDERS OF ACID BASE BALANCE; DNA FRAGMENTATION; DRUG EFFECT; HUMAN; PLASMID; SPECTROSCOPY;

ACID-BASE IMBALANCE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CATECHOLS; CELL CYCLE CHECKPOINTS; CHROMANS; COPPER; DNA; DNA FRAGMENTATION; HEP G2 CELLS; HUMANS; OXIDANTS; PLASMIDS; REACTIVE OXYGEN SPECIES; SPECTRUM ANALYSIS; STILBENES;

EID: 84865259421     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201545     Document Type: Article

References (53)

1. B. C. Dickinson, C. J. Chang, Nat. Chem. Biol. 2011, 7, 504-511
2. E. H. Sarsour, M. G. Kumar, L. Chaudhuri, A. L. Kalen, P. C. Goswami, Antioxid. Redox Signaling 2009, 11, 2985-3011.
3. T. Finkel, M. Serrano, M. A. Blasco, Nature 2007, 448, 767-774
4. T. Finkel, Nat. Rev. Mol. Cell Biol. 2005, 6, 971-976
5. K. J. Barnham, C. L. Masters, A. I. Bush, Nat. Rev. Drug Discovery 2004, 3, 205-214
6. J. E. Klaunig, L. M. Kamendulis, Annu. Rev. Pharmacol. Toxicol. 2004, 44, 239-267
7. S. P. Hussain, L. J. Hofseth, C. C. Harris, Nat. Rev. Cancer 2003, 3, 276-285
8. T. Finkel, N. J. Holbrook, Nature 2000, 408, 239-247.
9. B. D′Autréaux, M. B. Toledano, Nat. Rev. Mol. Cell Biol. 2007, 8, 813-824
10. S. G. Rhee, Science 2006, 312, 1882-1883
11. J. R. Stone, S. Yang, Antioxid. Redox Signaling 2006, 8, 243-270
12. J. D. Lambeth, Nat. Rev. Immunol. 2004, 4, 181-189.
13. D. Trachootham, J. Alexandre, P. Huang, Nat. Rev. Drug Discovery 2009, 8, 579-591
14. A. Gupte, R. J. Mumper, Cancer Treat. Rev. 2009, 35, 32-46
15. G. T. Wondrak, Antioxid. Redox Signaling 2009, 11, 3013-3069
16. N. Hail, Jr., M. Cortes, E. N. Drake, J. E. Spallholz, Free Radical Biol. Med. 2008, 45, 97-110
17. J. Antosiewicz, W. Ziolkowski, S. Kar, A. A. Powolny, S. V. Singh, Planta Med. 2008, 74, 1570-1579
18. H. Pelicano, D. Carney, P. Huang, Drug Resist. Updates 2004, 7, 97-110
19. V. Jamier, L. A. Ba, C. Jacob, Chem. Eur. J. 2010, 16, 10920-10928.
20. S. Quideau, D. Deffieux, C. Douat-Casassus, L. Pouységu, Angew. Chem. 2011, 123, 610-646
21. Angew. Chem. Int. Ed. 2011, 50, 586-621.
22. Y. Yoshida, S. Furuta, E. Niki, Biochim. Biophys. Acta 1993, 1210, 81-88.
23. S. M. Hadi, S. H. Bhat, A. S. Azmi, S. Hanif, U. Shamim, M. F. Ullah, Semin. Cancer Biol. 2007, 17, 370-376 and references therein
24. W. A. Spencer, J. Jeyabalan, S. Kichambre, R. C. Gupta, Free Radical Biol. Med. 2011, 50, 139-147
25. N. R. Perron, C. R. García, J. R. Pinzõn, M. N. Chaur, J. L. Brumaghim, J. Inorg. Biochem. 2011, 105, 745-753
26. M. F. Ullah, U. Shamim, S. Hanif, A. S. Azmi, S. M. Hadi, Mol. Nutr. Food Res. 2009, 53, 1376-1385
27. S. Hanif, U. Shamim, M. F. Ullah, A. S. Azmi, S. H. Bhat, S. M. Hadi, Toxicology 2008, 249, 19-25
28. K. Fukuhara, M. Nagakawa, I. Nakanishi, K. Ohkubo, K. Imai, S. Urano, S. Fukuzumi, T. Ozawa, N. Ikota, M. Mochizuki, N. Miyata, H. Okuda, Bioorg. Med. Chem. 2006, 14, 1437-1443
29. M. Yoshino, M. Haneda, M. Naruse, H. H. Htay, R. Tsubochi, S. L. Qiao, W. H. Li, K. Murakami, T. Yokochi, Toxicol. in Vitro 2004, 18, 783-789
30. Y.-J. Jung, Y.-J. Surh, Free Radical Biol. Med. 2001, 30, 1407-1417
31. N. Yamashita, H. Tanemura, S. Kawanishi, Mutat. Res. 1999, 425, 107-115
32. N. Yamashita, M. Murata, S. Inoue, M. J. BurKitt, L. Miline, S. Kawanishi, Chem. Res. Toxicol. 1998, 11, 855-862
33. K. Fukuhara, N. Miyata, Bioorg. Med. Chem. Lett. 1998, 8, 3187-3192
34. F. Hayakawa, T. Kimura, T. Maeda, M. Fujita, H. Sohmiya, M. Fujii, T. Ando, Biochim. Biophys. Acta 1997, 1336, 123-131.
35. J. R. Lou, X.-X. Zhang, J. Zheng, W.-Q. Ding, Anticancer Res. 2010, 30, 3249-3256
36. H.-N. Yu, J.-J. Yin, S.-R. Shen, J. Agric. Food Chem. 2004, 52, 462-466
37. K. Satoh, T. Kadofuku, H. Sakagami, Anticancer Res. 1997, 17, 2487-2490.
38. G.-J. Fan, X.-L. Jin, Y.-P. Qian, Q. Wang, R.-T. Yang, F. Dai, J.-J. Tang, Y.-J. Shang, L.-X. Cheng, J. Yang, B. Zhou, Chem. Eur. J. 2009, 15, 12889-12899
39. L.-F. Zheng, Q.-Y. Wei, Y.-J. Cai, J.-G. Fang, B. Zhou, L. Yang, Z.-L. Liu, Free Radical Biol. Med. 2006, 41, 1807-1816.
40. J. Yang, G.-Y. Liu, D.-L. Lu, F. Dai, Y.-P. Qian, X.-L. Jin, B. Zhou, Chem. Eur. J. 2010, 16, 12808-12813.
41. A. Rahman, F. Fazal, J. Greensill, K. Ainley, J. H. Parish, S. M. Hadi, Mol. Cell. Biochem. 1992, 111, 3-9.
42. A. Krishan, J. Cell Biol. 1975, 66, 188-193.
43. F. A. Oberhammer, M. Pavelka, S. Sharma, R. Tiefenbacher, A. F. Purchio, W. Bursch, R. Schulte-Hermann, Proc. Natl. Acad. Sci. USA 1992, 89, 5408-5412.
44. A. J. Winder, H. Harris, Eur. J. Biochem. 1991, 198, 317-326
45. M. Bai, J. Huang, X. Zheng, Z. Song, M. Tang, W. Mao, L. Yuan, J. Wu, X. Weng, X. Zhou, J. Am. Chem. Soc. 2010, 132, 15321-15327.
46. F. Kader, M. Irmouli, N. Zitouni, J. P. Nicolas, M. Metche, J. Agric. Food Chem. 1999, 47, 4625-4630
47. V. Cheynier, M. Moutounet, J. Agric. Food Chem. 1992, 40, 2038-2044
48. M. Sugumaran, Arch. Biochem. Biophys. 2000, 378, 404-410.
49. G. Litwinienko, K. U. Ingold, Acc. Chem. Res. 2007, 40, 222-230.
50. A. M. Samuni, E. Y. Chuang, M. C. Krishna, W. Stein, W. DeGraff, A. Russo, J. B. Mitchell, Proc. Natl. Acad. Sci. USA 2003, 100, 5390-5395
51. M. E. Haque, M. Asanuma, Y. Higashi, I. Miyazaki, K. I. Tanaka, N. Ogawa, Biochim. Biophys. Acta 2003, 1619, 39-52
52. Y. Li, X. Sun, J. T. LaMont, A. B. Pardee, C. J. Li, Proc. Natl. Acad. Sci. USA 2003, 100, 2674-2678
53. J. J. Pink, S. M. Planchon, C. Tagliarino, M. E. Varnes, D. Siegel, D. A. Boothman, J. Biol. Chem. 2000, 275, 5416-5424.