Novel pathways associated with quinone-induced stress in breast cancer cells

Drug Metabolism Reviews

Volumn 38, Issue 4, 2006, Pages 601-613

  Benz, Christopher C ^a   Atsriku, Christian ^a   Yau, Christina ^a   Britton, David ^a   Schilling, Birgit ^a   Gibson, Bradford W ^a   Baldwin, Michael A ^a   Scott, Gary K ^a  

^a BUCK INSTITUTE FOR RESEARCH ON AGING   (United States)

Author keywords

Arylating quinines; Breast cancer; Estrogen receptor; Menadione; Oxidative stress

Indexed keywords

CYTOKERATIN 8; CYTOSKELETON PROTEIN; ESTROGEN RECEPTOR; HISTONE H3; MENADIONE; MITOGEN ACTIVATED PROTEIN KINASE; QUINONE DERIVATIVE; THIOL DERIVATIVE; TRANSCRIPTION FACTOR;

ANTIBODY AFFINITY; ARYLATION; BREAST CANCER; BREAST EPITHELIUM; CANCER CELL; CONFERENCE PAPER; GENE EXPRESSION; GENE TRANSLOCATION; MASS SPECTROMETRY; NONHUMAN; OXIDATIVE STRESS; PROTEIN BINDING; PROTEIN DNA BINDING; PROTEIN DOMAIN; PROTEIN EXPRESSION; PROTEIN MODIFICATION; PROTEIN PHOSPHORYLATION;

AMINO ACID SEQUENCE; BREAST NEOPLASMS; CELL LINE, TUMOR; DNA, NEOPLASM; FEMALE; HUMANS; MOLECULAR SEQUENCE DATA; OXIDATIVE STRESS; QUINONES; SIGNAL TRANSDUCTION;

EID: 33845433862     PISSN: 03602532     EISSN: 10979883     Source Type: Journal    
DOI: 10.1080/03602530600959391     Document Type: Conference Paper

References (48)

1. Abdelmohsen. K., Gerber, P. A., von Montfort, C., Sies H., Klotz, L. O. (2003). Epidermal growth factor receptor is a common mediator of quinone-induced signaling leading to phosphorylation of connexin-43: Role of glutathione and tyrosine phosphatases. J. Biol. Chem. 278:38360-38367.
2. Atsriku, C., Scott, G. K., Benz, C. C., Baldwin, M. A. (2005). Reactivity of zinc finger cysteines: Chemical modifications within labile zinc fingers in estrogen receptor. J. Am. Soc. Mass. Spectrom. 16: 2017-2026.
3. Baldwin, M. A., Benz, C. C. (2002). Redox control of zinc finger proteins. Methods Enzymology 353:54-69.
4. Barchowsky, A., Williams, M. E., Benz, C. C., Chepenik, K. P. (1994). Oxidant-sensitive protein phoshorylation in endothelial cells. Free Radic. Biol. Med. 16: 771-777.
5. Benz, C. C. (2004). ErbB2/HER2 and other molecular pathways in estrogen receptor-positive breast cancer: impact on endocrine resistance and clinical outcome. In Advances in Endocrine Therapy of Breast Cancer, edited by J. N. Ingle and M. Dowsett, New York: Marcel Dekker, pp. 229-247.
6. Benz, C. C., Clarke, C. A., Moore, D. H. (2003). Geographic excess of estrogen receptor-positive breast cancer. Cancer Epidemiol. Biomarkers Prev. 12:1523-1527.
7. Bhat, H. K., Calaf, G., Hei, T. K., Loya, T., Vadgama, J. V. (2003). Proc. Natl. Acad. Sci. (USA), 100:3913-3918.
8. Bolton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G., Monks, T. J. (2000). Role in quinones in toxicology. Chem. Res. Toxicol. 13:135-160.
9. Bolton, J. L., Yu, L., Thatcher, G. R. J. (2004). Quinoids formed from estrogens and antiestrogens. Meth. Enzymol. 378:110-123.
10. Choi, B. K., Choi, C. H., Oh, H. L., Kim, Y. K. (2004). Role of ERK activation in cisplatin-induced apoptosis in A172 human glioma cells. Neurotoxicol. 25:915-924.
11. Clemons, M., Goss, P. (2001). Estrogen and the risk of breast cancer. New Engl. J. Med. 344:276-285.
12. Cross, J. V., Deak, J., Rich, E. A., Qian, Y., Lewis, M., Parrott, L. A., Mochida, K., Gustafson D., Sol, S. V., Templeton, D. J. (1999). Quinone reductase inhibitors block SAPK/JNK and NFκB pathways and potentiate apoptosis. J. Biol. Chem. 274:31150-31154.
13. De Bernardo, S., Canals, S., Casarejos, M. J., Solano, R. M., Menendez, J., Mena, M. A. (2004). Role of extracellular signal-regulated protein kinase in neuronal cell death induced by glutathione depletion in neuron/glia mesencephalic cultures. J. Neurochem. 91:667-682.
14. Dinkova-Kostova, A. T., Holtzclaw, W. D., Kensler, T. W. (2005). The role of Keap1 in cellular protective responses. Chem. Res. Toxicol. 18:1779-1791.
15. Dong, J., Everitt, J. I., Lau, S. S., Monks, T. J. (2004). Induction of ERK1/2 and histone H3 phosphorylation within the outer stripe of the outer medullar of the Eker rat by 2,3,4-tris-(glutathione-S-yl)hydroquinone. Toxicol. Sci. 80:350-357.
16. Fink, S. L. Cookson, B. T. 2005. Apoptosis, pyroptosis, and necrosis: mechanistic description of dead and dying eukaryotic cells. Infect. Immun. 73:1907-1916.
17. Finkel, T., Holbrook, N. J. (2000). Oxidants, oxidative stress and the biology of ageing. Nature 408:239-247.
18. Forman, H. J., Torres, M., Fukuto, J. (2002). Redox signaling. Mol. Cell. Biochem. 234/235:49-62.
19. Habu, D., Shiomi, S., Tamori, A., Takeda, T., Tanaka, T., Kubo, S., Nishiguchi S. (2004). Role of vitamin K2 in the development of hepatocellular carcinoma in women with viral cirrhosis of the liver. JAMA 292:358-361.
20. He, T., Stepulak, A., Holmstrom, T. H., Omary, M. B., Eriksson, J. E. (2002). The intermediate filament protein keratin 8 is a novel cytoplasmic substrate for c-jun N-terminal kinase. J. Biol. Chem. 277:10767-10774.
21. Klaunig, J. E. Kamendulis, L. M. (2004). The role of oxidative stress in carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 44:239-267.
22. Klotz, L. O., Patak, P., Ale-Agha, N., Bucheczyk, D. P., Abdelmohsen, K., Gerber, P. A., von Montfort, C., Sies, H. (2002). 2-Methyl-1,4-naphthoquinone, vitamin K3, decreases gap-junctional intercellular communication via activation of the epidermal growth factor receptor/extracellular signal-regulated kinase cascade. Cancer Res. 62:4922-4928.
23. Ku, N. O., Azhar, S., Omary, M. B. (2002). Keratin 8 phosphorylation by p38 kinase regulates cellular keratin filament reorganization: modulation by a keratin 1-like disease causing mutation. J. Biol. Chem. 277:10775-10782.
24. Kuriyama, S., Hitomi, M., Yoshiji, H., Nonomura, T., Tsujimoto, T., Mitoro, A., Akahane, T., Ogawa, M., Nakai, S., Deguchi, A., Masaki, T., Uchida, N. (2005). Vitamins K2, K3 and K5 exert in vivo antitumor effects on hepatocellular carcinoma by regulating the expression of G1 phase-related cell cycle molecules. Int. J. Oncol. 27:505-511.
25. Liang, X., Lu, B., Scott, G. K., Chang, C.-H., Baldwin, M. A., Benz, C. C. (1998). Oxidant stress impaired DNA-binding of estrogen receptor from human breast cancer. Mol. Cell. Endocrinol. 146:151-161.
26. Liao, J., Ku, N. O., Omary, M. B. (1997). Stress, apoptosis and mitosis induce phosphorylation of human keratin 8 at Ser-73 in tissues and cultured cells. J. Biol. Chem. 272:17565-17573.
27. Liehr, J. G. (2002). Breast carcinogensis and its prevention by inhibition of estrogen genotoxity. In Endocrine Therapy in Breast Cancer, (W. R. Miller, J. N. Ingle, eds.) New York: Marcel Dekker, pp. 287-301.
28. Lubec, G. (1996). The hydroxyl radical: from chemistry to human disease. J. Investig. Med. 44:324-346.
29. Meza, J. E., Scott, G. K., Benz, C. C., and Baldwin, M. A. (2003). Essential cysteine-alkylation strategies to monitor structurally altered estrogen receptor as found in oxidant-stress breast cancers. Analytical Biochem. 320:21-31.
30. Osada, S., Saji, S., Osada, K. (2001). Critical role of extracellular signal-regulated kinase phosphorylation on menadione (vitamin K3) induced growth inhibition. Cancer 91:1156-1165.
31. Parmar, H., Melov, S., Samper, E., Ljung, B.-M., Cunha, G. R., Benz, C. C. (2005). Hyperplasia, reduced E-cadherin expression, and developmental arrest in mammary glands oxidatively stressed by loss of mitochondrial superoxide dismutase. The Breast 14: 256-263.
32. Person, M. D., Mason, D. E., Liebler, D. C., Monks, T. J., and Lau, S. S. (2005). Alkylation of cytochrome c by (glutathione-S-yl)-1,4-benzoquinone and iodoacetamide demonstrates compound-dependent site specificity. Chem. Res. Toxicol. 18:41-50.
33. Romashko, J., Horowitz, S., Franek, W. R., Palaia, T., Miller, E. J., Lin, A., Birrer, M. J., Scott, W., Mantell, L. L. (2003). MAPK pathways mediate hyperoxia-induced oncotic cell death in lung epithelial cells. Free Radic. Biol. Med. 35:978-993.
34. Saxena, S. P., Israels, E. D., Israels, L. G. (2001). Novel vitamin K-dependent pathways regulating cell survival. Apoptosis 6:57-68.
35. Schmeider, P. K., Tapper, M. A., Kolanczyk, R. C., Hammermeister, D. E., Sheed, B. R., Denny, J. S. 2003. Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes. Toxicol. Sci. 72:66-76.
36. Scott, G. K., Atsriku, C., Kaminker, P., Held, J., Gibson, B., Baldwin, M. A., Benz, C. C. (2005). Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Mol. Pharmacol. 68:606-615.
37. Seanor, K. L., Cross, J. V., Nguyen, S. M., Yan, M., Templeton, D. J. (2003). Reactive quinones differentially regulated SAPK/JNK and p38/mHOG stress kinases. Antioxid. Redox Signal. 5:103-113.
38. Sullivan, S., Sink, D. W., Trout, K. L., Makalowska, I., Taylor, P. M., Baxevanis, A. D., Landsman, D. (2002). The histone database. Nucleic Acid Res. 30:341-342.
39. Sun, J. M., Chen, H. Y., Davie, J. R. (2002). Isolation of transcriptionally active chromatin from human breast cancer cells using Sulfolink coupling gel chromatography. J. Cell Biochem. 84:439-446.
40. Surh, Y.-J., Kundu, J. K., Na, H.-K., Lee, J.-S. (2005). Redox-sensitive transcription factors as prime targets for chemoprevention with anti-inflammatory and antioxidative phytochemicals. J. Nutr. 135:2993S-3001S.
41. Talay, P., DeLong, M., Prochaska, H. J. (1988). Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc. Natl. Acad. Sci (USA) 85:8261-8265.
42. Tikoo, K., Lau, S. S., Monks, T. J. (2001). Histone H3 phosphorylation is coupled to poly-(ADP-ribosylation) during reactive oxygen species-induced cell death in renal proximal tubular epithelial cells. Mol. Pharmacol. 60:394-402.
43. Trump, B. E., Berezesky, I. K., Chang, S. H., Phelps, P. C. (1997). The pathway of cell death: oncosis, apoptosis and necrosis. Toxicol. Pathol. 25:82-88.
44. Uht, R. M., Webb, P., Nguyen, P., Price, Jr., R. H., Valentine, C., Favre, H., Kushner, P. J. (2004). A conserved lysine in the estrogen receptor DNA binding domain regulates ligand activation profiles at AP-1 sites, possibly by controlling interactions with a modulatory repressor. Nucl. Recept. 2:2.
45. Van Cruchte, S., Van Den Broeck, W. (2002). Morphological and biochemical aspects of apoptosis, oncosis and necrosis. Anat. Histol. Embryol. 31:214-223.
46. Wang, X., Thomas, B., Sachdeva, R., Arterburn, L., Frye, L., Hatcher, P. G., Cornwell, D. G., Ma, J. (2006). Mechanism of arylating quinone toxicity involving Michael adduct formation and induction of endoplasmic reticulum stress. Proc. Natl. Acad. Sci. (USA). 103:3604-3609.
47. Webb, P., Lopez, G. N., Uht, R. M., Kushner, P. J. (1995). Tamoxifen activation of the estrogen receptor/AP-1 pathway: potential origin for the cell-specific estrogen-like effects of antiestrogens. Mol. Endocrinol. 9:443-456.
48. Whittal, R. M., Benz, C. C., Scott, G., Semyonov, J., Burlingame, A. L., Baldwin, M. A. (2000). Preferential oxidation of zinc finger 2 in estrogen receptor DNA-binding domain prevents dimerization and hence, DNA binding. Biochemistry 39:8406-8417.