Inhibition of DNA binding activity of cAMP response element-binding protein by 1,2-naphthoquinone through chemical modification of Cys-286

Chemico-Biological Interactions

Volumn 192, Issue 3, 2011, Pages 272-277

  Endo, Akiko ^a   Sumi, Daigo ^a   Iwamoto, Noriko ^a   Kumagai, Yoshito ^a,b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

CREB; Cysteine; Electrophile; Quinone

Indexed keywords

1,2 NAPHTHOQUINONE; CYCLIC AMP RESPONSIVE ELEMENT BINDING PROTEIN; CYSTEINE;

AMINO ACID SUBSTITUTION; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DNA BINDING; LOSS OF FUNCTION MUTATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR INTERACTION; MUTATIONAL ANALYSIS; NONHUMAN; PROTEIN BINDING; PROTEIN MODIFICATION;

CELL LINE, TUMOR; CYCLIC AMP RESPONSE ELEMENT-BINDING PROTEIN; CYSTEINE; ENVIRONMENTAL POLLUTANTS; GENE EXPRESSION; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; MUTAGENS; NAPHTHOQUINONES;

BOVINAE;

EID: 79957665131     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2011.04.003     Document Type: Article

References (43)

1. R.O. McClellan, Health effects of exposure to diesel exhaust particles, Annu. Rev. Pharmacol. Toxicol. 27 (1987) 279-300. (Pubitemid 17067236)
2. D.W. Dockery, C.A. Pope 3rd, X. Xu, J.D. Spengler, J.H. Ware, M.E. Fay, B.G. Ferris Jr., F.E. Speizer, An association between air pollution and mortality in six U.S. cities, N. Engl. J. Med. 329 (24) (1993) 1753-1759. (Pubitemid 23355547)
3. A.E. Nel, D. Diaz-Sanchez, N. Li, The role of particulate pollutants in pulmonary inflammation and asthma: evidence for the involvement of organic chemicals and oxidative stress, Curr. Opin. Pulm. Med. 7 (1) (2001) 20-26. (Pubitemid 32003169)
4. J.L. Bolton, M.A. Trush, T.M. Penning, G. Dryhurst, T.J. Monks, Role of quinones in toxicology, Chem. Res. Toxicol. 13 (3) (2000) 135-160. (Pubitemid 30169958)
5. Y. Kumagai, T. Hayashi, T. Miyauchi, A. Endo, A. Iguchi, M. Kiriya-Sakai, S. Sakai, K. Yuki, M. Kikushima, N. Shimojo, Phenanthraquinone inhibits eNOS activity and suppresses vasorelaxation, Am. J. Physiol. Regul. Integr. Comp. Physiol. 281 (1) (2001) R25-30.
6. Y. Sun, K. Taguchi, D. Sumi, S. Yamano, Y. Kumagai, Inhibition of endothelial nitric oxide synthase activity and suppression of endothelium-dependent vasorelaxation by 1,2-naphthoquinone, a component of diesel exhaust particles, Arch. Toxicol. 80 (5) (2006) 280-285.
7. K. Taguchi, S. Fujii, S. Yamano, A.K. Cho, S. Kamisuki, Y. Nakai, F. Sugawara, J.R. Froines, Y. Kumagai, An approach to evaluate two-electron reduction of 9,10-phenanthraquinone and redox activity of the hydroquinone associated with oxidative stress, Free Radic. Biol. Med. 43 (5) (2007) 789-799.
8. R. Sugimoto, Y. Kumagai, Y. Nakai, T. Ishii, 9,10-Phenanthraquinone in diesel exhaust particles downregulates Cu, Zn-SOD and HO-1 in human pulmonary epithelial cells: intracellular iron scavenger 1,10-phenanthroline affords protection against apoptosis, Free Radic. Biol. Med. 38 (3) (2005) 388-395.
9. K. Inoue, H. Takano, K. Hiyoshi, T. Ichinose, K. Sadakane, R. Yanagisawa, S. Tomura, Y. Kumagai, Naphthoquinone enhances antigen-related airway inflammation in mice, Eur. Respir. J. 29 (2) (2007) 259-267.
10. Y. Kumagai, S. Koide, K. Taguchi, A. Endo, Y. Nakai, T. Yoshikawa, N. Shimojo, Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles, Chem. Res. Toxicol. 15 (4) (2002) 483-489.
11. A.K. Cho, E.D. Stefano, Y. You, C.E. Rodriguez, D.A. Schmitz, Y. Kumagai, A.H. Miguel, A. Eiguren-Fernandez, T. Kobayashi, E. Avol, J.R. Fronines, Determination of four quinones in diesel exhaust particles, SRM 1649a and atmospheric PM2.5, Aerosol Sci. Technol. 38 (2004) 1-14.
12. M. Saeed, S. Higginbotham, E. Rogan, E. Cavalieri, Formation of depurinating N3adenine and N7guanine adducts after reaction of 1,2-naphthoquinone or enzyme-activated 1,2-dihydroxynaphthalene with DNA. Implications for the mechanism of tumor initiation by naphthalene, Chem. Biol. Interact. 165 (3) (2007) 175-188.
13. N. Iwamoto, D. Sumi, T. Ishii, K. Uchida, A.K. Cho, J.R. Froines, Y. Kumagai, Chemical knockdown of protein-tyrosine phosphatase 1B by 1,2-naphthoquinone through covalent modification causes persistent transactivation of epidermal growth factor receptor, J. Biol. Chem. 282 (46) (2007) 33396-33404. (Pubitemid 350159512)
14. B. Mayr, M. Montminy, Transcriptional regulation by the phosphorylation-dependent factor CREB, Nat. Rev. Mol. Cell Biol. 2 (8) (2001) 599-609. (Pubitemid 33674011)
15. J.C. Chrivia, R.P. Kwok, N. Lamb, M. Hagiwara, M.R. Montminy, R.H. Goodman, Phosphorylated CREB binds specifically to the nuclear protein CBP, Nature 365 (6449) (1993) 855-859. (Pubitemid 23341031)
16. C.T. Taylor, N. Fueki, A. Agah, R.M. Hershberg, S.P. Colgan, Critical role of cAMP response element binding protein expression in hypoxia-elicited induction of epithelial tumor necrosis factor-alpha, J. Biol. Chem. 274 (27) (1999) 19447-19454.
17. F.U. Muller, J. Neumann, W. Schmitz, Transcriptional regulation by cAMP in the heart, Mol. Cell. Biochem. 212 (1-2) (2000) 11-17.
18. M.D. Conkright, M. Montminy, CREB: the unindicted cancer co-conspirator, Trends Cell Biol. 15 (9) (2005) 457-459. (Pubitemid 41253464)
19. T. Tully, R. Bourtchouladze, R. Scott, J. Tallman, Targeting the CREB pathway for memory enhancers, Nat. Rev. Drug Discov. 2 (4) (2003) 267-277. (Pubitemid 37361685)
20. B.E. Wilson, E. Mochon, L.M. Boxer, Induction of bcl-2 expression by phosphorylated CREB proteins during B-cell activation and rescue from apoptosis, Mol. Cell. Biol. 16 (10) (1996) 5546-5556. (Pubitemid 26315074)
21. C. Desdouets, G. Matesic, C.A. Molina, N.S. Foulkes, P. Sassone-Corsi, C. Brechot, J. Sobczak-Thepot, Cell cycle regulation of cyclin A gene expression by the cyclic AMP-responsive transcription factors CREB and CREM, Mol. Cell. Biol. 15 (6) (1995) 3301-3309.
22. M.R. Montminy, K.A. Sevarino, J.A. Wagner, G. Mandel, R.H. Goodman, Identification of a cyclic-AMP-responsive element within the rat somatostatin gene, Proc. Natl. Acad. Sci. USA 83 (18) (1986) 6682-6686. (Pubitemid 16002298)
23. C. Vinson, A. Acharya, E.J. Taparowsky, Deciphering B-ZIP transcription factor interactions in vitro and in vivo, Biochim. Biophys. Acta 1759 (1-2) (2006) 4-12.
24. C. Abate, L. Patel, F.J. Rauscher 3rd, T. Curran, Redox regulation of fos and jun DNA-binding activity in vitro, Science 249 (4973) (1990) 1157-1161.
25. I. Goren, E. Tavor, A. Goldblum, A. Honigman, Two cysteine residues in the DNA-binding domain of CREB control binding to CRE and CREB-mediated gene expression, J. Mol. Biol. 313 (4) (2001) 695-709.
26. A. Endo, D. Sumi, Y. Kumagai, 1,2-Naphthoquinone disrupts the function of cAMP response element-binding protein through covalent modification, Biochem. Biophys. Res. Commun. 361 (1) (2007) 243-248.
27. J.P. Richards, H.P. Bachinger, R.H. Goodman, R.G. Brennan, Analysis of the structural properties of cAMP-responsive element-binding protein (CREB) and phosphorylated CREB, J. Biol. Chem. 271 (23) (1996) 13716-13723.
28. L.A. Berkowitz, M.Z. Gilman, Two distinct forms of active transcription factor CREB (cAMP response element binding protein), Proc. Natl. Acad. Sci. USA 87 (14) (1990) 5258-5262.
29. M.A. Schumacher, R.H. Goodman, R.G. Brennan, The structure of a CREB bZIP. Somatostatin CRE complex reveals the basis for selective dimerization and divalent cation-enhanced DNA binding, J. Biol. Chem. 275 (45) (2000) 35242-35247.
30. D. Bloom, S. Dhakshinamoorthy, A.K. Jaiswal, Site-directed mutagenesis of cysteine to serine in the DNA binding region of Nrf2 decreases its capacity to upregulate antioxidant response element-mediated expression and antioxidant induction of NAD(P)H:quinone oxidoreductase1 gene, Oncogene 21 (14) (2002) 2191-2200. (Pubitemid 34311373)
31. V.J. Dwarki, M. Montminy, I.M. Verma, Both the basic region and the 'leucine zipper' domain of the cyclic AMP response element binding (CREB) protein are essential for transcriptional activation, EMBO J. 9 (1) (1990) 225-232.
32. J.C. Craig, M.A. Schumacher, S.E. Mansoor, D.L. Farrens, R.G. Brennan, R.H. Goodman, Consensus and variant cAMP-regulated enhancers have distinct CREB-binding properties, J. Biol. Chem. 276 (15) (2001) 11719-11728.
33. M.A. Troester, A.B. Lindstrom, S. Waidyanatha, L.L. Kupper, S.M. Rappaport, Stability of hemoglobin and albumin adducts of naphthalene oxide, 1,2-naphthoquinone, and 1,4-naphthoquinone, Toxicol. Sci. 68 (2) (2002) 314-321.
34. S. Waidyanatha, M.A. Troester, A.B. Lindstrom, S.M. Rappaport, Measurement of hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone after administration of naphthalene to F344 rats, Chem. Biol. Interact. 141 (3) (2002) 189-210.
35. M. Kobayashi, L. Li, N. Iwamoto, Y. Nakajima-Takagi, H. Kaneko, Y. Nakayama, M. Eguchi, Y. Wada, Y. Kumagai, M. Yamamoto, The antioxidant defense system Keap1-Nrf2 comprises a multiple sensing mechanism for responding to a wide range of chemical compounds, Mol. Cell. Biol. 29 (2) (2009) 493-502.
36. O.M. Andrisani, J.E. Dixon, Involvement of lysine residues 289 and 291 of the cAMP-responsive element-binding protein in the recognition of the cAMP-responsive element, J. Biol. Chem. 266 (32) (1991) 21444-21450.
37. D. Sumi, M. Akimori, K. Inoue, H. Takano, Y. Kumagai, 1,2-Naphthoquinone suppresses lipopolysaccharide-dependent activation of IKKbeta/NF-kappaB/NO signaling: an alternative mechanism for the disturbance of inducible NO synthase-catalyzed NO formation, J. Toxicol. Sci. 35 (6) (2010) 891-898.
38. D. Sumi, Y. Numasawa, A. Endo, N. Iwamoto, Y. Kumagai, Catechol estrogens mediated activation of Nrf2 through covalent modification of its quinone metabolite to Keap1, J. Toxicol. Sci. 34 (6) (2009) 627-635.
39. S. Kikuno, K. Taguchi, N. Iwamoto, S. Yamano, A.K. Cho, J.R. Froines, Y. Kumagai, 1,2-Naphthoquinone activates vanilloid receptor 1 through increased protein tyrosine phosphorylation, leading to contraction of guinea pig trachea, Toxicol. Appl. Pharmacol. 210 (1-2) (2006) 47-54.
40. T. Ichiki, T. Tokunou, K. Fukuyama, N. Iino, S. Masuda, A. Takeshita, Cyclic AMP response element-binding protein mediates reactive oxygen species-induced c-fos expression, Hypertension 42 (2) (2003) 177-183. (Pubitemid 36944593)
41. H. Pham, B. Chong, R. Vincenti, L.W. Slice, Ang II and EGF synergistically induce COX-2 expression via CREB in intestinal epithelial cells, J. Cell. Physiol. 214 (1) (2008) 96-109.
42. K. Niwano, M. Arai, K. Tomaru, T. Uchiyama, Y. Ohyama, M. Kurabayashi, Transcriptional stimulation of the eNOS gene by the stable prostacyclin analogue beraprost is mediated through cAMP-responsive element in vascular endothelial cells: close link between PGI2 signal and NO pathways, Circ. Res. 93 (6) (2003) 523-530.
43. R.C. Fentzke, C.E. Korcarz, R.M. Lang, H. Lin, J.M. Leiden, Dilated cardiomyopathy in transgenic mice expressing a dominant-negative CREB transcription factor in the heart, J. Clin. Invest. 101 (11) (1998) 2415-2426.