Cell signaling mediated by nitrated cyclic guanine nucleotide

Nitric Oxide - Biology and Chemistry

Volumn 23, Issue 3, 2010, Pages 166-174

  Akaike, T ^a   Fujii, Shigemoto ^a   Sawa, Tomohiro ^a   Ihara, Hideshi ^b  

^a KUMAMOTO UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

8 Nitro cGMP; Cell signaling; Nitrated cyclic nucleotide; Nitric oxide; S guanylation

Indexed keywords

8 NITROGUANOSINE 3',5' CYCLIC MONOPHOSPHATE; CYCLIC GMP; GUANINE NUCLEOTIDE; HEME OXYGENASE 1; NITRIC OXIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

CELL CULTURE; CELL FUNCTION; GLIA CELL; LIQUID CHROMATOGRAPHY; MACROPHAGE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN MODIFICATION; REVIEW; SIGNAL TRANSDUCTION; TANDEM MASS SPECTROMETRY;

CYCLIC GMP; HUMANS; NITRIC OXIDE; SIGNAL TRANSDUCTION;

MAMMALIA;

EID: 77956009695     PISSN: 10898603     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.niox.2010.06.006     Document Type: Review

References (49)

1. Fridovich I. Superoxide anion radical (O2·-), superoxide dismutases, and related matters. J. Biol. Chem. 1997, 272:18515-18517.
2. Halliwell B. Biochemistry of oxidative stress. Biochem. Soc. Trans. 2007, 35(Pt. 5):1147-1150.
3. Beckman J.S., Beckman T.W., Chen J., Marshall P.A., Freeman B.A. Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. USA 1990, 87:1620-1624.
4. van der Vliet A., Cross C.E. Oxidants, nitrosants, and the lung. Am. J. Med. 2000, 109:398-421.
5. Szabó C. Role of nitrosative stress in the pathogenesis of diabetic vascular dysfunction. Br. J. Pharmacol. 2009, 156:713-727.
6. Estévez A.G., Crow J.P., Sampson J.B., Reiter C., Zhuang Y., Richardson G.J., Tarpey M.M., Barbeito L., Beckman J.S. Induction of nitric oxide-dependent apoptosis in motor neurons by zinc-deficient superoxide dismutase. Science 1999, 286:2498-2500.
7. Trachootham D., Alexandre J., Huang P. Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach?. Nat. Rev. Drug Discov. 2009, 8:579-591.
8. Sawa T., Zaki M.H., Okamoto T., Akuta T., Tokutomi Y., Kim-Mitsuyama S., Ihara H., Kobayashi A., Yamamoto M., Fujii S., Arimoto H., Akaike T. Protein S-guanylation by the biological signal 8-nitroguanosine 3',5'-cyclic monophosphate. Nat. Chem. Biol. 2007, 3:727-735.
9. Saito Y., Taguchi H., Fujii S., Sawa T., Kida E., Kabuto C., Akaike T., Arimoto H. 8-Nitroguanosines as chemical probes of the protein S-guanylation. Chem. Commun. 2008, (45):5984-5986.
10. Zaki M.H., Fujii S., Okamoto T., Islam S., Khan S., Ahmed K.A., Sawa T., Akaike T. Cytoprotective function of heme oxygenase 1 induced by a nitrated cyclic nucleotide formed during murine salmonellosis. J. Immunol. 2009, 182:3746-3756.
11. T. Sawa, H. Arimoto, T. Akaike, Regulation of redox signaling involving chemical conjugation of protein thiols by nitric oxide and electrophiles. Bioconjug. Chem. (2010), doi:10.1021/bc900396u.
12. S. Fujii, T. Sawa, H. Ihara, K.I. Tong, T. Ida, T. Okamoto, A.K. Ahtesham, Y. Ishima, H. Motohashi, M. Yamamoto, T. Akaike, The critical role of nitric oxide signaling, via protein S-guanylation and nitrated cyclic GMP, in the antioxidant adaptive response. J. Biol. Chem. (2010), doi:10.1074/jbc.M110.145441.
13. Akaike T., Okamoto S., Sawa T., Yoshitake J., Tamura F., Ichimori K., Miyazaki K., Sasamoto K., Maeda H. 8-Nitroguanosine formation in viral pneumonia and its implication for pathogenesis. Proc. Natl. Acad. Sci. USA 2003, 100:685-690.
14. Murad F. Cyclic guanosine monophosphate as a mediator of vasodilation. J. Clin. Invest. 1986, 78:1-5.
15. Bredt D.S., Hwang P.M., Snyder S.H. Localization of nitric oxide synthase indicating a neural role for nitric oxide. Nature 1990, 347:768-770.
16. Lima B., Forrester M.T., Hess D.T., Stamler J.S. S-Nitrosylation in cardiovascular signaling. Circ. Res. 2010, 106:633-646.
17. Bryan N.S., Bian K., Murad F. Discovery of the nitric oxide signaling pathway and targets for drug development. Front. Biosci. 2009, 14:1-18.
18. Schopfer F.J., Baker P.R., Freeman B.A. NO-dependent protein nitration: a cell signaling event or an oxidative inflammatory response?. Trends Biochem. Sci. 2003, 28:646-654.
19. Radi R. Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl. Acad. Sci. USA 2004, 101:4003-4008.
20. Eiserich J.P., Hristova M., Cross C.E., Jones A.D., Freeman B.A., Halliwell B., van der Vliet A. Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 1998, 391:393-397.
21. Ohshima H., Sawa T., Akaike T. 8-Nitroguanine, a product of nitrative DNA damage caused by reactive nitrogen species: formation, occurrence, and implications in inflammation and carcinogenesis. Antioxid. Redox Signal. 2006, 8:1033-1045.
22. Sawa T., Tatemichi M., Akaike T., Barbin A., Ohshima H. Analysis of urinary 8-nitroguanine, a marker of nitrative nucleic acid damage, by high-performance liquid chromatography-electrochemical detection coupled with immunoaffinity purification: association with cigarette smoking. Free Radic. Biol. Med. 2006, 40:711-720.
23. Yoshitake J., Akaike T., Akuta T., Tamura F., Ogura T., Esumi H., Maeda H. Nitric oxide as an endogenous mutagen for Sendai virus without antiviral activity. J. Virol. 2004, 78:8709-8719.
24. Terasaki Y., Akuta T., Terasaki M., Sawa T., Mori T., Okamoto T., Ozaki M., Takeya M., Akaike T. Guanine nitration in idiopathic pulmonary fibrosis and its implication for carcinogenesis. Am. J. Respir. Crit. Care Med. 2006, 174:665-673.
25. Sawa T., Akaike T., Ichimori K., Akuta T., Kaneko K., Nakayama H., Stuehr D.J., Maeda H. Superoxide generation mediated by 8-nitroguanosine, a highly redox-active nucleic acid derivative. Biochem. Biophys. Res. Commun. 2003, 311:300-306.
26. Motohashi H., Yamamoto M. Nrf2-Keap1 defines a physiologically important stress response mechanism. Trends Mol. Med. 2004, 10:549-557.
27. Dinkova-Kostova A.T., Holtzclaw W.D., Kensler T.W. The role of Keap1 in cellular protective responses. Chem. Res. Toxicol. 2005, 18:1779-1791.
28. Dinkova-Kostova A.T., Holtzclaw W.D., Cole R.N., Itoh K., Wakabayashi N., Katoh Y., Yamamoto M., Talalay P. Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc. Natl. Acad. Sci. USA 2002, 99:11908-11913.
29. Itoh K., Tong K.I., Yamamoto M. Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles. Free Radic. Biol. Med. 2004, 36:1208-1213.
30. Buckley B.J., Li S., Whorton A.R. Keap1 modification and nuclear accumulation in response to S-nitrosocysteine. Free Radic. Biol. Med. 2008, 44:692-698.
31. Jaffrey S.R., Erdjument-Bromage H., Ferris C.D., Tempst P., Snyder S.H. Protein S-nitrosylation: a physiological signal for neuronal nitric oxide. Nat. Cell Biol. 2001, 3:193-197.
32. Rudolph T.K., Freeman B.A. Transduction of redox signaling by electrophile-protein reactions. Sci. Signal. 2009, 2:re7.
33. Doorn J.A., Petersen D.R. Covalent adduction of nucleophilic amino acids by 4-hydroxynonenal and 4-oxononenal. Chem. Biol. Interact. 2003, 143-144:93-100.
34. Baker L.M., Baker P.R., Golin-Bisello F., Schopfer F.J., Fink M., Woodcock S.R., Branchaud B.P., Radi R., Freeman B.A. Nitro-fatty acid reaction with glutathione and cysteine. Kinetic analysis of thiol alkylation by a Michael addition reaction. J. Biol. Chem. 2007, 282:31085-31093.
35. Alam J., Cook J.L. How many transcription factors does it take to turn on the heme oxygenase-1 gene?. Am. J. Respir. Cell Mol. Biol. 2007, 36:166-174.
36. Levonen A.L., Landar A., Ramachandran A., Ceaser E.K., Dickinson D.A., Zanoni G., Morrow J.D., Darley-Usmar V.M. Cellular mechanisms of redox cell signalling: role of cysteine modification in controlling antioxidant defences in response to electrophilic lipid oxidation products. Biochem. J. 2004, 378:373-382.
37. Kobayashi A., Kang M.I., Watai Y., Tong K.I., Shibata T., Uchida K., Yamamoto M. Oxidative and electrophilic stresses activate Nrf2 through inhibition of ubiquitination activity of Keap1. Mol. Cell. Biol. 2006, 26:221-229.
38. 12,14-prostaglandin J2 adduct formation with Keap1 over time: effects on potency for intracellular antioxidant defence induction. Biochem. J. 2008, 411:297-306.
39. Kobayashi M., Li L., Iwamoto N., Nakajima-Takagi Y., Kaneko H., Nakayama Y., Eguchi M., Wada Y., Kumagai Y., Yamamoto M. The antioxidant defense system Keap1-Nrf2 comprises a multiple sensing mechanism for responding to a wide range of chemical compounds. Mol. Cell. Biol. 2009, 29:493-502.
40. Yamamoto T., Suzuki T., Kobayashi A., Wakabayashi J., Maher J., Motohashi H., Yamamoto M. Physiological significance of reactive cysteine residues of Keap1 in determining Nrf2 activity. Mol. Cell. Biol. 2008, 28:2758-2770.
41. Holland R., Hawkins A.E., Eggler A.L., Mesecar A.D., Fabris D., Fishbein J.C. Prospective type 1 and type 2 disulfides of Keap1 protein. Chem. Res. Toxicol. 2008, 21:2051-2060.
42. Tong K.I., Katoh Y., Kusunoki H., Itoh K., Tanaka T., Yamamoto M. Keap1 recruits Neh2 through binding to ETGE and DLG motifs: characterization of the two-site molecular recognition model. Mol. Cell. Biol. 2006, 26:2887-2900.
43. Tong K.I., Padmanabhan B., Kobayashi A., Shang C., Hirotsu Y., Yokoyama S., Yamamoto M. Different electrostatic potentials define ETGE and DLG motifs as hinge and latch in oxidative stress response. Mol. Cell. Biol. 2007, 27:7511-7521.
44. Padmanabhan B., Tong K.I., Ohta T., Nakamura Y., Scharlock M., Ohtsuji M., Kang M.I., Kobayashi A., Yokoyama S., Yamamoto M. Structural basis for defects of Keap1 activity provoked by its point mutations in lung cancer. Mol. Cell 2006, 21:689-700.
45. Ogura T., Tong K.I., Mio K., Maruyama Y., Kurokawa H., Sato C., Yamamoto M. Keap1 is a forked-stem dimer structure with two large spheres enclosing the intervening, double glycine repeat, and C-terminal domains. Proc. Natl. Acad. Sci. USA 2010, 107:2842-2847.
46. Lo S.C., Li X., Henzl M.T., Beamer L.J., Hannink M. Structure of the Keap1:Nrf2 interface provides mechanistic insight into Nrf2 signaling. EMBO J. 2006, 25:3605-3617.
47. Doi K., Akaike T., Fujii S., Tanaka S., Ikebe N., Beppu T., Shibahara S., Ogawa M., Maeda H. Induction of haem oxygenase-1 nitric oxide and ischaemia in experimental solid tumours and implications for tumour growth. Br. J. Cancer 1999, 80:1945-1954.
48. Tanaka S., Akaike T., Fang J., Beppu T., Ogawa M., Tamura F., Miyamoto Y., Maeda H. Antiapoptotic effect of haem oxygenase-1 induced by nitric oxide in experimental solid tumour. Br. J. Cancer 2003, 88:902-909.
49. Okamoto T., Khan S., Oyama K., Fujii S., Sawa T., Akaike T. A new paradigm for antimicrobial host defense mediated by a nitrated cyclic nucleotide. J. Clin. Biochem. Nutr. 2010, 46:14-19.