NO-releasing NSAIDs suppress NF-κB signaling in vitro and in vivo through S-nitrosylation

Cancer Letters

Volumn 298, Issue 2, 2010, Pages 204-211

  Chattopadhyay, Mitali ^a   Goswami, Satindra ^a   Rodes, Deborah B ^a   Kodela, Ravinder ^a   Velazquez, Carlos A ^b   Boring, Daniel ^c   Crowell, James A ^c   Kashfi, Khosrow ^a  

^a CITY UNIVERSITY OF NEW YORK MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Caspase 3; Chemoprevention; NF B; NO NSAIDs; S nitrosylation

Indexed keywords

2 (6 METHOXY 2 NAPTHYL)PROPIONIC ACID 4 NITROOXYBUTYL ESTER; 2 (ACETYLOXY) 3 [(NITROOXY)METHYL]PHENYL ESTER; ACETYLSALICYLIC ACID; CASPASE 3; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; NAPROXEN; NITRIC OXIDE; NONSTEROID ANTIINFLAMMATORY AGENT; O2 (ACETYLSALICYLOYLOXYMETHYL) 1 (PYRROLIDIN 1 YL)DIAZEN 1 IUM 1,2 DIOLATE; PROSTAGLANDIN E2; TRANSCRIPTION FACTOR RELA; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; APOPTOSIS; ARTICLE; CANCER INHIBITION; COLON ADENOCARCINOMA; CONTROLLED STUDY; DOSE RESPONSE; ENZYME ACTIVATION; ENZYME ACTIVITY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; MALE; NITROSYLATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN BLOOD LEVEL; RAT; SIGNAL TRANSDUCTION; STOMACH MUCOSA;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ASPIRIN; BLOTTING, WESTERN; CASPASE 3; CELL PROLIFERATION; COLONIC NEOPLASMS; DINOPROSTONE; DOSE-RESPONSE RELATIONSHIP, DRUG; GASTRIC MUCOSA; HT29 CELLS; HUMANS; MALE; NAPROXEN; NF-KAPPA B; NITRATES; NITRIC OXIDE; NITRIC OXIDE DONORS; RATS; RATS, WISTAR; S-NITROSOTHIOLS; SIGNAL TRANSDUCTION; STOMACH; TRANSCRIPTION FACTOR RELA; TUMOR NECROSIS FACTOR-ALPHA;

RATTUS;

EID: 77957938071     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.canlet.2010.07.006     Document Type: Article

References (32)

1. Rigas B., Kashfi K. Nitric-oxide-donating NSAIDs as agents for cancer prevention. Trends Mol. Med. 2004, 10:324-330.
2. Kashfi K., Rigas B. Molecular targets of nitric-oxide-donating aspirin in cancer. Biochem. Soc. Trans. 2005, 33:701-704.
3. Kashfi K., Ryan Y., Qiao L.L., Williams J.L., Chen J., Del Soldato P., Traganos F., Rigas B. Nitric oxide-donating nonsteroidal anti-inflammatory drugs inhibit the growth of various cultured human cancer cells: evidence of a tissue type-independent effect. J. Pharmacol. Exp. Ther. 2002, 303:1273-1282.
4. Kashfi K., Borgo S., Williams J.L., Chen J., Gao J., Glekas A., Benedini F., Del Soldato P., Rigas B. Positional isomerism markedly affects the growth inhibition of colon cancer cells by nitric oxide-donating aspirin in vitro and in vivo. J. Pharmacol. Exp. Ther. 2005, 312:978-988.
5. Hulsman N., Medema J.P., Bos C., Jongejan A., Leurs R., Smit M.J., de Esch I.J., Richel D., Wijtmans M. Chemical insights in the concept of hybrid drugs: the antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin. J. Med. Chem. 2007, 50:2424-2431.
6. Dunlap T., Chandrasena R.E., Wang Z., Sinha V., Wang Z., Thatcher G.R. Quinone formation as a chemoprevention strategy for hybrid drugs: balancing cytotoxicity and cytoprotection. Chem. Res. Toxicol. 2007, 20:1903-1912.
7. Kashfi K., Rigas B. The mechanism of action of nitric oxide-donating aspirin. Biochem. Biophys. Res. Commun. 2007, 358:1096-1101.
8. Kashfi K. Anti-inflammatory agents as cancer therapeutics. Adv. Pharmacol. 2009, 57:31-89.
9. Velazquez C., Praveen Rao P.N., Knaus E.E. Novel nonsteroidal antiinflammatory drugs possessing a nitric oxide donor diazen-1-ium-1, 2-diolate moiety: design, synthesis, biological evaluation, and nitric oxide release studies. J. Med. Chem. 2005, 48:4061-4067.
10. P. Lane, G. Hao, S.S. Gross, S-nitrosylation is emerging as a specific and fundamental posttranslational protein modification: head-to-head comparison with O-phosphorylation, Sci. STKE 2001 (2001) re1.
11. Son K., Kim Y.M. In vivo cisplatin-exposed macrophages increase immunostimulant-induced nitric oxide synthesis for tumor cell killing. Cancer Res. 1995, 55:5524-5527.
12. Li J., Billiar T.R., Talanian R.V., Kim Y.M. Nitric oxide reversibly inhibits seven members of the caspase family via S-nitrosylation. Biochem. Biophys. Res. Commun. 1997, 240:419-424.
13. Marshall H.E., Merchant K., Stamler J.S. Nitrosation and oxidation in the regulation of gene expression. FASEB J. 2000, 14:1889-1900.
14. Reynaert N.L., Ckless K., Korn S.H., Vos N., Guala A.S., Wouters E.F., van der Vliet A., Janssen-Heininger Y.M. Nitric oxide represses inhibitory kappaB kinase through S-nitrosylation. Proc. Natl. Acad. Sci. USA 2004, 101:8945-8950.
15. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., AndersonGd, Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., Isakson P.C. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J. Med. Chem. 1997, 40:1347-1365.
16. Forrester M.T., Foster M.W., Benhar M., Stamler J.S. Detection of protein S-nitrosylation with the biotin-switch technique. Free Radical. Biol. Med. 2009, 46:119-126.
17. Li S., Whorton A.R. Regulation of protein tyrosine phosphatase 1B in intact cells by S-nitrosothiols. Arch. Biochem. Biophys. 2003, 410:269-279.
18. Huang B., Chen C. An ascorbate-dependent artifact that interferes with the interpretation of the biotin switch assay. Free Radical. Biol. Med. 2006, 41:562-567.
19. S.R. Jaffrey, S.H. Snyder, The biotin switch method for the detection of S-nitrosylated proteins, Sci. STKE 2001 (2001) pl1.
20. Forrester M.T., Foster M.W., Stamler J.S. Assessment and application of the biotin switch technique for examining protein S-nitrosylation under conditions of pharmacologically induced oxidative stress. J. Biol. Chem. 2007, 282:13977-13983.
21. Velazquez C.A., Praveen Rao P.N., Citro M.L., Keefer L.K., Knaus E.E. O2-acetoxymethyl-protected diazeniumdiolate-based NSAIDs (NONO-NSAIDs): synthesis, nitric oxide release, and biological evaluation studies. Bioorg. Med. Chem. 2007, 15:4767-4774.
22. Hess D.T., Matsumoto A., Kim S.O., Marshall H.E., Stamler J.S. Protein S-nitrosylation: purview and parameters. Nat. Rev. Mol. Cell Biol. 2005, 6:150-166.
23. Gao J., Liu X., Rigas B. Nitric oxide-donating aspirin induces apoptosis in human colon cancer cells through induction of oxidative stress. Proc. Natl. Acad. Sci. USA 2005, 102:17207-17212.
24. Wong B.C., Jiang X.H., Lin M.C., Tu S.P., Cui J.T., Jiang S.H., Wong W.M., Yuen M.F., Lam S.K., Kung H.F. Cyclooxygenase-2 inhibitor (SC-236) suppresses activator protein-1 through c-Jun NH2-terminal kinase. Gastroenterology 2004, 126:136-147.
25. Mannick J.B., Schonhoff C., Papeta N., Ghafourifar P., Szibor M., Fang K., Gaston B. S-nitrosylation of mitochondrial caspases. J. Cell Biol. 2001, 154:1111-1116.
26. Marshall H.E., Stamler J.S. Inhibition of NF-kappa B by S-nitrosylation. Biochemistry 2001, 40:1688-1693.
27. Kim P.K., Kwon Y.G., Chung H.T., Kim Y.M. Regulation of caspases by nitric oxide. Ann. NY Acad. Sci. 2002, 962:42-52.
28. Lander H.M., Hajjar D.P., Hempstead B.L., Mirza U.A., Chait B.T., Campbell S., Quilliam L.A. A molecular redox switch on p21(ras). Structural basis for the nitric oxide-p21(ras) interaction. J. Biol. Chem. 1997, 272:4323-4326.
29. Kelleher Z.T., Matsumoto A., Stamler J.S., Marshall H.E. NOS2 regulation of NF-kappaB by S-nitrosylation of p65. J. Biol. Chem. 2007, 282:30667-30672.
30. Williams J.L., Ji P., Ouyang N., Liu X., Rigas B. NO-donating aspirin inhibits the activation of NF-kappaB in human cancer cell lines and Min mice. Carcinogenesis 2008, 29:390-397.
31. Li Q., Verma I.M. NF-kappaB regulation in the immune system. Nat. Rev. Immunol. 2002, 2:725-734.
32. Mannick J.B., Hausladen A., Liu L., Hess D.T., Zeng M., Miao Q.X., Kane L.S., Gow A.J., Stamler J.S. Fas-induced caspase denitrosylation. Science 1999, 284:651-654.