Synthesis and evaluation of the anti-inflammatory properties of selenium-derivatives of celecoxib

Chemico-Biological Interactions

Volumn 188, Issue 3, 2010, Pages 446-456

  Desai, Dhimant ^a   Kaushal, Naveen ^b   Gandhi, Ujjawal H ^b   Arner, Ryan J ^b   D'Souza, Christopher ^c   Chen, Gang ^a   Vunta, Hema ^b   El Bayoumy, Karam ^a   Amin, Shantu ^a   Prabhu, K Sandeep ^b  

^a PENN STATE COLLEGE OF MEDICINE   (United States)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

^c IMMUNOMEDICS INC   (United States)

Author keywords

Cyclooxygenase 2; Nuclear factor B; PGE2; Proinflammatory genes; Transcription

Indexed keywords

ACETYLCYSTEINE; ANTIINFLAMMATORY AGENT; CELECOXIB; CYCLOOXYGENASE 2; GLUTATHIONE PEROXIDASE 1; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; SELENIUM; SELENIUM DERIVATIVE; SELENOCOXIB 2; SELENOCOXIB 3; SULFAPHENAZOLE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BONE MARROW CELL; CELL VIABILITY; CONJUGATION; CONTROLLED STUDY; DOWN REGULATION; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; GENE EXPRESSION; IN VITRO STUDY; LIVER MICROSOME; MACROPHAGE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PROTEIN EXPRESSION; RAT; SIGNAL TRANSDUCTION; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; UPREGULATION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BONE MARROW CELLS; CELL LINE; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GLUTATHIONE PEROXIDASE; HUMANS; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; NF-KAPPA B; PYRAZOLES; RATS; SELENIUM; SIGNAL TRANSDUCTION; SULFONAMIDES;

MURINAE; RATTUS;

EID: 78149471569     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.09.021     Document Type: Article

References (32)

1. Smith W.L., Meade E.A., DeWitt D.L. Pharmacology of prostaglandin endoperoxide synthase isozymes-1 and -2. Ann. N. Y. Acad. Sci. 1994, 714:136-142.
2. Iezzi A., Ferri C., Mezzetti A., Cipollone F. COX-2: friend or foe?. Curr. Pharm. Des. 2007, 13:1715-1721.
3. Bunimov N., Laneuville O. Cyclooxygenase inhibitors: instrumental drugs to understand cardiovascular homeostasis and arterial thrombosis. Cardiovasc. Hematol. Disord. Drug Targets 2008, 8:268-277.
4. Zhu J., Song X., Lin H.P., Young D.C., Yan S., Marquez V.E., Chen C.S. Using cyclooxygenase-2 inhibitors as molecular platforms to develop a new class of apoptosis inducing agents. J. Natl. Cancer Inst. 2002, 94:1745-1757.
5. Thun M.J., Henley S.J., Patrono C. Nonsteroidal anti-inflammatory drugs as anticancer agents: mechanistic, pharmacologic, and clinical issues. J. Natl. Cancer Inst. 2002, 94:252-266.
6. Steinbach G., Lynch P.M., Phillips R.K., Wallace M.H., Hawk E., Gordon G.B., Wakabayashi N., Saunders B., Shen Y., Fujimura T., Su L.K., Levin B. The effect of celecoxib, a cyclooxygenase-2 inhibitor, in familial adenomatous polyposis. N. Engl. J. Med. 2000, 342:1946-1952.
7. Bertagnolli M.M., Eagle C.J., Zauber A.G., Redston M., Breazna A., Kim K., Tang J., Rosenstein R.B., Umar A., Bagheri D., Collins N.T., Burn J., Chung D.C., Dewar T., Foley T.R., Hoffman N., Macrae P., Pruitt R.E., Saltzman J.R., Salzberg B., Sylwestrowicz T., Hawk E.T. Five-year efficacy and safety analysis of the adenoma prevention with celecoxib trial. Cancer Prev. Res. 2009, 2:310-321.
8. Zamamiri-Davis F., Lu Y., Thompson J.T., Prabhu K.S., Reddy P.V., Sordillo L.M., Reddy C.C. Nuclear factor-kappaB mediates over-expression of cyclooxygenase-2 during activation of RAW 264.7 macrophages in selenium deficiency. Free Radic. Biol. Med. 2002, 32:890-897.
9. Vunta H., Davis F., Palempall U.D., Bhat D., Arner R.J., Thompson J.T., Peterson D.G., Reddy C.C., Prabhu K.S. The anti-inflammatory effects of selenium are mediated through 15-deoxy-delta12, 14-prostaglandin J2 in macrophages. J. Biol. Chem. 2007, 282:17964-17973.
10. Mugesh G., du Mont W.W., Sies H. Chemistry of biologically important synthetic organoselenium compounds. Chem. Rev. 2001, 101:2125-2179.
11. Combs G.F., Gray W.P. Chemopreventive agents: selenium. Pharmacol. Ther. 1998, 79:179-192.
12. Ip C. Lessons from basic research in selenium and cancer prevention. J. Nutr. 1998, 128:1845-1854.
13. Ganther H.E. Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thioredoxin reductase. Carcinogenesis 1999, 20:1657-1666.
14. Rayman M.P. The importance of selenium to human health. Lancet 2000, 356:233-241.
15. El-Bayoumy K. The protective role of selenium on genetic damage and on cancer. Mutat. Res. 2001, 475:123-139.
16. Birringer M., Pilawa S., Flohé L. Trends in selenium biochemistry. Nat. Prod. Rep. 2002, 19:693-718.
17. El-Bayoumy K., Upadhyaya P., Chae Y.H., Sohn O.S., Rao C.V., Fiala E., Reddy B.S. Chemoprevention of cancer by organoselenium compounds. J. Cell. Biochem. 1995, 22:92-100.
18. El-Bayoumy K., Das A., Narayanan B., Narayanan N., Fiala E.S., Desai D., Rao C.V., Amin S., Sinha R. Molecular targets of the chemopreventive agent 1, 4-phenylenebis(methylene)-selenocyanate in human non-small cell lung cancer. Carcinogenesis 2006, 27:1369-1376.
19. Desai D., Madhunapantula S.V., Gowdahalli K., Sharma A., Chandagaludoreswamy R., El-Bayoumy K., Robertson G.P., Amin S. Synthesis and characterization of a novel iNOS/Akt inhibitor Se, Se′-1,4-phenylenebis(1,2-ethanediyl)bisisoselenourea (PBISe) against colon cancer. Bioorg. Med. Chem. Lett. 2010, 20:2038-2043.
20. Frank D.H., Roe D.J., Chow H.H., Guillen J.M., Choquette K., Gracie D., Francis J., Fish A., Alberts D.S. Effects of a high-selenium yeast supplement on celecoxib plasma levels: a randomized phase II trial. Cancer Epidemiol. Biomarkers Prev. 2004, 13:299-303.
21. Penning T.D., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J. 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]benzenesulfonamide (SC-58635, celecoxib). J. Med. Chem. 1997, 40:1347-1365.
22. Gierse J.K., Koboldt C.M., Walker M.C., Seibert K., Isakson P.C. Kinetic basis for selective inhibition of cyclo-oxygenases. Biochem. J. 1999, 339:607-614.
23. Moore R.A., Derry S., McQuay H.J. Cyclo-oxygenase-2 selective inhibitors and nonsteroidal anti-inflammatory drugs: balancing gastrointestinal and cardiovascular risk. BMC Musculoskelet. Disord. 2007, 8:73.
24. Hirschowitz E.A., Hidalgo G.E., Doherty D.E. Induction of cyclo-oxygenase-2 in non-small cell lung cancer cells by adenovirus vector information. Chest 2002, 121:32S.
25. Shishodia S., Aggarwal B.B. Nuclear factor-kappaB activation: a question of life or death. J. Biochem. Mol. Biol. 2002, 35:28-40.
26. Grabacka M., Plonka P.M., Urbanska K., Reiss K. Peroxisome proliferator-activated receptor alpha activation decreases metastatic potential of melanoma cells in vitro via down-regulation of Akt. Clin. Cancer Res. 2006, 12:3028-3036.
27. Vunta H., Belda B.J., Arner R.J., Reddy C.C., Vanden Heuvel J.P., Prabhu K.S. Selenium attenuates pro-inflammatory gene expression in macrophages. Mol. Nutr. Food Res. 2008, 52:1316-1323.
28. Safir N., Wendel A., Saile R., Chabraoui L. The effect of selenium on immune functions of J774.1 cells. Clin. Chem. Lab. Med. 2003, 41:1005-1011.
29. Sohn O.S., Desai D.H., Das A., Rodriguez J.G., Amin S.G., El-Bayoumy K. Comparative excretion and tissue distribution of selenium in mice and rats following treatment with the chemopreventive agent 1, 4-phenylenebis (methylene) selenocyanate. Chem. Biol. Interact. 2005, 151:193-202.
30. Sandberg M., Yasar U., Stromberg P., Hoog J.O., Eliasson E. Oxidation of celecoxib by polymorphic cytochrome P450 2C9 and alcohol dehydrogenase. Br. J. Clin. Pharmacol. 2002, 54:423-429.
31. Kim S.R., Lee M.E., Park J.S., Park S.C., Han J.A. Selective COX-2 inhibitors modulate cellular senescence in human dermal fibroblasts in a catalytic activity-independent manner. Mech. Ageing Dev. 2008, 129:706-713.
32. Conaway C.C., Wang C.X., Pittman B., Yang Y.M., Schwartz J.E., Tian D., McIntee E.J., Hecht S.S., Chung F.L. Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice. Cancer Res. 2005, 65:8548-8557.