Analogues of 2-phenyl-ethenesulfonic acid phenyl ester have dual functions of inhibiting expression of inducible nitric oxide synthase and activating peroxisome proliferator-activated receptor γ

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 20, 2008, Pages 5676-5679

  Lee, Yue Zhi ^a   Yang, Cheng Wei ^a   Kang, Iou Jiun ^a   Wu, Ssu Hui ^a   Chao, Yu Sheng ^a   Chern, Jyh Haur ^a   Lee, Shiow Ju ^a  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

Author keywords

Anti inflammation; Nitric oxide; Peroxisome proliferator activated receptor gamma; Phenyl ethenesulfonic acid phenyl ester

Indexed keywords

2 PHENYLETHENESULFONIC ACID 4 CHLOROPHENYL ESTER; 2 PHENYLETHENESULFONIC ACID PHENYL ESTER; 2 PHENYLETHENESULFONIC ACID PHENYL ESTER DERIVATIVE; GAMMA INTERFERON; INDUCIBLE NITRIC OXIDE SYNTHASE; LIPOPOLYSACCHARIDE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE INHIBITOR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; ATHEROSCLEROSIS; CONTROLLED STUDY; DRUG DESIGN; ENZYME ASSAY; ENZYME INHIBITION; MOUSE; NONHUMAN; PROTEIN BINDING; PROTEIN EXPRESSION; SCINTILLATION PROXIMITY ASSAY; TRANSACTIVATION; VALIDATION PROCESS; WESTERN BLOTTING;

ALKANESULFONATES; ANIMALS; ANTI-INFLAMMATORY AGENTS; CELL LINE; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; ENZYME ACTIVATION; ESTERS; INHIBITORY CONCENTRATION 50; MICE; MODELS, CHEMICAL; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; PPAR GAMMA; SULFONIC ACIDS; TRANSCRIPTIONAL ACTIVATION;

EID: 53549113033     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.08.107     Document Type: Article

References (24)

1. Tiwari R.L., Singh V., and Barthwal M.K. Med. Res. Rev. 28 (2008) 483
2. Detmers P.A., Hernandez M., Mudgett J., Hassing H., Burton C., Mundt S., Chun S., Fletcher D., Card D.J., Lisnock J., Weikel R., Bergstrom J.D., Shevell D.E., Hermanowski-Vosatka A., Sparrow C.P., Chao Y.S., Rader D.J., Wright S.D., and Pure E. J. Immunol. 165 (2000) 3430
3. Kauser K., da Cunha V., Fitch R., Mallari C., and Rubanyi G.M. Am. J. Physiol. Heart Circ. Physiol. 278 (2000) H1679
4. Ricote M., Li A.C., Willson T.M., Kelly C.J., and Glass C.K. Nature 391 (1998) 79
5. Liang Y.C., Tsai S.H., Tsai D.C., Lin-Shiau S.Y., and Lin J.K. FEBS Lett. 496 (2001) 12
6. Tseng H.Y., Wu S.H., Huang W.H., Wang S.F., Yang Y.N., Mahindroo N., Hsu T., Jiaang W.T., and Lee S.J. Bioorg. Med. Chem. Lett. 15 (2005) 2027
7. Yang C.W., Chen W.L., Wu P.L., Tseng H.Y., and Lee S.J. Mol. Pharmacol. 69 (2006) 749
8. Yang C.W., Chuang T.H., Wu P.L., Huang W.H., and Lee S.J. Biochem. Biophys. Res. Commun. 354 (2007) 942
9. Collins A.R., Meehan W.P., Kintscher U., Jackson S., Wakino S., Noh G., Palinski W., Hsueh W.A., and Law R.E. Arterioscler. Thromb. Vasc. Biol. 21 (2001) 365
10. Duez H., Chao Y.S., Hernandez M., Torpier G., Poulain P., Mundt S., Mallat Z., Teissier E., Burton C.A., Tedgui A., Fruchart J.C., Fievet C., Wright S.D., and Staels B. J. Biol. Chem. 277 (2002) 48051
11. Li A.C., and Palinski W. Annu. Rev. Pharmacol. Toxicol. 46 (2006) 1
12. Li A.C., Brown K.K., Silvestre M.J., Willson T.M., Palinski W., and Glass C.K. J. Clin. Invest. 106 (2000) 523
13. Chen Z., Ishibashi S., Perrey S., Osuga J., Gotoda T., Kitamine T., Tamura Y., Okazaki H., Yahagi N., Iizuka Y., Shionoiri F., Ohashi K., Harada K., Shimano H., Nagai R., and Yamada N. Arterioscler. Thromb. Vasc. Biol. 21 (2001) 372
14. Gross B., and Staels B. Best Pract. Res. Clin. Endocrinol. Metab. 21 (2007) 687
15. Forman B.M., Tontonoz P., Chen J., Brun R.P., Spiegelman B.M., and Evans R.M. Cell 83 (1995) 803
16. Kliewer S.A., Sundseth S.S., Jones S.A., Brown P.J., Wisely G.B., Koble C.S., Devchand P., Wahli W., Willson T.M., Lenhard J.M., and Lehmann J.M. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 4318
17. Li M., Pascual G., and Glass C.K. Mol. Cell. Biol. 20 (2000) 4699
18. Pascual G., Fong A.L., Ogawa S., Gamliel A., Li A.C., Perissi V., Rose D.W., Willson T.M., Rosenfeld M.G., and Glass C.K. Nature 437 (2005) 759
19. Straus D.S., and Glass C.K. Trends Immunol. 28 (2007) 551
20. TM Microplate Scinetillation and Luminescence Counter (Packard).
21. Mahindroo N., Huang C.F., Peng Y.H., Wang C.C., Liao C.C., Lien T.W., Chittimalla S.K., Huang W.J., Chai C.H., Prakash E., Chen C.P., Hsu T.A., Peng C.H., Lu I.L., Lee L.H., Chang Y.W., Chen W.C., Chou Y.C., Chen C.T., Goparaju C.M., Chen Y.S., Lan S.J., Yu M.C., Chen X., Chao Y.S., Wu S.Y., and Hsieh H.P. J. Med. Chem. 48 (2005) 8194
22. TM Microplate Scinetillation and Luminescence Counter (Packard). The luciferase activity was normalized with β-galactosidase activity. The PPARγ transactivation-activity activated by the treatment of 10 μM 15d-PGJ2 was used at 100% to calculate the other assay activity with each individual compound treatment.
23. Chawla A., Lee C.H., Barak Y., He W., Rosenfeld J., Liao D., Han J., Kang H., and Evans R.M. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 1268
24. 1H NMR as spectra data of these compounds were examined for purity. A part of compounds were also verified on liquid chromatography/mass spectrometry (Agilent Technologies) at NHRI.