11,12-Epoxyeicosatrienoic acid (11,12-EET): Structural determinants for inhibition of TNF-α-induced VCAM-1 expression

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 22, 2003, Pages 4011-4014

  Falck, J R ^a   Reddy, L Manmohan ^a   Reddy, Y Krishna ^a   Bondlela, Muralidhar ^a   Krishna, U Murali ^a   Ji, Yu ^a   Sun, Jianxin ^b   Liao, James K ^b  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^b BRIGHAM AND WOMEN S HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

11,12 EPOXY 5,8,14 ICOSATRIENOIC ACID; ANTIINFLAMMATORY AGENT; AUTACOID; CYCLOPROPANE DERIVATIVE; EPOXIDE; ETHER DERIVATIVE; FURAN DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1;

ARTICLE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG SYNTHESIS; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; MOLECULAR RECOGNITION; PROTEIN DETERMINATION; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION;

EID: 0242285600     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.08.060     Document Type: Article

References (19)

1. Presented in part at the 225th ACS National Meeting, New Orleans, LA, March 23-27, 2003: MEDI 258.
2. Capdevila J.H., Falck J.R. Prostaglandins and Other Lipid Mediators. 68-69:2002;325.
3. (a) Zou A.-P., Fleming J.T., Falck J.R., Jacobs E.R., Gebremedhin D., Harder D.R., Roman R.J. Am. J. Physiol. 270:1996;F822 (b) Salvail D., Dumoulin M., Rousseau E. Am. J. Physiol. 275:1998;L432 (c) Archer S.L., Gragasin F.S., Wu X., Wang S., McMurtry S., Kim D.H., Platonov M., Koshal A., Hashimoto K., Campbell W.B., Falck J.R., Michelakis E.D. Circulation. 107:2003;769.
4. (a) Zou A.-P., Fleming J.T., Falck J.R., Jacobs E.R., Gebremedhin D., Harder D.R., Roman R.J. Am. J. Physiol. 270:1996;F822 (b) Salvail D., Dumoulin M., Rousseau E. Am. J. Physiol. 275:1998;L432 (c) Archer S.L., Gragasin F.S., Wu X., Wang S., McMurtry S., Kim D.H., Platonov M., Koshal A., Hashimoto K., Campbell W.B., Falck J.R., Michelakis E.D. Circulation. 107:2003;769.
5. (a) Zou A.-P., Fleming J.T., Falck J.R., Jacobs E.R., Gebremedhin D., Harder D.R., Roman R.J. Am. J. Physiol. 270:1996;F822 (b) Salvail D., Dumoulin M., Rousseau E. Am. J. Physiol. 275:1998;L432 (c) Archer S.L., Gragasin F.S., Wu X., Wang S., McMurtry S., Kim D.H., Platonov M., Koshal A., Hashimoto K., Campbell W.B., Falck J.R., Michelakis E.D. Circulation. 107:2003;769.
6. Li P.-L., Chen C.-L., Bortell R., Campbell W.B. Cir. Res. 85:1999;349.
7. Roman R.J., Maier K.G., Sun C.W., Harder D.R., Alonso-Galicia M. Clin. Exp. Pharm. Physiol. 27:2000;855.
8. Popp R., Brandes R.P., Ott G., Busse R., Fleming I. Cir. Res. 90:2002;800.
9. Node K., Huo Y., Ruan Z.X., Yang B., Spiecker M., Ley K., Zeldin D.C., Liao J.K. Science. 285:1999;1276.
10. Recognition and/or binding site is the preferred terminology at this time since insufficient data are available to satisfy acceptable criteria for the existence of a receptor. For a relevant discussion of the distinctions, see: Laduron P.M. Biochem. Pharmacol. 33:1984;833.
11. A stereospecific, membrane binding site for 14,15-EET has been reported: Wong P.Y.K., Lin K.T., Yan Y.T., Ahern D., Iles J., Shen S.Y., Bhatt R.K., Falck J.R. J. Lipid Mediators. 6:1993;199.
12. For an EET/fatty acid binding protein, see: Widstrom R.L., Norris A.W., Spector A.A. Biochemistry. 40:2001;1070.
13. (a) Fang X., Kaduce T.L., Weintraub N.L., Harmon S., Teesch L.M., Morisseau C., Thompson D.A., Hammock B.D., Spector A.A. J. Biol. Chem. 276:2001;14867 (b) Zeldin D.C., Wei S., Falck J.R., Hammock B.D., Snapper J.R., Capdevila J.H. Arch. Biochem. Biophys. 316:1995;443.
14. (a) Fang X., Kaduce T.L., Weintraub N.L., Harmon S., Teesch L.M., Morisseau C., Thompson D.A., Hammock B.D., Spector A.A. J. Biol. Chem. 276:2001;14867 (b) Zeldin D.C., Wei S., Falck J.R., Hammock B.D., Snapper J.R., Capdevila J.H. Arch. Biochem. Biophys. 316:1995;443.
15. Drummond J.T., Johnson G. Tetrahedron Lett. 29:1988;1653.
16. 1H NMR (400 MHz) of analogue 9: δ 0.88 (t, J=6.8 Hz, 3H), 1.20-1.63 (m, 22H), 1.99 (q, J=6.8 Hz, 2H), 2.14-2.22 (m, 1H), 2.27-2.38 (m, 3H), 2.64-2.70 (m, 2H), 5.31-5.40 (m, 1H), 5.42-5.51 (m, 1H). 11: δ 0.88 (t, J=6.7 Hz, 3H), 1.20-1.44 (m, 17H), 1.45-1.58 (m, 3H), 1.59-1.70 (m, 2H), 2.05 (q, J=6.7 Hz, 2H), 2.13-2.24 (m, 1H), 2.29-2.42 (m, 3H), 2.89-2.97 (m, 2H), 5.38-5.47 (m, 1H), 5.48-5.56 (m, 1H). 14: δ 0.88 (t, J=7.0 Hz, 3H), 1.20-1.41 (m, 6H), 1.72 (quintet, J=7.6 Hz, 2H), 2.05 (q, J=6.4 Hz, 2H), 2.13 (q, J=6.7 Hz, 2H), 2.20-2.45 (m, 4H), 2.48-2.61 (m, 2H), 2.80 (apparent t, J=6. 4 Hz, 2H) 2.92-3.00 (m, 2H), 5.33-5.58 (m, 6H). 15: δ 0.88 (t, J=6.4 Hz, 3H), 1.20-1.42 (m, 15H), 1.41-1.58 (m, 3H), 1.59-1.70 (m, 2H), 1.82-1.92 (m, 2H), 2.0-2.10 (m, 2H), 2.32-2.40 (m, 3H), 2.41-2.52 (m, 1H), 2.90-3.00 (m, 2H), 5.43-5.52 (m, 2H). 17: δ 0.88 (t, J=6.4 Hz, 3H), 1.22-1.40 (m, 18H), 1.53-1.65 (m, 4H), 1.98-2.08 (m, 2H), 2.33 (quintet, J=7 Hz, 4H), 3.38-3.43 (m, 4H), 5.33-5.40 (m, 1H), 5.41-5.47 (m, 1H).
17. Hopf H., Kruger A. Chem. Eur J. 7:2001;4378.
18. 2, 0°C, 1 h) of the corresponding alcohol, Kotsuki H., Ushio Y., Yoshimura N., Ochi M. J. Org. Chem. 52:1987;2594.
19. As in ref 15: using the alcohol described by Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647.