Chemometric rationalization of the structural and physicochemical basis for selective cyclooxygenase-2 inhibition: Toward more specific ligands

Journal of Computer-Aided Molecular Design

Volumn 14, Issue 3, 2000, Pages 277-291

  Filipponi, Enrica ^a   Cecchetti, Violetta ^a   Tabarrini, Oriana ^a   Bonelli, Daniela ^a   Fravolini, Arnaldo ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Cyclooxygenase 2; GRID characterization; Principal component analysis (PCA); Selectivity

Indexed keywords

CHEMICAL ANALYSIS; DISEASES; DRUG INTERACTIONS; ENZYMES; LEAD COMPOUNDS; LIGANDS;

CHEMOMETRICES; CYCLOOXYGENASE 2; CYCLOOXYGENASES; GRID CHARACTERIZATION; PHYSICO-CHEMICALS; PRINCIPAL COMPONENT ANALYSE; PRINCIPAL-COMPONENT ANALYSIS; RATIONALISATION; SELECTIVE INHIBITION; SELECTIVITY;

PRINCIPAL COMPONENT ANALYSIS;

4 [5 (4 BROMOPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 5 (4 FLUOROPHENYL) 1 [(4 METHYLSULFONYL)PHENYL] 3 TRIFLUOROMETHYLPYRAZOLE; 5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; ISOENZYME; LIGAND; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; NIMESULIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN;

ARTICLE; CHEMOMETRIC ANALYSIS; CRYSTAL STRUCTURE; DRUG EFFICACY; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME STRUCTURE; HUMAN; INFLAMMATORY DISEASE; METHODOLOGY; MOUSE; MULTIVARIATE ANALYSIS; NONHUMAN; PHYSICAL CHEMISTRY; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0034073943     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1008180108753     Document Type: Article

References (42)

1. a. Vane, J.R., Nature (New Biol.), 231 (1971) 232.
2. b. Smith, J.B. and Willis, A.L., Nature (New Biol.), 231 (1971) 235.
3. Vane, J.R., Mitchell, J.A., Appleton, I., Tomlinson, A., Bishop-Bailey, D., Croxtail, J. and Willoughby, D.A., Proc. Natl. Acad. Sci. USA, 91 (1994) 2046.
4. a. Hla, T. and Neilson, K., Proc. Natl. Acad. Sci. USA, 89 (1992) 7384.
5. b. Xie, W., Chipman, J.G., Robertson, D.L., Erokson, R.L. and Simmons, D.L., Proc. Natl. Acad. Sci. USA, 88 (1991) 2692.
6. c. Kujubu, D.A., Fletcher, B.S., Varnum, B.C., Lim, R.W. and Herschman, H.R., J. Biol. Chem., 14 (1971) 1171.
7. a. Masferrer, J.L., Zweifel, B.S., Manning, P.T., Hauser, S.D., Leahey, K.M., Smith, W.G., Isakson, P.C. and Seibert, K., Proc. Natl. Acad. Sci. USA, 91 (1994) 3228.
8. b. Seibert, K. and Masferrer, J.L., Receptor, 4 (1994) 17.
9. c. Meade, E.A., Smith, V.L. and DeWitt, D.L., J. Biol. Chem., 268 (1993) 6610.
10. d. Mitchell, J.A., Akarasereemont, P., Thiemerman, C., Flower, R.J. and Wane, J.R., Proc. Natl. Acad. Sci. USA, 90 (1993) 11693.
11. e. Harada, Y., Hatanaka, K., Saito, M., Majima, M., Ogina, M., Kawamura, M., Ohno, T., Yang, Q., Katori, M. and Yamamoto, S., Biomed. Res., 15 (1994) 127.
12. a. Vane, J.R., Nature, 367 (1994) 215.
13. b. Vane, J.R. and Botting, R.M., Inflamm. Res., 44 (1995) 1.
14. c. DeWitt, D.L., Meade, E.A. and Smith, V.L., Am. J. Med., 95 (1993) 2A-40S.
15. Wallance, J.L., TIPS, 20 (1999) 4.
16. Picot, D., Loll, P.J. and Garavito, M., Nature, 367 (1994) 243.
17. Kurumbail, R.G., Stevens, A.M., Gierse, J.K., McDonald, J.J., Stegeman, R.A., Pak, J.Y., Gildehaus, D., Miyshiro, J.M., Penning, T.D., Seibert, K., Isakson, P.C. and Stallings, W.C., Nature, 384 (1996) 644.
18. Luong, C., Miller, A., Barnett, J., Chow, J., Ramesha, C. and Browner, M.F., Nature Struct. Biol., 3 (1996) 927.
19. Gierse, J.K., McDonald, J.J., Hauser, S.D., Rangwala, S.H., Koboldt, C.M. and Seibert, K., J. Biol. Chem., 271 (1996) 15810.
20. Quipeng, G., Lee-Ho, W., Ke-He, R. and Richard, J.K., J. Biol. Chem., 271 (1996) 19134.
21. Futaki, N., Takahashi, S., Yokoyama, M., Arai, I. and Higuchi, S., Prostaglandins, 47 (1994) 55.
22. Swingle, K.P., Moore, G.G.I, and Grant, T.J., Arch. Int. Pharmacodyn., 221 (1976) 132.
23. Gans, K.R., Galbraith, W., Roman, R.J., Haber, S.B., Kerr, J.S., Schmidt, W.K., Smith, C., Hewes, W.E. and Ackerman, N.R., J. Pharmacol. Exp. Ther., 254 (1990) 180.
24. Seibert, K., Zhang, Y., Leahy, K., Hauser, S., Masferrer, J., Perkins, W., Lee, L. and Isakson, P., Proc. Natl. Acad. Sci. USA, 91 (1994) 12013.
25. Penning, T.D., Talley, J.J., Bertenshaw, S.R., Carter, J.S., Collins, P.W., Docter, S., Matthew, J.G., Lee, L.F., Malecha, J.W, Miyashiro, J.M., Rogers, R.S., Rogier, D.J., Yu, S.S., Anderson, G.D., Burton, E.G., Cogburn, J.N., Gregory, S.A., Koboldt, C.M., Perkins, W.E., Veenhuizen, A.W., Zhang, Y.Y. and Isakson, P.C., J. Med. Chem., 40 (1997) 1347.
26. a. Pouplana, R., Perez, C., Sanchez, J., Lozano, J.J. and Puig-Parellada, P., J. Comput.-Aided Mol. Design, 13 (1999) 287.
27. b. Gabriel, F.F., Vasantha, P. and Kuppuswamy, N., Bioorg. Med. Chem., 6 (1998) 2337.
28. c. Pedretti, A., Villa, A.M., Villa, L. and Vistoli, G., Il Farmaco, 52 (1997) 487.
29. d. Stewart, K.D., Loren, S., Frey, L., Otis, E., Klinghofer, V. and Hulkower, K., Bioorg. Med. Chem. Lett., 8 (1998) 529.
30. a. Cruciani, G. and Goodford, P.J., J. Mol. Graphics, 12 (1994) 116.
31. b. Pastor, M. and Cruciani, G., J. Med. Chem., 38 (1995) 4637.
32. c. Matter, H. and Schwab, E., J. Med. Chem., 42 (1999) 4506.
33. Goodford, P.J., J. Med. Chem., 28 (1985) 849.
34. GRID v. 16 Manuals, Molecular Discovery Ltd.
35. Wold, S., Esbensen, K. and Geladi, P., Chemom. Intell. Lab. Syst., 2 (1987) 37.
36. Brookhaven National Laboratories Protein Databank.
37. SYBYL 6.3 Molecular Modeling Software, Tripos, Inc.
38. Baroni, M. and Pastor, M., GOLPE v. 4.0.2, Multivariate Infometric Analysis 1998.
39. a. Cruciani, G., Baroni, M., Clementi, S., Costantino, G., Riganelli, D. and Skagerberg, B., J. Chemometrics, 6 (1992) 335.
40. b. Wold, S., Technometrics, 20 (1978) 397.
41. WO96/09304 PCT/US95/11403.
42. Loll, P.J., Picot, D. and Garavito, R.M., Nat. Struct. Biol., 2 (1995) 639.