Investigation of the binding pocket of human hematopoietic prostaglandin (PG) D2 synthase (hH-PGDS): A tale of two waters

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 11, 2012, Pages 3795-3799

  Trujillo, John I ^a,d   Kiefer, James R ^a,d   Huang, Wei ^a   Day, Jacqueline E ^a   Moon, Joseph ^b   Jerome, Gina M ^a   Bono, Christine P ^a   Kornmeier, Christine M ^a   Williams, Melanie L ^a   Kuhn, Cyrille ^c   Rennie, Glen R ^c   Wynn, Thomas A ^c   Carron, Christopher P ^a   Thorarensen, Atli ^a  

^a PFIZER INC   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^c Research Technology Center   (United States)

^d GENENTECH INC   (United States)

Author keywords

Isoquinoline; PGDS inhibitors; Prostaglandin D2 synthase; Water displacement

Indexed keywords

BINDING PROTEIN; PROSTAGLANDIN D SYNTHASE; PROSTAGLANDIN D2 SYNTHASE; PROSTAGLANDIN SYNTHASE INHIBITOR; UNCLASSIFIED DRUG; WATER;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; ENZYME BINDING; ENZYME INHIBITION; HEMATOPOIETIC SYSTEM; HUMAN; HUMAN CELL; MOLECULAR PROBE;

ANTI-ALLERGIC AGENTS; ANTI-INFLAMMATORY AGENTS; BINDING SITES; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HUMANS; INTRAMOLECULAR OXIDOREDUCTASES; ISOQUINOLINES; LIPOCALINS; NAPHTHALENES; PROTEIN STRUCTURE, TERTIARY; WATER;

EID: 84861202344     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.04.004     Document Type: Article

References (39)

1. H. Giles, and P. Leff Prostaglandins 35 1988 277
2. H. Nagai Allergology 57 2008 187
3. T. Oguma, K. Asano, and A. Ishizaka Allergology 57 2008 307
4. Y. Urade, and N. Eguchi Prostaglandins Other Lipid Mediat. 68 2002 375
5. For a review of hematopoietic prostaglandin D synthase see: Y. Kanaoka, and Y. Urade Prostaglandins Leukot. Essent. Fatty Acids 69 2003 163 and references cited therein
6. T. Matsuoka, M. Hirata, H. Tanaka, Y. Takahashi, T. Murata, K. Kabashima, Y. Sugimoto, T. Kobayashi, F. Ushikubi, Y. Aze, N. Eguchi, Y. Urade, N. Yoshida, K. Kimura, A. Mizoguchi, Y. Honda, H. Nagai, and S. Narumiya Science 287 2000 2013
7. K. Aritake, Y. Kado, T. Inoue, M. Miyano, and Y. Urade J. Biological Chemistry 281 2006 15277
8. M. Howhy, L. Spadola, B. Lundquist, P. Hawtin, J. Dahmen, I. Groth-Clausen, E. Nilsson, S. Persdotter, K. von Wachenfeldt, R.H.A. Folmer, and K. Edman J. Med. Chem. 51 2008 2178
9. Li, Z.; Xiong, J. Sabol, J.S.; WO 2004/016223 A2.
10. Cao, Y.; Sabol, J.S.; Ayers, S; WO 2006/015195 A1.
11. Aldous, S.C.; Jiang, J.Z.; Lu, J.; Ma, L.; Mu, L.; Munson, H.R.; Sabol, J.S.; Thurairatnam, S.; Vandeusen, C.L. WO 2007/041634 A1.
12. Aldous, S.C.; Fennie, M.W.; Jiang, J.Z.; John, S.; Mu, L.; Pedgrift, B.; Pribish, J.R.; Rauckman, B.; Sabol, J.S.; Stoklosa, G.T.; Thurairatnam, S.; Vandeusen, C.L. WO 2008/121670 A1.
13. Aldous, S.C.; Fennie, M.W.;Jiang, J.Z.; John, S.; Pedgrift, B.; Pribish, J.R.; Rauckman, B.; Sabol, J.S.; Stoklosa, G.T.; Thurairatnam, S.; Vandeusen, C.L. WO 2008/121670 A1.
14. T. Hesterkamp, J. Barker, A. Davenport, and M. Whittaker Curr. Top. Med. Chem. 7 2007 1582
15. Aicher, B.; Kelter, A.R.; Coulter, T.S.; Taylor, S.; Davenport, A.J.; Hesterkamp, T.; Kirchhoff, C. WO 2008/122787 A1.
16. Urade, Y.; Tanaka, Y.; Yamane, K.; Togawa, M. WO 2007/007778 A1.
17. Urade, Y.; Shigeno, K.; Tanaka, Y.; Kuze, J.; Tsuchikawa, M.; Hosoya, T. JP 2007051121 A.
18. Yamane, K.; Tanaka, Y.; Shigeno, K.; Hosoya, T.; Inoue, S.; Kitade, M.; Harada, T.; Aoyagi, H.; Miyoshi, N.; Mutoh, T.; Togawa, M.; Kiniwa, M.; Yamasaki, Y. Abstracts of Papers, 235th National Meeting of the American Chemical Society, New Orleans, LA, April 6-10, 2008; American Chemical Society: Washington, DC, 2008; MEDI 26.
19. Blake, T.; Hamper, B.C.; Huang, W.; Kiefer, J.R.; Moon, J.B.; Neal, B.E.; Olson, K.L.; Pelc, M.J.; Schweitzer, B.A.; Thorarensen, A.; Trujillo, J.I.; Turner, S.R. US 2008/0146569 A1.
20. C.P. Carron, J.I. Trujillo, K.L. Olson, W. Huang, B.C. Hamper, T. Dice, B.E. Neal, M.J. Pelc, J. Day, D.C. Rohrer, J.R. Kiefer, J.B. Moon, B.A. Schweitzer, T.D. Blake, S.R. Turner, R. Woerndle, B.L. Case, C.P. Bono, V.M. Dilworth, C.L. Funckes-Shippy, B.L. Hood, G.M. Jerome, C.M. Kornmeier, M.R. Radabaugh, M.L. Williams, M.S. Davies, C.D. Wegner, D.J. Welsch, W.M. Abraham, C.J. Warren, M.E. Dowty, F. Hua, A. Zutshi, J.Z. Yang, and A. Thorarensen ACS Med. Chem. Lett. 1 2010 59
21. P.Y.S. Lam, P.K. Jadhav, C.J. Eyermann, C.N. Hodge, R. Yu, L.T. Bacheler, J.L. Meek, M.J. Otto, M.M. Rayner, Y.N. Wong, C.-H. Chang, P.C. Weber, D.A. Jackson, T.R. Sharpe, and S. Erickson-Viitanen Science 263 1994 380
22. C.S. Poornima, and P.M. Dean J. Comput. Aided Mol. Des. 9 1995 500
23. C.S. Poornima, and P.M. Dean J. Comput. Aided Mol. Des. 9 1995 513
24. C.S. Poornima, and P.M. Dean J. Comput. Aided Mol. Des. 9 1995 521
25. J.E. Ladbury Chem. Biol. 3 1996 973 980
26. C. Barillari, J. Taylor, R. Viner, and J.W. Essex J. Am. Chem. Soc. 129 2007 2577
27. M.L. Raymer, P.C. Shanschagrin, W.F. Punch, S. Venkataraman, E.D. Goodman, and L.A. Kuhn J. Mol. Biol. 265 1997 445
28. A.T. Garcia-Sosa, R.L. Mancera, and P.M. Dean J. Mol. Model. 9 2003 172
29. A. Suzuki Mod. Arene Chem. 2002 53
30. C. Bissantz, B. Kuhn, and M. Stahl J. Med. Chem. 53 2010 5061 For a recent perspective on molecular interactions see
31. For recent publications regarding inhibitors of hHPGDS see: Smythe, M.L.; Flanagan, J.U. WO 2011/150457.
32. Urade, Y., Kitade, M.; Shigeno, K. Yamane, K.; Tanaka, K. WO 2011/090062.
33. Takada, Ch. Saeki, K.; Kawaski, H.; Tagaya, M.; Komai, M.; Ikemura, T.; Yamaguchi, S.; Iida, K. WO 2011/043359.
34. Urade, Y.; Kitade, M.; Shigeno, K.; Yamane, K.; Tanaka, K. WO 2010/0104024.
35. A. Christ, L. Labzin, G.T. Bourne, H. Fukunishi, J.E. Weber, M.J. Sweet, M.L. Smythe, and J.U. Flanagan J. Med. Chem. 53 2010 5536
36. J.E. Weber, A.J. Oakley, A.N. Christ, A.G. Clark, J.D. Hayes, R. Hall, D.A. Hume, P.G. Board, M.L. Smythe, and J.U. Flanagan Eur. J. Med. Chem. 45 2010 447
37. Endres, G.W.; Lee, P.H.; Olson, K.L.; Kramer, J.B.; Ciske, F.L.; Barret, S.D. WO 2010/033977 A2.
38. Huang, W.; Mantell, S.J.; Strang, R.S.; Thorarensen, A.; Trujillo, J.I.; Turner, S.R.; Yeap, S.K. WO 2009/153720 A1.
39. Trujillo, J.I. et al. manuscript in preparation.