Structure-based design of novel human Pin1 inhibitors (III): Optimizing affinity beyond the phosphate recognition pocket

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 17, 2014, Pages 4187-4191

  Guo, Chuangxing ^a   Hou, Xinjun ^a   Dong, Liming ^a   Marakovits, Joseph ^a   Greasley, Samantha ^a   Dagostino, Eleanor ^a   Ferre, Roseann ^a   Catherine Johnson, M ^a   Humphries, Paul S ^a   Li, Haitao ^a   Paderes, Genevieve D ^a   Piraino, Joseph ^a   Kraynov, Eugenia ^a   Murray, Brion W ^a  

^a PFIZER INC   (United States)

Author keywords

Anti cancer; Anti tumor; Cell permeability; Medicinal chemistry; Mitosis; Peptidyl prolyl isomerase; Phospho protein epitope; Pin1; PPIase; SBDD; Structural based drug design

Indexed keywords

ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ISOMERASE INHIBITOR; PEPTIDYLPROLYL ISOMERASE PIN1; PEPTIDYLPROLYL ISOMERASE PIN1 INHIBITOR; PHOSPHATE; PROLINE; UNCLASSIFIED DRUG; BENZIMIDAZOLE; CARBOXYLIC ACID; ENZYME INHIBITOR; NIMA-INTERACTING PEPTIDYLPROLYL ISOMERASE; PEPTIDYLPROLYL ISOMERASE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; CANCER CELL LINE; CATALYSIS; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; LIGAND BINDING; MOLECULAR RECOGNITION; PROCESS OPTIMIZATION; PROTEIN BINDING; PROTEIN FUNCTION; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENZYME ACTIVE SITE; METABOLISM; SYNTHESIS;

BENZIMIDAZOLES; CARBOXYLIC ACIDS; CATALYTIC DOMAIN; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; MOLECULAR STRUCTURE; PEPTIDYLPROLYL ISOMERASE; PHOSPHATES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84906935037     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.07.044     Document Type: Article

References (29)

1. Recent reviews on Pin1 research T.H. Lee, L. Pastorino, and K.P. Lu Expert Rev. Mol. Med. 20 13 2011 e21
2. Y.C. Liou, X.Z. Zhou, and K.P. Lu Trends Biochem. Sci. 36 2011 501
3. G. Finn, and K.P. Lu Curr. Cancer Drug Targets 8 2008 223
4. G. Lippens, I. Landrieu, and C. Smet FEBS J. 274 2007 5211
5. S. Esnault, Z.J. Shen, and J.S. Malter Crit. Rev. Immunol. 28 2008 45
6. C.J. Zhang, Z.H. Zhang, B.L. Xu, and Y.L. Wang Yao Xue Xue Bao 43 2008 9
7. K.P. Lu, S.D. Hanes, and T. Hunter Nature 380 1996 544
8. E.S. Yeh, and A.R. Means Nat. Rev. Cancer 7 2007 381 and references cited therein
9. A. Rustighi, L. Tiberi, A. Soldano, M. Napoli, P. Nuciforo, A. Rosato, F. Kaplan, A. Capobianco, S. Pece, P.P. Di Fiore, and G. Del Sal Nat. Cell Biol. 11 2009 133
10. Y. Zheng, Y. Xia, D. Hawke, M. Halle, M.L. Tremblay, X. Gao, X.Z. Zhou, K. Aldape, M.H. Cobb, K. Xie, J. He, and Z. Lu Mol. Cell. 35 2009 11
11. K.P. Lu Prog. Cell Cycle Res. 4 2000 83
12. K.E. Winkler, K.I. Swenson, S. Kornbluth, and A.R. Means Science 287 2000 1644
13. Lu, K. P.; Wulf, G.; Zhou, X. Z. PCT Int. Appl. WO 2001038878, 2001.
14. S. Daum, J. Fanghanel, D. Wildemann, and C. Schiene-Fischer Biochemistry 45 2006 12125
15. E. Pani, M. Menigatti, S. Schubert, D. Hess, B. Gerrits, K.H. Klempnauer, and S. Ferrari Biochim. Biophys. Acta 1783 2008 1121
16. C. Guo, X. Hou, L. Dong, E. Dagostino, S. Greasley, R.A. Ferre, J. Marakovits, M.C. Johnson, D. Matthews, B. Mroczkowski, H. Parge, T. VanArsdale, I. Popoff, J. Piraino, S. Margosiak, J. Thomson, G. Los, and B.W. Murray Bioorg. Med. Chem. Lett. 19 2009 5613
17. C. Guo, S. Reich, R. Showalter, E. Villafranca, and L. Dong Tetrahedron Lett. 41 28 2000 5307
18. R. Hudack, N. Barta, C. Guo, J. Deal, L. Dong, L. Fay, B. Caprathe, A. Chatterjee, D. Vanderpool, C. Bigge, R. Showalter, S. Bender, C. Augelli-Szafran, E. Lunney, and X. Hou J. Med. Chem. 49 2006 1202
19. D. Wildemann, F. Erdmann, B.H. Alvarez, G. Stoller, X.Z. Zhou, J. Fanghanel, M. Schutkowski, K.P. Lu, and G. Fischer J. Med. Chem. 49 2006 2147
20. L. Zhu, J. Jin, C. Liu, C. Zhang, Y. Sun, Y. Guo, D. Fu, X. Chen, and B. Xu BMC 19 9 2011 2797
21. T. Liu, Y. Liu, H. Kao, and D. Pei J. Med. Chem. 53 6 2010 2494
22. G.G. Xu, C. Slebodnick, and F.A. Etzkorn PLoS One 7 9 2012 e44226
23. K.E. Duncan, B.R. Dempsey, L.E. Killip, J. Adams, M.L. Bailey, G.A. Lajoie, D.W. Litchfield, C.J. Brandl, G.S. Shaw, and B.H. Shilton J. Med. Chem. 54 11 2011 3854
24. A.J. Potter, S. Ray, L. Gueritz, C.L. Nunns, C.J. Bryant, S.F. Scrace, N. Matassova, L. Baker, P. Dokurno, D.A. Robinson, A.E. Surgenor, B. Davis, J.B. Murray, C.M. Richardson, and J.D. Moore Bioorg. Med. Chem. Lett. 20 2 2010 586
25. A. Potter, V. Oldfield, C. Nunns, C. Fromont, S. Ray, C.J. Northfield, C.J. Bryant, S.F. Scrace, D. Robinson, N. Matossova, L. Baker, P. Dokurno, A.E. Surgenor, B. Davis, C.M. Richardson, J.B. Murray, and J.D. Moore Bioorg. Med. Chem. Lett. 20 22 2010 6483
26. L. Dong, J. Marakovits, X. Hou, C. Guo, S. Greasley, E. Dagostino, R.A. Ferre, M.C. Johnson, E. Kraynov, J. Thomson, V. Pathak, and B.W. Murray Bioorg. Med. Chem. Lett. 20 2010 2210
27. Synthetic procedures of the compounds cited herein were reported in WO Patent WO/2006/040,646, 2006. The purity of all compounds reported herein was 97% or higher determined by proton NMR and LCMS analyses.
28. Caco2 assay conditions and result interpretation reported previously C. Guo, I. McAlpine, J. Zhang, D. Knighton, S. Kephart, M. Johnson, H. Li, D. Bouzida, A. Yang, L. Dong, J. Marakovits, J. Tikhe, P. Richardson, L. Guo, R. Kania, M. Edwards, E. Kraynov, J. Christensen, J. Piraino, J. Lee, E. Dagostino, C. Del-Carmen, Y. Deng, T. Smeal, and B.W. Murray J. Med. Chem. 55 2012 4728
29. C. Guo, A. Linton, S. Kephart, M. Ornelas, M. Pairish, J. Gonzalez, S. Greasley, A. Nagata, B. Burke, M. Edwards, N. Hosea, P. Kang, W. Hu, J. Engebretsen, D. Briere, M. Shi, H. Gukasyan, P. Richardson, K. Dack, T. Underwood, P. Johnson, A. Morell, R. Felstead, H. Kuruma, H. Matsimoto, A. Zoubeidi, M. Gleave, G. Los, and A.N. Fanjul J. Med. Chem. 54 2013 7693