A reduced-amide inhibitor of pin1 binds in a conformation resembling a twisted-amide transition state

Biochemistry

Volumn 50, Issue 44, 2011, Pages 9545-9550

  Xu, Guoyan G ^a   Zhang, Yan ^b   Mercedes Camacho, Ana Y ^a   Etzkorn, Felicia A ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLUBILITY; CELL CYCLE; ETHYLAMINE; PEPTIDYL-PROLYL ISOMERASE; STRUCTURAL DETERMINATION; TRANSITION STATE; X-RAY STRUCTURE;

OLEFINS;

AMIDES;

AMIDE; ISOMERASE INHIBITOR; PEPTIDYLPROLYL ISOMERASE PIN1; PIPECOLIC ACID; PROLINE; PYRROLIDINE DERIVATIVE; REDUCED AMIDE INHIBITOR; SERINE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DRUG STRUCTURE; ENZYME CONFORMATION; PRIORITY JOURNAL; TWISTED AMIDE TRANSITION STATE;

AMIDES; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HUMANS; OXIDATION-REDUCTION; PEPTIDYLPROLYL ISOMERASE; PROTEIN BINDING; PROTEIN CONFORMATION; PYRROLIDINES; STEREOISOMERISM;

EID: 80155166010     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi201055c     Document Type: Article

References (41)

1. Lu, K. P., Hanes, S. D., and Hunter, T. (1996) A human peptidyl-prolyl isomerase essential for regulation of mitosis Nature 380, 544-547 (Pubitemid 26111332)
2. Fischer, G., Wittamann-Liebold, B., Lang, K., Kiefhaber, T., and Schmid, F. X. (1989) Cyclophilin and peptidyl-prolyl cis-trans isomerase are probably identical proteins Nature 337, 476-478
3. Harding, M. W., Galat, A., Uehling, D. E., and Schreiber, S. L. (1989) A receptor for the immuno-suppressant FK506 is a cis-trans peptidyl-prolyl isomerase Nature 341, 758-760 (Pubitemid 19260893)
4. Wiederrecht, G. and Etzkorn, F. A. (1994) Immunophilins. In Perspectives in Drug Discovery and Design (Sigal, N. and Wyvratt, M., Eds.) pp 57-84, ESCOM Science Publishers, B.V.
5. Lu, K. P. (2004) Pinning down cell signaling, cancer and Alzheimers disease Trends Biochem. Sci. 29, 200-209 (Pubitemid 38472025)
6. Yaffe, M. B., Schutkowski, M., Shen, M., Zhou, X. Z., Stukenberg, P. T., Rahfeld, J. U., Xu, J., Kuang, J., Kirschner, M. W., Fischer, G., Cantley, L. C., and Lu, K. P. (1997) Sequence-specific and phosphorylation-dependent proline isomerization: A potential mitotic regulatory mechanism Science 278, 1957-1960 (Pubitemid 28013239)
7. Stukenberg, P. T. and Kirschner, M. W. (2001) Pin1 acts catalytically to promote a conformational change in Cdc25 Mol. Cell 7, 1071-1083 (Pubitemid 32525753)
8. Satyanarayana, A. and Kaldis, P. (2009) Mammalian cell-cycle regulation: Several Cdks, numerous cyclins and diverse compensatory mechanisms Oncogene 28, 2925-2939
9. Ranganathan, R., Lu, K. P., Hunter, T., and Noel, J. P. (1997) Structural and functional analysis of the mitotic rotamase Pin1 suggests substrate recognition is phosphorylation dependent Cell 89, 875-886 (Pubitemid 27513514)
10. Joseph, J. D., Yeh, E. S., Swenson, K. I., Means, A. R., and Winkler (2003) The peptidyl-prolyl isomerase Pin1 Prog. Cell Cycle Res. 5, 477-487
11. Xu, G. G. and Etzkorn, F. A. (2009) Pin1 as an anticancer drug target Drug News Perspect. 22, 399-407
12. Fischer, G. (1994) Peptidyl-Prolyl cis/trans Isomerases and Their Effectors Angew. Chem., Int. Ed. 33, 1415-1436
13. Rosen, M. K., Standaert, R. F., Galat, A., Nakatsuka, M., and Schreiber, S. L. (1990) Inhibition of FKBP Rotamase Activity by Immunosuppressant FK506: Twisted Amide Surrogate Science 248, 863-866
14. Harrison, R. K., Caldwell, C. G., Rosegay, A., Melillo, D., and Stein, R. L. (1990) Confirmation of the Secondary Deuterium Isotope Effect for the Peptidyl Prolyl Cis-Trans Isomerase Activity of Cyclophilin by a Competitive, Double-Label Technique J. Am. Chem. Soc. 112, 7063-7064 (Pubitemid 20319140)
15. Zydowsky, L. D., Etzkorn, F. A., Chang, H., Ferguson, S. B., Stolz, L. A., Ho, S. I., and Walsh, C. T. (1992) Active Site Mutants of Human Cyclophilin A Separate Peptidyl-Prolyl Isomerase Activity from Cyclosporin A Binding and Calcineurin Inhibition Protein Sci. 1, 1092-1099 (Pubitemid 23016423)
16. Fischer, S., Michnick, S., and Karplus, M. (1993) A Mechanism for Rotamase Catalysis by the FK506 Binding Protein (FKBP) Biochemistry 32, 13830-13837 (Pubitemid 24018233)
17. Hur, S. and Bruice, T. C. (2002) The Mechanism of Cis-Trans Isomerization of Prolyl Peptides by Cyclophilin J. Am. Chem. Soc. 124, 7303-7313 (Pubitemid 34670439)
18. Schroeder, O. E., Carper, E., Wind, J. J., Poutsma, J. L., Etzkorn, F. A., and Poutsma, J. C. (2006) Theoretical and experimental investigation of the energetics of cis-trans proline isomerization in peptide models J. Phys. Chem. A 110, 6522-6530 (Pubitemid 44020306)
19. Szelke, M., Leckie, B., Hallett, A., Jones, D. M., Sueiras, J., Atrash, B., and Lever, A. F. (1982) Potent new inhibitors of human renin Nature 299, 555-557 (Pubitemid 12034214)
20. Zivec, M., Jakopin, Z., and Gobec, S. (2009) Recent advances in the synthesis and applications of reduced amide pseudopeptides Curr. Med. Chem. 16, 2289-2304
21. Wang, X. J., Xu, B., Mullins, A. B., Neiler, F. K., and Etzkorn, F. A. (2004) Conformationally locked isostere of phosphoSer- cis -Pro inhibits Pin1 23-fold better than phosphoSer- trans -Pro isostere J. Am. Chem. Soc. 126, 15533-15542 (Pubitemid 39577489)
22. Zhang, Y., Daum, S., Wildemann, D., Zhou, X. Z., Verdecia, M. A., Bowman, M. E., Lucke, C., Hunter, T., Lu, K. P., Fischer, G., and Noel, J. P. (2007) Structural basis for high-affinity peptide inhibition of human Pin1 ACS Chem. Biol. 2, 320-328 (Pubitemid 350001580)
23. Otwinowski, Z. and Minor, W. (1997) Processing of X-ray diffraction data collected in oscillation mode Methods Enzymol. 276, 307-326 (Pubitemid 27085611)
24. Navaza, J. (1994) AMoRe: An automated package for molecular replacement Acta Crystallogr. A50, 157-163
25. Collaborative Computational Project Number 4 (1994) The CCP4 suite: Programs for protein crystallography Acta Crystallogr. D50, 760-763
26. Brunger, A. T. (1992) Free R value: A novel statistical quantity for assessing the accuracy of crystal structures Nature 355, 472-475
27. Emsley, P. and Cowtan, K. (2004) Coot: Model-building tools for molecular graphics Acta Crystallogr. D60, 2126-2132 (Pubitemid 41742764)
28. Laskowski, R. A., MacArthur, M. W., Moss, D. S., and Thornton, J. M. (1993) PROCHECK: A program to check the stereochemical quality of protein structures J. Appl. Crystallogr. 26, 283-291
29. Roeske, R. W., Weitl, F. L., Prasad, K. U., and Thompson, R. M. (1976) Selective Reduction of the Amide Carbonyl Group in Dipeptides by Borane J. Org. Chem. 41, 1260-1261
30. 2N]Pro Linkages in HIV Protease Inhibitors J. Org. Chem. 56, 4161-4167
31. Verdecia, M. A., Bowman, M. E., Lu, K. P., Hunter, T., and Noel, J. P. (2000) Structural basis for phosphoserine-proline recognition by group IV WW domains Nat. Struct. Biol. 7, 639-643 (Pubitemid 30636673)
32. Lu, P. J., Zhou, X. Z., Shen, M., and Lu, K. P. (1999) Function of WW domains as phosphoserine- or phosphothreonine-binding modules Science 283, 1325-1328
33. SYBYL (2008) Tripos International, St. Louis.
34. Schramm, V. L. (2005) Enzymatic transition states and transition state analogues Curr. Opin. Struct. Biol. 15, 604-613 (Pubitemid 41668515)
35. Xu, G. (2010) Pin1 Inhibitors: Towards Understanding the Enzymatic Mechanism. Ph.D. Thesis, Virginia Polytechnic Institute and State University, Blacksburg, VA.
36. Etzkorn, F. A., Noel, J. P., Zhang, Y., and Wang, X. J. (2006) Pin1: Inhibitors and Mechanism. In Understanding Biology Using Peptides, Proceedings of the 19th American Peptide Symposium (Blondelle, S. E., Ed.), pp 759-762, Springer, Inc., San Diego.
37. Wildemann, D., Erdmann, F., Alvarez, B. H., Stoller, G., Zhou, X. Z., Fanghanel, J., Schutkowski, M., Lu, K. P., and Fischer, G. (2006) Nanomolar Inhibitors of the Peptidyl Prolyl Cis/Trans Isomerase Pin1 from Combinatorial Peptide Libraries J. Med. Chem. 49, 2147-2150
38. Namanja, A. T., Wang, X. J., Xu, B., Mercedes-Camacho, A. Y., Wilson, B. D., Wilson, K. A., Etzkorn, F. A., and Peng, J. W. (2010) Toward Flexibility-Activity Relationships by NMR Spectroscopy: Dynamics of Pin1 Ligands J. Am. Chem. Soc. 132, 5607-5609
39. Zhao, S. and Etzkorn, F. A. (2007) A phosphorylated prodrug for the inhibition of Pin1 Bioorg. Med. Chem. Lett. 17, 6615-6618 (Pubitemid 350026314)
40. Xu, G. G. and Etzkorn, F. A. (2010) Convergent Synthesis of α-Ketoamide Inhibitors of Pin1 Org. Lett. 12, 696-699
41. DeLano, W. L. (2002) The PyMOL Molecular Graphics System, DeLano Scientific, San Carlos, CA.