Discovery and binding studies on a series of novel pin1 ligands

Chemical Biology and Drug Design

Volumn 73, Issue 4, 2009, Pages 369-379

  Wu, Bainan ^a   Rega, Michele F ^a   Wei, Jun ^a   Yuan, Hongbin ^a   Dahl, Russell ^a   Zhang, Ziming ^a   Pellecchia, Maurizio ^a  

^a BURNHAM INSTITUTE   (United States)

Author keywords

Comparative molecular field analysis; NMR; Pin1; WW domain

Indexed keywords

BI 81; INDOLE; LIGAND; NAPHTHALENE; PEPTIDE HYDROLASE INHIBITOR; PEPTIDYLPROLYL ISOMERASE PIN1; PINTIDE; SERINE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CARCINOGENESIS; CONTROLLED STUDY; DRUG BINDING; DRUG BLOOD LEVEL; DRUG DESIGN; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG TARGETING; LIGAND BINDING; MEMBRANE TRANSPORT; MOLECULAR PROBE; MOLECULAR WEIGHT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN PHOSPHORYLATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SPECTROSCOPY;

COMPUTER SIMULATION; ESCHERICHIA COLI; HUMANS; LIGANDS; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDYLPROLYL ISOMERASE; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SERINE; SMALL MOLECULE LIBRARIES;

EID: 61849109430     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00795.x     Document Type: Article

References (44)

1. Gothel S.F., Marahiel M.A. (1999) Peptidyl-prolyl cis-trans isomerases, a superfamily of ubiquitous folding catalysts. Cell Mol Life Sci 55 : 423 436.
2. Schmid F.X., Mayr L.M., Mucke M., Schonbrunner E.R. (1993) Prolyl isomerases: role in protein folding. Adv Protein Chem 44 : 25 66.
3. Shaw P.E. (2002) Peptidyl-prolyl isomerases: a new twist to transcription. EMBO Rep 3 : 521 526.
4. Handschumacher R.E., Harding M.W., Rice J., Drugge R.J., Speicher D.W. (1984) Cyclophilin: a specific cytosolic binding protein for cyclosporin A. Science 226 : 544 547.
5. Harding M.W., Galat A., Uehling D.E., Schreiber S.L. (1989) A receptor for the immunosuppressant FK506 is a cis-trans peptidyl-prolyl isomerase. Nature 341 : 758 760.
6. Rahfeld J.U., Schierhorn A., Mann K., Fischer G. (1994) A novel peptidyl-prolyl cis/trans isomerase from Escherichia coli. FEBS Lett 343 : 65 69.
7. Lu K.P., Hanes S.D., Hunter T. (1996) A human peptidyl-prolyl isomerase essential for regulation of mitosis. Nature 380 : 544 547.
8. Ranganathan R., Lu K.P., Hunter T., Noel J.P. (1997) Structural and functional analysis of the mitotic rotamase Pin1 suggests substrate recognition is phosphorylation dependent. Cell 89 : 875 886.
9. Zheng H., You H., Zhou X.Z., Murray S.A., Uchida T., Wulf G., Gu L., Tang X., Lu K.P., Xiao Z.X. (2002) The prolyl isomerase Pin1 is a regulator of p53 in genotoxic response. Nature 419 : 849 853.
10. Zhou X.Z., Kops O., Werner A., Lu P.J., Shen M., Stoller G., Kullertz G., Stark M., Fischer G., Lu K.P. (2000) Pin1-dependent prolyl isomerization regulates dephosphorylation of Cdc25C and tau proteins. Mol Cell 6 : 873 883.
11. Ryo A., Nakamura M., Wulf G., Liou Y.C., Lu K.P. (2001) Pin1 regulates turnover and subcellular localization of beta-catenin by inhibiting its interaction with APC. Nat Cell Biol 3 : 793 801.
12. Lu K.P., Liou Y.C., Vincent I. (2003) Proline-directed phosphorylation and isomerization in mitotic regulation and in Alzheimer's disease. BioEssays 25 : 174 181.
13. Lee M.S., Kao S.C., Lemere C.A., Xia W., Tseng H.C., Zhou Y., Neve R., Ahlijanian M.K., Tsai L.H. (2003) APP processing is regulated by cytoplasmic phosphorylation. J Cell Biol 163 : 83 95.
14. Liou Y.C., Ryo A., Huang H.K., Lu P.J., Bronson R., Fujimori F., Uchida T., Hunter T., Lu K.P. (2002) Loss of Pin1 function in the mouse causes phenotypes resembling cyclin D1-null phenotypes. Proc Natl Acad Sci USA 99 : 1335 1340.
15. Ryo A., Liou Y.C., Wulf G., Nakamura M., Lee S.W., Lu K.P. (2002) PIN1 is an E2F target gene essential for Neu/Ras-induced transformation of mammary epithelial cells. Mol Cell Biol 22 : 5281 5295.
16. Wulf G.M., Ryo A., Wulf G.G., Lee S.W., Niu T., Petkova V., Lu K.P. (2001) Pin1 is overexpressed in breast cancer and cooperates with Ras signaling in increasing the transcriptional activity of c-Jun towards cyclin D1. EMBO J 20 : 3459 3472.
17. Dominguez-Sola D., Dalla-Favera R. (2004) PINning down the c-Myc oncoprotein. Nat Cell Biol 6 : 288 289.
18. Ryan K.M., Vousden K.H. (2002) Cancer: pinning a change on p53. Nature 419 : 795 797.
19. Zacchi P., Gostissa M., Uchida T., Salvagno C., Avolio F., Volinia S., Ronai Z., Blandino G., Schneider C., Del Sal G. (2002) The prolyl isomerase Pin1 reveals a mechanism to control p53 functions after genotoxic insults. Nature 419 : 853 857.
20. Wintjens R., Wieruszeski J.M., Drobecq H., Rousselot-Pailley P., Buee L., Lippens G., Landrieu I. (2001) 1H NMR study on the binding of Pin1 Trp-Trp domain with phosphothreonine peptides. J Biol Chem 276 : 25150 25156.
21. Verdecia M.A., Bowman M.E., Lu K.P., Hunter T., Noel J.P. (2000) Structural basis for phosphoserine-proline recognition by group IV WW domains. Nat Struct Biol 7 : 639 643.
22. Bayer E., Goettsch S., Mueller J.W., Griewel B., Guiberman E., Mayr L.M., Bayer P. (2003) Structural analysis of the mitotic regulator hPin1 in solution: insights into domain architecture and substrate binding. J Biol Chem 278 : 26183 26193.
23. Jacobs D.M., Saxena K., Vogtherr M., Bernado P., Pons M., Fiebig K.M. (2003) Peptide binding induces large scale changes in inter-domain mobility in human Pin1. J Biol Chem 278 : 26174 26182.
24. Kim C.J., Cho Y.G., Park Y.G., Nam S.W., Kim S.Y., Lee S.H., Yoo N.J., Lee J.Y., Park W.S. (2005) Pin1 overexpression in colorectal cancer and its correlation with aberrant beta-catenin expression. World J Gastroenterol 11 : 5006 5009.
25. Ayala G., Wang D., Wulf G., Frolov A., Li R., Sowadski J., Wheeler T.M., Lu K.P., Bao L. (2003) The prolyl isomerase Pin1 is a novel prognostic marker in human prostate cancer. Cancer Res 63 : 6244 6251.
26. Nakashima M. et al. (2004) Cyclin D1 overexpression in thyroid tumours from a radio-contaminated area and its correlation with Pin1 and aberrant beta-catenin expression. J Pathol 202 : 446 455.
27. Wildemann D., Erdmann F., Alvarez B.H., Stoller G., Zhou X.Z., Fanghanel J., Schutkowski M., Lu K.P., Fischer G. (2006) Nanomolar inhibitors of the peptidyl prolyl cis/trans isomerase Pin1 from combinatorial peptide libraries. J Med Chem 49 : 2147 2150.
28. Zhang Y., Daum S., Wildemann D., Zhou X.Z., Verdecia M.A., Bowman M.E., Lucke C., Hunter T., Lu K.P., Fischer G., Noel J.P. (2007) Structural basis for high-affinity peptide inhibition of human Pin1. ACS Chem Biol 2 : 320 328.
29. Lu K.P., Zhou X.Z. (2007) The prolyl isomerase PIN1: a pivotal new twist in phosphorylation signalling and disease. Nat Rev Mol Cell Biol 8 : 904 916.
30. Smet C., Duckert J.F., Wieruszeski J.M., Landrieu I., Buee L., Lippens G., Deprez B. (2005) Control of protein-protein interactions: structure-based discovery of low molecular weight inhibitors of the interactions between Pin1 WW domain and phosphopeptides. J Med Chem 48 : 4815 4823.
31. Cramer R.D., III., Patterson D.E., Bunce J.D. (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steriods to carrier proteins. J Am Chem Soc 110 : 5959 5967.
32. Goddard T.D., Kneller D.G. (2008) SPARKY 3. San Francisco : University of California.
33. Farmer B.T., II., Constantine K.L., Goldfarb V., Friedrichs M.S., Wittekind M., Yanchunas J., Jr., Robertson J.G., Mueller L. (1996) Localizing the NADP+ binding site on the MurB enzyme by NMR. Nat Struct Biol 3 : 995 997.
34. Seydel J.K., Wiese M. (2002) Drug-Membrane Interactions: Analysis, Drug Distribution, Modeling. Weinheim : Wiley-VCH.
35. Jones G., Willett P., Glen R.C. (1995) Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation. J Mol Biol 245 : 43 53.
36. Jones G., Willett P., Glen R.C., Leach A.R., Taylor R. (1997) Development and validation of a genetic algorithm for flexible docking. J Mol Biol 267 : 727 748.
37. 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., Lu K.P. (1997) Sequence-specific and phosphorylation-dependent proline isomerization: a potential mitotic regulatory mechanism. Science 278 : 1957 1960.
38. Ramelot T.A., Nicholson L.K. (2001) Phosphorylation-induced structural changes in the amyloid precursor protein cytoplasmic tail detected by NMR. J Mol Biol 307 : 871 884.
39. Pastorino L., Sun A., Lu P.J., Zhou X.Z., Balastik M., Finn G., Wulf G., Lim J., Li S.H., Li X., Xia W., Nicholson L.K., Lu K.P. (2006) The prolyl isomerase Pin1 regulates amyloid precursor protein processing and amyloid-beta production. Nature 440 : 528 534.
40. Lian L.Y., Barsukov I.L., Derrick J.P., Roberts G.C. (1994) Mapping the interactions between streptococcal protein G and the Fab fragment of IgG in solution. Nat Struct Biol 1 : 355 357.
41. Williamson R.A., Carr M.D., Frenkiel T.A., Feeney J., Freedman R.B. (1997) Mapping the binding site for matrix metalloproteinase on the N-terminal domain of the tissue inhibitor of metalloproteinases-2 by NMR chemical shift perturbation. Biochemistry 36 : 13882 13889.
42. Shuker S.B., Hajduk P.J., Meadows R.P., Fesik S.W. (1996) Discovering high-affinity ligands for proteins: SAR by NMR. Science 274 : 1531 1534.
43. Zhang Y., Fussel S., Reimer U., Schutkowski M., Fischer G. (2002) Substrate-based design of reversible Pin1 inhibitors. Biochemistry 41 : 11868 11877.
44. Daum S., Lucke C., Wildemann D., Schiene-Fischer C. (2007) On the benefit of bivalency in peptide ligand/pin1 interactions. J Mol Biol 374 (1 147 161.