Selective targeting of disease-relevant protein binding domains by O-phosphorylated natural product derivatives

ACS Chemical Biology

Volumn 6, Issue 10, 2011, Pages 1008-1014

  Gra, ^a,b   Janczyk, Weronika ^a   Sperl, Bianca ^a   Elumalai, Nagarajan ^b   Kozany, Christian ^c   Hausch, Felix ^c   Holak, Tad A ^a   Berg, Thorsten ^a,b  

^a MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

^c MAX PLANCK INSTITUTE OF PSYCHIATRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DEXAMETHASONE SODIUM PHOSPHATE; FOSFOSAL; NATURAL PRODUCT; PEPTIDYLPROLYL ISOMERASE; PROTEIN SH2; STAT5B PROTEIN;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; DRUG TARGETING; ENZYME ACTIVITY; FLUORESCENCE POLARIZATION; LIGAND BINDING; NITROGEN NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN DOMAIN; PROTEIN PHOSPHORYLATION; PROTEIN PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; BINDING SITES; DEXAMETHASONE; HUMANS; MODELS, MOLECULAR; PEPTIDYLPROLYL ISOMERASE; PHOSPHORIC ACID ESTERS; PHOSPHORYLATION; PROTEIN BINDING; SRC HOMOLOGY DOMAINS; STAT5 TRANSCRIPTION FACTOR;

EID: 80054999462     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb2001796     Document Type: Article

References (38)

1. Wells, J. A. and McClendon, C. L. (2007) Reaching for high-hanging fruit in drug discovery at protein-protein interfaces Nature 450, 1001-9 (Pubitemid 350273630)
2. Breinbauer, R., Vetter, I. R., and Waldmann, H. (2002) From protein domains to drug candidates-natural products as guiding principles in the design and synthesis of compound libraries Angew. Chem., Int. Ed. 41, 2879-90
3. Corson, T. W. and Crews, C. M. (2007) Molecular understanding and modern application of traditional medicines: triumphs and trials Cell 130, 769-74 (Pubitemid 47332575)
4. Sperl, B., Seifert, M. H., and Berg, T. (2009) Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains Bioorg. Med. Chem. Lett. 19, 3305-9
5. Ramis, J., Gich, I., Torrent, J., Mis, R., Jane, F., and Forn, J. (1989) Bioavailability study of fosfosal and codeine administered alone or in combination Int. J. Clin. Pharmacol. Ther. Toxicol. 27, 352-7 (Pubitemid 19179093)
6. Nirschl, R. P., Rodin, D. M., Ochiai, D. H., and Maartmann-Moe, C. (2003) Iontophoretic administration of dexamethasone sodium phosphate for acute epicondylitis. A randomized, double-blinded, placebo-controlled study Am. J. Sports Med. 31, 189-95 (Pubitemid 36343322)
7. Reindl, W., Yuan, J., Krämer, A., Strebhardt, K., and Berg, T. (2008) Inhibition of Polo-like Kinase 1 by blocking Polo-Box domain-dependent protein-protein interactions Chem. Biol. 15, 459-66 (Pubitemid 351645109)
8. Schust, J., Sperl, B., Hollis, A., Mayer, T. U., and Berg, T. (2006) Stattic: a small-molecule inhibitor of STAT3 activation and dimerization Chem. Biol. 13, 1235-42 (Pubitemid 44750735)
9. Reindl, W., Yuan, J., Krämer, A., Strebhardt, K., and Berg, T. (2009) A Pan-specific inhibitor of the Polo-Box domains of Polo-like kinases arrests cancer cells in mitosis ChemBioChem 10, 1145-1148
10. Neculai, D., Neculai, A. M., Verrier, S., Straub, K., Klumpp, K., Pfitzner, E., and Becker, S. (2005) Structure of the unphosphorylated STAT5a dimer J. Biol. Chem. 280, 40782-7 (Pubitemid 41780569)
11. Trott, O. and Olson, A. J. (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 31, 455-61
12. Mao, X., Ren, Z., Parker, G. N., Sondermann, H., Pastorello, M. A., Wang, W., McMurray, J. S., Demeler, B., Darnell, J. E., Jr., and Chen, X. (2005) Structural bases of unphosphorylated STAT1 association and receptor binding Mol. Cell 17, 761-71 (Pubitemid 40386938)
13. Burke, T. R., Jr., Yao, Z. J., Liu, D. G., Voigt, J., and Gao, Y. (2001) Phosphoryltyrosyl mimetics in the design of peptide-based signal transduction inhibitors Biopolymers 60, 32-44
14. Müller, J., Sperl, B., Reindl, W., Kiessling, A., and Berg, T. (2008) Discovery of chromone-based inhibitors of the transcription factor STAT5 ChemBioChem 9, 723-7
15. Wetzel, S., Wilk, W., Chammaa, S., Sperl, B., Roth, A. G., Yektaoglu, A., Renner, S., Berg, T., Arenz, C., Giannis, A., Oprea, T. I., Rauh, D., Kaiser, M., and Waldmann, H. (2010) A scaffold-tree-merging strategy for prospective bioactivity annotation of gamma-pyrones Angew. Chem., Int. Ed. 49, 3666-70
16. Kozany, C., Marz, A., Kress, C., and Hausch, F. (2009) Fluorescent probes to characterise FK506-binding proteins ChemBioChem 10, 1402-10
17. Bayer, E., Goettsch, S., Mueller, J. W., Griewel, B., Guiberman, E., Mayr, L. M., and Bayer, P. (2003) Structural analysis of the mitotic regulator hPin1 in solution: insights into domain architecture and substrate binding J. Biol. Chem. 278, 26183-93 (Pubitemid 36835387)
18. 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, 320-8 (Pubitemid 350001580)
19. 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, 1957-60 (Pubitemid 28013239)
20. 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, 1325-8
21. 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, 875-86 (Pubitemid 27513514)
22. Daum, S., Erdmann, F., Fischer, G., Feaux de Lacroix, B., Hessamian-Alinejad, A., Houben, S., Frank, W., and Braun, M. (2006) Aryl indanyl ketones: efficient inhibitors of the human peptidyl prolyl cis / trans isomerase Pin1 Angew. Chem., Int. Ed. 45, 7454-8 (Pubitemid 44786984)
23. Potter, A., Oldfield, V., Nunns, C., Fromont, C., Ray, S., Northfield, C. J., Bryant, C. J., Scrace, S. F., Robinson, D., Matossova, N., Baker, L., Dokurno, P., Surgenor, A. E., Davis, B., Richardson, C. M., Murray, J. B., and Moore, J. D. (2010) Discovery of cell-active phenyl-imidazole Pin1 inhibitors by structure-guided fragment evolution Bioorg. Med. Chem. Lett. 20, 6483-8
24. Zhu, L., Jin, J., Liu, C., Zhang, C., Sun, Y., Guo, Y., Fu, D., Chen, X., and Xu, B. (2011) Synthesis and biological evaluation of novel quinazoline-derived human Pin1 inhibitors Bioorg. Med. Chem. 19, 2797-807
25. Uchida, T., Takamiya, M., Takahashi, M., Miyashita, H., Ikeda, H., Terada, T., Matsuo, Y., Shirouzu, M., Yokoyama, S., Fujimori, F., and Hunter, T. (2003) Pin1 and Par14 peptidyl prolyl isomerase inhibitors block cell proliferation Chem. Biol. 10, 15-24 (Pubitemid 36154470)
26. Hennig, L., Christner, C., Kipping, M., Schelbert, B., Rucknagel, K. P., Grabley, S., Kullertz, G., and Fischer, G. (1998) Selective inactivation of parvulin-like peptidyl-prolyl cis / trans isomerases by juglone Biochemistry 37, 5953-60 (Pubitemid 28196748)
27. Xu, G. G. and Etzkorn, F. A. (2009) Pin1 as an anticancer drug target Drug News Perspect. 22, 399-407
28. Duncan, K. E., Dempsey, B. R., Killip, L. E., Adams, J., Bailey, M. L., Lajoie, G. A., Litchfield, D. W., Brandl, C. J., Shaw, G. S., and Shilton, B. H. (2011) Discovery and characterization of a nonphosphorylated cyclic peptide inhibitor of the peptidylprolyl isomerase, pin1 J. Med. Chem. 54, 3854-65
29. Guo, C., Hou, X., Dong, L., Dagostino, E., Greasley, S., Ferre, R., Marakovits, J., Johnson, M. C., Matthews, D., Mroczkowski, B., Parge, H., Vanarsdale, T., Popoff, I., Piraino, J., Margosiak, S., Thomson, J., Los, G., and Murray, B. W. (2009) Structure-based design of novel human Pin1 inhibitors (I) Bioorg. Med. Chem. Lett. 19, 5613-6
30. Dong, L., Marakovits, J., Hou, X., Guo, C., Greasley, S., Dagostino, E., Ferre, R., Johnson, M. C., Kraynov, E., Thomson, J., Pathak, V., and Murray, B. W. (2010) Structure-based design of novel human Pin1 inhibitors (II) Bioorg. Med. Chem. Lett. 20, 2210-4
31. Potter, A. J., Ray, S., Gueritz, L., Nunns, C. L., Bryant, C. J., Scrace, S. F., Matassova, N., Baker, L., Dokurno, P., Robinson, D. A., Surgenor, A. E., Davis, B., Murray, J. B., Richardson, C. M., and Moore, J. D. (2010) Structure-guided design of alpha-amino acid-derived Pin1 inhibitors Bioorg. Med. Chem. Lett. 20, 586-90
32. Stankovic, C. J., Surendran, N., Lunney, E. A., Plummer, M. S., Para, K. S., Shahripour, A., Fergus, J. H., Marks, J. S., Herrera, R., Hubbell, S. E., Humblet, C., Saltiel, A. R., Stewart, B. H., and Sawyer, T. K. (1997) The role of 4-phosphonodifluoromethyl- and 4-phosphono-phenylalanine in the selectivity and cellular uptake of SH2 ligands Bioorg. Med. Chem. Lett. 7, 1909-1914 (Pubitemid 27317813)
33. Liu, W. Q., Vidal, M., Olszowy, C., Million, E., Lenoir, C., Dhotel, H., and Garbay, C. (2004) Structure-activity relationships of small phosphopeptides, inhibitors of Grb2 SH2 domain, and their prodrugs J. Med. Chem. 47, 1223-33 (Pubitemid 38229124)
34. Mandal, P. K., Gao, F., Lu, Z., Ren, Z., Ramesh, R., Birtwistle, J. S., Kaluarachchi, K. K., Chen, X., Bast, R. C., Liao, W. S., and McMurray, J. S. (2011) Potent and selective phosphopeptide mimetic prodrugs targeted to the Src Homology 2 (SH2) domain of signal transducer and activator of transcription 3 J. Med. Chem. 54, 3549-63
35. Laketa, V., Zarbakhsh, S., Morbier, E., Subramanian, D., Dinkel, C., Brumbaugh, J., Zimmermann, P., Pepperkok, R., and Schultz, C. (2009) Membrane-permeant phosphoinositide derivatives as modulators of growth factor signaling and neurite outgrowth Chem. Biol. 16, 1190-6
36. Nikolovska-Coleska, Z., Wang, R., Fang, X., Pan, H., Tomita, Y., Li, P., Roller, P. P., Krajewski, K., Saito, N. G., Stuckey, J. A., and Wang, S. (2004) Development and optimization of a binding assay for the XIAP BIR3 domain using fluorescence polarization Anal. Biochem. 332, 261-73 (Pubitemid 39485734)
37. DeLano, W. L. (2002) The PyMOL Molecular Graphics System.: DeLano Scientific, Palo Alto, CA.
38. Goddard, T. D. and Kneller, D. G. SPARKY 3, University of California, San Francisco, CA.