Conformationally constrained peptide analogues of pTyr-Glu-Glu-Ile as inhibitors of the Src SH2 domain binding

Journal of Medicinal Chemistry

Volumn 47, Issue 12, 2004, Pages 3131-3141

  Nam, Nguyen Hai ^a   Ye, Guofeng ^a   Sun, Gongqin ^a   Parang, Keykavous ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [2 [8 (2 CARBOXYETHYL) 3,6,9 TRIOXO 5 (4 PHOSPHONOOXYBENZYL) 1,4,7 TRIAZONAN 2 YL]ACETYLAMINO] 3 METHYLPENTANOIC ACID; 2 [3 [8 (2 CARBOXYETHYL) 3,6,9 TRIOXO 5 (4 PHOSPHONOOXYBENZYL) 1,4,7 TRIAZONAN 2 YL]PROPIONYLAMINO] 3 METHYLPENTANOIC ACID; 2 [4 CARBOXY 2 [3 [3,6 DIOXO 5 (4 PHOSPHONOOXYBENZYL)PIPERAZIN 2 YL]PROPIONYLAMINO]BUTYRYLAMINO] 3 METHYLPENTANOIC ACID; PROTEIN INHIBITOR; PROTEIN SH2; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; BINDING SITE; COMPARATIVE STUDY; CYCLIZATION; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; FLUORESCENCE POLARIZATION; HYDROPHOBICITY; MOLECULAR MODEL; NONHUMAN; STRUCTURE ANALYSIS;

BINDING SITES; BINDING, COMPETITIVE; FLUORESCENCE POLARIZATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; OLIGOPEPTIDES; PHOSPHOPEPTIDES; PROTO-ONCOGENE PROTEINS PP60(C-SRC); SRC HOMOLOGY DOMAINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2542528563     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040008+     Document Type: Article

References (34)

1. Luttrell, D. K.; Lee, A.; Lansing, T. J.; Crosby, R. M.; Jung, K. D.; Willard, D.; Luther, M.; Rodriguez, M.; Berman, J.; Gilmer, T. M. Involvement of pp60c-src with two major signaling pathways in human breast cancer. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 83-87.
2. Boyce, B. F.; Yoneda, T.; Lowe, C.; Soriano, P.; Mundy, G. R. Requirement of pp60c-src expression for osteoclasts to form ruffled borders and resorb bone in mice. J. Clin. Invest. 1992, 90, 1622-1627.
3. Soriano, P.; Montgomery, C.; Geske, R.; Bradley, A. Targeted disruption of the c-src proto-oncogene leads to osteopetrosis in mice. Cell 1991, 64, 693-702.
4. Alonso, G.; Koegl, M.; Mazurenko, N.; Courtneidge, S. A. Sequence requirements for binding of Src family tyrosine kinases to activated growth factor receptors. J. Biol. Chem. 1995, 270, 9840-9848.
5. Roussel, R. R.; Brodeur, S. R.; Shalloway, D.; Laudano, A. P. Selective binding of activated pp60c-src by an immobilized synthetic phosphopeptide modeled on the carboxyl terminus of pp60c-src. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10696-10700.
6. Payne, G.; Shoelson, S. E.; Gish, G. D.; Pawson, T.; Walsh, C. T. Kinetics of p56lck and p60src Src homology 2 domain binding to tyrosine-phosphorylated peptides determined by a competition assay or surface plasmon resonance. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 4902-4906.
7. Payne, G.; Stolz, L. A.; Pei, D.; Band, H.; Shoelson, S. E.; Walsh, C. T. The phosphopeptide-binding specificity of Src family SH2 domains. Chem. Biol. 1994, 1, 99-105.
8. Songyang, Z.; Shoelson, S. E.; Chaudhuri, M.; Gish, G.; Pawson, T.; Haser, W. G.; King, F.; Roberts, T.; Ratnofsky, S.; Lechleider, R. J.; Neel, B. G.; Birge, R. B.; Fajardo, J. E.; Chou, M. M.; Hanafusa, H.; Schaffhausen, B.; Cantley, L. C. SH2 domains recognize specific phosphopeptide sequences. Cell 1993, 72, 767-778.
9. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowburn, D.; Kuriyan, J. Binding of a high affinity phosphotyrosyl peptide to the Src SH2 domain: crystal structures of the complexed and peptide-free forms. Cell 1993, 72, 779-789.
10. Waksman, G.; Kominos, D.; Robertson, S. C.; Pant, N.; Baltimore, D.; Birge, R. B.; Cowburn, D.; Hanafusa, H.; Mayer, B. J.; Overduin, M.; Resh, M. D.; Rios, C. B.; Silverman, L.; Kuriyan, J. Crystal structure of the phosphotyrosine recognition domain SH2 of v-src complexed with tyrosine-phosphorylated peptides. Nature 1992, 358, 646-653.
11. Eck, M. J.; Shoelson, S. E.; Harrison, S. C. Recognition of a high-affinity phosphotyrosyl peptide by the Src homology-2 domain of p56lck. Nature 1993, 362, 87-91.
12. Lesuisse, D.; Deprez, P.; Albert, E.; Duc, T. T.; Sortais, B.; Gofflo, D.; Jean-Baptiste, V.; Marquette, J.; Schoot, B.; Sarubbi, E.; Lange, G.; Broto, P.; Mandine, E. Discovery of thioazepinone ligands for Src SH2: from non-specific to specific binding. Bioorg. Med. Chem. Lett. 2001, 11, 2127-2131.
13. Deprez, P.; Mandine, E.; Vermond, A.; Lesuisse, D. Imidazole-based ligands of the Src SH2 protein. Bioorg. Med. Chem. Lett. 2002, 12, 1287-1289.
14. Deprez, P.; Baholet, I.; Burlet, S.; Lange, G.; Amengual, R.; Schoot, B. ; Vermond, A.; Mandine, E.; Lesuisse, D. Discovery of highly potent Src SH2 binders: Structure-activity studies and X-ray structures. Bioorg. Med. Chem. Lett. 2002, 12, 1291-1294.
15. Buchanan, J. L.; Bohacek, R. S.; Luke, G. P.; Hatada, M.; Lu, X.; Dalgarno, D. C.; Narula, S. S.; Yuan, R.; Holt, D. A. Structure-based design and synthesis of a novel class of Src SH2 inhibitors. Bioorg. Med. Chem. Lett. 1999, 9, 2353-2358.
16. Buchanan, J. L.; Vu, C. B.; Merry, T. J.; Corpuz, E. G.; Pradeepan, S. G.; Mani, U. N.; Yang, M.; Plake, H. R.; Varkhedkar, V. M.; Lynch, B. A.; MacNeil, I. A.; Loiacono, K. A.; Tiong, C. L.; Holt, D. A. Structure-activity relationships of a novel class of Src SH2 inhibitors. Bioorg. Med. Chem. Lett. 1999, 9, 2359-2364.
17. Humphrey, J. M.; Chamberlin, A. R. Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides. Chem. Rev. 1997, 97, 2243-2266.
18. Khan, A. R.; Parrish, J. C.; Fraser, M. E.; Smith, W. W.; Bartlett, P. A.; James, M. N. G. Lowering the entropic barrier for binding conformationally flexible inhibitors to enzymes. Biochemistry 1998, 37, 16839-16845.
19. Smith, W. W.; Bartlett, P. A. Macrocyclic inhibitors of penicillopepsin. 3. Design, synthesis, and evaluation of an inhibitor bridged between P2 and P1′. J. Am. Chem. Soc. 1998, 120, 4622-4628.
20. Davidson, J. P.; Lubman, O.; Rose, T.; Waksman, G.; Martin, S. F. Calorimetric and structural studies of 1,2,3-trisubstituted cyclopropanes as conformationally constrained peptide inhibitors of Src SH2 domain binding. J. Am. Chem. Soc. 2002, 124, 205-215.
21. Ettmayer, P.; France, D.; Gounarides, J.; Jarosinski, M.; Martin, M. S.; Rondeau, J. M.; Sabio, M.; Topiol, S.; Weidmann, B.; Zurini, M.; Bair, K. W. Structural and conformational requirements for high-affinity binding to the SH2 domain of Grb2. J. Med. Chem. 1999, 42, 971-980.
22. Lesuisse, D.; Lange, G.; Deprez, P.; Benard, D.; Schoot, B.; Delettre, G.; Marquette, J. P.; Broto, P.; Jean-Baptiste, V.; Bichet, P.; Sarubbi, E.; Mandine, E. SAR and X-ray. A new approach combining fragment-based screening and rational drug design: Application to the discovery of nanomolar inhibitors of Src SH2. J. Med. Chem. 2002, 45, 2379-2387.
23. Shakespeare, W.; Yang, M.; Bohacek, R.; Cerasoli, F.; Stebbins, K.; Sundaramoorthi, R.; Azimioara, M.; Vu, C.; Pradeepan, S.; Metcalf, C., 3rd; Haraldson, C.; Merry, T.; Dalgarno, D.; Narula, S.; Hatada, M.; Lu, X.; van Schravendijk, M. R.; Adams, S.; Violette, S.; Smith, J.; Guan, W.; Bartlett, C. ; Herson, J.; Iuliucci, J.; Weigele, M.; Sawyer, T. Structure-based design of an osteoclast-selective, nonpeptide Src homology 2 inhibitor with in vivo antiresorptive activity. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9373-9378.
24. El Haddadi, M.; Cavelier, F.; Vives, E.; Azmani, A.; Verducci, J.; Martinez, J. All-L-Leu-Pro-Leu-Pro: a challenging cyclization. J. Pept. Sci. 2000, 6, 560-570.
25. Meutermans, W. D. F.; Bourne, G. T.; Golding, S. W.; Horton, D. A.; Campitelli, M. R.; Craik, D.; Scanlon, M.; Smythe, M. L. Difficult macrocyclizations: New strategies for synthesizing highly strained cyclic tetrapeptides. Org. Lett. 2003, 5, 2711-2714.
26. Yoon, U. C.; Jin, Y. X.; Oh, S. W.; Park, C. H.; Park, J. H.; Campana, C. F.; Cai, X.; Duesler, E. N.; Mariano, P. S. A synthetic strategy for the preparation of cyclic peptide mimetics based on SET-promoted photocyclization processes. J. Am. Chem. Soc. 2003, 125, 10664-10671.
27. Miranda, L. P.; Meutermans, W. D.; Smythe, M. L.; Alewood, P. F. An activated O → N acyl transfer auxiliary: efficient amide-backbone substitution of hindered "difficult" peptides. J. Org. Chem. 2000, 65, 5460-5468.
28. Meutermans, W. D. F.; Golding, S. W.; Bourne, G. T.; Miranda, L. P.; Dooley, M. J.; Alewood, P. F.; Smythe, M. L. Synthesis of difficult cyclic peptides by inclusion of a novel photolabile auxiliary in a ring contraction strategy. J. Am. Chem. Soc. 1999, 121, 9790-9796.
29. Lynch, B. A.; Loiacono, K. A.; Tiong, C. L.; Adams, S. E.; MacNeil, I. A. A fluorescence polarization based Src-SH2 binding assay. Anal. Biochem. 1997, 247, 77-82.
30. Adamczyk, M.; Fishpaugh, J. R.; Heuser, K. J. Preparation of succinimidyl and pentafluorophenyl active esters of 5- and 6-carboxyfluorescein. Bioconjugate Chem. 1997, 8, 253-255.
31. Kawahata, N. H.; Yang, M. H.; Luke, G. P.; Shakespeare, W. C.; Sundaramoorthi, R.; Wang, Y.; Johnson, D.; Merry, T.; Violette, S.; Guan, W.; Bartlett, C.; Smith, J.; Hatada, M.; Lu, X.; Dalgarno, D. C.; Eyermann, C. J.; Bohacek, R. S.; Sawyer, T. K. A novel phosphotyrosine mimetic 4'-carboxymethyloxy-3′-phosphonophenylalanine (Cpp): exploitation in the design of nonpeptide inhibitors of pp60(Src) SH2 domain. Bioorg. Med. Chem. Lett. 2001, 11, 2319-2323.
32. Metcalf, C. A., III; van Schravendijk, M. R.; Dalgarno, D. C.; Sawyer, T. K. Targeting protein kinases for bone disease: discovery and development of Src inhibitors. Curr. Pharm. Des. 2002, 8, 2049-2075.
33. Burke, T. R., Jr.; Yao, Z. J.; Liu, D. G.; Voigt, J.; Gao, Y. Phosphoryltyrosyl mimetics in the design of peptide-based signal transduction inhibitors. Biopolymers 2001, 60, 32-44.
34. Burke, T. R., Jr.; Lee, K. Phosphotyrosyl mimetics in the development of signal transduction inhibitors. Acc. Chem. Res. 2003, 36, 424-433.