Structure-based design of peptidomimetic ligands of the Grb2-SH2 domain

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 20, 1998, Pages 2865-2870

  Schoepfer, Joseph ^a   Gay, Brigitte ^a   Caravatti, Giorgio ^a   Garcia Echeverria, Carlos ^a   Fretz, Heinz ^a   Rahuel, Joseph ^a   Furet, Pascal ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

GROWTH FACTOR RECEPTOR; PROTEIN DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; LIGAND BINDING; STRUCTURE ACTIVITY RELATION;

ADAPTOR PROTEINS, SIGNAL TRANSDUCING; DRUG DESIGN; GRB2 ADAPTOR PROTEIN; INHIBITORY CONCENTRATION 50; LIGANDS; MODELS, MOLECULAR; MOLECULAR MIMICRY; PHOSPHOPEPTIDES; PROTEINS; RECEPTOR, EPIDERMAL GROWTH FACTOR; SIGNAL TRANSDUCTION; SRC HOMOLOGY DOMAINS;

EID: 0032552917     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00513-7     Document Type: Article

References (20)

1. 1. Traxler, P.; Lydon, N. Drugs Future 1996, 20, 1261.
2. 2. Groundwater, P. W.; Solomons, K. R. H.; Drewe, J. A.; Munawar, M. A. Prog. Med. Chem. 1996, 33, 233.
3. 3. Smithgall, T. E. J. Pharmacol. Toxicol Methods 1995, 34, 125.
4. 4. Gishizky, M. L. Annu. Rep. Med. Chem. 1995, 30, 247.
5. 5. Rojas, M.; Yao, S.; Lin, Y.-Z. J. Biol. Chem. 1996, 271, 27456.
6. 6. Lowenstein, E. J.; Daly, R. J.; Batzer, A. G.; Li, W.; Margolis, B.; Lammers, R.; Ullrich, A.; Skolnik, E. Y.; Bar-Sagi, D.; Schlessinger, J. Cell (Cambridge, Mass. ) 1992, 70, 431.
7. 7. Phosphopeptide residues are numbered relative to the position of phosphotyrosine which is denoted 0. Positive numbers are used for amino acids C-terminal to phosphotyrosine.
8. 8. Furet, P.; Gay, B.; Garcia-Echeverria, C.; Rahuel, J.; Fretz, H.; Schoepfer, J.; Caravatti, G. J. Med. Chem. 1997, 40, 3551.
9. +1 is more versatile: valine, isoleucine, glutamine and glutamic acid being the preferred natural amino acids at this position (Garcia-Echeverria, C.; et al. Novartis Pharma Inc., Oncology Research Department, unpublished results).
10. 10. Rahuel, J.; Gay, B.; Erdmann, D.; Strauss, A.; Garcia-Echeverria; Furet, P.; Caravatti, G.; Fretz, H.; Schoepfer, J.; Gruetter, M. G. Nat. Struct. Biol. 1996, 3, 586. PDB code 1TZE.
11. 11. MacroModel v.4.0: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
12. 12. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S. Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765. A dielectric constant of 4r was used in the calculations.
13. 13. For the definition of β-turn types see: Wilmot, C. M.; Thornton, J. M. Protein Eng. 1990, 3, 479.
14. 14. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G.; Kennard, O.; et al. Acta Crystallogr., Sect. B 1979, B35, 2331.
15. 15. Martin, E. L. J. Am. Chem. Soc. 1936, 58, 1438.
16. 16. Curran, W. V.; Ross, A. J. Med. Chem. 1974, 17, 273.
17. 17. Florence, G. J. Bull. Sci. Pharm. 1933, 40, 325.
18. 18. Staskun, B.; Van Es, T. J. Chem. Soc. (C) 1966, 40, 531.
19. 19. Gay, B.; Furet, P.; Garcia-Echeverria, C.; Rahuel, J.; Chene, P.; Fretz, H.; Schoepfer, J.; Caravatti, G. Biochemistry 1997, 36, 5712.
20. 20. Eck, M. J.; Shoelson, S. E.; Harrison, S. C. Nature (London) 1993, 362, 87.