Development and characterization of potent and specific peptide inhibitors of p60c-src protein tyrosine kinase using pseudosubstrate-based inhibitor design approach

Journal of Peptide Research

Volumn 62, Issue 6, 2003, Pages 260-268

  Kamath, J R ^a   Liu, R ^a   Enstrom, A M ^a   Lou, Q ^a   Lam, K S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

p60c src protein tyrosine kinase; Protein kinase assay with thin layer chromatography; Pseudosubstrate based peptide inhibitors; Structure activity relationship study

Indexed keywords

ANTINEOPLASTIC AGENT; CYSTEINYLISOLEUCYLTYROSYLLYSINE; CYSTEINYLISOLEUCYLTYROSYLLYSYLTYROSYLTYROSINE; CYSTEINYLISOLEUCYLTYROSYLLYSYLTYROSYLTYROSYLPHENYLALANINE; CYTOPLASM PROTEIN; METHIONYLISOLEUCYLTYROSYLLYSYLTYROSYLTYROSYLPHENYLALANINE; PEPTIDE DERIVATIVE; PEPTIDOMIMETIC AGENT; PHENYLALANINE; PROTEIN INHIBITOR; PROTEIN KINASE P60; PROTEIN TYROSINE KINASE; TETRAPEPTIDE; TYROSINE; TYROSYLISOLEUCYLTYROSYLGLYCYLSERYLPHENYLALANYLLYSINE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SPECIFICITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME SUBSTRATE; HUMAN; IC 50; KNOCKOUT MOUSE; OSTEOPOROSIS; PHENOTYPE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TECHNIQUE;

AMINO ACID SEQUENCE; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PEPTIDE FRAGMENTS; PEPTIDES; PROTO-ONCOGENE PROTEINS PP60(C-SRC); STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0346122849     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1399-3011.2003.00094.x     Document Type: Article

References (49)

1. 3 domain: the same residues of the ligand binding surface are important for intra-and intermolecular interactions. EMBO J. 14, 963-975.
2. Parsons, J.T. & Parsons, S.J. (1997) Src family protein tyrosine kinases: cooperating with growth factor and adhesion signaling pathways. Curr. Opin. Cell Biol. 9, 187-192.
3. Brown, M.T. & Cooper, J.A. (1996) Regulation, substrates and function of src. Biochim. Biophys. Acta 1287, 121-149.
4. Elder, J.T., Fisher, G.J., Lindquist, P.B., Bennett, G.L., Pittelkow, M.R., Coffey, R.J. Jr, Ellingsworth, L., Derynck, R. & Voorthees, J.J. (1989) Overexpression of transforming growth factor alpha in psoriatic epidermis. Science 243, 811-814.
5. Libby, P., Schwartz, D., Brogi, E., Tanaka, H. & Clinton, S.K. (1992) A cascade model for restenosis. A special case of atherosclerosis progression. Circulation 86, III47-52.
6. Powis, G. & Workman, P. (1994) Signalling targets for the development of cancer drugs. Anticancer Drug Des. 9, 555-568.
7. Al-Obeidi, F.A., Wu, J.J. & Lam, K.S. (1998) Protein tyrosine kinases: structure, substrate specificity, and drug discovery. Biopolymers (Peptide Sci.) 47, 197-223.
8. Al-Obeidi, F.A. & Lam, K.S. (2000) Development of inhibitors for protein tyrosine kinases. Oncogens 19, 5690-5701.
9. Lam, K.S. (1997) Application of combinatorial library methods in cancer research and drug discovery. Anticancer Drug Des. 12, 145-167.
10. Sawyers, C.L. (2002) Rational therapeutic intervention in cancer: kinases as drug targets. Curr. Opin. Genetics Dev. 12, 111-115.
11. c-src in human colon carcinoma and normal human colon mucosal cells. Oncogene Res. 1, 149-168.
12. c-src with two major signaling pathways in human breast cancer. Proc. Natl. Acad. Sci. U.S.A. 91, 83-87.
13. c-src in human small cell and non-small cell lung carcinomas. Eur. J. Cancer 28, 372-377.
14. c-src in low grade human bladder carcinoma. Cancer Res. 52, 1457-1462.
15. Barnekow, A., Paul, E. & Schartl, M. (1987) Expression of the c-src protooncogene in human skin tumors. Cancer Res. 47, 235-240.
16. Lynch, S.A., Brugge, J.S., Fromowitz, F., Glantz, L., Wang, P., Caruso, R. & Viola, M.V. (1993) Increased expression of the src proto-oncogene in hairy cell leukemia and a subgroup of B-cell lymphomas. Leukemia 7, 1416-1422.
17. c-src in neuroblastoma in relation to clinical stage and prognosis. Cancer Res. 50, 6908-6914.
18. Garcia-Echeverria, C., Traxler, P. & Evans, D.B. (2000) ATP site-directed competitive and irreversible inhibitors of protein kinases. Med. Res. Rev. 20, 28-57.
19. Traxler, P.M., Furet, P., Mett, H., Buchdunger, E., Meyer, T. & Lydon, N. (1996) 4-(Phenylamino)pyrrolopyrimidines: potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase. J. Med. Chem. 39, 2285-2292.
20. 2 domain. J. Med. Chem. 41, 1894-1908.
21. 2 domains have overlapping specificities. Nature 373, 536-539.
22. Young, S.W., Poole, R.C., Hudson, A.T., Halestrap, A.P., Denton, R.M. & Tavare, J.M. (1993) Effects of tyrosine kinase inhibitors on protein kinase-independent systems. FEBS Lett. 316, 278-282.
23. Kemp, B.E., Pearson, R.B. & House, C.M. (1991) Pseudosubstrate-based peptide inhibitors. Methods Enzymol. 201, 287-304.
24. Fry, D.W. (1996) Recent advances in tyrosine kinase inhibitors. Annu. Rep. Med. Chem. 31, 151-160.
25. Lam, K.S., Wu, J. & Lou, Q. (1995) Identification and characterization of a novel synthetic peptide substrate specific for src-family protein tyrosine kinases. Intl. J. Pept. Protein Res. 45, 587-592.
26. c-src. J. Med. Chem. 38, 4276-4283.
27. c-src. Arch. Biochem. Biophys. 316, 73-78.
28. c-src protein tyrosine kinase: conformational and topographical constraints in peptide design. J. Med. Chem. 41, 2252-2260.
29. c-src protein tyrosine kinase. Cancer Res. 57, 1877-1881.
30. c-src protein tyrosine kinase. Bioorg. Med. Chem. 4, 677-682.
31. Wu, J.J., Afar, D.E.H., Phan, H., Witte, O.N. & Lam, K.S. (2002) Recognition of multiple substrate motifs by the c-ABL protein tyrosine kinase. Comb. Chem. High Throughput Screening 5, 83-91.
32. Fields, G.B. & Noble, R.L. (1990) Solid-phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 35, 161-214 and references therein.
33. Lou, Q., Wu, J. & Lam, K.S. (1996) A protein kinase assay system for both acidic and basic peptides. Anal. Biochem. 235, 107-109.
34. v-src kinase activity in vitro. Biochem. Biophys. Res. Commun. 173, 276-282.
35. Levitzki, A. & Gazit, A. (1995) Tyrosine kinase inhibition: an approach to drug development. Science 267, 1782-1788.
36. Morin, M.J. (2000) From oncogene to drug: development of small molecule tyrosine kinase inhibitors as antitumor and antiangiogenic agents. Oncogene 19, 6574-6583.
37. Fabbro, D., Parkinson, D. & Matter, A. (2002) Protein tyrosine kinase inhibitors: new treatment modalities? Curr. Opin. Pharmacol. 2, 374-381.
38. Shawver, L.K., Slamon, D. & Ullrich, A. (2002) Smart drugs: tyrosine kinase inhibitors in cancer therapy. Cancer Cell 1, 117-123.
39. Hanks, S.K., Quinn, A.M. & Hunter, T. (1988) The protein kinase family: conserved features and deduced phylogeny of the catalytic domains. Science 241, 42-52.
40. Klutchko, S.R., Hamby, J.M., Boschelli, D.H., Wu, Z., Kraker, A.J., Amar, A.M., Hartl, E.G., Shen, C., Klohs, W.D., Steinkampf, R.W., Driscoll, D.L., Nelson, J.M., Elliot, W.L., Roberts, B.J., Stoner, C.L., Vincent, P.W., Dykes, D.J., Panek, R.L., Lu, G.H., Major, T.C., Dahring, T.K., Hallak, H., Bradford, L.A., Showalter, H.D. & Doherty, A.M. (1998) 2-Substituted aminopyrido [2,3-d]pyrimidin-7(8H)-ones. Structure-activity relationships against selected tyrosine kinases and in vitro and in vivo anticancer activity. J. Med. Chem. 41, 3276-3292.
41. Trumpp-Kallmeyer, S., Rubin, J.R., Humblet, C., Hamby, J.M. & Showalter, H.D. (1998) Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors. J. Med. Chem. 41, 1752-1763.
42. Lam, K.S. & Wu, J. (1994) Use of selectide technology to identify protein kinase A substrate motif. Methods 6, 401-403.
43. Wu, J., Ma, Q.N. & Lam, K.S. (1994) Identifying substrate motifs of protein kinases by a random library approach. Biochemistry 33, 14825-14833.
44. Furka, A., Sebestyen, F., Asgedom, M. & Dibo, G. (1991) General method for rapid synthesis of multicomponent peptide mixtures. Int. J. Pept. Protein Res. 37, 487-493.
45. Lam, K.S., Salmon, S.E., Hersh, E.M., Hruby, V.J., Kazmierski, W.M. & Knapp, R.J. (1991) One-bead, one-peptide: a new type of synthetic peptide library for identifying ligand-binding activity. Nature 354, 82-84.
46. c-src protein tyrosine kinase. Lett. Pept. Sci. 2, 289-296.
47. c-src protein tyrosine kinase. Lett. Pept. Sci. 3, 309-316.
48. c-src. J. Am. Chem. Soc. 119, 3844-3845.
49. Cheng, H.C., Matsuura, I. & Wang, J.H. (1993) In vitro substrate specificity of protein tyrosine kinases. Mol. Cell. Biochem. 117-128, 103-112.