Biochemical and antiproliferative properties of 4-[ar(alk)ylamino]pyridopyrimidines, a new chemical class of potent and specific epidermal growth factor receptor tyrosine kinase inhibitor

Biochemical Pharmacology

Volumn 54, Issue 8, 1997, Pages 877-887

  Fry, David W ^a   Nelson, James M ^a   Slintak, Veronika ^a   Keller, Paul R ^a   Rewcastle, Gordon W ^b   Denny, William A ^b   Zhou, Hairong ^a   Bridges, Alexander J ^a  

^a PFIZER INC   (United States)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Anticancer; EGF receptor; Inhibitor; Pyridopyrimidine; Tumor; Tyrosine kinase

Indexed keywords

4 (3 BROMOANILINO) 6 (METHYLAMINO)PYRIDO[3,4 D]PYRIMIDINE; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR; PD 153717; PD 69896; PROTEIN TYROSINE KINASE INHIBITOR; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; AUTOPHOSPHORYLATION; BREAST CARCINOMA; CELL PROLIFERATION; CELL STRAIN 3T3; CONTROLLED STUDY; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; TUMOR CELL;

CARRIER PROTEINS; ENZYME INHIBITORS; GLYCOPROTEINS; GROWTH INHIBITORS; HUMANS; KINETICS; MOLECULAR STRUCTURE; NEUREGULIN-1; PEPTIDE FRAGMENTS; PHOSPHORYLATION; PYRIMIDINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; TUMOR CELLS, CULTURED;

EID: 0030870071     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00242-6     Document Type: Article

References (62)

1. Glenney JR Jr, Tyrosine-phosphorylated proteins: Mediators of signal transduction from the tyrosine kinases. Biochim Biophys Acta 1134: 113-127, 1992.
2. Cadena DL and Gill GN, Receptor tyrosine kinases. FASEB J 6: 2332-2337, 1992.
3. Schlessinger J and Ullrich A, Growth factor signaling by receptor tyrosine kinases. Neuron 9: 383-391, 1992.
4. Vandergeer P, Hunter T and Lindberg RA, Receptor protein-tyrosine kinases and their signal transduction pathways. Annu Rev Cell Biol 10: 251-337, 1994.
5. Chiao PJ, Bischoff FZ, Strong LC and Tainsky MA, The current status of oncogenes and cancer: Experimental approaches for analyzing oncogenetic events in human cancer. Cancer Metastasis Rev 9: 63-80, 1990.
6. Hunter T, Cooperation between oncogenes. Cell 64: 249-270, 1991.
7. Aaronson SA, Growth factors and cancer. Science 254: 1146-1153, 1991.
8. Cantley LC, Auger KR, Carpenter C, Duckworth B, Graziani A, Kapeller R and Soltoff S, Oncogenes and signal transduction. Cell 64: 281-302, 1991.
9. Kaplan DR, Perkins A and Morrison DK, Signal transduction by receptor tyrosine kinases. In: Oncogenes and Tumor Suppressor Genes in Human Malignancies (Eds. Benz CC and Liu ET), pp. 265-279. Kluwer Academic Publishers, Boston, 1993.
10. Ullrich A and Schlessinger J, Signal transduction by receptors with tyrosine kinase activity. Cell 61: 203-212, 1990.
11. Brunton VG and Workman P, Cell-signaling targets for antitumour drug development. Cancer Chemother Pharmacol 32: 1-19, 1993.
12. Powis G, Signalling pathways as targets for anticancer drug development. Pharmacol Ther 62: 57-95, 1994.
13. Levitzki A and Gazit A, Tyrosine kinase inhibition: An approach to drug development. Science 267: 1782-1788, 1995.
14. Fry DW, Protein tyrosine kinases as therapeutic targets in cancer chemotherapy and recent advances in the development of new inhibitors. Expert Opin Invest Drugs 3: 577-595, 1994.
15. Langdon SP and Smyth JF, Inhibition of cell signalling pathways. Cancer Treat Rev 21: 65-89, 1995.
16. Elder JT, Fisher GJ, Lindquist PB, Bennet GL, Pittelkow MR, Coffey RJ, Ellingsworth L, Denrynck R and Voorhees JJ, Overexpression of transforming growth factor α in psoriatic epidermis. Science 243: 811-814, 1989.
17. Vassar R and Fuchs E, Transgenic mice provide new insights into the role of TGFα during epidermal development and differentiation. Genes Dev 5: 714-727, 1991.
18. Hajjar DP and Pomerantz KB, Signal transduction in atherosclerosis: Integration of cytokines and the eicosanoid network. FASEB J 6: 2933-2941, 1992.
19. Libby P, Schwartz D, Brogi E, Tanaka H and Clinton SK, A cascade model for restenosis. A special case of atherosclerosis progression. Circulation 86(Suppl 6): III47-III52, 1992.
20. Schwartz RS, Holmes DR and Topol EJ, The restenosis paradigm revisited: An alternative proposal for cellular mechanisms. J Am Coll Cardiol 20: 1284-1293, 1992.
21. Modjtahedi H and Dean C, The receptor for EGF and its ligands - Expression, prognostic value and target for therapy in cancer. Int J Oncol 4: 277-296, 1994.
22. Dougall WC, Qian X, Peterson NC, Miller MJ, Samanta A and Greene MI, The neu-oncogene: Signal transduction pathways, transformation mechanisms and evolving therapies. Oncogene 9: 2109-2123, 1994.
23. Bacus SS, Zelnick CR, Plowman G and Yarden Y, Expression of the erbB-2 family of growth factor receptors and their ligands in breast cancers. Implication for tumor biology and clinical behavior. Am J Clin Pathol 102: S13-S24, 1994.
24. Hynes NE and Stern DF, The biology of erbB-2/neu/HER-2 and its role in cancer. Biochim Biophys Acta 1198: 165-184, 1994.
25. Hayman MJ and Enrietto PJ, Cell transformation by the epidermal growth factor receptor and v-erbB. Cancer Cells 3: 302-307, 1991.
26. Fry DW and Bridges AJ, Inhibitors of protein tyrosine kinases. Curr Opin Biotechnol 6: 662-667, 1995.
27. Fry DW, Recent advances in tyrosine kinase inhibitors. Annu Rep Med Chem 31: 151-160, 1996.
28. Bridges AJ, The current status of tyrosine kinase inhibitors: Do the diarylamine inhibitors of the EGF receptor represent a new beginning? Exp Opin Ther Patents 5: 1245-1257, 1995.
29. Spada AP and Myers MR, Small molecule inhibitors of tyrosine kinase activity. Exp Opin Ther Patents 5: 805-817, 1995.
30. Rewcastle GW, Denny WA, Bridges AJ, Zhou HR, Cody DR, McMichael A and Fry DW, Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5′-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth factor receptor. J Med Chem 38: 3482-3487, 1995.
31. Denny WA, Rewcastle GW, Bridges AJ, Fry DW and Kraker AJ, Structure-activity relationships for 4-anilinoquinazolines as potent inhibitors at the ATP binding site of the epidermal growth factor receptor in vitro. Clin Exp Pharmacol Physiol 23: 424-427, 1996.
32. Bridges AJ, Cody DR, Zhou H, McMichael A and Fry DW, Enantioselective inhibition of the epidermal growth factor receptor tyrosine kinase by 4-(a-phenethylamino)quinazolines. Bioorg Med Chem 3: 1651-1656, 1995.
33. Bridges AJ, Zhou H, Cody DR, Rewcastle GW, McMichael A, Showalter HDH, Fry DW, Kraker AJ and Denny WA, Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor. J Med Chem 39: 267-276, 1996.
34. Rewcastle GW, Palmer BD, Bridges AJ, Showalter HDH, Li S, Nelson JM, McMichael A, Kraker AJ, Fry DW and Denny WA, Tyrosine kinase inhibitors. 9. Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J Med Chem 39: 918-928, 1996.
35. Osherov N and Levitzki A, Epidermal-growth-factor-dependent activation of the src-family kinases. Eur J Biochem 225: 1047-1053, 1994.
36. Ward WHJ, Cook PN, Slater AM, Davies H, Holdgate GA and Green LR, Epidermal growth factor receptor tyrosine kinase. Investigation of catalytic mechanism, structure-based searching and discovery of a potent inhibitor. Biochem Pharmacol 48: 659-666, 1994.
37. Wakeling AE, Barker AJ, Davies DH, Brown DS, Green LR, Cartlidge SA and Woodburn JR, Specific inhibition of epidermal growth factor receptor tyrosine kinase by 4-anilinoquinazolines. Breast Cancer Res Treat 38: 67-73, 1996.
38. Thompson AM, Bridges AJ, Fry DW, Kraker AJ and Denny WA, Tyrosine kinase inhibitors. 7. 7-Amino-4-(phenylamino)- and 7-amino-4-[(phenylmethyl)amino]pyrido[4,3-d] pyrimidines: A new class of inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J Med Chem 38: 3780-3788, 1995.
39. Rewcastle GW, Palmer BD, Thompson AM, Bridges AJ, Cody DR, Zhou H, Fry DW, McMichael A and Denny WA, Tyrosine kinase inhibitors. 10. Isomeric 4-[(3-bromophenyl)amino]pyrido[d]pyrimidines are potent ATP binding site inhibitors of the tyrosine kinase function of the epidermal growth factor receptor. J Med Chem 39: 1823-1835, 1996.
40. Traxler PM, Furet P, Mett H, Buchdunger E, Meyer T and Lydon N, 4-(Phenylamino)pyrrolopyrimidines: potent and selective ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase. J Med Chem 39: 2285-2292, 1996.
41. Woodburn JR, Barker AJ, Wakeling AE, Valcaccia BE, Cartlidge SA and Davies DH, 6-Amino-4-(3-methylphenylamino)-quinazoline: An EGF receptor tyrosine kinase inhibitor with activity in a range of human tumour xenografts. Proc Am Assoc Cancer Res 37: 390-391, 1996.
42. Holmes WE, Sliwkowski MX, Akita RW, Henzel WJ, Lee J, Park JW, Yansura D, Abadi N, Raab H, Lewis GD, Shepard HM, Kuang WJ, Wood WI, Goeddel DV and Vandlen RL, Identification of heregulin, a specific activator of p185(erbB2). Science 256: 1205-1210, 1992.
43. Gill GN and Weber W, Purification of functionally active epidermal growth factor receptor protein using a competitive antagonist monoclonal antibody and competitive elution with epidermal growth factor. Methods Enzymol 146: 82-88, 1987.
44. 50 values and the type of inhibition for enzyme-catalyzed reactions. Biochem Med Metab Biol 40: 204-212, 1988.
45. Wen D, Suggs SV, Karunagaran D, Liu N, Cupples RL, Luo Y, Janssen AM, Ben-Baruch N, Trollinger DB, Jacobsen VL, Meng S-Y, Lu HS, Hu S, Chang D, Yang W, Yanigahara D, Koski RA and Yarden Y, Structural and functional aspects of the multiplicity of neu differentiation factors. Mol Cell Biol 14: 1909-1919, 1994.
46. Sliwkowski MX, Schaefer G, Akita RW, Lofgren JA, Fitzpatrick VD, Nuijens A, Fendly BM, Cerione RA, Vandlen RL and Carraway KL, Coexpression of erbB2 and erbB3 proteins reconstitutes a high affinity receptor for heregulin. J Biol Chem 269: 14661-14665, 1994.
47. Carraway KL, Sliwkowski MX, Akita R, Platko JV, Guy PM, Nuijens A, Diamonti AJ, Vandlen RL, Cantley LC and Cerione RA, The erbB3 gene product is a receptor for heregulin. J Biol Chem 269: 14303-14306, 1994.
48. Tzahar E, Levkowitz G, Karunagaran D, Yi L, Peles E, Lavi S, Chang D, Liu N, Yayon A, Wen D and Yarden Y, ErbB-3 and ErbB-4 function as the respective low and high affinity receptors of all neu differentiation factor/heregulin isoforms. J Biol Chem 269: 25226-25233, 1994.
49. Plowman GD, Green JM, Culouscou JM, Carlton GW, Rothwell VM and Buckley S, Heregulin induces tyrosine phosphorylation of HER4/P180(erbB4). Nature 366: 473-475, 1993.
50. Kita YA, Barff J, Luo Y, Wen DZ, Brankow D, Hu S, Liu NL, Prigent SA, Gullick WJ and Nicolson M, NDF/heregulin stimulates the phosphorylation of Her3/erbB3. FEBS Lett 349: 139-143, 1994.
51. Carraway KL III and Cantley LC, A neu acquaintance for ErbB3 and ErbB4: A role for receptor heterodimerization in growth signaling. Cell 78: 5-8, 1994.
52. Earp HS, Dawson TL, Li X and Yu H, Heterodimerization and functional interaction between EGF receptor family members: A new signaling paradigm with implications for breast cancer research. Breast Cancer Res Treat 35: 115-132, 1995.
53. Riese DJ II, van Raaij TM, Plowman GD, Andrews GC and Stern DF, The cellular response to neuregulins is governed by complex interactions of the erbB receptor family. Mol Cell Biol 15: 5770-5776, 1995.
54. Wallasch C, Weiß FU, Niederfellner G, Jallal B, Issing W and Ullrich A, Heregulin-dependent regulation of HER2/neu oncogenic signaling by heterodimerization with HER3. EMBO J 14: 4267-4275, 1995.
55. Kraus MH, Popescu NC, Amsbaugh SC and King CR, Overexpression of the EGF receptor-related proto-oncogene erbB-2 in human mammary tumor cell lines by different molecular mechanisms. EMBO J 6: 605-610, 1987.
56. Alimandi M, Romano A, Curia MC, Muraro R, Fedi P, Aaronson SA, Di Fiore PP and Kraus MH, Cooperative signaling of erbB3 and erbB2 in neoplastic transformation and human mammary carcinomas. Oncogene 10: 1813-1821, 1995.
57. Lemoine NR, Barnes DM, Hollywood DP, Hughes CM, Smith P, Dublin E, Prigent SA, Gullick WJ and Hurst HC, Expression of the erbB3 gene product in breast cancer. Br J Cancer 66: 1116-1121, 1992.
58. Kraus MH, Fedi P, Starks V, Muraro R and Aaronson SA, Demonstration of ligand-dependent signaling by the erbB-3 tyrosine kinase and its constitutive activation in human breast tumor cells. Proc Natl Acad Sci USA 90: 2900-2904, 1993.
59. Plowman GD, Culouscou J-M, Whitney GS, Green JM, Carlton GW, Foy L, Neubauer MG and Shoyab M, Proc Natl Acad Sci USA 90: 1746-1750, 1993.
60. Guy PM, Platko JV, Cantley LC, Cerione RA and Carraway KL, Insect cell-expressed p180(erbB3) possesses an impaired tyrosine kinase activity. Proc Natl Acad Sci USA 91: 8132-8136, 1994.
61. Baselga J and Mendelsohn J, Receptor blockade with monoclonal antibodies as anti-cancer therapy. Pharmacol Ther 64: 127-154, 1994.
62. Ohnishi Y, Nakamura H, Yoshimura M, Tokuda Y, Iwasawa M, Ueyama Y, Tamaoki N and Shimamura K, Prolonged survival of mice with human gastric cancer treated with an anti-c-erbB-2 monoclonal antibody. Br J Cancer 71: 969-973, 1995.