Inhibition of the epidermal growth factor receptor family of tyrosine kinases as an approach to cancer chemotherapy progression from reversible to irreversible inhibitors

Pharmacology and Therapeutics

Volumn 82, Issue 2-3, 1999, Pages 207-218

  Fry, David W ^a  

^a PFIZER INC   (United States)

Author keywords

Cancer chemotherapy; EGF; erbB2; Inhibitor; Phosphorylation; Tyrosine kinase

Indexed keywords

4 (3 BROMOANILINO) 6 (METHYLAMINO)PYRIDO[3,4 D]PYRIMIDINE; ADENOSINE TRIPHOSPHATE; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; ERLOTINIB; GEFITINIB; N [4 (3 BROMOANILINO) 6 QUINAZOLINYL]ACRYLAMIDE; PD 169414; PD 174265; PROTEIN TYROSINE KINASE INHIBITOR; PYRIDOPYRIMIDINE DERIVATIVE; PYRROLOPYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL MODEL; BINDING SITE; CANCER; CANCER CHEMOTHERAPY; CLINICAL TRIAL; CONFERENCE PAPER; DRUG SPECIFICITY; ENZYME INHIBITION; HUMAN; NONHUMAN; PRIORITY JOURNAL; PROGNOSIS; PROTEIN FAMILY; PROTEIN PHOSPHORYLATION;

ANIMALS; ANTINEOPLASTIC AGENTS; BINDING, COMPETITIVE; CLINICAL TRIALS; ENZYME INHIBITORS; HUMANS; NEOPLASMS; PHOSPHOTRANSFERASES; PROTEIN-TYROSINE KINASES; RECEPTOR, EPIDERMAL GROWTH FACTOR;

EID: 0033025369     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(98)00050-3     Document Type: Conference Paper

References (141)

1. Aaronson S.A. Growth factors and cancer. Science. 254:1991;1146-1153.
2. Bacus S.S., Zelnick C.R., Plowman G., 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. 102:1994;S13-S24.
3. Baker B.R. Design of Active-Site Directed Irreversible Enzyme Inhibitors; the Organic Chemistry of the Enzyme Active-Site. 1967;John Wiley & Sons, New York.
4. Bartlett J.M., Langdon S.P., Simpson B.J., Stewart M., Datsaros D., Sismondi P., Love S., Scott W.N., Williams A.R., Lessells A.M., Macleod K.G., Smyth J.F., Miller W.R. The prognostic value of epidermal growth factor receptor mRNA expression in primary ovarian cancer. Br. J. Cancer. 73:1996;301-306.
5. Ben-Levy R., Paterson H.F., Marshall C.J., Yarden Y. A single autophosphorylation site confers oncogenicity to the neu/erbB-2 receptor and enables coupling to the MAP kinase pathway. EMBO J. 13:1994;3302-3311.
6. Bridges A.J. The current status of tyrosine kinase inhibitors. do the diarylamine inhibitors of the EGF receptor represent a new beginning? Exp. Opin. Ther. Patents. 5:1995;1245-1257.
7. Bridges A.J., Cody D.R., Zhou H., McMichael A., Fry D.W. Enantioselective inhibition of the epidermal growth factor receptor tyrosine kinase by 4-(α-phenethylamino)quinazolines. Bioorg. Med. Chem. 3:1995;1651-1656.
8. Bridges A.J., Zhou H., Cody D.R., Rewcastle G.W., McMichael A., Showalter H.D.H., Fry D.W., Kraker A.J., Denny W.A. 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 epdiermal growth factor receptor. J. Med. Chem. 39:1996;267-276.
9. Bridges, A. J., Denny, W. A., Dobrusin, E. M., Doherty, A. M., Fry, D. W., McNamara, D. J., Showalter, H. D. H., Smaill, J. B. and Zhou, H. (1997) Preparation of N-quinazolinylacrylamides and analogs as tyrosine kinase inhibitors. World Patent Application WO 9738983.
10. Brunton V.G., Workman P. Cell-signaling targets for antitumour drug development. Cancer Chemother. Pharmacol. 32:1993;1-19.
11. Bucci B., D'Agnano I., Botti C., Mottolese M., Carico E., Zupi G., Vecchione A. EGF-R expression in ductal breast cancer. proliferation and prognostic implications Anticancer Res. 17:1997;769-774.
12. Buhrow S.A., Cohen S., Staros J.V. Affinity labeling of the protein kinase associated with the epidermal growth factor receptor in membrane vesicles from A431 cells. J. Biol. Chem. 257:1982;4019-4022.
13. Buhrow S.A., Cohen S., Garbers D.L., Staros J.V. Characterization of the interaction of 5′-p-fluorosulfonylbenzoyl adenosine with the epidermal growth factor receptor/protein kinase in A431 cell membranes. J. Biol. Chem. 258:1983;7824-7827.
14. Burke C.L., Lemmon M.A., Coren B.A., Engelman D.M., Stern D.F. Dimerization of the p185(neu) transmembrane domain is necessary but not sufficient for transformation. Oncogene. 14:1997;687-696.
15. Burke T.R. Protein-tyrosine kinase inhibitors. Drugs Fut. 17:1992;119-131.
16. Cadena D.L., Gill G.N. Receptor tyrosine kinases. FASEB J. 6:1992;2332-2337.
17. Cantley L.C., Auger K.R., Carpenter C., Duckworth B., Graziani A., Kapeller R., Soltoff S. Oncogenes and signal transduction. Cell. 64:1991;281-302.
18. Carraway K.L. III Involvement of the neuregulins and their receptors in cardiac and neural development. Bioessays. 18:1996;263-266.
19. Carraway K.L., Cantley L.C. A neu acquaintance for ErbB3 and ErbB4. a role for receptor heterodimerization in growth signaling Cell. 78:1994;5-8.
20. Carraway K.L., Weber J.L., Unger M.J., Ledesma J., Yu N., Gassmann M., Lai C. Neuregulin-2, a new ligand of ErbB3/ErbB4-receptor tyrosine kinases. Nature. 387:1997;512-516.
21. Chang H., Riese D.J., Gilbert W., Stern D.F., McMahan U.J. Ligands for ErbB-family receptors encoded by a newly characterized neuregulin-like gene. Nature. 387:1997;509-512.
22. Chiao P.J., Bischoff F.Z., Strong L.C., Tainsky M.A. The current state of oncogenes and cancer. experimental approaches for analyzing oncogenetic events in human cancer Cancer Metast. Rev. 9:1990;63-80.
23. Clark S., Konstantopoulos N. Sulphhydryl agents modulate insulin- and epidermal growth factor (EGF)-receptor kinase via reaction with intracellular receptor domains. differential effects on basal versus activated receptors Biochem. J. 292:1993;217-223.
24. Cobleigh M.A., Vogel C.L., Tripathy D., Robert N.J., Scholl R.S., Fehrenbacher L., Paton V., Shak S., Lieberman G., Slamon D. Efficacy and safely of herceptin™ (humanized anti-HER2 antibody) as a single agent in 222 women with HER2 overexpression who relapsed following chemotherapy for metastatic breast cancer. Proc. Am. Soc. Clin. Oncol. 17:1998;97a.
25. Colman R.F. Affinity labeling of purine nucleotide sites in proteins. Annu. Rev. Biochem. 52:1983;67-91.
26. Colman R.F., Bailey J.M., DeCamp D.L., Huang Y.-C., Vollmer S.H. Affinity labeling of adenine nucleotide sites in enzymes. Ann. NY Acad. Sci. 603:1990;417-426.
27. Dankort D.L., Wang Z., Blackmore V., Moran M.F., Muller W.J. Distinct tyrosine autophosphorylation sites negatively and positively modulate neu-mediated transformation. Mol. Cell. Biol. 17:1997;5410-5425.
28. Davies D.E., Chamberlin S.G. Targeting the epidermal growth factor receptor for therapy of carcinomas. Biochem. Pharmacol. 51:1996;1101-1110.
29. Decker S.J. Aspects of the metabolism of the epidermal growth factor receptor in A431 human epidermoid carcinoma cells. Mol. Cell. Biol. 4:1984;571-575.
30. Denhardt D.T. Signal-transducing protein phosphorylation cascades mediated by Ras/Rho proteins in the mammalian cell. the potential for multiplex signalling Biochem. J. 318:1996;729-747.
31. Denny W.A., Rewcastle G.W., Bridges A.J., Fry D.W., Kraker A.J. 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. 23:1996;424-427.
32. Denny W.A., Palmer B.D., Rewcastle G.W., Thompson A.M., Bridges A.J., Doherty A.M., Fry D.W., Nelson J.M., Rubin J.R., Showalter H.D.H., Trumpp-Kallmeyer S. Pyrido[d]pyrimidine inhibitors of the tyrosine kinase activity of the EGF receptor. a binding model and structure-activity relationships for soluble analogues Proc. Am. Assoc. Cancer Res. 38:1997;633.
33. Depotter C.R. The neu-oncogene. more than a prognostic indicator? Hum. Pathol. 25:1994;1264-1268.
34. Dougall W.C., Qian X., Greene M.I. Interaction of the neu/p185 and EGF receptor tyrosine kinases. implications for cellular transformation and tumor therapy J. Cell. Biochem. 53:1993;61-73.
35. Elliott W.L., Fry D.W., Vincent P.W., Roberts B.J., Howard C.T., Slintak V., Nelson J.M., Hook K.E., Showalter H.D.H., Winters T.R., Denny W.A., Thompson A.M. In vitro and in vivo activity of 4-anilinopyridopyridimine EGF family specific tyrosine kinase inhibitors. Proc. Am. Assoc. Cancer Res. 38:1997;470.
36. Fazioli F., Kim U.-H., Rhee S.G., Molloy C.J., Segatto O., DiFiore P.P. The erbB-2 mitogenic signaling pathway. tyrosine phosphorylation of phopholipase C-γ and GTPase-activating protein does not correlate with erbB-2 mitogenic potency Mol. Cell. Biol. 11:1991;2040-2048.
37. Fiddes R.J., Janes P.W., Sanderson G.M., Sivertsen S.P., Sutherland R.L., Daly R.J. Heregulin (HRG)-induced mitogenic signaling and cytotoxic activity of a HRG/PE40 ligand toxin in human breast cancer cells. Cell Growth Differ. 6:1995;1567-1577.
38. Fiddes R.J., Campbell D.H., Janes P.W., Sivertsen S.P., Sasaki H., Wallasch C., Daly R.J. Analysis of Grb7 recruitment by heregulin-activated erbB receptors reveals a novel target selectivity for erbB3. J. Biol. Chem. 273:1998;7717-7724.
39. Fischbach G.D., Rosen K.M. ARIA. a neuromuscular junction neuregulin Annu. Rev. Neurosci. 20:1997;429-458.
40. Fry D.W. Protein tyrosine kinases as therapeutic targets in cancer chemotherapy and recent advances in the development of new inhibitors. Exp. Opin. Invest. Drugs. 3:1994;577-595.
41. Fry D.W. Recent advances in tyrosine kinase inhibitors. Annu. Rep. Med. Chem. 31:1996;151-160.
42. Fry D.W., Bridges A.J. Inhibitors of protein tyrosine kinases. Curr. Opin. Biotech. 6:1995;662-667.
43. Fry D.W., Kraker A.J., McMichael A., Ambroso L.A., Nelson J.M., Leopold W.R., Connors R.W., Bridges A.J. Specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science. 265:1994;1093-1095.
44. Fry D.W., Nelson J.M., McMichael A., Rewcastle G.W., Denny W.A., Zhou H.R., Bridges A.J. Specific suppression of the epidermal growth factor receptor tyrosine kinase in tumor cells and ensuing inhibition of clone formation in soft agar. Proc. Am. Assoc. Cancer Res. 37:1996;424.
45. Fry D.W., Nelson J.M., Slintak V., Keller P.R., Rewcastle G.W., Denny W.A., Zhou H.R., Bridges A.J. 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. Biochem. Pharmacol. 54:1997;877-887.
46. Fry D.W., Bridges A.J., Denny W.A., Doherty A., Greis K., Hicks J.L., Hook K.E., Keller P.R., Leopold W.R., Loo J., McNamara D.J., Nelson J.M., Sherwood V., Smaill J.B., Trumpp-Kallmeyer S., Dobrusin E.M. Specific, irreversible inactivation of the epidermal growth factor receptor and erbb2, by a new class of tyrosine kinase inhibitor. Proc. Natl. Acad. Sci. USA. 95:1998;12022-12027. a.
47. Fry D.W., Nelson J.M., Slintak V., Keller P.R., Loo J., Greis K., Trumpp-Kallmeyer S., Denny W.A., Smaill J.B., Showalter H.D.H., Bridges A.J., Zhou H., McNamara D.J., Dobrusin E.M. Specific, irreversible inhibitors of the epidermal growth factor receptor (EGFR) family of tyrosine kinases. Proc. Am. Assoc. Cancer Res. 39:1998;560. b.
48. Gazit A., Chen J., App H., McMahon G., Hirth P., Chen I., Levitzki A. Tyrphostins IV - highly potent inhibitors of EGF receptor kinase. Structure-activity relationship study of 4-anilidoquinazolines. Bioorg. Med. Chem. 4:1996;1203-1207.
49. Gibson, K. (1996) Quinazoline derivatives. World Patent Application WO 96/33980.
50. Gibson K.H., Grundy W., Godfrey A.A., Woodburn J.R., Ashton S.E., Curry B.J., Scarlett L., Barker A.J., Brown D.S. Epidermal growth factor receptor tyrosine kinase. structure-activity relationships and antitumour activity of novel quinazolines Bioorg. Med. Chem. Lett. 7:1997;2723-2728.
51. Goldman R., Ben Levy R., Peles E., Yarden Y. Heterodimerization of the ErbB1 and ErbB2 receptors in human breast carcinoma cells. a mechanism for receptor transregulation Biochemistry. 29:1990;11024-11028.
52. Grasso A.W., Wen D., Miller C.M., Rhim J.S., Pretlow T.G., Kung H.-J. ErbB kinases and NDF signaling in human prostate cancer cells. Oncogene. 15:1997;2705-2716.
53. Graus-Porta D., Beerli R.R., Daly J.M., Hynes N.E. ErbB-2, the preferred heterodimerization partner of all ErbB receptors, is a mediator of lateral signaling. EMBO J. 16:1997;1647-1655.
54. 6-(6-idodoacetamido-n-hexyl)adenosine 5′-triphosphate. J. Med. Chem. 19:1976;1279-1283. a.
55. Hampton A., Slotin L.A., Kappler F., Sasaki T., Perini F. Design of substrate-site-directed inhibitors of adenylate kinase and hexokinase. Effect of substrate substituents on affinity for the adenine nucleotide sites. J. Med. Chem. 19:1976;1371-1377. b.
56. Hanks S.K., Hunter T. Protein kinases 6 - the eukaryotic protein kinase superfamily. kinase (catalytic) domain structure and classification FASEB J. 9:1995;576-596.
57. Hanks S.K., Quinn A.M., Hunter T. The protein kinase family. conserved features and deduced phylogeny of the catalytic domains Science. 241:1988;42-51.
58. Hook K.E., Vincent P.W., Elliott W.L., Lathia C.D., Smail J., Dobrusin E.M., Bridges A.J., Leopold W.R. Comparative antitumor activity of the irreversible EGF receptor tyrosine kinase inhibitor PD 168393 and its reversible congener PD 174265 in nude mice. Proc. Am. Assoc. Cancer Res. 39:1998;316.
59. Hunter T. Cooperation between oncogenes. Cell. 64:1991;249-270.
60. Hunter T. Tyrosine phosphorylation. past, present and future Biochem. Soc. Trans. 24:1996;307-327.
61. Hynes N.E., Stern D.F. The biology of erbB-2/neu/HER-2 and its role in cancer. Biochim. Biophys. Acta. 1198:1994;165-184.
62. Iwata K., Miller P.E., Barbacci E.G., Arnold L., Doty J., DiOrio C.I., Pustilnik L.R., Reynolds M., Thelemann A., Sloan D., Moyer J.D. CP-358,774. a selective EGFR kinase inhibitor with potent antiproliferative activity against HN5 head and neck tumor cells Proc. Am. Assoc. Cancer Res. 38:1997;633.
63. Jallal B., Schlessinger J., Ullrich A. Tyrosine phosphatase inhibition permits analysis of signal transduction complexes in p185HER2/neu-overexpressing human tumor cells. J. Biol. Chem. 267:1992;4357-4363.
64. Janes P.W., Daly R.J., deFazio A., Sutherland R.L. Activation of the ras signalling pathway in human breast cancer cells overexpressing erbB-2. Oncogene. 9:1994;3601-3608.
65. erB2. J. Biol. Chem. 268:1993;2924-2931.
66. Kaplan, D. R., Perkins, A. and Morrison, D. K. (1993) Signal transduction by receptor tyrosine kinases. In: Oncogenes and Tumor Suppressor Genes in Human Malignancies, pp. 265-279, Benz, C. C. and Liu, E. T. (eds.) Kluwer Academic Publisher, Boston.
67. Khazaie K., Schirrmacher V., Lichtner R.B. EGF receptor in neoplasia and metastasis. Cancer Metastasis Rev. 12:1993;255-274.
68. King C.R., Borrello I., Bellot F., Comoglio P., Schlessinger J. EGF binding to its receptor triggers a rapid tyrosine phosphorylation of the erbB-2 protein in the mammary tumor cell line SK-BR-3. EMBO J. 7:1988;1647-1651.
69. Klijn J.G.M., Berns P.M.J.J., Schmitz P.I.M., Foekens J.A. The clinical significance of epidermal growth factor receptor (EGF-R) in human breast cancer - a review on 5232 patients. Endocr. Rev. 13:1992;3-17.
70. Klijn J.G., Look M.P., Portengen H., Alexieva-Figusch J., van Putten W.L., Foekens J.A. The prognostic value of epidermal growth factor receptor (EGF-R) in primary breast cancer. results of a 10 year follow-up study Breast Cancer Res. Treat. 29:1994;73-83.
71. Klohs W.D., Fry D.W., Kraker A.J. Inhibitors of tyrosine kinase. Curr. Opin. Oncol. 9:1997;562-568.
72. Komurasaki T., Toyoda H., Uchida D., Morimoto S. Epiregulin binds to epidermal growth factor receptor and ErbB-4 and induces tyrosine phosphorylation of epidermal growth factor receptor, ErbB-2, ErbB-3 and ErbB-4. Oncogene. 15:1997;2841-2848.
73. Kurganov B.I., Nagradova N.K., Lavrik O.I. Chemical Modification of Enzymes. 1996;Nova Science Publishers, Commack.
74. Laird A.D., Shalloway D. Oncoprotein signalling and mitosis. Cell. Signal. 9:1997;249-255.
75. Langdon S.P., Smyth J.F. Inhibition of cell signalling pathways. Cancer Treat. Rev. 21:1995;65-89.
76. Lawrence D.S., Niu J. Protein kinase inhibitors. the tyrosine-specific protein kinases Pharmacol. Ther. 77:1998;81-114.
77. Levitzki A. Tyrphostins. tyrosine kinase blockers as novel antiproliferative agents and dissectors of signal transduction FASEB J. 6:1992;3275-3282.
78. Levitzki A., Gazit A. Tyrosine kinase inhibition. an approach to drug development Science. 267:1995;1782-1788.
79. Levitzki A., Gilon C. Tyrphostins as molecular tools and potential antiproliferative drugs. Trends Pharmacol. Sci. 12:1991;171-174.
80. Lutrell D.K., Lee A., Lansing T.J., Crosby R.M., Jung K.D., Willard 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. USA. 19:1994;83-97.
81. Marchionni M.A., Goodearl A.D.J., Chen M.S., Berminghan-McDonogh O., Kirk C., Hendricks M., Danehy F., Misumi D., Sudhalter J., Kobayashi K., Wroblewski D., Lynch C., Baldassare M., Hiles I., Davis J.B., Hsuan J.J., Totty N.F., Otsu M., McBurney R.N., Waterfield M.D., Stroobant P., Gwynne D. Glial growth factors are alternatively spliced erbB2 ligands expressed in the nervous system. Nature. 362:1993;312-318.
82. Meden H., Marx D., Raab T., Schauer K.M., Kuhn W. EGF-R and overexpression of the oncogene c-erbB-2 in ovarian cancer. immunohistochemical findings and prognostic value J. Obstet. Gynaecol. 21:1995;167-178.
83. Meyer D., Birchmeier C. Multiple essential functions of neuregulin in development. Nature. 378:1995;386-398.
84. Moolenaar W.H., Bierman A.J., Tilly B.C., Verlaan I., Defize L.H.K., Honegger A.M., Ullrich A., Schlessinger J. A point mutation at the ATP-binding site of the EGF-receptor abolishes signal transduction. EMBO J. 7:1988;707-710.
85. Moyer J.D., Barbacci E.G., Iwata K.K., Arnold L., Boman B., Cunningham A., DiOrio C., Doty J., Morin M.J., Moyer M.P., Neveu M., Pollack V.A., Pustilnik L.R., Reynolds M.M., Sloan D., Theleman A., Miller P. Induction of apoptosis and cell cycle arrest by CP-358,774, an inhibitor of epidermal growth factor receptor tyrosine kinase. Cancer Res. 57:1997;4838-4848.
86. Muller W.J., Arteaga C.L., Muthuswamy S.K., Siegel P.M., Webster M.A., Cardiff R.D., Meise K.S., Li F., Halter S.A., Coffey R.J. Synergistic interaction of the neu proto-oncogene product and transforming growth factor alpha in the mammary epithelium of transgenic mice. Mol. Cell. Biol. 16:1996;5726-5736.
87. Muthuswamy S.K., Siegel P.S., Dankort D.L., Webster M.A., Muller W.J. Mammary tumors expressing the new proto-oncogene possess elevated c-src tyrosine kinase activity. Mol. Cell. Biol. 14:1994;735-743.
88. Nelson J.M., Slintak V., Denny W.A., Smaill J.B., Rewcastle G.W., Showalter H.D.H., Bridges A.J., Zhou H., McNamara D.J., Dobrusin E.M., Fry D.W. In vitro comparison of irreversible versus reversible inhibition for a series of substituted quinazolines and pyridopyrimidines that are potent and specific inhibitors of the epidermal growth factor receptor (EGFR) family of tyrosine kinases. Proc. Am. Assoc. Cancer Res. 39:1998;316.
89. Osherov N., Levitzki A. Epidermal-growth-factor-dependent activation of the Src-family kinases. Eur. J. Biochem. 225:1994;1047-1053.
90. Palfreyman M.G., McCann P.P., Lovenberg W., Temple J.G., Sjoerdsma A. Enzymes as Targets for Drug Design. 1989;Academic Press, San Diego.
91. Palmer B.D., Trumpp-Kallmeyer S., Fry D.W., Nelson J.M., Showalter H.D.H., Denny W.A. Tyrosine kinase inhibitors. 11. Soluble analogues of pyrrolo- and pyrazoloquinazolines as epidermal growth factor receptor inhibitors. synthesis, biological evaluation, and modeling of the mode of binding J. Med. Chem. 40:1997;1519-1529.
92. Patmore S.J., Roberts B.J., Stoner C.L., Vincent P.W., Leopold W.R., Dykes D.J., Denny W.A., Smaill J.B., Elliott W.L. In vivo evaluation of the irreversible EGF receptor tyrosine kinase inhibitor PD 168393. Proc. Am. Assoc. Cancer Res. 39:1998;560.
93. Pawson T., Schlessinger J. SH2 and SH3 domains. Curr. Biol. 3:1993;434-442.
94. Pinkas-Kramarski R., Soussan L., Waterman H., Levkowitz G., Alroy I., Klapper L., Lavi S., Seger R., Ratzkin B.J., Sela M., Yarden Y. Diversification of Neu differentiation factor and epidermal growth factor signaling by combinatorial receptor interactions. EMBO J. 15:1996;2452-2467.
95. Pollack V.A., Savage D.M., Baker D.A., Tsaparikos K.E., Sloan D.E., Barbacci E.G., Pustilnik L.R., Smolarek T.A., Davis J.A., Vaidya M.P., Iwata K. Therapy of human carcinomas in athymic mice by inhibition of EGF receptor-mediated signal transduction with CP-358774. dynamics of receptor inhibition and anti-tumor effects Proc. Am. Assoc. Cancer Res. 38:1997;633.
96. Powis G. Signalling pathways as targets for anticancer drug development. Pharmacol. Ther. 62:1994;57-95.
97. Qian X., Greene M.I. Her2/neu. a receptor tyrosine kinase with developmental and oncogenic activity Encycl. Cancer. 2:1997;835-856.
98. Qian X.L., Dougall W.C., Fei Z.Z., Greene M.I. Intermolecular association and trans-phosphorylation of different neu-kinase forms permit SH2-dependent signaling and oncogenic transformation. Oncogene. 10:1995;211-219.
99. Rajkumar T., Gullick W.J. The type I growth factor receptors in human breast cancer. Breast Cancer Res. Treat. 29:1994;3-9.
100. Ram T.G., Ethier S.P. Phosphatidylinositol 3-kinase recruitment by p185erbB-2 and erbB-3 is potently induced by neu differentiation factor/heregulin during mitogenesis and is constitutively elevated in growth factor-independent breast carcinoma cells with c-erbB-2 gene amplification. Cell Growth Differ. 7:1996;551-561.
101. Reese D.M., Slamon D.J. HER-2/neu signal transduction in human breast and ovarian cancer. Stem Cells. 15:1997;1-8.
102. Rewcastle G.W., Denny W.A., Bridges A.J., Zhou H.R., Cody D.R., McMichael A., Fry D.W. 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. 38:1995;3482-3487.
103. Rewcastle G.W., Palmer B.D., Bridges A.J., Showalter H.D.H., Li S., Nelson J., McMichael A., Kraker A.J., Fry D.W., Denny W.A. 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. 39:1996;918-928. a.
104. Rewcastle G.W., Palmer B.D., Thompson A.M., Bridges A.J., Cody D.R., Zhou H., Fry D.W., McMichael A., Denny W.A. 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. 39:1996;1823-1835. b.
105. Rewcastle G.W., Bridges A.J., Fry D.W., Rubin J.R., Denny W.A. Tyrosine kinase inhibitors. 12. Synthesis and structure-activity relationships for 6-substituted 4-(phenylamino)pyrimido-[5,4-d]pyrimidines designed as inhibitors of the epidermal growth factor receptor. J. Med. Chem. 40:1997;1820-1826.
106. Riese D.J., Stern D.F. Specificity within the EGF family/erbB receptor family signaling network. Bioessays. 20:1998;41-48.
107. Riese D.J. II, Bermingham Y., van Raaij T.M., Buckely S., Plowman G.D., Stern D.F. Betacellulin activates the epidermal growth factor receptor and ErbB4, and induces cellular response patterns distinct from those stimulated by epidermal growth factor or neuregulin-β Oncogene. 12:1996;345-353. a.
108. Riese D.J. II, Kim E.D., Elinius K., Buckely S., Klagsbrun M., Plowman G.D., Stern D.F. The epidermal growth factor receptor couples transforming growth factor-α, heparin-binding epidermal growth factor-like factor, and amphiregulin to Neu, ErbB3, and ErbB4. J. Biol. Chem. 271:1996;20047-20052. b.
109. Russo M.W., Lukas T.J., Cohen S., Staros J.V. Identification of residues in the nucleotide binding site of the epidermal growth factor receptor kinase. J. Biol. Chem. 260:1985;5205-5208.
110. Salomon D.S., Brandt R., Ciardiello F., Normanno N. Epidermal growth factor-related peptides and their receptors in human malignancies. Crit. Rev. Oncol. Hematol. 19:1995;183-232.
111. Scambia G., Benedetti-Panici P., Ferrandina G., Distefano M., Salerno G., Romanini M.E., Fagotti A., Mancuso S. Epidermal growth factor, oestrogen and progesterone receptor expression in primary ovarian cancer. correlation with clinical outcome and response to chemotherapy Br. J. Cancer. 72:1995;361-366.
112. Schlessinger J., Ullrich A. Growth factor signaling by receptor tyrosine kinases. Neuron. 9:1992;383-391.
113. Schnur, R. C. and Arnold, L. D. (1996) Quinazoline derivatives. World Patent Application WO 96/30347.
114. Scoggins R.M., Summerfield A.E., Stein R.A., Guyer C.A., Staros J.V. 5′-(p-Fluorosulfonylbenzoyl)-2′(or 3′)-(methylanthraniloyl)adenosine, fluorescent affinity labels for adenine nucleotide binding sites. interaction with the kinase active site of the receptor for epidermal growth factor Biochemistry. 35:1996;9197-9203.
115. Segatto O., Lonardo F., Helin K., Wexler D., Fazioli F., Rhee S.G., Di Fiore P.P. erbB-2 autophosphorylation is required for mitogenic action and high-affinity substrate coupling. Oncogene. 7:1992;1339-1346.
116. Sepp-Lorenzino L., Eberhard I., Ma Z., Cho C., Serve H., Liu F., Rosen N., Lupu R. Signal transduction pathways induced by heregulin in MDA-MB-453 breast cancer cells. Oncogene. 12:1996;1679-1687.
117. Singh J., Dobrusin E.M., Fry D.W., Haske T., Whitty A., McNamara D.J. Structure-based design of a potent, selective, and irreversible inhibitor of the catalytic domain of the erbB receptor subfamily of protein tyrosine kinases. J. Med. Chem. 40:1997;1130-1135.
118. Songyang Z., Carraway K.L. III, Eck M.J., Harrison S.C., Feldman R.A., Mohammadi M., Schlessinger J., Hubbard S.R., Smith D.P., Eng C., Lorenzo M.J., Ponder B.A.J., Mayer B.J., Cantley L.C. Catalytic specificity of protein-tyrosine kinases is critical for selective signalling. Nature. 373:1995;536-539.
119. Spada A.P., Myers M.R. Small molecule inhibitors of tyrosine kinase activity. Opin. Ther. Patents. 5:1995;805-817.
120. Stein D., Wu J., Fuqua S.A., Roonprapunt C., Yajnik V., D'Eustachio P., Moskow J.J., Buchberg A.M., Osborne C.K., Margolis B. The SH2 domain protein GRB7 is co-amplified, overexpressed and in a tight complex with HER2 in breast cancer. EMBO J. 13:1994;1331-1340.
121. neu. A potential model for receptor interactions. EMBO J. 7:1988;995-1001.
122. Stern D.F., Heffernan P.A., Weinberg R.A. P185, a product of the neu proto-oncogene, is a receptor-like protein associated with tyrosine kinase activity. Mol. Cell. Biol. 6:1986;1729-1740.
123. Thompson A.M., Bridges A.J., Fry D.W., Kraker A.J., Denny W.A. 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. 38:1995;3780-3788.
124. Thompson A.M., Murray D.K., Elliott W.L., Fry D.W., Nelson J.A., Showalter H.D.H., Roberts B.J., Vincent P.W., Denny W.A. Tyrosine kinase inhibitors. 13. Structure-activity relationships for soluble 7-substituted 4-[(3-bromophenyl)amino]pyrido[4,3-d]-pyrimidines designed as inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J. Med. Chem. 40:1997;3915-3925.
125. Toi M., Tominaga T., Osaki A., Toge T. Role of epidermal growth factor receptor expression in primary breast cancer. results of a biochemical study and an immunocytochemical study Breast Cancer Res. 29:1994;51-58.
126. Traxler, P. (1996) Pyrazole derivatives and processes for the preparation thereof. World Patent Application, WO96/31510.
127. Traxler P.M., Furet P., Mett H., Buchdunger E., Meyer T., Lydon N. 4-(Phenylamino)pyrrolopyrimidines. potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase J. Med. Chem. 39:1996;2285-2292.
128. Traxler P., Bold G., Frei J., Lang M., Lydon N., Mett H., Buchdunger E., Meyer T., Mueller M., Furet P. Use of a pharmacophore model for the design of EGF-R tyrosine kinase inhibitors. 4-(phenylamino)pyrazolo[3,4-d]pyrimidines J. Med. Chem. 40:1997;3601-3616.
129. Tzahar E., Waterman H., Chen X.M., Levkowitz G., Karunagaran D., Lavi S., Ratzkin B.J., Yarden Y. A hierarchical network of interreceptor interactions determines signal transduction by neu differentiation factor/neuregulin and epidermal growth factor. Mol. Cell. Biol. 16:1996;5276-5287.
130. Tzahar E., Pinkas-Kramarski R., Moyer J.D., Kapper L.N., Alroy I., Levkowitz G., Shelly M., Henis S., Eisenstein M., Ratzkin B.J., Sela M., Andrews G.C., Yarden Y. Bivalence of EGF-like ligands drives the ErbB signaling network. EMBO J. 16:1997;4938-4950.
131. Ullrich A., Schlessinger J. Signal transduction by receptors with tyrosine kinase activity. Cell. 61:1990;203-212.
132. Vandergeer P., Hunter T., Lindberg R.A. Receptor protein-tyrosine kinases and their signal transduction pathways. Annu. Rev. Cell Biol. 10:1994;251-337.
133. Vincent P.W., Akinson B.E., Zhou H., Dykes D., Leopold W.R., Patmore S.J., Roberts B.J., Bridges A., Elliott W.L. Characterization of the in vivo activity of a novel EGF receptor family kinase inhibitor, PD 168414. Proc. Am. Assoc. Cancer Res. 39:1998;560.
134. Wada T., Qian X., Green M.I. Intermolecular association of the p185neu protein and EGF receptor modulates EGF receptor function. Cell. 61:1990;1339-1347.
135. Ward N.E., Gravitt K.R., O'Brian C.A. Irreversible inactivation of protein kinase C by a peptide-substrate analog. J. Biol. Chem. 270:1995;8056-8060.
136. Ward W.H.J., Cook P.N., Slater A.M., Davies H., Holdgate G.A., Green L.R. Epidermal growth factor receptor tyrosine kinase. Investigation of catalytic mechanism, structure-based searching and discovery of a potent inhibitor. Biochem. Pharmacol. 48:1994;659-666.
137. Wissner, A., Johnson, B. D., Floyd, M. B. and Kitchen, D. B. (1997) Substituted quinazoline derivatives. European Patent Application, EP 0 787 722 A1.
138. Woltjer R.L., Staros J.V. Effects of sulfhydryl modification reagents on the kinase activity of the epidermal growth factor receptor. Biochemistry. 36:1997;9911-9916.
139. Woodburn J.R., Barker A.J., Gibson K.H., Ashton S.E., Wakeling A.E., Curry B.J., Scarlett L., Henthorn L.R. ZD1839, an epidermal growth factor tyrosine kinase inhibitor selected for clinical development. Proc. Am. Assoc. Cancer Res. 38:1997;633.
140. Yount R.G., Babcock D., Ballantyne W., Ojala D. Adenylyl immidodiphosphate, an adenosine triphosphate analog containing a P-N-P linkage. Biochemistry. 10:1971;2484-2489.
141. Zheng J., Knighton D.R., Ten Eyck L.F., Darlsson R., Xuong N., Taylor S.S., Sowadski J.M. Crystal structure of the catalytic subunit of the cAMP Ser/Thr-dependent protein kinase complexed with MgATP and peptide inhibitor. Biochemistry. 32:1993;2154-2161.