In vivo Positron Emission Tomography (PET) imaging of Mesenchymal - Epithelial Transition (MET) receptor

Journal of Medicinal Chemistry

Volumn 53, Issue 1, 2010, Pages 139-146

  Wu, Chunying ^a   Tang, Zhe ^b   Fan, Weiwen ^b   Zhu, Wenxia ^a   Wang, Changning ^a   Somoza, Edurado ^a   Owino, Norbert ^a   Li, Ruoshi ^a   Ma, Patrick C ^b   Wang, Yanming ^a  

^a CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 14; N (3 CHLOROPHENYL) 3 [3,5 DIMETHYL 4 (4 METHYL 1 PIPERAZINYLCARBONYL) 1H PYRROL 2 YLMETHYLENE] 2,3 DIHYDRO N METHYL 2 OXO 1H INDOLE 5 SULFONAMIDE; N (3 CHLOROPHENYL) 3 [3,5 DIMETHYL 4 (4 METHYL 1 PIPERAZINYLCARBONYL) 1H PYRROL 2 YLMETHYLENE] 2,3 DIHYDRO N METHYL 2 OXO 1H INDOLE 5 SULFONAMIDE C 11; SCATTER FACTOR RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CANCER SCINTISCANNING; CONTROLLED STUDY; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IMMUNOHISTOCHEMISTRY; ISOTOPE LABELING; LUNG CANCER; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; NUDE MOUSE; POSITRON EMISSION TOMOGRAPHY; RADIOCHEMISTRY; RADIOISOTOPE DISTRIBUTION; REACTION ANALYSIS; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG EVALUATION; HUMANS; INDOLES; LUNG NEOPLASMS; MICE; MICE, NUDE; MOLECULAR IMAGING; PIPERAZINES; POSITRON-EMISSION TOMOGRAPHY; RECEPTOR PROTEIN-TYROSINE KINASES; RECEPTOR, EPIDERMAL GROWTH FACTOR; SULFONAMIDES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 74849102049     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900803q     Document Type: Article

References (44)

1. Sun, S.; Schiller, J. H.; Spinola, M.; Minna, J. D. New molecularly targeted therapies for lung cancer. J. Clin. Invest. 2007, 117, 2740-2750.
2. Savage, D. G.; Antman, K. H. Imatinib mesylate - a new oral targeted therapy. N. Engl. J. Med. 2002, 346, 683-693.
3. Ryan, Q.; Ibrahim, A.; Cohen, M. H.; Johnson, J.; Ko, C. W.; Sridhara, R.; Justice, R.; Pazdur, R.FDAdrug approval summary: lapatinib in combination with capecitabine for previously treated metastatic breast cancer that overexpresses HER-2. Oncologist 2008, 13, 1114-1119.
4. Goodman, V. L.; Rock, E. P.; Dagher, R.; Ramchandani, R. P.; Abraham, S.; Gobburu, J. V.; Booth, B. P.; Verbois, S. L.; Morse, D. E.; Liang, C. Y.; Chidambaram, N.; Jiang, J. X.; Tang, S.; Mahjoob, K.; Justice, R.; Pazdur, R. Approval summary: sunitinib for the treatment of imatinib refractory or intolerant gastrointestinal stromal tumors and advanced renal cell carcinoma. Clin. Cancer Res. 2007, 13, 1367-1373.
5. Wilhelm, S.; Carter, C.; Lynch, M.; Lowinger, T.; Dumas, J.; Smith, R. A.; Schwartz, B.; Simantov, R.; Kelley, S. Discovery and development of sorafenib: a multikinase inhibitor for treating cancer. Nat. Rev. Drug Discovery 2006, 5, 835-844.
6. Birchmeier, C.; Birchmeier, W.; Gherardi, E.; Vande Woude, G. F. Met, metastasis, motility and more. Nat. Rev. Mol. Cell Biol. 2003, 4, 915-925.
7. Ma, P. C.; Maulik, G.; Christensen, J.; Salgia, R. c-Met: structure, functions and potential for therapeutic inhibition. Cancer Metastasis Rev 2003, 22, 309-325.
8. Birchmeier, C.; Gherardi, E. Developmental roles of HGF/SF and its receptor, the c-Met tyrosine kinase. Trends Cell Biol 1998, 8, 404-410.
9. Rosario, M.; Birchmeier, W. How to make tubes: signaling by the Met receptor tyrosine kinase. Trends Cell Biol 2003, 13, 328-335.
10. Dietrich, S.; Uppalapati, R.; Seiwert, T. Y.; Ma, P. C. Role of c-MET in upper aerodigestive malignancies - from biology to novel therapies. J. Environ. Pathol., Toxicol. Oncol. 2005, 24, 149-162.
11. Sattler, M.; Pride, Y. B.; Ma, P.; Gramlich, J. L.; Chu, S. C.; Quinnan, L. A.; Shirazian, S.; Liang, C.; Podar, K.; Christensen, J. G.; Salgia, R. A novel small molecule met inhibitor induces apoptosis in cells transformed by the oncogenic TPR-MET tyrosine kinase. Cancer Res. 2003, 63, 5462-5469.
12. Corso, S.; Comoglio, P. M.; Giordano, S. Cancer therapy: can the challenge be MET? Trends Mol. Med. 2005, 11, 284-292.
13. Eder, J. P.; Vande Woude, G. F.; Boerner, S. A.; LoRusso, P. M. Novel therapeutic inhibitors of the c-Met signaling pathway in cancer. Clin. Cancer Res. 2009, 15, 2207-2214.
14. Knudsen, B. S.; Vande Woude, G. Showering c-MET-dependent cancers with drugs. Curr. Opin. Genet. Dev. 2008, 18, 87-96.
15. Ma, P. C.; Tretiakova, M. S.; Nallasura, V.; Jagadeeswaran, R.; Husain, A. N.; Salgia, R. Downstream signalling and specific inhibition of c-MET/HGF pathway in small cell lung cancer: implications for tumour invasion. Br. J. Cancer 2007, 97, 368-377.
16. Ma, P. C.; Jagadeeswaran, R.; Jagadeesh, S.; Tretiakova, M. S.; Nallasura, V.; Fox, E. A.; Hansen, M.; Schaefer, E.; Naoki, K.; Lader, A.; Richards, W.; Sugarbaker, D.; Husain, A. N.; Christensen, J. G.; Salgia, R. Functional expression and mutations of c-Met and its therapeutic inhibition with SU11274 and small interfering RNA in non-small cell lung cancer. Cancer Res. 2005, 65, 1479-1488.
17. Ma, P. C.; Schaefer, E.; Christensen, J. G.; Salgia, R. A selective small molecule c-MET inhibitor, PHA665752, cooperates with rapamycin. Clin. Cancer Res. 2005, 11, 2312-2319.
18. Shaharabany, M.; Abramovitch, R.; Kushnir, T.; Tsarfaty, G.; Ravid-Megido, M.; Horev, J.; Ron, R.; Itzchak, Y.; Tsarfaty, I. In vivo molecular imaging of met tyrosine kinase growth factor receptor activity in normal organs and breast tumors. Cancer Res. 2001, 61, 4873-4878.
19. Tsarfaty, G.; Stein, G. Y.; Moshitch-Moshkovitz, S.; Kaufman, D. W.; Cao, B.; Resau, J. H.; Vande Woude, G. F.; Tsarfaty, I. HGF/SF increases tumor blood volume: a novel tool for the in vivo functional molecular imaging of Met. Neoplasia 2006, 8, 344-352.
20. Towner, R. A.; Smith, N.; Tesiram, Y. A.; Abbott, A.; Saunders, D.; Blindauer, R.; Herlea, O.; Silasi-Mansat, R.; Lupu, F. In vivo detection of c-MET expression in a rat hepatocarcinogenesis model using molecularly targeted magnetic resonance imaging. Mol. Imaging 2007, 6, 18-29.
21. 89Zr-labelled monoclonal antibody DN30. Eur. J. Nucl. Med. Mol. Imaging 2008, 35, 1857-1867.
22. Hay, R. V.; Cao, B.; Skinner, R. S.; Su, Y.; Zhao, P.; Gustafson, M. F.; Qian, C. N.; Teh, B. T.; Knudsen, B. S.; Resau, J. H.; Shen, S.; Waters, D. J.; Gross, M. D.; Vande Woude, G. F. Nuclear imaging of Met-expressing human and canine cancer xenografts with radiolabeled monoclonal antibodies (MetSeek). Clin. Cancer Res. 2005, 11, 7064s-7069s.
23. Schroeder, G. M.; An, Y.; Cai, Z. W.; Chen, X. T.; Clark, C.; Cornelius, L. A.; Dai, J.; Gullo-Brown, J.; Gupta, A.; Henley, B.; Hunt, J. T.; Jeyaseelan, R.; Kamath, A.; Kim, K.; Lippy, J.; Lombardo, L. J.; Manne, V.; Oppenheimer, S.; Sack, J. S.; Schmidt, R. J.; Shen, G.; Stefanski, K.; Tokarski, J. S.; Trainor, G. L.; Wautlet, B. S.; Wei, D.; Williams, D. K.; Zhang, Y.; Fargnoli, J.; Borzilleri,R.M.Discovery of N-(4-(2-amino-3-chloropyridin-4-yloxy)-3- fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3- carboxamide (BMS-777607), a selective and orally efficacious inhibitor of the Met kinase superfamily. J. Med. Chem. 2009, 52, 1251-1254.
24. Zhang, Y.; Kaplan-Lefko, P. J.; Rex, K.; Yang, Y.; Moriguchi, J.; Osgood, T.; Mattson, B.; Coxon, A.; Reese, M.; Kim, T. S.; Lin, J.; Chen, A.; Burgess, T. L.; Dussault, I. Identification of a novel recepteur d'origine nantais/c-met small-molecule kinase inhibitor with antitumor activity in vivo. Cancer Res. 2008, 68, 6680-6687.
25. Liu, L.; Siegmund, A.; Xi, N.; Kaplan-Lefko, P.; Rex, K.; Chen, A.; Lin, J.; Moriguchi, J.; Berry, L.; Huang, L.; Teffera, Y.; Yang, Y.; Zhang, Y.; Bellon, S. F.; Lee, M.; Shimanovich, R.; Bak, A.; Dominguez, C.; Norman, M. H.; Harmange, J. C.; Dussault, I.; Kim, T. S. Discovery of a potent, selective, and orally bioavailable c-Met inhibitor: 1-(2-hydroxy-2-methylpropyl)-N-(5- (7-methoxyquinolin-4-yloxy)pyridin-2-yl)-5-methyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazole-4-carboxamide (AMG 458). J. Med. Chem. 2008, 51, 3688-3691.
26. Yang, Y.; Wislez, M.; Fujimoto, N.; Prudkin, L.; Izzo, J. G.; Uno, F.; Ji, L.; Hanna, A. E.; Langley, R. R.; Liu, D.; Johnson, F. M.; Wistuba, I.; Kurie, J. M. A selective small molecule inhibitor of c-Met, PHA-665752, reverses lung premalignancy induced by mutant K-ras. Mol. Cancer Ther. 2008, 7, 952-960.
27. Chattopadhyay, C.; El-Naggar, A. K.; Williams, M. D.; Clayman, G. L. Small molecule c-MET inhibitor PHA665752: effect on cell growth and motility in papillary thyroid carcinoma. Head Neck 2008, 30, 991-1000.
28. Tseng, J. R.; Kang, K. W.; Dandekar, M.; Yaghoubi, S.; Lee, J. H.; Christensen, J. G.; Muir, S.; Vincent, P. W.; Michaud, N. R.; Gambhir, S. S. Preclinical efficacy of the c-Met inhibitor CE-355621 in a U87 MG mouse xenograft model evaluated by 18F-FDG small-animal PET. J. Nucl. Med. 2008, 49, 129-134.
29. Koon, E. C.; Ma, P. C.; Salgia, R.; Welch, W. R.; Christensen, J. G.; Berkowitz, R. S.; Mok, S. C. Effect of a c-Met-specific, ATP-competitive small-molecule inhibitor SU11274 on human ovarian carcinoma cell growth, motility, and invasion. Int. J. Gynecol. Cancer 2008, 18, 976-984.
30. Zou, H. Y.; Li, Q.; Lee, J. H.; Arango, M. E.; McDonnell, S. R.; Yamazaki, S.; Koudriakova, T. B.; Alton, G.; Cui, J. J.; Kung, P. P.; Nambu, M. D.; Los, G.; Bender, S. L.; Mroczkowski, B.; Christensen, J. G. An orally available small-molecule inhibitor of c-Met, PF-2341066, exhibits cytoreductive antitumor efficacy through antiproliferative and antiangiogenic mechanisms. Cancer Res. 2007, 67, 4408-4417.
31. Puri, N.; Khramtsov, A.; Ahmed, S.; Nallasura, V.; Hetzel, J. T.; Jagadeeswaran, R.; Karczmar, G.; Salgia, R. A selective small molecule inhibitor of c-Met, PHA665752, inhibits tumorigenicity and angiogenesis in mouse lung cancer xenografts. Cancer Res. 2007, 67, 3529-3534.
32. Smolen, G. A.; Sordella, R.; Muir, B.; Mohapatra, G.; Barmettler, A.; Archibald, H.; Kim, W. J.; Okimoto, R. A.; Bell, D. W.; Sgroi, D. C.; Christensen, J. G.; Settleman, J.; Haber, D. A. Amplification of MET may identify a subset of cancers with extreme sensitivity to the selective tyrosine kinase inhibitor PHA-665752. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 2316-2321.
33. Wang, S. Y.; Chen, B.; Zhan, Y. Q.; Xu, W. X.; Li, C. Y.; Yang, R. F.; Zheng, H.; Yue, P. B.; Larsen, S. H.; Sun, H. B.; Yang, X. SU5416 is a potent inhibitor of hepatocyte growth factor receptor (c-Met) and blocks HGF-induced invasiveness of human HepG2 hepatoma cells. J. Hepatol. 2004, 41, 267-273.
34. Christensen, J. G.; Schreck, R.; Burrows, J.; Kuruganti, P.; Chan, E.; Le, P.; Chen, J.; Wang, X.; Ruslim, L.; Blake, R.; Lipson, K. E.; Ramphal, J.; Do, S.; Cui, J. J.; Cherrington, J. M.; Mendel, D. B.A selective small molecule inhibitor of c-Met kinase inhibits c-Metdependent phenotypes in vitro and exhibits cytoreductive antitumor activity in vivo. Cancer Res. 2003, 63, 7345-7355.
35. Christensen, J. G.; Burrows, J.; Salgia, R. c-Met as a target for human cancer and characterization of inhibitors for therapeutic intervention. Cancer Lett. 2005, 225, 1-26.
36. Kopka, K.; Faust, A.; Keul, P.; Wagner, S.; Breyholz, H. J.; Holtke, C.; Schober, O.; Schafers, M.; Levkau, B. 5-Pyrrolidinylsulfonyl isatins as a potential tool for the molecular imaging of caspases in apoptosis. J. Med. Chem. 2006, 49, 6704-6715.
37. Li, H. H.; Zheng, X. H.; Tan, J. Z.; Chen, L. L.; Liu, H.; Luo, X. M.; Shen, X.; Lin, L. P.; Chen, K. X.; Ding, J.; Jiang, H. L. Design, synthesis, antitumor evaluations and molecular modeling studies of novel 3,5-substituted indolin-2-one derivatives. Acta Pharmacol. Sin. 2007, 28, 140-152.
38. Sun, L.; Liang, C.; Shirazian, S.; Zhou, Y.; Miller, T.; Cui, J.; Fukuda, J. Y.; Chu, J. Y.; Nematalla, A.; Wang, X.; Chen, H.; Sistla, A.; Luu, T. C.; Tang, F.; Wei, J.; Tang, C. Discovery of 5-[5-fluoro-2-oxo-1,2- dihydroindol-(3Z)-ylidenemethyl]-2,4- dimethyl-1H-pyrrole-3- carboxylic acid (2-diethylaminoethyl)amide, a novel tyrosine kinase inhibitor targeting vascular endothelial and platelet-derived growth factor receptor tyrosine kinase. J. Med. Chem. 2003, 46, 1116-1119.
39. Bell, I. M.; Stirdivant, S. M.; Ahern, J.; Culberson, J. C.; Darke, P. L.; Dinsmore, C. J.; Drakas, R. A.; Gallicchio, S. N.; Graham, S. L.; Heimbrook, D. C.; Hall, D. L.; Hua, J.; Kett, N. R.; Kim, A. S.; Kornienko, M.; Kuo, L. C.; Munshi, S. K.; Quigley, A. G.; Reid, J. C.; Trotter, B. W.; Waxman, L. H.; Williams, T. M.; Zartman, C. B. Biochemical and structural characterization of a novel class of inhibitors of the type 1 insulin-like growth factor and insulin receptor kinases. Biochemistry 2005, 44, 9430-9440.
40. Manley, J. M.; Kalman, M. J.; Conway, B. G.; Ball, C. C.; Havens, J. L.; Vaidyanathan, R. Early amidation approach to 3-[(4-amido)pyrrol-2-yl]-2- indolinones. J. Org. Chem. 2003, 68, 6447-6450.
41. Sun, L.; Cui, J.; Liang, C.; Zhou, Y.; Nematalla, A.; Wang, X.; Chen, H.; Tang, C.; Wei, J. Rational design of 4,5-disubstituted-5,7-dihydro-pyrrolo[2,3- d]pyrimidin-6-ones as a novel class of inhibitors of epidermal growth factor receptor (EGF-R) and Her2-(p185(erbB)) tyrosine kinases. Bioorg. Med. Chem. Lett. 2002, 12, 2153-2157.
42. Tang, Z.; Du, R.; Jiang, S.; Wu, C.; Barkauskas, D. S.; Richey, J.; Molter, J.; Lam, M.; Flask, C.; Gerson, S.; Dowlati, A.; Liu, L.; Lee, Z.; Halmos, B.; Wang, Y.; Kern, J. A.; Ma, P. C. Dual MET-EGFR combinatorial inhibition against T790M-EGFR-mediated erlotinib-resistant lung cancer. Br. J. Cancer 2008, 99, 911-922.
43. 11C-methyl-L-methionine. Int. J. Appl. Radiat. Isot. 1976, 27, 357-363.
44. Ma, P. C.; Tretiakova, M. S.; MacKinnon, A. C.; Ramnath, N.; Johnson, C.; Dietrich, S.; Seiwert, T.; Christensen, J. G.; Jagadeeswaran, R.; Krausz, T.; Vokes, E. E.; Husain, A. N.; Salgia, R. Expression and mutational analysis of MET in human solid cancers. Genes, Chromosomes Cancer 2008, 47, 1025-1037.