Bioorthogonal small molecule imaging agents allow single-cell imaging of MET

PLoS ONE

Volumn 8, Issue 11, 2013, Pages

  Kim, Eunha ^a   Yang, Katherine S ^a   Weissleder, Ralph ^a,b  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 [3 (QUINOLIN 6 YLMETHYL) 3H [1,2,3]TRIAZOLO[4,5 B]PYRAZIN 5 YL] 1H PYRAZOL 1 YL]ETHANOL; BODIPY; FLUOROCHROME; FORETINIB; GSK 13630898; PF 04217903; PROTEIN TYROSINE KINASE INHIBITOR; SCATTER FACTOR RECEPTOR; TRANSCYCLOOCTENE; UNCLASSIFIED DRUG;

ARTICLE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; FLUORESCENCE MICROSCOPY;

BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; INTRACELLULAR SPACE; MICROSCOPY, FLUORESCENCE; MODELS, MOLECULAR; MOLECULAR IMAGING; MOLECULAR STRUCTURE; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTO-ONCOGENE PROTEINS C-MET; SINGLE-CELL ANALYSIS; SMALL MOLECULE LIBRARIES; TIME FACTORS;

EID: 84893017777     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0081275     Document Type: Article

References (33)

1. Overington JP, Al-Lazikani B, Hopkins AL (2006) How many drug targets are there? Nat Rev Drug Discov 5: 993-996. doi:10.1038/nrd2199. PubMed: 17139284. (Pubitemid 44835126)
2. Hopkins AL (2008) Network pharmacology: the next paradigm in drug discovery. Nat Chem Biol 4: 682-690. doi:10.1038/nchembio.118. PubMed: 18936753.
3. Fabian MA, Biggs WH, Treiber DK, Atteridge CE, Azimioara MD et al. (2005) A small molecule-kinase interaction map for clinical kinase inhibitors. Nat Biotechnol 23: 329-336. doi:10.1038/nbt1068. PubMed: 15711537. (Pubitemid 41094421)
4. Frantz S (2005) Drug discovery: playing dirty. Nature 437: 942-943. doi:10.1038/437942a. PubMed: 16222266.
5. Jalencas X, Mestres J (2013) On the origins of drug polypharmacology. MedChemComm 4: 80-87
6. Apsel B, Blair JA, Gonzalez B, Nazif TM, Feldman ME et al. (2008) Targeted polypharmacology: discovery of dual inhibitors of tyrosine and phosphoinositide kinases. Nat Chem Biol 4: 691-699. doi:10.1038/nchembio.117. PubMed: 18849971.
7. Lemmon MA, Schlessinger J (2010) Cell signaling by receptor tyrosine kinases. Cell.
8. Laird AD, Cherrington JM (2003) Small molecule tyrosine kinase inhibitors: clinical development of anticancer agents. Expert Opin Investig Drugs 12: 51-64. doi:10.1517/13543784.12.1.51. PubMed: 12517254. (Pubitemid 36104643)
9. Trusolino L, Bertotti A, Comoglio PM (2010) MET signalling: principles and functions in development, organ regeneration and cancer. Nat Rev Mol Cell Biol 11: 834-848. doi:10.1038/nrm3012. PubMed: 21102609.
10. Comoglio PM, Giordano S, Trusolino L (2008) Drug development of MET inhibitors: targeting oncogene addiction and expedience. Nat Rev Drug Discov 7: 504-516. doi:10.1038/nrd2530. PubMed: 18511928. (Pubitemid 351767118)
11. Ghoussoub RA, Dillon DA, D'Aquila T, Rimm EB, Fearon ER et al. (1998) Expression of c-met is a strong independent prognostic factor in breast carcinoma. Cancer 82: 1513-1520. doi:10.1002/(SICI)1097-0142(19980415)82:8. PubMed: 9554529. (Pubitemid 28164998)
12. Di Renzo MF, Olivero M, Giacomini A, Porte H, Chastre E et al. (1995) Overexpression and amplification of the met/HGF receptor gene during the progression of colorectal cancer. Clin Cancer Res 1: 147-154. PubMed: 9815967.
13. Kammula US, Kuntz EJ, Francone TD, Zeng Z, Shia J et al. (2007) Molecular co-expression of the c-Met oncogene and hepatocyte growth factor in primary colon cancer predicts tumor stage and clinical outcome. Cancer Lett 248: 219-228. doi:10.1016/j.canlet.2006.07.007. PubMed: 16945480. (Pubitemid 46330555)
14. Ponzo MG, Lesurf R, Petkiewicz S, O'Malley FP, Pinnaduwage D et al. (2009) Met induces mammary tumors with diverse histologies and is associated with poor outcome and human basal breast cancer. Proc Natl Acad Sci U S A 106: 12903-12908. doi:10.1073/pnas.0810402106. PubMed: 19617568.
15. Underiner TL, Herbertz T, Miknyoczki SJ (2010) Discovery of small molecule c-Met inhibitors: Evolution and profiles of clinical candidates. Anticancer Agents Med Chem 10: 7-27. doi:10.2174/1871520611009010007. PubMed: 20015007.
16. Kim EM, Park EH, Cheong SJ, Lee CM, Jeong HJ et al. (2009) In vivo imaging of mesenchymal-epithelial transition factor (c-Met) expression using an optical imaging system. Bioconjug Chem 20: 1299-1306. doi:10.1021/bc8005539. PubMed: 19534520.
17. Zou HY, Li Q, Lee JH, Arango ME, Burgess K et al. (2012) Sensitivity of selected human tumor models to PF-04217903, a novel selective c-Met kinase inhibitor. Mol Cancer Ther 11: 1036-1047. doi:10.1158/1535-7163.MCT-11-0839. PubMed: 22389468.
18. Qian F, Engst S, Yamaguchi K, Yu P, Won KA et al. (2009) Inhibition of tumor cell growth, invasion, and metastasis by EXEL-2880 (XL880, GSK1363089), a novel inhibitor of HGF and VEGF receptor tyrosine kinases. Cancer Res 69: 8009-8016. doi:10.1158/0008-5472.CAN-08-4889. PubMed: 19808973.
19. Yang KS, Budin G, Reiner T, Vinegoni C, Weissleder R (2012) Bioorthogonal imaging of aurora kinase A in live cells. Angewandte Chemie (International ed. in English) 51: 6598-6603
20. Devaraj NK, Upadhyay R, Haun JB, Hilderbrand SA, Weissleder R (2009) Fast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition. Angew Chem Int Ed Engl 48:7013-7016. doi:10.1002/anie.200903233. PubMed: 19697389.
21. Karlan BY, Amin W, Band V, Zurawski... (1988) Plasminogen activator secretion by established lines of human ovarian carcinoma cells〈i〉 in vitro〈/i〉. Gynecologic ....
22. Behrens BC, Hamilton TC, Masuda H, Grotzinger, (1987) Characterization of a cis-diamminedichloroplatinum (II)-resistant human ovarian cancer cell line and its use in evaluation of platinum analogues. Cancer Research.
23. Tiedt R, Degenkolbe E, Furet P, Appleton BA, Wagner S et al. (2011) A drug resistance screen using a selective MET inhibitor reveals a spectrum of mutations that partially overlap with activating mutations found in cancer patients. Cancer Res 71: 5255-5264. doi:10.1158/0008-5472.CAN-10-4433. PubMed: 21697284.
24. Lui VW, Wong EY, Ho K, Ng PK, Lau CP et al. (2011) Inhibition of c-Met downregulates TIGAR expression and reduces NADPH production leading to cell death. Oncogene 30: 1127-1134. doi:10.1038/onc.2010.490. PubMed: 21057531.
25. Ding S, Merkulova-Rainon T, Han ZC, Tobelem G (2003) HGF receptor up-regulation contributes to the angiogenic phenotype of human endothelial cells and promotes angiogenesis in vitro. Blood 101: 4816-4822. doi:10.1182/blood- 2002-06-1731. PubMed: 12595309. (Pubitemid 36857740)
26. Tam NN, Chung SS, Lee DT, Wong YC (2000) Aberrant expression of hepatocyte growth factor and its receptor, c-Met, during sex hormone-induced prostatic carcinogenesis in the Noble rat. Carcinogenesis 21: 2183-2191. doi:10.1093/carcin/21.12.2183. PubMed: 11133807. (Pubitemid 32049224)
27. Ichimura E, Maeshima A, Nakajima T, Nakamura T (1996) Expression of c-met/HGF receptor in human non-small cell lung carcinomas in vitro and in vivo and its prognostic significance. Jpn J Cancer Res 87: 1063-1069. doi:10.1111/j.1349-7006.1996.tb03111.x. PubMed: 8957065. (Pubitemid 26392044)
28. Liu HS, Hsu PY, Lai MD, Chang HY, Ho CL et al. (2010) An unusual function of RON receptor tyrosine kinase as a transcriptional regulator in cooperation with EGFR in human cancer cells. Carcinogenesis 31: 1456-1464. doi:10.1093/carcin/bgq100. PubMed: 20498137.
29. Davis MI, Hunt JP, Herrgard S, Ciceri P, Wodicka LM et al. (2011) Comprehensive analysis of kinase inhibitor selectivity. Nat Biotechnol 29: 1046-1051. doi:10.1038/nbt.1990. PubMed: 22037378.
30. Thurber GM, Yang KS, Reiner T, Kohler RH, Sorger P et al. (2013) Single-cell and subcellular pharmacokinetic imaging allows insight into drug action in vivo. Nat Commun 4: 1504. doi:10.1038/ncomms2506. PubMed: 23422672.
31. Lukinavičius G, Umezawa K, Olivier N, Honigmann A, Yang G et al. (2013) A near-infrared fluorophore for live-cell super-resolution microscopy of cellular proteins. Nat Chem 5: 132-139. doi:10.1038/nchem.1546. PubMed: 23344448.
32. Devaraj NK, Hilderbrand S, Upadhyay R, Mazitschek R, Weissleder R (2010) Bioorthogonal turn-on probes for imaging small molecules inside living cells. Angew Chem Int Ed Engl 49: 2869-2872. doi:10.1002/anie.200906120. PubMed: 20306505.
33. Hendricks JA, Keliher EJ, Wan D, Hilderbrand SA, Weissleder R et al. (2012) Synthesis of [18F] BODIPY: Bifunctional Reporter for Hybrid Optical/Positron Emission Tomography Imaging. Angewandte Chemie (International ed. in English) 51: 4603-4606