Covalent targeting of acquired cysteines in cancer

Current Opinion in Chemical Biology

Volumn 30, Issue , 2016, Pages 61-67

  Visscher, Marieke ^a   Arkin, Michelle R ^b   Dansen, Tobias B ^a  

^a UNIVERSITY MEDICAL CENTER UTRECHT   (Netherlands)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABIRATERONE ACETATE; AMINO ACID; ANTINEOPLASTIC AGENT; BETA CATENIN; BORTEZOMIB; CYSTEINE; DNA METHYLTRANSFERASE 3A; FIBROBLAST GROWTH FACTOR RECEPTOR 3; IMBRUTINIB; ISOCITRATE DEHYDROGENASE 1; K RAS PROTEIN; MUTANT PROTEIN; OSIMERTINIB; PHOSPHOTRANSFERASE INHIBITOR; PROTEIN; PROTEIN FBXW7; PROTEIN P53; ROCILETINIB; SML 8731; STIMULATORY GUANINE NUCLEOTIDE BINDING PROTEIN; UNCLASSIFIED DRUG; KRAS PROTEIN, HUMAN; PROTEIN P21;

BINDING SITE; CANCER CELL; CANCER CELL LINE; CARCINOGENESIS; COVALENT BOND; DRUG BINDING SITE; DRUG TARGETING; ENZYME ACTIVE SITE; HUMAN; MISSENSE MUTATION; NEOPLASM; NONHUMAN; ONCOGENE; OXIDATION REDUCTION REACTION; PERSONALIZED MEDICINE; PROTEIN STRUCTURE; REVIEW; SIGNAL TRANSDUCTION; SOMATIC MUTATION; ANTAGONISTS AND INHIBITORS; CHEMISTRY; GENETICS; METABOLISM; MOLECULARLY TARGETED THERAPY; MUTATION; NEOPLASMS; PROCEDURES;

CYSTEINE; HUMANS; MOLECULAR TARGETED THERAPY; MUTATION; NEOPLASMS; PRECISION MEDICINE; PROTO-ONCOGENE PROTEINS P21(RAS);

EID: 84949008215     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2015.11.004     Document Type: Review

References (33)

1. DeSantis C.E., Lin C.C., Mariotto A.B., Siegel R.L., Stein K.D., Kramer J.L., Alteri R., Robbins A.S., Jemal A. Cancer treatment and survivorship statistics, 2014. CA Cancer J Clin 2014, 64:252-271.
2. Rimawi M.F., Schiff R., Osborne C.K. Targeting HER2 for the treatment of breast cancer. Annu Rev Med 2015, 66:111-128.
3. Mulcahy N: Top 10 best-selling cancer drugs globally, June 2014. Medscape.
4. Bollag G., Tsai J., Zhang J., Zhang C., Ibrahim P., Nolop K., Hirth P. Vemurafenib: the first drug approved for BRAF-mutant cancer. Nat Rev Drug Discov 2012, 11:873-886.
5. Bauer R.A. Covalent inhibitors in drug discovery: from accidental discoveries to avoided liabilities and designed therapies. Drug Discov Today 2015, 20:1061-1073.
6. Liu Q., Sabnis Y., Zhao Z., Zhang T., Buhrlage S.J., Jones L.H., Gray N.S. Developing irreversible inhibitors of the protein kinase cysteinome. Chem Biol 2013, 20:146-159.
7. Singh J., Petter R.C., Baillie T.A., Whitty A. The resurgence of covalent drugs. Nat Rev Drug Discov 2011, 10:307-317.
8. Tucker D.L., Rule S.A. A critical appraisal of ibrutinib in the treatment of mantle cell lymphoma and chronic lymphocytic leukemia. Ther Clin Risk Manag 2015, 11:979-990.
9. Finlay M.R., Anderton M., Ashton S., Ballard P., Bethel P.A., Box M.R., Bradbury R.H., Brown S.J., Butterworth S., Campbell A., et al. Discovery of a potent and selective EGFR inhibitor (AZD9291) of both sensitizing and T790M resistance mutations that spares the wild type form of the receptor. J Med Chem 2014, 57:8249-8267.
10. Walter A.O., Sjin R.T., Haringsma H.J., Ohashi K., Sun J., Lee K., Dubrovskiy A., Labenski M., Zhu Z., Wang Z., et al. Discovery of a mutant-selective covalent inhibitor of EGFR that overcomes T790M-mediated resistance in NSCLC. Cancer Discov 2013, 3:1404-1415.
11. Zhou W., Ercan D., Chen L., Yun C.H., Li D., Capelletti M., Cortot A.B., Chirieac L., Iacob R.E., Padera R., et al. Novel mutant-selective EGFR kinase inhibitors against EGFR T790M. Nature 2009, 462:1070-1074.
12. Bradshaw J.M., McFarland J.M., Paavilainen V.O., Bisconte A., Tam D., Phan V.T., Romanov S., Finkle D., Shu J., Patel V., et al. Prolonged and tunable residence time using reversible covalent kinase inhibitors. Nat Chem Biol 2015, 11:525-531.
13. Tan L., Wang J., Tanizaki J., Huang Z., Aref A.R., Rusan M., Zhu S.J., Zhang Y., Ercan D., Liao R.G., et al. Development of covalent inhibitors that can overcome resistance to first-generation FGFR kinase inhibitors. Proc Natl Acad Sci USA 2014, 111:E4869-E4877.
14. Kwiatkowski N., Zhang T., Rahl P.B., Abraham B.J., Reddy J., Ficarro S.B., Dastur A., Amzallag A., Ramaswamy S., Tesar B., et al. Targeting transcription regulation in cancer with a covalent CDK7 inhibitor. Nature 2014, 511:616-620.
15. Johansson M.H. Reversible Michael additions: covalent inhibitors and prodrugs. Mini Rev Med Chem 2012, 12:1330-1344.
16. Forbes S.A., Beare D., Gunasekaran P., Leung K., Bindal N., Boutselakis H., Ding M., Bamford S., Cole C., Ward S., et al. COSMIC: exploring the world's knowledge of somatic mutations in human cancer. Nucleic Acids Res 2015, 43:D805-D811.
17. Tekaia F., Yeramian E., Dujon B. Amino acid composition of genomes, lifestyles of organisms, and evolutionary trends: a global picture with correspondence analysis. Gene 2002, 297:51-60.
18. Flanagan M.E., Abramite J.A., Anderson D.P., Aulabaugh A., Dahal U.P., Gilbert A.M., Li C., Montgomery J., Oppenheimer S.R., Ryder T., et al. Chemical and computational methods for the characterization of covalent reactive groups for the prospective design of irreversible inhibitors. J Med Chem 2014, 57:10072-10079.
19. Kozakov D., Grove L.E., Hall D.R., Bohnuud T., Mottarella S.E., Luo L., Xia B., Beglov D., Vajda S. The FTMap family of web servers for determining and characterizing ligand-binding hot spots of proteins. Nat Protoc 2015, 10:733-755.
20. Kathman S.G., Xu Z., Statsyuk A.V. A fragment-based method to discover irreversible covalent inhibitors of cysteine proteases. J Med Chem 2014, 57:4969-4974.
21. Miller R.M., Paavilainen V.O., Krishnan S., Serafimova I.M., Taunton J. Electrophilic fragment-based design of reversible covalent kinase inhibitors. J Am Chem Soc 2013, 135:5298-5301.
22. Ostrem J.M., Peters U., Sos M.L., Wells J.A., Shokat K.M. K-Ras(G12C) inhibitors allosterically control GTP affinity and effector interactions. Nature 2013, 503:548-551.
23. Wilson C.G., Arkin M.R. Probing structural adaptivity at PPI interfaces with small molecules. Drug Discov Today Technol 2013, 10:e501-e508.
24. Erlanson D.A., Braisted A.C., Raphael D.R., Randal M., Stroud R.M., Gordon E.M., Wells J.A. Site-directed ligand discovery. Proc Natl Acad Sci USA 2000, 97:9367-9372.
25. Krishnan S., Miller R.M., Tian B., Mullins R.D., Jacobson M.P., Taunton J. Design of reversible, cysteine-targeted Michael acceptors guided by kinetic and computational analysis. J Am Chem Soc 2014, 136:12624-12630.
26. Holmstrom K.M., Finkel T. Cellular mechanisms and physiological consequences of redox-dependent signalling. Nat Rev Mol Cell Biol 2014, 15:411-421.
27. Nagy P., Karton A., Betz A., Peskin A.V., Pace P., O'Reilly R.J., Hampton M.B., Radom L., Winterbourn C.C. Model for the exceptional reactivity of peroxiredoxins 2 and 3 with hydrogen peroxide: a kinetic and computational study. J Biol Chem 2011, 286:18048-18055.
28. Weerapana E., Wang C., Simon G.M., Richter F., Khare S., Dillon M.B., Bachovchin D.A., Mowen K., Baker D., Cravatt B.F. Quantitative reactivity profiling predicts functional cysteines in proteomes. Nature 2010, 468:790-795.
29. Sullivan L.B., Chandel N.S. Mitochondrial reactive oxygen species and cancer. Cancer Metab 2014, 2:17.
30. Paulsen C.E., Truong T.H., Garcia F.J., Homann A., Gupta V., Leonard S.E., Carroll K.S. Peroxide-dependent sulfenylation of the EGFR catalytic site enhances kinase activity. Nat Chem Biol 2012, 8:57-64.
31. Furdui C.M., Poole L.B. Chemical approaches to detect and analyze protein sulfenic acids. Mass Spectrom Rev 2014, 33:126-146.
32. Lim S.M., Westover K.D., Ficarro S.B., Harrison R.A., Choi H.G., Pacold M.E., Carrasco M., Hunter J., Kim N.D., Xie T., et al. Therapeutic targeting of oncogenic K-Ras by a covalent catalytic site inhibitor. Angew Chem Int Ed Engl 2014, 53:199-204.
33. Rudolph J., Stokoe D. Selective inhibition of mutant Ras protein through covalent binding. Angew Chem Int Ed Engl 2014, 53:3777-3779.