Targeted Covalent Enzyme Inhibitors

Annual Reports in Medicinal Chemistry

Volumn 47, Issue , 2012, Pages 413-439

  Noe, Mark C ^a   Gilbert, Adam M ^a  

^a PFIZER INC   (United States)

Author keywords

Irreversible covalent enzyme inhibitors; Kinase inhibitors; Protease inhibitors; Reversible covalent enzyme inhibitors; Targeted covalent enzyme inhibitors

Indexed keywords

EID: 84866772206     PISSN: 00657743     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-396492-2.00027-8     Document Type: Chapter

References (88)

1. Singh J., Petter R.C., Baillie T.A., Whitty A. Nat. Rev. Drug Discov. 2011, 10:307.
2. Robertson J.G. Biochemistry 2005, 44:5561.
3. Swinney D.C. Curr. Opin. Drug Discov. Devel. 2009, 12:31.
4. Wells J.A., McClendon C.L. Nature 2007, 450:1001.
5. Yun C.-H., Mengwasser K.E., Toms A.V., Woo M.S., Greulich H., Wong K.-K., Meyerson M., Eck M.J. Proc. Natl. Acad. Sci. U.S.A. 2008, 105:2070.
6. Bonanno L., Jirillo A., Favaretto A. Curr. Drug Targets 2011, 12:922.
7. Singh J., Petter R.C., Kluge A.F. Curr. Opin. Chem. Biol. 2010, 14:475.
8. Garuti L., Roberti M., Bottegoni G. Curr. Med. Chem. 2011, 18:2981.
9. Leproult E., Barluenga S., Moras D., Wurtz J.-M., Winssinger N. J. Med. Chem. 2011, 54:1347.
10. Smith A.J.T., Zhang X., Leach A.G., Houk K.N. J. Med. Chem. 2009, 52:225.
11. Kitz R., Wilson I.B. J. Biol. Chem. 1962, 237:3245.
12. Kluter S., Simard J.R., Rode H.B., Grutter C., Pawar V., Raaijmakers H.C.A., Barf T.A., Rabiller M., van Otterlo Willem A.L., Rauh D. Chembiochem 2010, 11:2557.
13. Krippendorff B.-F., Neuhaus R., Lienau P., Reichel A., Huisinga W. J. Biomol. Screen. 2009, 14:913.
14. Johnson D.S., Weerapana E., Cravatt B.F. Future Med. Chem. 2010, 2:949.
15. Naisbitt D.J., Gordon S.F., Pirmohamed M., Park B.K. Drug Saf. 2000, 23:483.
16. Stepan A.F., Walker D.P., Bauman J., Price D.A., Baillie T.A., Kalgutkar A.S., Aleo M.D. Chem. Res. Toxicol. 2011, 24:1345.
17. Hughes J.D., Blagg J., Price D.A., Bailey S., DeCrescenzo G.A., Devraj R.V., Ellsworth E., Fobian Y.M., Gibbs M.E., Gilles R.W., Greene N., Huang E., Krieger-Burke T., Loesel J., Wager T., Whiteley L., Zhang Y. Bioorg. Med. Chem. Lett. 2008, 18:4872.
18. Park B.K., Boobis A., Clarke S., Goldring C.E.P., Jones D., Kenna J.G., Lambert C., Laverty H.G., Naisbitt D.J., Nelson S., Nicoll-Griffith D.A., Obach R.S., Routledge P., Smith D.A., Tweedie D.J., Vermeulen N., Williams D.P., Wilson I.D., Baillie T.A. Nat. Rev. Drug Discov. 2011, 10:292.
19. Nakayama S., Atsumi R., Takakusa H., Kobayashi Y., Kurihara A., Nagai Y., Nakai D., Okazaki O. Drug Metab. Dispos. 2009, 37:1970.
20. Potashman M.H., Duggan M.E. J. Med. Chem. 2009, 52:1231.
21. Bachovchin D.A., Cravatt B.F. Nat. Rev. Drug Discov. 2012, 11:52.
22. Prongay A.J., Guo Z., Yao N., Pichardo J., Fischmann T., Strickland C., Myers J., Weber P.C., Beyer B.M., Ingram R., Hong Z., Prosise W.W., Ramanathan L., Taremi S.S., Yarosh-Tomaine T., Zhang R., Senior M., Yang R.-S., Malcolm B., Arasappan A., Bennett F., Bogen S.L., Chen K., Jao E., Liu Y.-T., Lovey R.G., Saksena A.K., Venkatraman S., Girijavallabhan V., Njoroge F.G., Madison V. J. Med. Chem. 2007, 50:2310.
23. Venkatraman S., Bogen S.L., Arasappan A., Bennett F., Chen K., Jao E., Liu Y.-T., Lovey R., Hendrata S., Huang Y., Pan W., Parekh T., Pinto P., Popov V., Pike R., Ruan S., Santhanam B., Vibulbhan B., Wu W., Yang W., Kong J., Liang X., Wong J., Liu R., Butkiewicz N., Chase R., Hart A., Agrawal S., Ingravallo P., Pichardo J., Kong R., Baroudy B., Malcolm B., Guo Z., Prongay A., Madison V., Broske L., Cui X., Cheng K.-C., Hsieh T.Y., Brisson J.-M., Prelusky D., Korfmacher W., White R., Bogdanowich-Knipp S., Pavlovsky A., Bradley P., Saksena A.K., Ganguly A., Piwinski J., Girijavallabhan V., Njoroge F.G. J. Med. Chem. 2006, 49:6074.
24. Lin C., Kwong A.D., Perni R.B. Infect. Disord. Drug Targets 2006, 6:3.
25. Perni R.B., Almquist S.J., Byrn R.A., Chandorkar G., Chaturvedi P.R., Courtney L.F., Decker C.J., Dinehart K., Gates C.A., Harbeson S.L., Heiser A., Kalkeri G., Kolaczkowski E., Lin K., Luong Y.-P., Rao B.G., Taylor W.P., Thomson J.A., Tung R.D., Wei Y., Kwong A.D., Lin C. Antimicrob. Agents Chemother. 2006, 50:899.
26. Malcolm B.A., Liu R., Lahser F., Agrawal S., Belanger B., Butkiewicz N., Chase R., Gheyas F., Hart A., Hesk D., Ingravallo P., Jiang C., Kong R., Lu J., Pichardo J., Prongay A., Skelton A., Tong X., Venkatraman S., Xia E., Girijavallabhan V., Njoroge F.G. Antimicrob. Agents Chemother. 2006, 50:1013.
27. Tong X., Arasappan A., Bennett F., Chase R., Feld B., Guo Z., Hart A., Madison V., Malcolm B., Pichardo J., Prongay A., Ralston R., Skelton A., Xia E., Zhang R., Njoroge F.G. Antimicrob. Agents Chemother. 2010, 54:2365.
28. Bennett F., Huang Y., Hendrata S., Lovey R., Bogen S.L., Pan W., Guo Z., Prongay A., Chen K.X., Arasappan A., Venkatraman S., Velazquez F., Nair L., Sannigrahi M., Tong X., Pichardo J., Cheng K.-C., Girijavallabhan V.M., Saksena A.K., Njoroge F.G. Bioorg. Med. Chem. Lett. 2010, 20:2617.
29. Garfunkle J., Ezzili C., Rayl T.J., Hochstatter D.G., Hwang I.B., Dale L. J. Med. Chem. 2008, 51:4392.
30. Romero F.A., Inkyu H., Boger D.L. J. Am. Chem. Soc. 2006, 128:14004.
31. Kimball F.S., Romero F.A., Ezzili C., Garfunkle J., Rayl T.J., Hochstatter D.G., Hwang I., Boger D.L. J. Med. Chem. 2008, 51:937.
32. Hardouin C., Kelso M.J., Romero F.A., Rayl T.J., Leung D., Hwang I., Cravatt B.F., Boger D.L. J. Med. Chem. 2007, 50:3359.
33. Romero F.A., Du W., Hwang I., Rayl T.J., Kimball F.S., Leung D., Hoover H.S., Apodaca R.L., Breitenbucher J.G., Cravatt B.F., Boger D.L. J. Med. Chem. 2007, 50:1058.
34. Boger D.L., Miyauchi H., Du W., Hardouin C., Fecik R.A., Cheng H., Hwang I., Hedrick M.P., Leung D., Acevedo O., Guimaraes C.R.W., Jorgensen W.L., Cravatt B.F. J. Med. Chem. 2005, 48:1849.
35. Lichtman A.H., Leung D., Shelton C.C., Saghatelian A., Hardouin C., Boger D.L., Cravatt B.F. J. Pharmacol. Exp. Ther. 2004, 311:441.
36. Chang L., Luo L., Palmer J.A., Sutton S., Wilson S.J., Barbier A.J., Breitenbucher J.G., Chaplan S.R., Webb M. Br. J. Pharmacol. 2006, 148:102.
37. Racys D.T., Rea D., Fueloep V., Wills M. Bioorg. Med. Chem. 2010, 18:4775.
38. Lawandi J., Toumieux S., Seyer V., Campbell P., Thielges S., Juillerat-Jeanneret L., Moitessier N. J. Med. Chem. 2009, 52:6672.
39. Mansour T.S., Bradford P.A., Venkatesan A.M. Annu. Rep. Med. Chem. 2008, 43:247.
40. Stachyra T., Pechereau M.-C., Bruneau J.-M., Claudon M., Frere J.-M., Miossec C., Coleman K., Black M.T. Antimicrob. Agents Chemother. 2010, 54:5132.
41. Eidam O., Romagnoli C., Caselli E., Babaoglu K., Pohlhaus D.T., Karpiak J., Bonnet R., Shoichet B.K., Prati F. J. Med. Chem. 2010, 53:7852.
42. Tan Q., Ogawa A.M., Painter R.E., Park Y.-W., Young K., DiNinno F.P. Bioorg. Med. Chem. Lett. 2010, 20:2622.
43. Bachovchin D.A., Wolfe M.R., Masuda K., Brown S.J., Spicer T.P., Fernandez-Vega V., Chase P., Hodder P.S., Rosen H., Cravatt B.F. Bioorg. Med. Chem. Lett. 2010, 20:2254.
44. Laine D.I., Busch-Petersen J. Expert Opin. Ther. Pat. 2010, 20:497.
45. Wiener J.J.M., Sun S., Thurmond R.L. Curr. Top. Med. Chem. 2010, 10:717.
46. Lluis M., Wang Y., Monzingo A.F., Fast W., Robertus J.D. ChemMedChem 2011, 6:81.
47. Powers J.P., Piper D.E., Li Y., Mayorga V., Anzola J., Chen J.M., Jaen J.C., Lee G., Liu J., Peterson M.G., Tonn G.R., Ye Q., Walker N.P.C., Wang Z. J. Med. Chem. 2006, 49:1034.
48. Tsou H.-R., Overbeek-Klumpers E.G., Hallett W.A., Reich M.F., Floyd M.B., Johnson B.D., Michalak R.S., Nilakantan R., Discafani C., Golas J., Rabindran S.K., Shen R., Shi X., Wang Y.-F., Upeslacis J., Wissner A. J. Med. Chem. 2005, 48:1107.
49. Wong K.-K., Fracasso P.M., Bukowski R.M., Lynch T.J., Munster P.N., Shapiro G.I., Jaenne P.A., Eder J.P., Naughton M.J., Ellis M.J., Jones S.F., Mekhail T., Zacharchuk C., Vermette J., Abbas R., Quinn S., Powell C., Burris H.A. Clin. Cancer Res. 2009, 15:2552.
50. Sequist L.V., Besse B., Lynch T.J., Miller V.A., Wong K.K., Gitlitz B., Eaton K., Zacharchuk C., Freyman A., Powell C., Ananthakrishnan R., Quinn S., Soria J.-C. J. Clin. Oncol. 2010, 28:3076.
51. Burstein H.J., Sun Y., Dirix L.Y., Jiang Z., Paridaens R., Tan A.R., Awada A., Ranade A., Jiao S., Schwartz G., Abbas R., Powell C., Turnbull K., Vermette J., Zacharchuk C., Badwe R. J. Clin. Oncol. 2010, 28:1301.
52. Li D., Ambrogio L., Shimamura T., Kubo S., Takahashi M., Chirieac L.R., Padera R.F., Shapiro G.I., Baum A., Himmelsbach F., Rettig W.J., Meyerson M., Solca F., Greulich H., Wong K.K. Oncogene 2008, 27:4702.
53. Subramaniam D.S., Hwang J. Expert Opin. Investig. Drugs 2011, 20:415.
54. Engelman J.A., Zejnullahu K., Gale C.-M., Lifshits E., Gonzales A.J., Shimamura T., Zhao F., Vincent P.W., Naumov G.N., Bradner J.E., Althaus I.W., Gandhi L., Shapiro G.I., Nelson J.M., Heymach J.V., Meyerson M., Wong K.-K., Jänne P.A. Cancer Res. 2007, 67:11924.
55. Gonzales A.J., Hook K.E., Althaus I.W., Ellis P.A., Trachet E., Delaney A.M., Harvey P.J., Ellis T.A., Amato D.M., Nelson J.M., Fry D.W., Zhu T., Loi C.-M., Fakhoury S.A., Schlosser K.M., Sexton K.E., Winters R.T., Reed J.E., Bridges A.J., Lettiere D.J., Baker D.A., Yang J., Lee H.T., Tecle H., Vincent P.W. Mol. Cancer Ther. 2008, 7:1880.
56. Janne P.A., Boss D.S., Camidge D.R., Britten C.D., Engelman J.A., Garon E.B., Guo F., Wong S., Liang J., Letrent S., Millham R., Taylor I., Eckhardt S.G., Schellens J.H.M. Clin. Cancer Res. 2011, 17:1131.
57. Wood E.R., Shewchuk L.M., Ellis B., Brignola P., Brashear R.L., Caferro T.R., Dickerson S.H., Dickson H.D., Donaldson K.H., Gaul M., Griffin R.J., Hassell A.M., Keith B., Mullin R., Petrov K.G., Reno M.J., Rusnak D.W., Tadepalli S.M., Ulrich J.C., Wagner C.D., Vanderwall D.E., Waterson A.G., Williams J.D., White W.L., Uehling D.E. Proc. Natl. Acad. Sci. U.S.A. 2008, 105:2773.
58. Petro J.B., Rahman S.M.J., Ballard D.W., Khan W.N. J. Exp. Med. 2000, 191:1745.
59. Heinonen J.E., Smith C.I.E., Nore B.F. FEBS Lett. 2002, 527:274.
60. Pan Z., Scheerens H., Li S.-J., Schultz B.E., Sprengeler P.A., Burrill L.C., Mendonca R.V., Sweeney M.D., Scott K.C.K., Grothaus P.G., Jeffery D.A., Spoerke J.M., Honigberg L.A., Young P.R., Dalrymple S.A., Palmer J.T. ChemMedChem 2007, 2:58.
61. Honigberg L.A., Smith A.M., Sirisawad M., Verner E., Loury D., Chang B., Li S., Pan Z., Thamm D.H., Miller R.A., Buggy J.J. Proc. Natl. Acad. Sci. U.S.A. 2010, 107:13075.
62. Herman S.E.M., Gordon A.L., Hertlein E., Ramanunni A., Zhang X., Jaglowski S., Flynn J., Jones J., Blum K.A., Buggy J.J., Hamdy A., Johnson A.J., Byrd J.C. Blood 2011, 117:6287.
63. MacGlashan D., Honigberg L.A., Smith A., Buggy J., Schroeder J.T. Int. Immunopharmacol. 2011, 11:475.
64. Honigberg, L.A.; Smith, A.M.; Chen, J.; Thiemann, P.; Verner, E. Poster Presented at the American Society for Hematology Annual Meeting, Atlanta, GA, 2007.
65. Advani, R.; Sharman, J.; Smith, S.; Pollyea, D.; Boyd, T.; Grant, B.; Kolibaba, K.; Buggy, J.; Hamdy, A.; Fowler, N. Oral Presentation at the American Society for Clinical Oncology Meeting, Chicago, Il, 2010.
66. Evans, E.; Tester, R.; Aslanian, S.; Mazdiyasni, H.; Ponader, S.; Tesar, B.; Chaturverdi, P.; Nacht, M.; Stiede, K.; Witowski, S.; Lounsbury, H.; Silver, B.; Burger, J.; Mahadevan, D.; Sharman, J.; Harb, W.; Petter, R.; Singh, J.; Westlin, W. Poster Presented at the ASH Annual Meeting, San Diego, CA, 2011.
67. Singh, J.; Petter, R.; Tester, R.; Kluge, A. F.; Mazdiyasni, H.; Westlin, W.; Niu, D.; Qiao, L. US Patent US 2010/0249092, 2010.
68. Witowski, S.; Westlin, W.; Tester, R. Patent Application WO 2012/021444A1, 2012.
69. Henise J.C., Taunton J. J. Med. Chem. 2011, 54:4133.
70. Zhou W., Hur W., McDermott U., Dutt A., Xian W., Ficarro S.B., Zhang J., Sharma S.V., Brugge J., Meyerson M., Settleman J., Gray N.S. Chem. Biol. 2010, 17:285.
71. Hagel M., Niu D., St Martin T., Sheets M.P., Qiao L., Bernard H., Karp R.M., Zhu Z., Labenski M.T., Chaturvedi P., Nacht M., Westlin W.F., Petter R.C., Singh J. Nat. Chem. Biol. 2011, 7:22.
72. Perez D.I., Palomo V., Peérez C.N., Gil C., Dans P.D., Luque F.J., Conde S., Martiénez A. J. Med. Chem. 2011, 54:4042.
73. Verhelst S.H.L., Witte M.D., Arastu-Kapur S., Fonovic M., Bogyo M. Chembiochem 2006, 7:943.
74. Greenberg C.S., Birckbichler P.J., Rice R.H. FASEB J. 1991, 5:3071.
75. Prime M.E., Andersen O.A., Barker J.J., Brooks M.A., Cheng R.K.Y., Toogood-Johnson I., Courtney S.M., Brookfield F.A., Yarnold C.J., Marston R.W., Johnson P.D., Johnsen S.F., Palfrey J.J., Vaidya D., Erfan S., Ichihara O., Felicetti B., Palan S., Pedret-Dunn A., Schaertl S., Sternberger I., Ebneth A., Scheel A., Winkler D., Toledo-Sherman L., Beconi M., Macdonald D., Muñoz-Sanjuan I., Dominguez C., Wityak J. J. Med. Chem. 2012, 55:1021.
76. Johnson D.S., Stiff C., Lazerwith S.E., Kesten S.R., Fay L.K., Morris M., Beidler D., Liimatta M.B., Smith S.E., Dudley D.T., Sadagopan N., Bhattachar S.N., Kesten S.J., Nomanbhoy T.K., Cravatt B.F., Ahn K. ACS Med. Chem. Lett. 2011, 2:91.
77. Liu Y., Patricelli M.P., Cravatt B.F. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:14694.
78. Meyers M.J., Long S.A., Pelc M.J., Wang J.L., Bowen S.J., Schweitzer B.A., Wilcox M.V., McDonald J., Smith S.E., Foltin S., Rumsey J., Yang Y.-S., Walker M.C., Kamtekar S., Beidler D., Thorarensen A. Bioorg. Med. Chem. Lett. 2011, 21:6545.
79. Meyers M.J., Long S.A., Pelc M.J., Wang J.L., Bowen S.J., Walker M.C., Schweitzer B.A., Madsen H.M., Tenbrink R.E., McDonald J., Smith S.E., Foltin S., Beidler D., Thorarensen A. Bioorg. Med. Chem. Lett. 2011, 21:6538.
80. Zvonok N., Pandarinathan L., Williams J., Johnston M., Karageorgos I., Janero D.R., Krishnan S.C., Makriyannis A. Chem. Biol. 2008, 15:854.
81. Matuszak N., Muccioli G.G., Labar G., Lambert D.M. J. Med. Chem. 2009, 52:7410.
82. Maione S., Morera E., Marabese I., Ligresti A., Luongo L., Ortar G., Di M.V. Br. J. Pharmacol. 2008, 155:775.
83. Bachovchin D.A., Mohr J.T., Speers A.E., Wang C., Berlin J.M., Spicer T.P., Fernandez-Vega V., Chase P., Hodder P.S., Schürer S.C., Nomura D.K., Rosen H., Fu G.C., Cravatt B.F. Proc. Natl. Acad. Sci. U.S.A. 2011, 108:6811.
84. Bachovchin D.A., Zuhl A.M., Speers A.E., Wolfe M.R., Weerapana E., Brown S.J., Rosen H., Cravatt B.F. J. Med. Chem. 2011, 54:5229.
85. Davies S., Pandian R., Bolos J., Castaner R. Drugs Future 2009, 34:708.
86. Demo S.D., Kirk C.J., Aujay M.A., Buchholz T.J., Dajee M., Ho M.N., Jiang J., Laidig G.J., Lewis E.R., Parlati F., Shenk K.D., Smyth M.S., Sun C.M., Vallone M.K., Woo T.M., Molineaux C.J., Bennett M.K. Cancer Res. 2007, 67:6383.
87. Kim J.-H., Lee S.-K., Ki M.-H., Choi W.-K., Ahn S.-K., Shin H.-J., Hong C.I. Int. J. Pharm. 2004, 272:79.
88. McLean L.R., Zhang Y., Li H., Li Z., Lukasczyk U., Choi Y.-M., Han Z., Prisco J., Fordham J., Tsay J.T., Reiling S., Vaz R.J., Li Y. Bioorg. Med. Chem. Lett. 2009, 19:6717.