A potent and selective inhibitor of KIAA1363/AADACL1 that impairs prostate cancer pathogenesis

Chemistry and Biology

Volumn 18, Issue 4, 2011, Pages 476-484

  Chang, Jae Won ^a   Nomura, Daniel K ^a   Cravatt, Benjamin F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CHOLESTEROL ESTERASE; GLYCEROL ETHER; KIAA1363 PROTEIN, MOUSE; PROTEINASE INHIBITOR; SERINE PROTEINASE;

ANIMAL; ARTICLE; CANCER INVASION; CELL MOTION; CELL SURVIVAL; CHEMISTRY; DRUG ANTAGONISM; DRUG DEVELOPMENT; DRUG EFFECT; ENZYME SPECIFICITY; ENZYMOLOGY; HUMAN; MALE; METABOLISM; MOUSE; PATHOLOGY; PROSTATE TUMOR; TIME; TUMOR CELL LINE;

ANIMALS; CARBAMATES; CELL LINE, TUMOR; CELL MOVEMENT; CELL SURVIVAL; DRUG DISCOVERY; GLYCERYL ETHERS; HUMANS; MALE; MICE; NEOPLASM INVASIVENESS; PROSTATIC NEOPLASMS; PROTEASE INHIBITORS; SERINE PROTEASES; STEROL ESTERASE; SUBSTRATE SPECIFICITY; TIME FACTORS;

EID: 79955396596     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2011.02.008     Document Type: Article

References (37)

1. K. Ahn, D.S. Johnson, M. Mileni, D. Beidler, J.Z. Long, M.K. McKinney, E. Weerapana, N. Sadagopan, M. Liimatta, and S.E. Smith Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain Chem. Biol. 16 2009 411 420
2. D.H. Albert, and C.E. Anderson Ether-linked glycerolipids in human brain tumors Lipids 12 1977 188 192 (Pubitemid 8052083)
3. J.P. Alexander, and B.F. Cravatt Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes Chem. Biol. 12 2005 1179 1187 (Pubitemid 41628253)
4. S. Arastu-Kapur, E.L. Ponder, U.P. Fonovic, S. Yeoh, F. Yuan, M. Fonovic, M. Grainger, C.I. Phillips, J.C. Powers, and M. Bogyo Identification of proteases that regulate erythrocyte rupture by the malaria parasite Plasmodium falciparum Nat. Chem. Biol. 4 2008 203 213 (Pubitemid 351264129)
5. D.A. Bachovchin, T. Ji, W. Li, G.M. Simon, H. Hoover, S. Niessen, and B.F. Cravatt A superfamily-wide portrait of serine hydrolase inhibition achieved by library-versus-library screening Proc. Natl. Acad. Sci. USA 107 2010 20941 20946
6. A.B. Berger, P.M. Vitorino, and M. Bogyo Activity-based protein profiling: applications to biomarker discovery, in vivo imaging and drug discovery Am. J. Pharmacogenomics 4 2004 371 381 (Pubitemid 40052846)
7. M.L. Blank, Z.L. Smith, E.A. Cress, and F. Snyder Characterization of the enzymatic hydrolysis of acetate from alkylacetylglycerols in the de novo pathway of PAF biosynthesis Biochim. Biophys. Acta 1042 1990 153 158 (Pubitemid 20043441)
8. G. Blum, S.R. Mullins, K. Kernen, M. Fonovic, C. Jedeszko, M.J. Rice, B.F. Sloane, and M. Bogyo Dynamic imaging of protease activity with fluorescently quenched activity-based probes Nat. Chem. Biol. 1 2005 203 209
9. M. Buchebner, T. Pfeifer, N. Rathke, P.G. Chandak, A. Lass, R. Schreiber, A. Kratzer, R. Zimmermann, W. Sattler, and H. Koefeler Cholesteryl ester hydrolase activity is abolished in HSL-/- macrophages but unchanged in macrophages lacking KIAA1363 J. Lipid Res. 51 2010 2896 2908
10. J.E. Casida, and G.B. Quistad Serine hydrolase targets of organophosphorus toxicants Chem. Biol. Interact. 157-158 2005 277 283 (Pubitemid 41757663)
11. K.P. Chiang, S. Niessen, A. Saghatelian, and B.F. Cravatt An enzyme that regulates ether lipid signaling pathways in cancer annotated by multidimensional profiling Chem. Biol. 13 2006 1041 1050 (Pubitemid 44557068)
12. B.F. Cravatt, A.T. Wright, and J.W. Kozarich Activity-based protein profiling: from enzyme chemistry to proteomic chemistry Annu. Rev. Biochem. 77 2008 383 414
13. E. Deu, M.J. Leyva, V.E. Albrow, M.J. Rice, J.A. Ellman, and M. Bogyo Functional studies of Plasmodium falciparum dipeptidyl aminopeptidase I using small molecule inhibitors and active site probes Chem. Biol. 17 2010 808 819
14. G.L. Ellman, K.D. Courtney, V. Andres Jr., and R.M. Feather-Stone A new and rapid colorimetric determination of acetylcholinesterase activity Biochem. Pharmacol. 7 1961 88 95
15. D.A. Ferguson, M.R. Muenster, Q. Zang, J.A. Spencer, J.J. Schageman, Y. Lian, H.R. Garner, R.B. Gaynor, J.W. Huff, and A. Pertsemlidis Selective identification of secreted and transmembrane breast cancer markers using Escherichia coli ampicillin secretion trap Cancer Res. 65 2005 8209 8217 (Pubitemid 41330584)
16. P.M. Haverty, L.S. Hon, J.S. Kaminker, J. Chant, and Z. Zhang High-resolution analysis of copy number alterations and associated expression changes in ovarian tumors BMC Med. Genomics 2 2009 21
17. N.M. Hoosein, D.D. Boyd, W.J. Hollas, A. Mazar, J. Henkin, and L.W. Chung Involvement of urokinase and its receptor in the invasiveness of human prostatic carcinoma cell lines Cancer Commun. 3 1991 255 264
18. C.A. Iacobuzio-Donahue, A. Maitra, G.L. Shen-Ong, T. van Heek, R. Ashfaq, R. Meyer, K. Walter, K. Berg, M.A. Hollingsworth, and J.L. Cameron Discovery of novel tumor markers of pancreatic cancer using global gene expression technology Am. J. Pathol. 160 2002 1239 1249 (Pubitemid 34411628)
19. M. Igarashi, J. Osuga, H. Uozaki, M. Sekiya, S. Nagashima, M. Takahashi, S. Takase, M. Takanashi, Y. Li, and K. Ohta The critical role of neutral cholesterol ester hydrolase 1 in cholesterol removal from human macrophages Circ. Res. 107 2010 1387 1395
20. N. Jessani, Y. Liu, M. Humphrey, and B.F. Cravatt Enzyme activity profiles of the secreted and membrane proteome that depict cancer invasiveness Proc. Natl. Acad. Sci. USA 99 2002 10335 10340
21. N. Jessani, S. Niessen, B.Q. Wei, M. Nicolau, M. Humphrey, Y. Ji, W. Han, D.Y. Noh, J.R. Yates 3rd, and S.S. Jeffrey A streamlined platform for high-content functional proteomics of primary human specimens Nat. Methods 2 2005 691 697 (Pubitemid 41223096)
22. S. Kathuria, S. Gaetani, D. Fegley, F. Valino, A. Duranti, A. Tontini, M. Mor, G. Tarzia, G. La Rana, and A. Calignano Modulation of anxiety through blockade of anandamide hydrolysis Nat. Med. 9 2003 76 81 (Pubitemid 36098263)
23. S. Krishnasamy, A.L. Teng, R. Dhand, R.M. Schultz, and N.J. Gross Molecular cloning, characterization, and differential expression pattern of mouse lung surfactant convertase Am. J. Physiol. 275 1998 L969 L975
24. D. Leung, C. Hardouin, D.L. Boger, and B.F. Cravatt Discovering potent and selective reversible inhibitors of enzymes in complex proteomes Nat. Biotechnol. 21 2003 687 691 (Pubitemid 36638097)
25. W. Li, J.L. Blankman, and B.F. Cravatt A functional proteomic strategy to discover inhibitors for uncharacterized hydrolases J. Am. Chem. Soc. 129 2007 9594 9595 (Pubitemid 47237463)
26. H.J. Lin, F.C. Ho, and C.L. Lee Abnormal distribution of O-alkyl groups in the neutral glycerolipids from human hepatocellular carcinomas Cancer Res. 38 1978 946 949 (Pubitemid 8393760)
27. Y. Liu, M.P. Patricelli, and B.F. Cravatt Activity-based protein profiling: the serine hydrolases Proc. Natl. Acad. Sci. USA 96 1999 14694 14699 (Pubitemid 30019702)
28. J.Z. Long, W. Li, L. Booker, J.J. Burston, S.G. Kinsey, J.E. Schlosburg, F.J. Pavon, A.M. Serrano, D.E. Selley, and L.H. Parsons Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects Nat. Chem. Biol. 5 2009 37 44
29. J.Z. Long, D.K. Nomura, and B.F. Cravatt Characterization of monoacylglycerol lipase inhibition reveals differences in central and peripheral endocannabinoid metabolism Chem. Biol. 16 2009 744 753
30. D.K. Nomura, J.Z. Long, S. Niessen, H.S. Hoover, S.W. Ng, and B.F. Cravatt Monoacylglycerol lipase regulates a fatty acid network that promotes cancer pathogenesis Cell 140 2010 49 61
31. H. Okazaki, M. Igarashi, M. Nishi, M. Sekiya, M. Tajima, S. Takase, M. Takanashi, K. Ohta, Y. Tamura, and S. Okazaki Identification of neutral cholesterol ester hydrolase, a key enzyme removing cholesterol from macrophages J. Biol. Chem. 283 2008 33357 33364
32. M.P. Patricelli, D.K. Giang, L.M. Stamp, and J.J. Burbaum Direct visualization of serine hydrolase activities in complex proteome using fluorescent active site-directed probes Proteomics 1 2001 1067 1071 (Pubitemid 33696471)
33. D.S. Roos, and P.W. Choppin Tumorigenicity of cell lines with altered lipid composition Proc. Natl. Acad. Sci. USA 81 1984 7622 7626 (Pubitemid 15196236)
34. G.M. Simon, and B.F. Cravatt Activity-based proteomics of enzyme superfamilies: serine hydrolases as a case study J. Biol. Chem. 285 2010 11051 11055
35. F. Snyder, and R. Wood Alkyl and alk-1-enyl ethers of glycerol in lipids from normal and neoplastic human tissues Cancer Res. 29 1969 251 257
36. I. Staub, and S.A. Sieber Beta-lactam probes as selective chemical-proteomic tools for the identification and functional characterization of resistance associated enzymes in MRSA J. Am. Chem. Soc. 131 2009 6271 6276
37. R. Wood, and F. Snyder Characterization and identification of glyceryl ether diesters present in tumor cells J. Lipid Res. 8 1967 494 500