Discovery of halopyridines as quiescent affinity labels: Inactivation of dimethylarginine dimethylaminohydrolase

Journal of the American Chemical Society

Volumn 133, Issue 5, 2011, Pages 1553-1562

  Johnson, Corey M ^a   Linsky, Thomas W ^a   Yoon, Dae Wi ^a   Person, Maria D ^a   Fast, Walter ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-METHYLPYRIDINE; BIOLOGICAL APPLICATIONS; CONCENTRATION-DEPENDENT; DIMETHYLARGININE; FACILE REACTION; GLUTATHIONES; HIGH-THROUGHPUT; INACTIVATION MECHANISMS; NUCLEOPHILICITIES; PYRIDINIUM; STRUCTURAL CLASS; TIME-DEPENDENT;

DIMETHYLARGININASE; GLUTATHIONE; HALOPYRIDINE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; COVALENT BOND; ENZYME ACTIVE SITE; ENZYME INACTIVATION; HIGH THROUGHPUT SCREENING; NUCLEOPHILICITY;

AFFINITY LABELS; AMIDOHYDROLASES; AMINO ACID SEQUENCE; BROMIDES; CATALYTIC DOMAIN; ENZYME ACTIVATION; ENZYME INHIBITORS; HALOGENS; HIGH-THROUGHPUT SCREENING ASSAYS; MOLECULAR SEQUENCE DATA; PSEUDOMONAS AERUGINOSA; PYRIDINES; PYRIDINIUM COMPOUNDS; TIME FACTORS;

EID: 79551695255     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109207m     Document Type: Article

References (30)

1. Pope, A. J.; Karuppiah, K.; Kearns, P. N.; Xia, Y.; Cardounel, A. J. J. Biol. Chem. 2009, 284, 35338
2. Linsky, T. W.; Fast, W. In Comprehensive Natural Products II Chemistry and Biology; Mander, L.; Liu, H.-W., Eds.; Elsevier: Oxford, 2010; Vol. 8, p 125.
3. Linsky, T.; Fast, W. Biochim. Biophys. Acta 2010, 1804, 1943
4. Stuhlinger, M. C.; Tsao, P. S.; Her, J. H.; Kimoto, M.; Balint, R. F.; Cooke, J. P. Circulation 2001, 104, 2569
5. Stone, E. M.; Schaller, T. H.; Bianchi, H.; Person, M. D.; Fast, W. Biochemistry 2005, 44, 13744
6. Luo, Y.; Knuckley, B.; Lee, Y. H.; Stallcup, M. R.; Thompson, P. R. J. Am. Chem. Soc. 2006, 128, 1092
7. Powers, J. C.; Asgian, J. L.; Ekici, O. D.; James, K. E. Chem. Rev. 2002, 102, 4639
8. Cravatt, B. F.; Wright, A. T.; Kozarich, J. W. Annu. Rev. Biochem. 2008, 77, 383
9. Congreve, M.; Carr, R.; Murray, C.; Jhoti, H. Drug Discovery Today 2003, 8, 876
10. Knuckley, B.; Jones, J. E.; Bachovchin, D. A.; Slack, J.; Causey, C. P.; Brown, S. J.; Rosen, H.; Cravatt, B. F.; Thompson, P. R. Chem. Commun. (Cambridge) 2010, 46, 7175
11. Stone, E. M.; Person, M. D.; Costello, N. J.; Fast, W. Biochemistry 2005, 44, 7069
12. Forbes, S. P.; Druhan, L. J.; Guzman, J. E.; Parinandi, N.; Zhang, L.; Green-Church, K. B.; Cardounel, A. J. Biochemistry 2008, 47, 1819
13. Livers, M.; Miller, J. J. Chem. Soc. 1963, 3486
14. Reinheimer, J. D.; Gerig, J. T.; Garst, R.; Schrier, B. J. Am. Chem. Soc. 1962, 84, 2770
15. MARVIN 5.2.0; ChemAxon, 2009; http://www.chemaxon.com
16. Luo, Y.; Arita, K.; Bhatia, M.; Knuckley, B.; Lee, Y. H.; Stallcup, M. R.; Sato, M.; Thompson, P. R. Biochemistry 2006, 45, 11727
17. Stone, E. M.; Costello, A. L.; Tierney, D. L.; Fast, W. Biochemistry 2006, 45, 5618
18. Tajc, S. G.; Tolbert, B. S.; Basavappa, R.; Miller, B. L. J. Am. Chem. Soc. 2004, 126, 10508
19. Pinitglang, S.; Watts, A. B.; Patel, M.; Reid, J. D.; Noble, M. A.; Gul, S.; Bokth, A.; Naeem, A.; Patel, H.; Thomas, E. W.; Sreedharan, S. K.; Verma, C.; Brocklehurst, K. Biochemistry 1997, 36, 9968
20. Silverman, R. B. Methods Enzymol. 1995, 249, 240
21. Krantz, A. Bioorg. Med. Chem. Lett. 1992, 2, 1327
22. Krantz, A. Adv. Med. Chem. 1992, 1, 235
23. Krantz, A.; Copp, L. J.; Coles, P. J.; Smith, R. A.; Heard, S. B. Biochemistry 1991, 30, 4678
24. Smith, R. A.; Copp, L. J.; Coles, P. J.; Pauls, H. W.; Robinson, V. J.; Spencer, R. W.; Heard, S. B.; Krantz, A. J. Am. Chem. Soc. 1988, 110, 4429
25. Boger, D. L.; Marsilje, T. H.; Castro, R. A.; Hedrick, M. P.; Jin, Q.; Baker, S. J.; Shim, J. H.; Benkovic, S. J. Bioorg. Med. Chem. Lett. 2000, 10, 1471
26. Hiebert, C. K.; Sayre, L. M.; Silverman, R. B. J. Biol. Chem. 1989, 264, 21516
27. Eliot, A. C.; Kirsch, J. F. Annu. Rev. Biochem. 2004, 73, 383
28. Hershfield, R.; Richards, F. M. J. Biol. Chem. 1976, 251, 5141
29. Knipp, M.; Vasak, M. Anal. Biochem. 2000, 286, 257
30. Evans, B. L.; Knopp, J. A.; Horton, H. R. Arch. Biochem. Biophys. 1981, 206, 362