Tyrosine-385 is critical for acetylation of cyclooxygenase-2 by aspirin [14]

Journal of the American Chemical Society

Volumn 122, Issue 27, 2000, Pages 6514-6515

  Hochgesang Jr , G Phillip ^a   Rowlinson, Scott W ^a   Marnett, Lawrence J ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; CYCLOOXYGENASE 2; TYROSINE;

ACETYLATION; CATALYSIS; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG PROTEIN BINDING; ENZYME ACTIVE SITE; HYDROGEN BOND; LETTER; SITE DIRECTED MUTAGENESIS;

EID: 12944309750     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0003932     Document Type: Letter

References (22)

1. Vane, J. R.; Flower, R. J.; Botting, R. M. Stroke 1990, 21(suppl IV), IV-12-IV-23.
2. Vane, J. R.; Bakhle, Y. S.; Botting, R. M. Annu. Rev. Pharmacol. Toxicol. 1998, 38, 97-120. There are two COX isoforms that exhibit differential cellular regulation and tissue distribution. In the present contribution, we use the abbreviation COX to refer to the proteins and the unabbreviated cyclooxygenase to refer to the catalytic activity or the active site where the reaction occurs.
3. Rome, L. H.; Lands, W. E. M.; Roth, G. J.; Majerus, P. W. Prostaglandins 1976, 11, 23-30.
4. Van Der Ouderaa, F. J.; Buytenhek, M.; Nugteren, D. H.; Van Dorp. D. A. Eur. J. Biochem. 1980, 109, 1-8.
5. DeWitt, D. L.; El-Harith, E. A.: Kraemer, S. A.; Andrews, M. J.; Yao, E. F.; Armstrong, R. L.; Smith, W. L. J. Biol. Chem. 1990, 265, 5192-5198.
6. Lecomte, M.; Laneuville, O.; Ji, C.; DeWitt, D. L.; Smith, W. L. J. Biol. Chem. 1994, 269, 13207-13215.
7. Rowlinson, S. W.; Crews, B. C.; Goodwin, D. C.; Schneider, C.; Gierse, J. K.; Marnett, L. J. J. Biol. Chem. 2000, 274, 6586-6591.
8. Chen, Y.-N. P.; Marnett, L. J. FASEB J. 1989, 3, 2294-2297.
9. Wells, I.; Marnett, L. J. Biochemistry 1992, 31, 9520-9525.
10. Loll, P. J.; Picot, D.; Garavito, R. M. Nat. Struct. Biol. 1995, 2, 637-642.
11. Bhattacharyya, D. K.; Lecomte, M.; Rieke, C. J.; Garavito, R. M.; Smith, W. L. J. Biol. Chem. 1996, 271, 2179-2184.
12. By convention, the COX-1 numbering system is used for all residues.
13. Rowlinson, S. W.; Crews, B. C.; Lanzo, C. A.; Marnett, L. J. J. Biol. Chem. 1999, 274, 23305-23310.
14. Shimokawa, T.; Kulmacz, R. J.; DeWitt, D. L.; Smith, W. L. J. Biol. Chem. 1990, 265, 20073-20076.
15. Tsai, A.-L.; Palmer, G.; Xiao, G.; Swinney, D. C.; Kulmacz, R. J. J. Biol. Chem. 1998, 273, 3888-3894.
16. Goodwin, D. C.; Gunther, M. H.; Hsi, L. H.; Crews, B. C.; Eling, T. E.; Mason, R. P.; Marnett, L. J. J. Biol. Chem. 1998, 273, 8903-8909.
17. 14C-acetyl]-salicylic acid in 100 mM tris-hydroxymethylaminomethane (pH 7.0) buffer containing 500 μM phenol in a final volume of 70 μL. After the initial 3 h incubation with aspirin, 10 μL of 1.05 M hydroxylamine was added, and the solution was incubated for an additional 1 h at 25 °C. Finally, 20 μL aliquots of the solution were added to each of three separate tubes containing 10 μL of sample buffer (3% sodium dodecyl sulfate, 10% glycerol, 62.5 μM tris-hydroxymethylaminomethane, 50 μM dithiothreitol) and then heated to 95 °C for three min prior to loading onto a 7.5% sodium dodecyl sulfate-polyacrylamide gel. Following electrophoresis, the gels were dried and autoradiographed on an Instant Imager (Packard Instruments, Meriden, CT).
18. Luong, C.; Miller, A.; Barnett, J.; Chow, J.; Ramesha, C.; Browner, M. F. Nat. Struct. Biol. 1996, 3, 927-933.
19. Kurumbail, R. G.; Stevens, A. M.; Gierse, J. K.; McDonald, J. J.; Stegeman, R. A.; Pak, J. Y.; Gildehaus, D.; Miyashiro, J. M.; Penning, T. D.; Seibert, K.; Isakson, P. C.; Stallings, W. C. Nature 1996, 384, 644-648.
20. Menard, R.; Storer, A. C. Biol. Chem. Hoppe Seyler 1992, 373, 393-400.
21. Picot, D.; Loll, P. J.; Garavito, R. M. Nature 1994, 367, 243-249.
22. Odenwaller, R.; Maddipati, K. R.; Marnett, L. J. J. Biol. Chem. 1992, 267, 13863-13869.