Substrate-selective inhibition of cyclooxygenase-2: Development and evaluation of achiral profen probes

ACS Medicinal Chemistry Letters

Volumn 3, Issue 9, 2012, Pages 759-763

  Windsor, Matthew A ^a   Hermanson, Daniel J ^a   Kingsley, Philip J ^a   Xu, Shu ^a   Crews, Brenda C ^a   Ho, Winnie ^b   Keenan, Catherine M ^b   Banerjee, Surajit ^c,d   Sharkey, Keith A ^b   Marnett, Lawrence J ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF CALGARY   (Canada)

^c Department of Obstetrics Gynecology   (United States)

^d ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

(R) profens; COX 2; endocannabinoids; prostaglandins; Substrate selective

Indexed keywords

2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; ARACHIDONIC ACID; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; DESMETHYLFLURBIPROFEN; FLURBIPROFEN; IBUPROFEN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG BLOOD LEVEL; DRUG HALF LIFE; DRUG METABOLISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; IC 50; IN VIVO STUDY; MOLECULAR SIZE; MOUSE; NONHUMAN; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

MUS;

EID: 84866355094     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3001616     Document Type: Article

References (23)

1. Turini, M. E.; DuBois, R. N. Cyclooxygenase-2: A Therapeutic Target Annu. Rev. Med. 2002, 53, 35-57
2. Rouzer, C. A.; Marnett, L. J. Endocannabinoid Oxygenation by Cyclooxygenases, Lipoxygenases, and Cytochromes P450: Cross-Talk between the Eicosanoid and Endocannabinoid Signaling Pathways Chem. Rev. 2011, 111 (10) 5899-5921
3. Funk, C. D. Prostaglandins and Leukotrienes: Advances in Eicosanoid Biology Science 2001, 298, 1871-1875
4. Rouzer, C. A.; Marnett, L. J. Cyclooxygenases: Structural and Functional Insights J. Lipid Res. 2009, April Supplement, S29-S34
5. Woodward, D. F.; Carling, R. W. C.; Cornell, C. L.; Fliri, H. G.; Martos, J. L.; Pettit, S. N.; Liang, Y.; Wang, J. W. The pharmacology and therapeutic relevance of endocannabinoid derived cyclo-oxygenase (COX)-2 products Pharmacol. Ther. 2008, 120 (1) 71-80
6. Sang, N.; Zhang, J.; Chen, C. COX-2 oxidative metabolite of endocannabinoid 2-AG enhances excitatory glutamatergic synaptic transmission and induces neurotoxicity J. Neurochem. 2007, 102 (6) 1966-1977
7. Svizenska, I.; Dubovy, P.; Sulcova, A. Cannabinoid Receptors 1 and 2 (CB1 and CB2), their Distribution, Ligands and Functional Involvement in the Nervous System Structures-A Short Review Pharmacol., Biochem. Behav. 2008, 90, 501-511
8. Nomura, D. K.; Morrison, B. E.; Blankman, J. L.; Long, J. Z.; Kinsey, S. G.; Marcondes, M. C. G.; Ward, A. M.; Hahn, Y. K.; Lichtman, A. H.; Conti, B.; Cravatt, B. F. Endocannabinoid Hydrolysis Generates Brain Prostaglandins That Promote Neuroinflammation Science 2011, 334 (6057) 809-813
9. Wang, D.; Wang, H.; Ning, W.; Backlund, M. G.; Dey, S. K.; DuBois, R. N. Loss of Cannabinoid Receptor 1 Accelerates Intestinal Tumor Growth Cancer Res. 2008, 68 (15) 6468-6476
10. Fowler, C. J.; Rojo, M. L.; Rodriguez-Gaztelumendi, A. Modulation of the endocannabinoid system: Neuroprotection or neurotoxicity? Exp. Neurol. 2010, 224 (1) 37-47
11. Ueda, N.; Tsuboi, K.; Uyama, T.; Ohnishi, T. Biosynthesis and degradation of the endocannabinoid 2-arachidonoylglycerol BioFactors 2011, 37 (1) 1-7
12. Kozak, K. R.; Crews, B. C.; Ray, J. L.; Tai, H.-H.; Morrow, J. D.; Marnett, L. J. Metabolism of Prostaglandin Glycerol Esters and Prostaglandin Ethanolamides in Vitro and in Vivo J. Biol. Chem. 2001, 276 (40) 36993-36998
13. Prusakiewicz, J. J.; Duggan, K. C.; Rouzer, C. A.; Marnett, L. J. Differential Sensitivity and Mechanism of Inhibition of COX-2 Oxygenation of Arachidonic Acid and 2-Arachidonoylglycerol by Ibuprofen and Mefenamic Acid Biochemistry 2009, 48 (31) 7353-7355
14. Dong, L.; Vecchio, A. J.; Sharma, N. P.; Jurban, B. J.; Malkowski, M. G.; Smith, W. L. Human Cyclooxygenase-2 Is a Sequence Homodimer That Functions as a Conformational Heterodimer J. Biol. Chem. 2011, 286 (21) 19035-19046
15. Rimon, G.; Sidhu, R. S.; Lauver, D. A.; Lee, J. Y.; Sharma, N. P.; Yuan, C.; Frieler, R. A.; Trievel, R. C.; Lucchesi, B. R.; Smith, W. L. Coxibs interfere with the action of aspirin by binding tightly to one monomer of cyclooxygenase-1 Proc. Natl. Acad. Sci. 2010, 107 (1) 28-33
16. Duggan, K. C.; Hermanson, D. J.; Musee, J.; Prusakiewicz, J. J.; Scheib, J. L.; Carter, B. D.; Banerjee, S.; Oates, J. A.; Marnett, L. J. (R)-Profens are substrate-selective inhibitors of endocannabinoid oxygenation by COX-2 Nat. Chem. Biol. 2011, 7 (11) 803-809
17. Leipold, D. D.; Kantoci, D.; Murray, E. D.; Quiggle, D. D.; Wechter, W. J. Bioinversion of (R)-flurbiprofen to (S)-flurbiprofen at various dose levels in rat, mouse, and monkey Chirality 2004, 16 (6) 379-387
18. Woodman, T. J.; Wood, P. J.; Thompson, A. S.; Hutchings, T. J.; Steel, G. R.; Jiao, P.; Threadgill, M. D.; Lloyd, M. D. Chiral inversion of 2-arylpropionyl-CoA esters by human alpha-methylacyl-CoA racemase 1A (P504S)-a potential mechanism for the anti-cancer effects of ibuprofen Chem. Commun. 2011, 47, 7332-7334
19. Ossipov, M. H.; Jerussi, T. P.; Ren, K.; Sun, H.; Porreca, F. Differential effects of spinal (R)-ketoprofen and (S)-ketoprofen against signs of neuropathic pain and tonic nociception: evidence for a novel mechanism of action of (R)-ketoprofen against tactile allodynia Pain 2000, 87 (2) 193-199
20. Davie, I. T.; Slawson, K. B.; Burt, R. A. P. A Double-Blind Comparison of Parenteral Morphine, Placebo, and Oral Fenoprofen in Management of Postoperative Pain Anesth. Analg. 1982, 61 (12) 1002-1005
21. Blobaum, A. L.; Marnett, L. J. Molecular Determinants for the Selective Inhibition of Cyclooxygenase-2 by Lumiracoxib J. Biol. Chem. 2007, 282 (22) 16379-16390
22. Rainsford, K. Ibuprofen: pharmacology, efficacy and safety Inflammopharmacology 2009, 17 (6) 275-342
23. Bhattacharyya, D. K.; Lecomte, M.; Rieke, C. J.; Garavito, R. M.; Smith, W. L. Involvement of Arginine 120, Glutamate 524, and Tyrosine 355 in the Binding of Arachidonate and 2-Phenylpropionic Acid Inhibitors to the Cyclooxygenase Active Site of Ovine Prostaglandin Endoperoxide H Synthase-1 J. Biol. Chem. 1996, 271 (4) 2179-2184