Long-chain carboxychromanols, metabolites of vitamin E, are potent inhibitors of cyclooxygenases

Proceedings of the National Academy of Sciences of the United States of America

Volumn 105, Issue 51, 2008, Pages 20464-20469

  Jiang, Qing ^a   Yin, Xinmin ^a   Lil, Markus A ^b   Danielson, Matthew L ^b   Freiser, Helene ^a   Huang, Jianjie ^a  

^a PURDUE UNIVERSITY   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

Cancer; Inflammation; PGE2; Tocopherol; Tocotrienol

Indexed keywords

13' CARBOXYCHROMANOL; 9' CARBOXYCHROMANOL; ALPHA TOCOPHEROL; ARACHIDONIC ACID; BETA TOCOPHEROL; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DELTA TOCOPHEROL; DRUG METABOLITE; GAMMA TOCOPHEROL; GAMMA TOCOTRIENOL; IBUPROFEN; INTERLEUKIN 1BETA; PARACETAMOL; PEROXIDASE; PROSTAGLANDIN E2; SESAMIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CELL STIMULATION; COMPETITIVE INHIBITION; COMPUTER SIMULATION; CONTROLLED STUDY; DRUG POTENCY; DRUG PROTEIN BINDING; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME PURIFICATION; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; PROTEIN EXPRESSION; VITAMIN METABOLISM;

CELL LINE; CHROMANS; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; INHIBITORY CONCENTRATION 50; STRUCTURE-ACTIVITY RELATIONSHIP; VITAMIN E;

EID: 58149488676     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0810962106     Document Type: Article

References (41)

1. Dubois RN, et al. (1998) Cyclooxygenase in biology and disease. FASEB J 12:1063-1073.
2. Rouzer CA, Marnett LJ (2003) Mechanism of free radical oxygenation of polyunsaturated fatty acids by cyclooxygenases. Chem Rev 103:2239-2304.
3. Vane JR, Bakhle YS, Botting RM (1998) Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol 38:97-120.
4. Vane JR, Botting RM (1998) Mechanism of action of antiinflammatory drugs. Int J Tissue React 20:3-15.
5. Coussens LM, Werb Z (2002) Inflammation and cancer. Nature 420:860-867.
6. Gupta RA, Dubois RN (2001) Colorectal cancer prevention and treatment by inhibition of cyclooxygenase-2. Nat Rev Cancer 1:11-21.
7. Grosser T, Fries S, FitzGerald GA (2006) Biological basis for the cardiovascular consequences of COX-2 inhibition: Therapeutic challenges and opportunities. J Clin Invest 116:4-15.
8. McKellar G, Madhok R, Singh G (2007) The problem with NSAIDs: What data to believe? Curr Pain Headache Rep 11:423-427.
9. Lee IM, Gaziano JM, Buring JE (2006) Vitamin E in the prevention of prostate cancer: Where are we today? J Natl Cancer Inst 98:225-227.
10. Singh U, Devaraj S, Jialal I (2005) Vitamin E, oxidative stress, and inflammation. Annu Rev Nutr 25:151-174.
11. Upston JM, Kritharides L, Stocker R (2003) The role of vitamin E in atherosclerosis. Prog Lipid Res 42:405-422.
12. Jiang Q, Christen S, Shigenaga MK, Ames BN (2001) γ-tocopherol, the major form of vitamin E in the US diet, deserves more attention. Am J Clin Nutr 74:714-722.
13. Jiang Q, Elson-Schwab I, Courtemanche C, Ames BN (2000) γ-tocopherol and its major metabolite, in contrast to alpha-tocopherol, inhibit cyclooxygenase activity in macrophages and epithelial cells. Proc Natl Acad Sci USA 97:11494-11499.
14. Jiang Q, Ames BN (2003) Gamma-tocopherol, but not alpha-tocopherol, decreases proinflammatory eicosanoids and inflammation damage in rats. FASEB J 17:816-822.
15. Jiang Q, Wong J, Fyrst H, Saba JD, Ames BN (2004) γ-tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Proc Natl Acad Sci USA 101:17825-17830.
16. Brigelius-Flohe R, Traber MG (1999) Vitamin E: Function and metabolism. FASEB J 13:1145-1155.
17. Jiang Q, Freiser H, Wood KV, Yin X (2007) Identification and quantitation of novel vitamin E metabolites, sulfated long-chain carboxychromanols, in human A549 cells and in rats. J Lipid Res 48:1221-1230.
18. You CS, Sontag TJ, Swanson JE, Parker RS (2005) Long-chain carboxychromanols are the major metabolites of tocopherols and tocotrienols in A549 lung epithelial cells but not HepG2 cells. J Nutr 135:227-232.
19. Mitchell JA, Saunders M, Barnes PJ, Newton R, Belvisi MG (1997) Sodium salicylate inhibits cyclo-oxygenase-2 activity independently of transcription factor (nuclear factor kappaB) activation: Role of arachidonic acid. Mol Pharmacol 51:907-912.
20. Parker RS, Sontag TJ, Swanson JE (2000) Cytochrome P4503A-dependent metabolism of tocopherols and inhibition by sesamin. Biochem Biophys Res Commun 277:531-534.
21. Grammas P, et al. (2004) Anti-inflammatory effects of tocopherol metabolites. Biochem Biophys Res Commun 319:1047-1052.
22. Kurumbail RG, Kiefer JR, Marnett LJ (2001) Cyclooxygenase enzymes: Catalysis and inhibition. Curr Opin Struct Biol 11:752-760.
23. Marnett LJ, Kalgutkar AS (1999) Cyclooxygenase 2 inhibitors: Discovery, selectivity and the future. Trends Pharmacol Sci 20:465-469.
24. Bhattacharyya DK, Lecomte M, Rieke CJ, Garavito M, Smith WL (1996) 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 271:2179-2184.
25. Mancini JA, Riendeau D, Falgueyret JP, Vickers PJ, O'Neill GP (1995) Arginine 120 of prostaglandin G/H synthase-1 is required for the inhibition by nonsteroidal antiinflammatory drugs containing a carboxylic acid moiety. J Biol Chem 270:29372-29377.
26. Aronoff DM, Boutaud O, Marnett LJ, Oates JA (2003) Inhibition of prostaglandin H2 synthases by salicylate is dependent on the oxidative state of the enzymes. J Pharmacol Exp Ther 304:589-595.
27. Boutaud O, Aronoff DM, Richardson JH, Marnett LJ, Oates JA (2002) Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H(2) synthases. Proc Natl Acad Sci USA 99:7130-7135.
28. Reiter E, Jiang Q, Christen S (2007) Anti-inflammatory properties of alpha- and gammatocopherol. Mol Aspects Med 28:668-691.
29. Sontag TJ, Parker RS (2007) Influence of major structural features of tocopherols and tocotrienols on their omega-oxidation by tocopherol-omega- hydroxylase. J Lipid Res 48:1090-1098.
30. Devaraj S, Leonard S, Traber MG, Jialal I (2008) Gamma-tocopherol supplementation alone and in combination with alpha-tocopherol alters biomarkers of oxidative stress and inflammation in subjects with metabolic syndrome. Free Radic Biol Med 44:1203-1208.
31. Jiang Q, et al. (2002) Gamma-tocopherol supplementation inhibits protein nitration and ascorbate oxidation in rats with inflammation. Free Radic Biol Med 33:1534-1542.
32. Takahashi K, et al. (2006) Gamma-tocopherol, but not alpha-tocopherol, potently inhibits neointimal formation induced by vascular injury in insulin resistant rats. J Mol Cell Cardiol 41:544-554.
33. Wagner JG, et al. (2008) Ozone enhancement of lower airway allergic inflammation is prevented by gamma-tocopherol. Free Radic Biol Med 43:1176-1188.
34. Himmelfarb J, et al. (2003) Alpha and gamma tocopherol metabolism in healthy subjects and patients with end-stage renal disease. Kidney Int 64:978-991.
35. Newmark HL, Huang MT, Reddy BS (2006) Mixed tocopherols inhibit azoxymethane-induced aberrant crypt foci in rats. Nutr Cancer 56:82-85.
36. van der Ouderaa FJ, Buytenhek M (1982) Purification of PGH synthase from sheep vesicular glands. Methods Enzymol 86:60-68.
37. Morris GM, et al. (1998) Automated docking using a lamarckian genetic algorithm and empirical binding free energy function. J Comput Chem 19:1639-1662.
38. Kollman PA, et al. (2000) Calculating structures and free energies of complex molecules: Combining molecular mechanics and continuum models. Acc Chem Res 33:889-897.
39. Aqvist J (1996) Calculation of absolute binding free energies for charged ligands and effects of long-range electrostatic interactions. J Comput Chem 17:1587-1597.
40. Popov VM, Yee WA, Anderson AC (2007) Towards in silico lead optimization: Scores from ensembles of protein/ligand conformations reliably correlate with biological activity. Proteins 66:375-387.
41. Eldridge MD, Murray CW, Auton TR, Paolini GV, Mee RP (1997) Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J Comp Aided Molec 11:425-445.