Caffeic acid phenethyl ester and its amide analogue are potent inhibitors of leukotriene biosynthesis in human polymorphonuclear leukocytes

PLoS ONE

Volumn 7, Issue 2, 2012, Pages

  Boudreau, Luc H ^a,b   Maillet, Jacques ^a   LeBlanc, Luc M ^a   Jean François, Jacques ^a   Touaibia, Mohamed ^a   Flamand, Nicolas ^b   Surette, Marc E ^a  

^a UNIVERSITÉ DE MONCTON   (Canada)

^b LAVAL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONIC ACID; CAFFEIC ACID DERIVATIVE; CAFFEIC ACID PHENETHYL ESTER; LEUKOTRIENE; ZILEUTON; AMIDE; ANTIINFLAMMATORY AGENT; DRUG DERIVATIVE; LEUKOTRIENE RECEPTOR BLOCKING AGENT; LIPOXYGENASE INHIBITOR; PHENETHYL ALCOHOL;

ANTIOXIDANT ACTIVITY; ARTICLE; BLOOD SAMPLING; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; NEUTROPHIL; NORMAL HUMAN; BIOSYNTHESIS; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; METABOLISM; STRUCTURE ACTIVITY RELATION;

AMIDES; ANTI-INFLAMMATORY AGENTS; ARACHIDONATE 5-LIPOXYGENASE; ARACHIDONIC ACID; CAFFEIC ACIDS; HUMANS; LEUKOTRIENE ANTAGONISTS; LEUKOTRIENES; LIPOXYGENASE INHIBITORS; NEUTROPHILS; PHENYLETHYL ALCOHOL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84856803352     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0031833     Document Type: Article

References (49)

1. Samuelsson B, (1983) Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation. Science 220: 568-575.
2. Mehrabian M, Allayee H, Wong J, Shi W, Wang XP, et al. (2002) Identification of 5-lipoxygenase as a major gene contributing to atherosclerosis susceptibility in mice. Circ Res 91: 120-126.
3. Leff JA, Busse WW, Pearlman D, Bronsky EA, Kemp J, et al. (1998) Montelukast, a leukotriene-receptor antagonist, for the treatment of mild asthma and exercise-induced bronchoconstriction. N Engl J Med 339: 147-152.
4. Chen M, Lam BK, Kanaoka Y, Nigrovic PA, Audoly LP, et al. (2006) Neutrophil-derived leukotriene B4 is required for inflammatory arthritis. J Exp Med 203: 837-842.
5. Gupta S, Srivastava M, Ahmad N, Sakamoto K, Bostwick DG, et al. (2001) Lipoxygenase-5 is overexpressed in prostate adenocarcinoma. Cancer 91: 737-743.
6. Chen Y, Li D, Li S, (2009) The Alox5 gene is a novel therapeutic target in cancer stem cells of chronic myeloid leukemia. Cell Cycle 8: 3488-3492.
7. Pergola C, Werz O, (2010) 5-Lipoxygenase inhibitors: a review of recent developments and patents. Expert Opin Ther Pat 20: 355-375.
8. Berger W, De Chandt MT, Cairns CB, (2007) Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract 61: 663-676.
9. Liu MC, Dube LM, Lancaster J, (1996) Acute and chronic effects of a 5-lipoxygenase inhibitor in asthma: a 6-month randomized multicenter trial. Zileuton Study Group. J Allergy Clin Immunol 98: 859-871.
10. Garcia-Marcos L, Schuster A, Perez-Yarza EG, (2003) Benefit-risk assessment of antileukotrienes in the management of asthma. Drug Saf 26: 483-518.
11. Parlakpinar H, Tasdemir S, Polat A, Bay-Karabulut A, Vardi N, et al. (2005) Protective role of caffeic acid phenethyl ester (cape) on gentamicin-induced acute renal toxicity in rats. Toxicology 207: 169-177.
12. Gokalp O, Uz E, Cicek E, Yilmaz HR, Ozer MK, et al. (2006) Ameliorating role of caffeic acid phenethyl ester (CAPE) against isoniazid-induced oxidative damage in red blood cells. Mol Cell Biochem 290: 55-59.
13. Sud'ina GF, Mirzoeva OK, Pushkareva MA, Korshunova GA, Sumbatyan NV, et al. (1993) Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties. FEBS Lett 329: 21-24.
14. Mirzoeva OK, Calder PC, (1996) The effect of propolis and its components on eicosanoid production during the inflammatory response. Prostaglandins Leukot Essent Fatty Acids 55: 441-449.
15. Michaluart P, Masferrer JL, Carothers AM, Subbaramaiah K, Zweifel BS, et al. (1999) Inhibitory effects of caffeic acid phenethyl ester on the activity and expression of cyclooxygenase-2 in human oral epithelial cells and in a rat model of inflammation. Cancer Res 59: 2347-2352.
16. Boudreau LH, Picot N, Doiron J, Villebonet B, Surette ME, et al. (2009) Caffeoyl and cinnamoyl clusters with anti-inflammatory and anti-cancer effects. Synthesis and structure-activity relationship. New J Chem 33: 1932-1940.
17. Doiron J, Boudreau LH, Picot N, Villebonet B, Surette ME, et al. (2009) Synthesis and 5-lipoxygenase inhibitory activity of new cinnamoyl and caffeoyl clusters. Bioorg Med Chem Lett 19: 1118-1121.
18. Chamulitrat W, Mason RP, Riendeau D, (1992) Nitroxide metabolites from alkylhydroxylamines and N-hydroxyurea derivatives resulting from reductive inhibition of soybean lipoxygenase. J Biol Chem 267: 9574-9579.
19. Wang X, Stavchansky S, Bowman PD, Kerwin SM, (2006) Cytoprotective effect of caffeic acid phenethyl ester (CAPE) and catechol ring-fluorinated CAPE derivatives against menadione-induced oxidative stress in human endothelial cells. Bioorg Med Chem 14: 4879-4887.
20. Brückner R, (2002) Advanced organic chemistry: reaction mechanisms. Harcourt/Academic Press pp. 238-240.
21. Kunishima M, Kawachi C, Morita J, Terao K, Iwasaki F, et al. (1999) 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: an efficient condensing agent leading to the formation of amides and esters Tetrahedron 55: 13159-13170.
22. Mahapatra T, Amarendra P, Mitra AK, (2005) A green procedure for the synthesis of cinnamate esters using Aliquat®336. J Chem Res 10: 629-631.
23. Rajan P, Vedernikova I, Cos P, Berghe DV, Augustyns K, et al. (2001) Synthesis and evaluation of caffeic acid amides as antioxidants. Bioorg Med Chem Lett 11: 215-217.
24. Son S, Lobkowsky EB, Lewis BA, (2001) Caffeic acid phenethyl ester (CAPE): synthesis and X-ray crystallographic analysis. Chem Pharm Bull (Tokyo) 49: 236-238.
25. Boyum A, (1968) Isolation of mononuclear cells and granulocytes from human blood. Isolation of monuclear cells by one centrifugation, and of granulocytes by combining centrifugation and sedimentation at 1 g. Scand J Clin Lab Invest Suppl 97: 77-89.
26. Borgeat P, Picard S, Vallerand P, Bourgoin S, Odeimat A, et al. (1990) Automated on-line extraction and profiling of lipoxygenase products of arachidonic acid by high-performance liquid chromatography. Methods Enzymol 187: 98-116.
27. Flamand N, Surette ME, Picard S, Bourgoin S, Borgeat P, (2002) Cyclic AMP-mediated inhibition of 5-lipoxygenase translocation and leukotriene biosynthesis in human neutrophils. Mol Pharmacol 62: 250-256.
28. Surette ME, Winkler JD, Fonteh AN, Chilton FH, (1996) Relationship between arachidonate-phospholipid remodeling and apoptosis. Biochemistry 35: 9187-9196.
29. Surette ME, Odeimat A, Palmantier R, Marleau S, Poubelle PE, et al. (1994) Reverse-phase high-performance liquid chromatography analysis of arachidonic acid metabolites in plasma after stimulation of whole blood ex vivo. Anal Biochem 216: 392-400.
30. Surette ME, Koumenis IL, Edens MB, Tramposch KM, Chilton FH, (2003) Inhibition of leukotriene synthesis, pharmacokinetics, and tolerability of a novel dietary fatty acid formulation in healthy adult subjects. Clin Ther 25: 948-971.
31. Liegeois C, Lermusieau G, Collin S, (2000) Measuring antioxidant efficiency of wort, malt, and hops against the 2,2′-azobis(2-amidinopropane) dihydrochloride-induced oxidation of an aqueous dispersion of linoleic acid. J Agric Food Chem 48: 1129-1134.
32. Hatano T, Edamastu R, Mori A, Fiujita Y, Yasahura T, et al. (1989) Effects of the interaction of tannins with co-existing substances. VI. Effects of tannins and related polyphenols on superoxide anion radical and on 1,1-diphenyl-picrylhydrazyl radical. Chem. Pharm. Bull 37: 2016-2021.
33. Lin CF, Chang TC, Chiang CC, Tsai HJ, Hsu LY, (2005) Synthesis of selenium-containing polyphenolic acid esters and evaluation of their effects on antioxidation and 5-lipoxygenase inhibition. Chem Pharm Bull (Tokyo) 53: 1402-1407.
34. Rossi A, Pergola C, Koeberle A, Hoffmann M, Dehm F, et al. (2010) The 5-lipoxygenase inhibitor, zileuton, suppresses prostaglandin biosynthesis by inhibition of arachidonic acid release in macrophages. Br J Pharmacol 161: 555-570.
35. Walsh CE, Waite BM, Thomas MJ, DeChatelet LR, (1981) Release and metabolism of arachidonic acid in human neutrophils. J Biol Chem 256: 7228-7234.
36. Radmark O, (2002) Arachidonate 5-lipoxygenase. Prostaglandins Other Lipid Mediat 68-69: 211-234.
37. Krump E, Picard S, Mancini J, Borgeat P, (1997) Suppression of leukotriene B4 biosynthesis by endogenous adenosine in ligand-activated human neutrophils. J Exp Med 186: 1401-1406.
38. Cronstein BN, (1994) Adenosine, an endogenous anti-inflammatory agent. J Appl Physiol 76: 5-13.
39. Thibault N, Burelout C, Harbour D, Borgeat P, Naccache PH, et al. (2002) Occupancy of adenosine A2a receptors promotes fMLP-induced cyclic AMP accumulation in human neutrophils: impact on phospholipase D activity and recruitment of small GTPases to membranes. J Leukoc Biol 71: 367-377.
40. Ham EA, Soderman DD, Zanetti ME, Dougherty HW, McCauley E, et al. (1983) Inhibition by prostaglandins of leukotriene B4 release from activated neutrophils. Proc Natl Acad Sci U S A 80: 4349-4353.
41. Fonteh AN, Winkler JD, Torphy TJ, Heravi J, Undem BJ, et al. (1993) Influence of isoproterenol and phosphodiesterase inhibitors on platelet-activating factor biosynthesis in the human neutrophil. J Immunol 151: 339-350.
42. Flamand N, Plante H, Picard S, Laviolette M, Borgeat P, (2004) Histamine-induced inhibition of leukotriene biosynthesis in human neutrophils: involvement of the H2 receptor and cAMP. Br J Pharmacol 141: 552-561.
43. Surette ME, Krump E, Picard S, Borgeat P, (1999) Activation of leukotriene synthesis in human neutrophils by exogenous arachidonic acid: inhibition by adenosine A(2a) receptor agonists and crucial role of autocrine activation by leukotriene B(4). Mol Pharmacol 56: 1055-1062.
44. Boudreau LH, Bertin J, Robichaud PP, Laflamme M, Ouellette RJ, et al. (2011) Novel 5-lipoxygenase isoforms affect the biosynthesis of 5-lipoxygenase products. FASEB J 25: 1097-1105.
45. Chouinard F, Lefebvre JS, Navarro P, Bouchard L, Ferland C, et al. The endocannabinoid 2-arachidonoyl-glycerol activates human neutrophils: critical role of its hydrolysis and de novo leukotriene B4 biosynthesis. J Immunol 186: 3188-3196.
46. Flamand N, Lefebvre J, Surette ME, Picard S, Borgeat P, (2006) Arachidonic acid regulates the translocation of 5-lipoxygenase to the nuclear membranes in human neutrophils. J Biol Chem 281: 129-136.
47. Surette ME, Dallaire N, Jean N, Picard S, Borgeat P, (1998) Mechanisms of the priming effect of lipopolysaccharides on the biosynthesis of leukotriene B4 in chemotactic peptide-stimulated human neutrophils. FASEB J 12: 1521-1531.
48. Flamand N, Picard S, Lemieux L, Pouliot M, Bourgoin SG, et al. (2006) Effects of pyrrophenone, an inhibitor of group IVA phospholipase A2, on eicosanoid and PAF biosynthesis in human neutrophils. Br J Pharmacol 149: 385-392.
49. Gilbert NC, Bartlett SG, Waight MT, Neau DB, Boeglin WE, et al. (2011) The structure of human 5-lipoxygenase. Science 331: 217-219.