Anti-inflammatory activity of N-(3-Florophenyl)ethylcaffeamide in mice

International Journal of Molecular Sciences

Volumn 14, Issue 8, 2013, Pages 15199-15211

  Liao, Jung Chun ^a   Tsai, Jen Chieh ^b   Peng, Wen Huang ^a   Chiu, Yung Jia ^a   Sung, Ping Jyun ^c,d   Tsuzoki, Minoru ^e   Kuo, Yueh Hsiung ^a  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b ASIA UNIVERSITY   (Taiwan)

^c Museum of Marine Biology and Aquarium   (Taiwan)

^d NATIONAL DONG HWA UNIVERSITY   (Taiwan)

^e Nihon Pharmaceutica University   (Japan)

Author keywords

Anti inflammatory; Caffeamide; Synthesis

Indexed keywords

ANTIINFLAMMATORY AGENT; CARRAGEENAN; CYCLOOXYGENASE 2; GLUTATHIONE PEROXIDASE; GLUTATHIONE REDUCTASE; INDOMETACIN; INTERLEUKIN 1BETA; MALONALDEHYDE; N (3 FLUOROPHENYL)ETHYLCAFFEAMIDE; NITRIC OXIDE; SUPEROXIDE DISMUTASE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DOSE COMPARISON; DRUG EFFICACY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME LINKED IMMUNOSORBENT ASSAY; LIVER PARENCHYMA; MALE; MOUSE; NONHUMAN; PAW EDEMA; PROTEIN ANALYSIS; TISSUE LEVEL;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CAFFEIC ACIDS; CARRAGEENAN; CYCLOOXYGENASE 2; EDEMA; GLUTATHIONE PEROXIDASE; GLUTATHIONE REDUCTASE; INFLAMMATION; INTERLEUKIN-1BETA; LIVER; MALE; MALONDIALDEHYDE; MICE; MICE, INBRED ICR; NITRIC OXIDE; SUPEROXIDE DISMUTASE; TUMOR NECROSIS FACTOR-ALPHA; UPPER EXTREMITY;

EID: 84880757597     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms140815199     Document Type: Article

References (38)

1. Janero, D.R. Malondialdehyde and thiobarbituric acid reactivity as diagnostic indices of lipid peroxidation and peroxidative tissue injury. Free Radic. Biol. Med. 1990, 9, 515-540.
2. Hwang, J.T.; Kwon, D.Y.; Yoon, S.H. AMP-activated protein kinase: A potential target for the diseases prevention by natural occurring polyphenols. N. Biotechnol. 2009, 26, 17-22.
3. Collins, Q.F.; Liu, H.Y.; Pi, J.; Liu, Z.; Quon, M.J.; Cao, W. Epigallocatechin-3-gallate (EGCG), a green tea polyphenol, suppresses hepatic gluconeogenesis through 50-AMP-activated protein kinase. J. Biol. Chem. 2007, 282, 30143-30149.
4. Breen, D.M.; Sanli, T.; Giacca, A.; Tsiani, E. Stimulation of muscle cell glucose uptake by resveratrol through sirtuins and AMPK. Biochem. Biophys. Res. Commun. 2008, 374, 117-122.
5. Fang, X.K.; Gao, J.; Zhu, D.N. Kaempferol and quercetin isolated from Euonymus alatus improve glucose uptake of 3T3-L1 cells without adipogenesis activity. Life Sci. 2008, 82, 615-622.
6. Hwang, J.T.; Kim, S.H.; Lee, M.S.; Kim, S.H.; Yang, H.J.; Kim, M.J.; Kim, H.S.; Ha, J.; Kim, M.S.; Kwon, D.Y. Anti-obesity effects of ginsenoside Rh2 are associated with the activation of AMPK signaling pathway in 3T3-L1 adipocyte. Biochem. Biophys. Res. Commun. 2007, 364, 1002-1008.
7. Lee, E.S.; Uhm, K.O.; Lee, Y.M.; Han, M.; Lee, M.; Park, J.M.; Suh, P.G.; Park, S.H.; Kim, H.S. CAPE (caffeic acid phenethyl ester) stimulates glucose uptake through AMPK (AMP-activated protein kinase) activation in skeletal muscle cells. Biochem. Biophys. Res. Commun. 2007, 361, 854-858.
8. Cheng, Z.; Pang, T.; Gu, M.; Gao, A.H.; Xie, C.M.; Li, J.Y.; Nan, F.J.; Li, J. Berberine-stimulated glucose uptake in L6 myotubes involves both AMPK and p38 MAPK. Biochem. Biophys. Res. Commun. 2006, 1760, 1682-1689.
9. Lee, Y.S.; Kim, W.S.; Kim, K.H.; Yoon, M.J.; Cho, H.J.; Shen, Y.; Ye, J.M.; Lee, C.H.; Oh, W.K.; Kim C.T.; et al. Berberine, a natural plant product, activates AMP-activated protein kinase with beneficial metabolic effects in diabetic and insulin-resistant states. Diabetes 2006, 55, 2256-2264.
10. Lin, C.L.; Huang, H.C.; Lin, J.K. Theaflavins attenuate hepatic lipid accumulation through activating AMPK in human HepG2 cells. J. Lipid Res. 2007, 48, 2334-2243.
11. Sud'Ina, G.F.; Mirzoeva, O.K.; Pushkareva, M.A.; Korshunova, G.A.; Sumbatyan, N.V.; Varfolomeev, S.D. Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties. FEBS Lett. 1993, 329, 21-24.
12. Michaluart, P.; Masferrer, J.L.; Carothers, A.M.; Subbaramaiah, K.; Zweifel, B.S.; Koboldt, C.; Mestre, J.R.; Grunberger, D.; Sacks, P.G.; Tanabe T.; et al. 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. 1999, 59, 2347-2352.
13. Hung, M.W.; Shiao, M.S.; Tsai, L.C.; Chang, G.G.; Chang, T.C. Apoptotic effect of caffeic acid phenethyl ester and its ester and amide analogues in human cervical cancer ME180 cells. Anticancer Res. 2003, 23, 4773-4780.
14. Fesen, M.R.; Pommier, Y.; Leteurtre, F.; Hiroguchi, S.; Yung, J.; Kohn, K.W. Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. Biochem. Pharmacol. 1994, 48, 595-608.
15. Park, E.H.; Kahng, J.H. Suppressive effects of propolis in rat adjuvant arthritis. Arch. Pharm. Res. 1999, 22, 554-558.
16. Di Rosa, M. Biological properties of carrageenan. J. Pharm. Pharmacol. 1972, 24, 89-102.
17. Seibert, K.; Zhang, Y.; Leahy, K.; Hauser, S.; Masferrer, J.; Perkins, W.; Lee, L.; Isakson, P. Pharmacological and biochemical demonstration of the role of cyclooxygenase 2 in inflammation and pain. Proc. Natl. Acad. Sci. USA 1994, 91, 12013-12017.
18. Spector, W.G.; Willoughby, D.A. The inflammatory response. Bacteriol. Rev. 1963, 27, 117-154.
19. Sawatzky, D.A.; Megson, I.L.; Rossi, A.G. Sildenafil offers protection against NSAID-induced gastric injury. Br. J. Pharmacol. 2005, 146, 477-478.
20. Dinarello, C.A. Proinflammatory and anti-inflammatory cytokines as mediators in the pathogenesis of septic shock. Chest 1997, 112, 321-329.
21. Beutler, B.; Cerami, A. The biology of cachectin/TNF-A primary mediator of the host response. Annu. Rev. Immunol. 1989, 7, 625-655.
22. Park, W.H.; Park, S.Y.; Kim, H.M.; Kim, C.H. Effect of a Korean traditional formulation, Hwaotang, on superoxide generation in human neutrophils, platelet aggregation in human blood, and nitric oxide, prostaglandin E2 production and paw oedema induced by carrageenan in mice. Immunopharmacol. Immunotoxicol. 2004, 26, 53-73.
23. Strieter, R.M.; Belperio, J.A.; Keane, M.P. Cytokines in innate host defense in the lung. Clin. Invest. 2002, 109, 699-705.
24. Salvemini, D.Z.; Wang, D.M.; Bourdon, M.K.; Stern, M.K.; Curne, M.G.; Manning, P.T. Evidence of peroxynitrite involvement in the carrageenan induced rat paw edema. Eur. J. Pharmacol. 1996, 303, 217-220.
25. Daniela, S.; Wang, Z.Q.; Wyatt, P.S.; Bourdon, D.M.; Marino, M.H.; Manning, P.T.; Currie, M.G. Nitric oxide: A key mediator in the early and late phase of carrageenan-induced rat paw inflammation. Br. J. Pharmacol. 1996, 118, 829-838.
26. Dawson, J.; Sedgwick, A.D.; Edwards, J.C.; Lees, P. A comparative study of the cellular, exudative and histological responses to carrageenan, dextran and zymosan in the mouse. Int. J. Tissue React. 1991, 13, 171-185.
27. Lu, T.C.; Ko, Y.Z.; Huang, H.W.; Hung, Y.C.; Lin, Y.C.; Peng, W.H. Analgesic and anti-inflamatory activities of aqueous extract from Glycine tomentella root in mice. J. Ethnopharmacol. 2007, 113, 142-148.
28. Flemming, N.; Mikkelsen, B.B.; Nielsen, J.B.; Andersen, H.R.; Grandjean, P. Plasma malondialdehyde as biomarker for oxidative stress: Reference interval and effects of life-style factors. Clin. Chem. 1997, 43, 1209-1214.
29. Boudreau, L.H.; Maillet, J.; LeBlanc, L.M.; Jean-François, J.; Touaibia, M.; Flamand, N.; Surette, M.E. Caffeic acid phenethyl ester and its amide analogue are potent inhibitors of leukotriene biosynthesis in human polymorphonuclear leukocytes. PLoS One 2012, 7, e31833.
30. Zimmermann, M. Ethical guidelines for investigations of experimental pain in conscious animals. Pain 1983, 16, 109-110.
31. Vinegar, R.; Schreiber, W.; Hugo, R. Biphasic development of carrageenan oedema in rats. J. Pharmacol. Exp. Ther. 1969, 166, 96-103.
32. Hung, S.H.; Shen, K.H.; Wu, C.H.; Liu, C.L.; Shih, Y.W. α-Mangostin suppresses PC-3 human prostate carcinoma cell metastasis by inhibiting matrix metalloproteinase-2/9 and urokinase-plasminogen expression through the JNK signaling pathway. J. Agric. Food Chem. 2009, 57, 1291-1298.
33. Moshage, H.; Kok, B.; Huizenga, J.R.; Jansen, P.L. Nitrite and nitrate determinations in plasma: A critical evaluation. Clin. Chem. 1995, 41, 892-896.
34. Nims, R.W.; Darbyshire, J.F.; Saavedra, J.E.; Christodoulou, D.; Hanbauer, I.; Cox, G.W.; Grisham, M.B.; Laval, F.; Cook, J.A.; Krishna M.C. et al. Colorimetric methods for the determination of nitric oxide concentration in neutral aqueous solutions. Methods 1995, 7, 48-54.
35. Tatum, V.L.; Changchit, C.C.; Chow, K. Measurement of malondialdehyde by high performance liquid chromatography with fluorescence detection. Lipids 1990, 25, 226-229.
36. Misra, H.P.; Fridovich, I. The univalent reduction of oxygen by reduced flavins and quinones. J. Biol. Chem. 1972, 247, 188-192.
37. Flohe, L.; Günzler, W.A. Assays of glutathione peroxidase. Methods Enzymol. 1984, 105, 114-121.
38. Carlberg, I.; Mannervik, B. Glutathione reductase. Methods Enzymol. 1985, 113, 484-490.