Caffeic acid phenethyl ester activation of Nrf2 pathway is enhanced under oxidative state: Structural analysis and potential as a pathologically targeted therapeutic agent in treatment of colonic inflammation

Free Radical Biology and Medicine

Volumn 65, Issue , 2013, Pages 552-562

  Kim, Hyunjeong ^a   Kim, Wooseong ^a   Yum, Soohwan ^a   Hong, Sungchae ^a   Oh, Jeong Eun ^a   Lee, Ji Woo ^a   Kwak, Mi Kyoung ^b   Park, Eun Ji ^c   Na, Dong Hee ^c   Jung, Yunjin ^a  

^a Pusan National University   (South Korea)

^b The Catholic University of Korea   (South Korea)

^c Kyungpook National University   (South Korea)

Author keywords

Caffeic acid phenethyl ester; Electrophile; Kelch like ECH associated protein 1; Nuclear factor erythroid 2 p45 (NF E2) related factor 2; Oxidation of catechol; Pathologically targeted therapeutic agent; Structural analysis

Indexed keywords

AGAROSE; BIOTIN; CAFFEIC ACID PHENETHYL ESTER; CATECHOL; HYPOCHLORITE SODIUM; KELCH LIKE ECH ASSOCIATED PROTEIN 1; STREPTAVIDIN; TRANSCRIPTION FACTOR NRF2; TRINITROBENZENESULFONIC ACID; ANTIINFLAMMATORY AGENT; CAFFEIC ACID DERIVATIVE; NFE2L2 PROTEIN, RAT; PHENETHYL ALCOHOL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CELL LYSATE; CHEMICAL MODIFICATION; COLITIS; CONTROLLED STUDY; DRUG EFFECT; DRUG PROTEIN BINDING; DRUG STRUCTURE; ELECTROPHILICITY; HUMAN; HUMAN CELL; NONHUMAN; OXIDATION; PRECIPITATION; PRIORITY JOURNAL; RAT; TRANSCRIPTION INITIATION; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; DISEASE MODEL; DRUG EFFECTS; ENZYME LINKED IMMUNOSORBENT ASSAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOPRECIPITATION; METABOLISM; OXIDATIVE STRESS; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; WESTERN BLOTTING;

RATTUS;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BLOTTING, WESTERN; CAFFEIC ACIDS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLITIS; DISEASE MODELS, ANIMAL; ENZYME-LINKED IMMUNOSORBENT ASSAY; HUMANS; IMMUNOPRECIPITATION; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; PHENYLETHYL ALCOHOL; RATS; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84889685829     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2013.07.015     Document Type: Article

References (37)

1. S. Son, and B.A. Lewis Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: structure-activity relationship J Agric Food Chem 50 2002 468 472
2. F. Borrelli, P. Maffia, L. Pinto, A. Ianaro, A. Russo, F. Capasso, and A. Ialenti Phytochemical compounds involved in the anti-inflammatory effect of propolis extract Fitoterapia 73 1 2002 S53 63
3. C.C. Ho, S.S. Lin, M.Y. Chou, F.L. Chen, C.C. Hu, C.S. Chen, G.Y. Lu, and C.C. Yang Effects of CAPE-like compounds on HIV replication in vitro and modulation of cytokines in vivo J Antimicrob Chemother 56 2005 372 379
4. J.H. Park, J.K. Lee, H.S. Kim, S.T. Chung, J.H. Eom, K.A. Kim, S.J. Chung, S.Y. Paik, and H.Y. Oh Immunomodulatory effect of caffeic acid phenethyl ester in Balb/c mice Int Immunopharmacol 4 2004 429 436
5. H.F. Liao, Y.Y. Chen, J.J. Liu, M.L. Hsu, H.J. Shieh, H.J. Liao, C.J. Shieh, M.S. Shiao, and Y.J. Chen Inhibitory effect of caffeic acid phenethyl ester on angiogenesis, tumor invasion, and metastasis J Agric Food Chem 51 2003 7907 7912
6. M. Calikoglu, L. Tamer, N. Sucu, B. Coskun, B. Ercan, A. Gul, I. Calikoglu, and A. Kanik The effects of caffeic acid phenethyl ester on tissue damage in lung after hindlimb ischemia-reperfusion Pharmacol Res 48 2003 397 403
7. H. Parlakpinar, E. Sahna, A. Acet, B. Mizrak, and A. Polat Protective effect of caffeic acid phenethyl ester (CAPE) on myocardial ischemia- reperfusion-induced apoptotic cell death Toxicology 209 2005 1 14
8. H. Ozyurt, S. Sogut, Z. Yildirim, L. Kart, M. Iraz, F. Armutcu, I. Temel, S. Ozen, A. Uzun, and O. Akyol Inhibitory effect of caffeic acid phenethyl ester on bleomycine-induced lung fibrosis in rats Clin Chim Acta 339 2004 65 75
9. H.J. Hwang, H.J. Park, H.J. Chung, H.Y. Min, E.J. Park, J.Y. Hong, and S.K. Lee Inhibitory effects of caffeic acid phenethyl ester on cancer cell metastasis mediated by the down-regulation of matrix metalloproteinase expression in human HT1080 fibrosarcoma cells J Nutr Biochem 17 2006 356 362
10. M.J. Weyant, A.M. Carothers, M.E. Bertagnolli, and M.M. Bertagnolli Colon cancer chemopreventive drugs modulate integrin-mediated signaling pathways Clin Cancer Res 6 2000 949 956
11. Y.S. Song, E.H. Park, G.M. Hur, Y.S. Ryu, Y.S. Lee, J.Y. Lee, Y.M. Kim, and C. Jin Caffeic acid phenethyl ester inhibits nitric oxide synthase gene expression and enzyme activity Cancer Lett 175 2002 53 61
12. M.R. Fesen, K.W. Kohn, F. Leteurtre, and Y. Pommier Inhibitors of human immunodeficiency virus integrase Proc Natl Acad Sci U S A 90 1993 2399 2403
13. G.F. Sud′ina, O.K. Mirzoeva, M.A. Pushkareva, G.A. Korshunova, N.V. Sumbatyan, and S.D. Varfolomeev Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties FEBS Lett 329 1993 21 24
14. P. Michaluart, J.L. Masferrer, A.M. Carothers, K. Subbaramaiah, B.S. Zweifel, C. Koboldt, J.R. Mestre, D. Grunberger, P.G. Sacks, T. Tanabe, and A.J. Dannenberg 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 1999 2347 2352
15. E. Balogun, M. Hoque, P. Gong, E. Killeen, C.J. Green, R. Foresti, J. Alam, and R. Motterlini Curcumin activates the haem oxygenase-1 gene via regulation of Nrf2 and the antioxidant-responsive element Biochem J 371 2003 887 895
16. K. Natarajan, S. Singh, T.R. Burke Jr, D. Grunberger, and B.B. Aggarwal Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B Proc Natl Acad Sci U S A 93 1996 9090 9095
17. K.I. Tong, A. Kobayashi, F. Katsuoka, and M. Yamamoto Two-site substrate recognition model for the Keap1-Nrf2 system: a hinge and latch mechanism Biol Chem 387 2006 1311 1320
18. H. Motohashi, and M. Yamamoto Nrf2-Keap1 defines a physiologically important stress response mechanism Trends Mol Med 10 2004 549 557
19. W. Li, and A.N. Kong Molecular mechanisms of Nrf2-mediated antioxidant response Mol Carcinog 48 2009 91 104
20. M. Kobayashi, and M. Yamamoto Molecular mechanisms activating the Nrf2-Keap1 pathway of antioxidant gene regulation Antioxid Redox Signal 7 2005 385 394
21. A.L. Levonen, A. Landar, A. Ramachandran, E.K. Ceaser, D.A. Dickinson, G. Zanoni, J.D. Morrow, and V.M. Darley-Usmar Cellular mechanisms of redox cell signalling: role of cysteine modification in controlling antioxidant defences in response to electrophilic lipid oxidation products Biochem J 378 2004 373 382
22. J.Y. Oh, N. Giles, A. Landar, and V. Darley-Usmar Accumulation of 15-deoxy-delta(12,14)-prostaglandin J2 adduct formation with Keap1 over time: effects on potency for intracellular antioxidant defence induction Biochem J 411 2008 297 306
23. D. Choi, J. Han, Y. Lee, J. Choi, S. Han, S. Hong, H. Jeon, Y.M. Kim, and Y. Jung Caffeic acid phenethyl ester is a potent inhibitor of HIF prolyl hydroxylase: structural analysis and pharmacological implication J Nutr Biochem 2009
24. Y. Lee, D.H. Shin, J.H. Kim, S. Hong, D. Choi, Y.J. Kim, M.K. Kwak, and Y. Jung Caffeic acid phenethyl ester-mediated Nrf2 activation and IkappaB kinase inhibition are involved in NFkappaB inhibitory effect: structural analysis for NFkappaB inhibition Eur J Pharmacol 643 2010 21 28
25. N.C. Andrews, and D.V. Faller A rapid micropreparation technique for extraction of DNA-binding proteins from limiting numbers of mammalian cells Nucleic Acids Res 19 1991 2499
26. G.P. Morris, P.L. Beck, M.S. Herridge, W.T. Depew, M.R. Szewczuk, and J.L. Wallace Hapten-induced model of chronic inflammation and ulceration in the rat colon Gastroenterology 96 1989 795 803
27. H. Yano, F. Hirayama, M. Kamada, H. Arima, and K. Uekama Colon-specific delivery of prednisolone-appended alpha-cyclodextrin conjugate: alleviation of systemic side effect after oral administration J Control Release 79 2002 103 112
28. Y. Nakamura, T. Kumagai, C. Yoshida, Y. Naito, M. Miyamoto, H. Ohigashi, T. Osawa, and K. Uchida Pivotal role of electrophilicity in glutathione S-transferase induction by tert-butylhydroquinone Biochemistry 42 2003 4300 4309
29. F. Ishii, and K. Kishi Oxidation of Hydroquinone and Catechols with Aqueous Sodium Hypochlorite under Phase-Transfer Catalysis Synthesis 9 1980 706 708
30. R.O. Ek, M. Serter, K. Ergin, Y. Yildiz, S. Cecen, T. Kavak, and C. Yenisey The effects of caffeic acid phenethyl ester (CAPE) on TNBS-induced colitis in ovariectomized rats Dig Dis Sci 53 2008 1609 1617
31. J. Kim, Y.N. Cha, and Y.J. Surh A protective role of nuclear factor-erythroid 2-related factor-2 (Nrf2) in inflammatory disorders Mutat Res 690 2010 12 23
32. T.O. Khor, M.T. Huang, K.H. Kwon, J.Y. Chan, B.S. Reddy, and A.N. Kong Nrf2-deficient mice have an increased susceptibility to dextran sulfate sodium-induced colitis Cancer Res 66 2006 11580 11584
33. T. Yamada, and M.B. Grisham Role of neutrophil-derived oxidants in the pathogenesis of intestinal inflammation Klin Wochenschr 69 1991 988 994
34. T. Satoh, K. Kosaka, K. Itoh, A. Kobayashi, M. Yamamoto, Y. Shimojo, C. Kitajima, J. Cui, J. Kamins, S. Okamoto, M. Izumi, T. Shirasawa, and S.A. Lipton Carnosic acid, a catechol-type electrophilic compound, protects neurons both in vitro and in vivo through activation of the Keap1/Nrf2 pathway via S-alkylation of targeted cysteines on Keap1 J Neurochem 104 2008 1116 1131
35. A.T. Dinkova-Kostova, M.A. Massiah, R.E. Bozak, R.J. Hicks, and P. Talalay Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups Proc Natl Acad Sci U S A 98 2001 3404 3409
36. P. Sawle, B.E. Moulton, M. Jarzykowska, C.J. Green, R. Foresti, I.J. Fairlamb, and R. Motterlini Structure-activity relationships of methoxychalcones as inducers of heme oxygenase-1 Chem Res Toxicol 21 2008 1484 1494
37. Y. Jung, and Y.M. Kim What should be considered on design of a colon-specific prodrug? Expert Opin Drug Deliv 7 2010 245 258