Curcumin analog 1, 5-bis (2-trifluoromethylphenyl)-1, 4-pentadien-3-one exhibits enhanced ability on Nrf2 activation and protection against acrolein-induced ARPE-19 cell toxicity

Toxicology and Applied Pharmacology

Volumn 272, Issue 3, 2013, Pages 726-735

  Li, Yuan ^a   Zou, Xuan ^a   Cao, Ke ^a   Xu, Jie ^a   Yue, Tingting ^a   Dai, Fang ^b   Zhou, Bo ^b   Lu, Wuyuan ^a   Feng, Zhihui ^a   Liu, Jiankang ^a  

^a XI'AN JIAOTONG UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Age related macular degeneration; Glutathione; Mitochondrial membrane potential; Oxidative stress; Reactive oxygen species

Indexed keywords

1,5 BIS(2 TRIFLUOROMETHYLPHENYL) 1,4 PENTADIEN 3 ONE DERIVATIVE; ACROLEIN; ADENOSINE TRIPHOSPHATE; CURCUMIN; GLUTATHIONE; GLUTATHIONE TRANSFERASE; KELCH LIKE ECH ASSOCIATED PROTEIN 1; PHOSPHATIDYLINOSITOL 3 KINASE; PROTEIN KINASE B; REACTIVE OXYGEN METABOLITE; SMALL INTERFERING RNA; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BIOAVAILABILITY; CELL NUCLEUS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; EYE PROTECTION; GENE SILENCING; GENETIC TRANSCRIPTION; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; MITOCHONDRIAL MEMBRANE POTENTIAL; OXIDATIVE STRESS; OXYGEN CONSUMPTION; PIGMENT EPITHELIUM; PROTEIN CARBONYLATION; PROTEIN TRANSPORT; RETINA MACULA AGE RELATED DEGENERATION; SIGNAL TRANSDUCTION;

AGE-RELATED MACULAR DEGENERATION; GLUTATHIONE; MITOCHONDRIAL MEMBRANE POTENTIAL; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES;

ACROLEIN; ANTIOXIDANTS; CELL LINE; CELL SURVIVAL; CURCUMIN; CYTOPROTECTION; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; RETINAL PIGMENT EPITHELIUM;

EID: 84884726738     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2013.07.029     Document Type: Article

References (50)

1. Adams B.K., Ferstl E.M., Davis M.C., Herold M., Kurtkaya S., Camalier R.F., Hollingshead M.G., Kaur G., Sausville E.A., Rickles F.R., Snyder J.P., Liotta D.C., Shoji M. Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents. Bioorg. Med. Chem. 2004, 12:3871-3883.
2. Ascensao A.A., Magalhaes J.F., Soares J.M., Ferreira R.M., Neuparth M.J., Appell H.J., Duarte J.A. Cardiac mitochondrial respiratory function and oxidative stress: the role of exercise. Int. J. Sports Med. 2005, 26:258-267.
3. Balogun E., Hoque M., Gong P., Killeen E., Green C.J., Foresti R., Alam J., Motterlini R. Curcumin activates the haem oxygenase-1 gene via regulation of Nrf2 and the antioxidant-responsive element. Biochem. J. 2003, 371:887-895.
4. Bryan H.K., Olayanju A., Goldring C.E., Park B.K. The Nrf2 cell defence pathway: Keap1-dependent and -independent mechanisms of regulation. Biochem. Pharmacol. 2013, 85:705-717.
5. Calabrese V., Cornelius C., Mancuso C., Pennisi G., Calafato S., Bellia F., Bates T.E., Giuffrida Stella A.M., Schapira T., Dinkova Kostova A.T., Rizzarelli E. Cellular stress response: a novel target for chemoprevention and nutritional neuroprotection in aging, neurodegenerative disorders and longevity. Neurochem. Res. 2008, 33:2444-2471.
6. Chen H.H., Chen Y.T., Huang Y.W., Tsai H.J., Kuo C.C. 4-Ketopinoresinol, a novel naturally occurring ARE activator, induces the Nrf2/HO-1 axis and protects against oxidative stress-induced cell injury via activation of PI3K/AKT signaling. Free Radic. Biol. Med. 2012, 52:1054-1066.
7. Clemons T.E., Milton R.C., Klein R., Seddon J.M., Ferris F.L. Risk factors for the incidence of advanced age-related macular degeneration in the Age-Related Eye Disease Study (AREDS) AREDS Report No. 19. Ophthalmology 2005, 112:533-539.
8. Feng Z., Liu Z., Li X., Jia H., Sun L., Tian C., Jia L., Liu J. alpha-Tocopherol is an effective Phase II enzyme inducer: protective effects on acrolein-induced oxidative stress and mitochondrial dysfunction in human retinal pigment epithelial cells. J. Nutr. Biochem. 2010, 21:1222-1231.
9. Furukawa M., Xiong Y. BTB protein Keap1 targets antioxidant transcription factor Nrf2 for ubiquitination by the Cullin 3-Roc1 ligase. Mol. Cell. Biol. 2005, 25:162-171.
10. Goel A., Aggarwal B.B. Curcumin, the golden spice from Indian saffron, is a chemosensitizer and radiosensitizer for tumors and chemoprotector and radioprotector for normal organs. Nutr. Cancer 2010, 62:919-930.
11. Granado-Serrano A.B., Martin M.A., Haegeman G., Goya L., Bravo L., Ramos S. Epicatechin induces NF-kappaB, activator protein-1 (AP-1) and nuclear transcription factor erythroid 2p45-related factor-2 (Nrf2) via phosphatidylinositol-3-kinase/protein kinase B (PI3K/AKT) and extracellular regulated kinase (ERK) signalling in HepG2 cells. Br. J. Nutr. 2010, 103:168-179.
12. Hatcher H., Planalp R., Cho J., Torti F.M., Torti S.V. Curcumin: from ancient medicine to current clinical trials. Cell. Mol. Life Sci. 2008, 65:1631-1652.
13. Henchcliffe C., Beal M.F. Mitochondrial biology and oxidative stress in Parkinson disease pathogenesis. Nat. Clin. Pract. Neurol. 2008, 4:600-609.
14. Itoh K., Chiba T., Takahashi S., Ishii T., Igarashi K., Katoh Y., Oyake T., Hayashi N., Satoh K., Hatayama I., Yamamoto M., Nabeshima Y. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem. Biophys. Res. Commun. 1997, 236:313-322.
15. Itoh K., Wakabayashi N., Katoh Y., Ishii T., Igarashi K., Engel J.D., Yamamoto M. Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain. Genes Dev. 1999, 13:76-86.
16. Jarmi T., Agarwal A. Heme oxygenase and renal disease. Curr. Hypertens. Rep. 2009, 11:56-62.
17. Jia L., Liu Z., Sun L., Miller S.S., Ames B.N., Cotman C.W., Liu J. Acrolein, a toxicant in cigarette smoke, causes oxidative damage and mitochondrial dysfunction in RPE cells: protection by (R)-alpha-lipoic acid. Investig. Ophthalmol. Vis. Sci. 2007, 48:339-348.
18. Kang E.S., Woo I.S., Kim H.J., Eun S.Y., Paek K.S., Chang K.C., Lee J.H., Lee H.T., Kim J.H., Nishinaka T., Yabe-Nishimura C., Seo H.G. Up-regulation of aldose reductase expression mediated by phosphatidylinositol 3-kinase/Akt and Nrf2 is involved in the protective effect of curcumin against oxidative damage. Free Radic. Biol. Med. 2007, 43:535-545.
19. Kelsey N.A., Wilkins H.M., Linseman D.A. Nutraceutical antioxidants as novel neuroprotective agents. Molecules 2010, 15:7792-7814.
20. Khan J.C., Thurlby D.A., Shahid H., Clayton D.G., Yates J.R., Bradley M., Moore A.T., Bird A.C. Smoking and age related macular degeneration: the number of pack years of cigarette smoking is a major determinant of risk for both geographic atrophy and choroidal neovascularisation. Br. J. Ophthalmol. 2006, 90:75-80.
21. Kinnunen K., Petrovski G., Moe M.C., Berta A., Kaarniranta K. Molecular mechanisms of retinal pigment epithelium damage and development of age-related macular degeneration. Acta Ophthalmol. 2012, 90:299-309.
22. Kobayashi M., Yamamoto M. Nrf2-Keap1 regulation of cellular defense mechanisms against electrophiles and reactive oxygen species. Adv. Enzym. Regul. 2006, 46:113-140.
23. Kobayashi A., Kang M.I., Okawa H., Ohtsuji M., Zenke Y., Chiba T., Igarashi K., Yamamoto M. Oxidative stress sensor Keap1 functions as an adaptor for Cul3-based E3 ligase to regulate proteasomal degradation of Nrf2. Mol. Cell. Biol. 2004, 24:7130-7139.
24. LeBel C.P., Ischiropoulos H., Bondy S.C. Evaluation of the probe 2',7'-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chem. Res. Toxicol. 1992, 5:227-231.
25. Li W., Kong A.N. Molecular mechanisms of Nrf2-mediated antioxidant response. Mol. Carcinog. 2009, 48:91-104.
26. Li X., Liu Z., Luo C., Jia H., Sun L., Hou B., Shen W., Packer L., Cotman C.W., Liu J. Lipoamide protects retinal pigment epithelial cells from oxidative stress and mitochondrial dysfunction. Free Radic. Biol. Med. 2008, 44:1465-1474.
27. Liu Z., Sun L., Zhu L., Jia X., Li X., Jia H., Wang Y., Weber P., Long J., Liu J. Hydroxytyrosol protects retinal pigment epithelial cells from acrolein-induced oxidative stress and mitochondrial dysfunction. J. Neurochem. 2007, 103:2690-2700.
28. Liu Z., Sun L., Zhu L., Jia X., Li X., Jia H., Wang Y., Weber P., Long J., Liu J. Hydroxytyrosol protects retinal pigment epithelial cells from acrolein-induced oxidative stress and mitochondrial dysfunction. J. Neurochem. 2007, 103:2690-2700.
29. Ma W., Zhao L., Fontainhas A.M., Fariss R.N., Wong W.T. Microglia in the mouse retina alter the structure and function of retinal pigmented epithelial cells: a potential cellular interaction relevant to AMD. PLoS One 2009, 4:e7945.
30. Maliakel D.M., Kagiya T.V., Nair C.K. Prevention of cisplatin-induced nephrotoxicity by glucosides of ascorbic acid and alpha-tocopherol. Exp. Toxicol. Pathol. 2008, 60:521-527.
31. Merry B.J. Oxidative stress and mitochondrial function with aging-the effects of calorie restriction. Aging Cell 2004, 3:7-12.
32. Moi P., Chan K., Asunis I., Cao A., Kan Y.W. Isolation of NF-E2-related factor 2 (Nrf2), a NF-E2-like basic leucine zipper transcriptional activator that binds to the tandem NF-E2/AP1 repeat of the beta-globin locus control region. Proc. Natl. Acad. Sci. U. S. A. 1994, 91:9926-9930.
33. Nguyen T., Nioi P., Pickett C.B. The Nrf2-antioxidant response element signaling pathway and its activation by oxidative stress. J. Biol. Chem. 2009, 284:13291-13295.
34. Pae H.O., Jeong G.S., Jeong S.O., Kim H.S., Kim S.A., Kim Y.C., Yoo S.J., Kim H.D., Chung H.T. Roles of heme oxygenase-1 in curcumin-induced growth inhibition in rat smooth muscle cells. Exp. Mol. Med. 2007, 39:267-277.
35. Rahman I., Biswas S.K., Kirkham P.A. Regulation of inflammation and redox signaling by dietary polyphenols. Biochem. Pharmacol. 2006, 72:1439-1452.
36. Ramkumar H.L., Zhang J., Chan C.C. Retinal ultrastructure of murine models of dry age-related macular degeneration (AMD). Prog. Retin. Eye Res. 2010, 29:169-190.
37. Schmidt S., Hauser M.A., Scott W.K., Postel E.A., Agarwal A., Gallins P., Wong F., Chen Y.S., Spencer K., Schnetz-Boutaud N., Haines J.L., Pericak-Vance M.A. Cigarette smoking strongly modifies the association of LOC387715 and age-related macular degeneration. Am. J. Hum. Genet. 2006, 78:852-864.
38. Sekhar K.R., Rachakonda G., Freeman M.L. Cysteine-based regulation of the CUL3 adaptor protein Keap1. Toxicol. Appl. Pharmacol. 2010, 244:21-26.
39. Shehzad A., Ha T., Subhan F., Lee Y.S. New mechanisms and the anti-inflammatory role of curcumin in obesity and obesity-related metabolic diseases. Eur. J. Nutr. 2011, 50:151-161.
40. Singh S. From exotic spice to modern drug?. Cell 2007, 130:765-768.
41. Smith W., Assink J., Klein R., Mitchell P., Klaver C.C.W., Klein B.E.K., Hofman A., Jensen S., Wang J.J., de Jong P.T.V.M. Risk factors for age related macular degeneration - pooled findings from three continents. Ophthalmology 2001, 108:697-704.
42. Suh J.H., Shenvi S.V., Dixon B.M., Liu H., Jaiswal A.K., Liu R.M., Hagen T.M. Decline in transcriptional activity of Nrf2 causes age-related loss of glutathione synthesis, which is reversible with lipoic acid. Proc. Natl. Acad. Sci. U. S. A. 2004, 101:3381-3386.
43. Sun L., Luo C., Long J., Wei D., Liu J. Acrolein is a mitochondrial toxin: effects on respiratory function and enzyme activities in isolated rat liver mitochondria. Mitochondrion 2006, 6:136-142.
44. Weber W.M., Hunsaker L.A., Roybal C.N., Bobrovnikova-Marjon E.V., Abcouwer S.F., Royer R.E., Deck L.M., Vander Jagt D.L. Activation of NFkappaB is inhibited by curcumin and related enones. Bioorg. Med. Chem. 2006, 14:2450-2461.
45. White C.C., Viernes H., Krejsa C.M., Botta D., Kavanagh T.J. Fluorescence-based microtiter plate assay for glutamate-cysteine ligase activity. Anal. Biochem. 2003, 318:175-180.
46. Xiao H., Lv F., Xu W., Zhang L., Jing P., Cao X. Deprenyl prevents MPP(+)-induced oxidative damage in PC12 cells by the upregulation of Nrf2-mediated NQO1 expression through the activation of PI3K/Akt and Erk. Toxicology 2011, 290:286-294.
47. Yang C., Zhang X., Fan H., Liu Y. Curcumin upregulates transcription factor Nrf2, HO-1 expression and protects rat brains against focal ischemia. Brain Res. 2009, 1282:133-141.
48. Yildirim Z., Ucgun N.I., Yildirim F. The role of oxidative stress and antioxidants in the pathogenesis of age-related macular degeneration. Clinics (Sao Paulo) 2011, 66:743-746.
49. Zhang D.D., Hannink M. Distinct cysteine residues in Keap1 are required for Keap1-dependent ubiquitination of Nrf2 and for stabilization of Nrf2 by chemopreventive agents and oxidative stress. Mol. Cell. Biol. 2003, 23:8137-8151.
50. Zou X., Feng Z., Li Y., Wang Y., Wertz K., Weber P., Fu Y., Liu J. Stimulation of GSH synthesis to prevent oxidative stress-induced apoptosis by hydroxytyrosol in human retinal pigment epithelial cells: activation of Nrf2 and JNK-p62/SQSTM1 pathways. J. Nutr. Biochem. 2012, 23:994-1006.