Novel curcumin analogue 14p protects against myocardial ischemia reperfusion injury through Nrf2-activating anti-oxidative activity

Toxicology and Applied Pharmacology

Volumn 282, Issue 2, 2015, Pages 175-183

  Li, Weixin ^a,b   Wu, Mingchai ^c   Tang, Longguang ^b   Pan, Yong ^b   Liu, Zhiguo ^b   Zeng, Chunlai ^a   Wang, Jingying ^b   Wei, Tiemin ^a   Liang, Guang ^b  

^a LISHUI CENTRAL HOSPITAL   (China)

^b WENZHOU MEDICAL UNIVERSITY   (China)

^c THE THIRD AFFILIATED HOSPITAL OF WENZHOU MEDICAL UNIVERSITY   (China)

Author keywords

Anti oxidative activity; Cardiac ischemia reperfusion injury; Curcumin; Mono carbonyl analogues; Nrf2

Indexed keywords

CASPASE 3; CREATINE KINASE MB; CURCUMIN; HYDROGEN PEROXIDE; MALONALDEHYDE; PROTEIN BAX; PROTEIN BCL 2; SUPEROXIDE DISMUTASE; TRANSCRIPTION FACTOR NRF2; ANTIOXIDANT; NFE2L2 PROTEIN, MOUSE; SMALL INTERFERING RNA;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CELL DEATH; CELL LYSATE; CELL PROLIFERATION; CELL STRUCTURE; CELL VIABILITY; CONTROLLED STUDY; DRUG EFFECT; DRUG MEGADOSE; ENZYME ACTIVATION; ENZYME INHIBITION; HEART INFARCTION SIZE; HEART MUSCLE ISCHEMIA; HEART PROTECTION; IMMUNOBLOTTING; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; MTT ASSAY; NICK END LABELING; NONHUMAN; OXIDATIVE STRESS; QUANTITATIVE ANALYSIS; REAL TIME POLYMERASE CHAIN REACTION; REPERFUSION INJURY; WESTERN BLOTTING; ANALOGS AND DERIVATIVES; ANIMAL; C57BL MOUSE; DRUG EFFECTS; HEART INFARCTION; HEART MUSCLE; METABOLISM; MYOCARDIAL ISCHEMIA; MYOCARDIAL REPERFUSION INJURY; PATHOLOGY;

ANIMALIA;

ANIMALS; ANTIOXIDANTS; APOPTOSIS; CASPASE 3; CURCUMIN; MALE; MICE; MICE, INBRED C57BL; MYOCARDIAL INFARCTION; MYOCARDIAL ISCHEMIA; MYOCARDIAL REPERFUSION INJURY; MYOCARDIUM; NF-E2-RELATED FACTOR 2; RNA, SMALL INTERFERING;

EID: 84919922469     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2014.12.001     Document Type: Article

References (36)

1. Aggarwal B.B., Sundaram C., Malani N., Ichikawa H. Curcumin: the Indian solid gold. Adv. Exp. Med. Biol. 2007, 595:1-75.
2. Anand P., Kunnumakkara A.B., Newman R.A., Aggarwal B.B. Bioavailability of curcumin: problems and promises. Mol. Pharm. 2007, 4:807-818.
3. Ashrafian H., Czibik G., Bellahcene M., Aksentijevic D., Smith A.C., Mitchell S.J., Dodd M.S., Kirwan J., Byrne J.J., Ludwig C., Isackson H., Yavari A., Stottrup N.B., Contractor H., Cahill T.J., Sahgal N., Ball D.R., Birkler R.I., Hargreaves I., Tennant D.A., Land J., Lygate C.A., Johannsen M., Kharbanda R.K., Neubauer S., Redwood C., de Cabo R., Ahmet I., Talan M., Gunther U.L., Robinson A.J., Viant M.R., Pollard P.J., Tyler D.J., Watkins H. Fumarate is cardioprotective via activation of the Nrf2 antioxidant pathway. Cell Metab. 2012, 15:361-371.
4. Baird L., Dinkova-Kostova A.T. The cytoprotective role of the Keap1-Nrf2 pathway. Arch. Toxicol. 2011, 85:241-272.
5. Balasubramanyam M., Koteswari A.A., Kumar R.S., Monickaraj S.F., Maheswari J.U., Mohan V. Curcumin-induced inhibition of cellular reactive oxygen species generation: novel therapeutic implications. J. Biosci. 2003, 28:715-721.
6. Buja L.M. Myocardial ischemia and reperfusion injury. Cardiovasc. Pathol. 2005, 14:170-175.
7. Calvert J.W., Jha S., Gundewar S., Elrod J.W., Ramachandran A., Pattillo C.B., Kevil C.G., Lefer D.J. Hydrogen sulfide mediates cardioprotection through Nrf2 signaling. Circ. Res. 2009, 105:365-374.
8. Goel A., Kunnumakkara A.B., Aggarwal B.B. Curcumin as "Curecumin": from kitchen to clinic. Biochem. Pharmacol. 2008, 75:787-809.
9. Gupta S.C., Prasad S., Kim J.H., Patchva S., Webb L.J., Priyadarsini I.K., Aggarwal B.B. Multitargeting by curcumin as revealed by molecular interaction studies. Nat. Prod. Rep. 2011, 28:1937-1955.
10. 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.
11. Hung L.M., Chen J.K., Huang S.S., Lee R.S., Su M.J. Cardioprotective effect of resveratrol, a natural antioxidant derived from grapes. Cardiovasc. Res. 2000, 47:549-555.
12. Hung L.M., Su M.J., Chu W.K., Chiao C.W., Chan W.F., Chen J.K. The protective effect of resveratrols on ischaemia-reperfusion injuries of rat hearts is correlated with antioxidant efficacy. Br. J. Pharmacol. 2002, 135:1627-1633.
13. Jennings R.B., Sommers H.M., Smyth G.A., Flack H.A., Linn H. Myocardial necrosis induced by temporary occlusion of a coronary artery in the dog. Arch. Pathol. 1960, 70:68-78.
14. Kannan K., Jain S.K. Oxidative stress and apoptosis. Pathophysiology 2000, 7:153-163.
15. Kaspar J.W., Niture S.K., Jaiswal A.K. Nrf2:INrf2 (Keap1) signaling in oxidative stress. Free Radic. Biol. Med. 2009, 47:1304-1309.
16. Kim Y.S., Kwon J.S., Cho Y.K., Jeong M.H., Cho J.G., Park J.C., Kang J.C., Ahn Y. Curcumin reduces the cardiac ischemia-reperfusion injury: involvement of the toll-like receptor 2 in cardiomyocytes. J. Nutr. Biochem. 2012, 23:1514-1523.
17. Liu Z., Tang L., Zou P., Zhang Y., Wang Z., Fang Q., Jiang L., Chen G., Xu Z., Zhang H., Liang G. Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents. Eur. J. Med. Chem. 2014, 74:671-682.
18. Marczin N., El-Habashi N., Hoare G.S., Bundy R.E., Yacoub M. Antioxidants in myocardial ischemia-reperfusion injury: therapeutic potential and basic mechanisms. Arch. Biochem. Biophys. 2003, 420:222-236.
19. Mazumder A., Raghavan K., Weinstein J., Kohn K.W., Pommier Y. Inhibition of human immunodeficiency virus type-1 integrase by curcumin. Biochem. Pharmacol. 1995, 49:1165-1170.
20. Motterlini R., Foresti R., Bassi R., Green C.J. Curcumin, an antioxidant and anti-inflammatory agent, induces heme oxygenase-1 and protects endothelial cells against oxidative stress. Free Radic. Biol. Med. 2000, 28:1303-1312.
21. Niture S.K., Jaiswal A.K. INrf2 (Keap1) targets Bcl-2 degradation and controls cellular apoptosis. Cell Death Differ. 2011, 18:439-451.
22. Parmley L.F., Mufti A.G., Downey J.M. Allopurinol therapy of ischemic heart disease with infarct extension. Can. J. Cardiol. 1992, 8:280-286.
23. Ray P.S., Maulik G., Cordis G.A., Bertelli A.A., Bertelli A., Das D.K. The red wine antioxidant resveratrol protects isolated rat hearts from ischemia reperfusion injury. Free Radic. Biol. Med. 1999, 27:160-169.
24. Reimer K.A., Ideker R.E. Myocardial ischemia and infarction: anatomic and biochemical substrates for ischemic cell death and ventricular arrhythmias. Hum. Pathol. 1987, 18:462-475.
25. Sharma R.A., Euden S.A., Platton S.L., Cooke D.N., Shafayat A., Hewitt H.R., Marczylo T.H., Morgan B., Hemingway D., Plummer S.M. Phase I clinical trial of oral curcumin biomarkers of systemic activity and compliance. Clin. Cancer Res. 2004, 10:6847-6854.
26. Sharma R.A., Euden S.A., Platton S.L., Cooke D.N., Shafayat A., Hewitt H.R., Marczylo T.H., Morgan B., Hemingway D., Plummer S.M., Pirmohamed M., Gescher A.J., Steward W.P. Phase I clinical trial of oral curcumin: biomarkers of systemic activity and compliance. Clin. Cancer Res. 2004, 10:6847-6854.
27. Sharma R.A., Steward W.P., Gescher A.J. Pharmacokinetics and pharmacodynamics of curcumin. Adv. Exp. Med. Biol. 2007, 595:453-470.
28. Sharma R.A., Steward W.P., Gescher A.J. Pharmacokinetics and pharmacodynamics of curcumin, the molecular targets and therapeutic uses of curcumin in health and disease 2007, 453-470. Springer.
29. Shehzad A., Lee Y.S. Molecular mechanisms of curcumin action: signal transduction. Biofactors 2013, 39:27-36.
30. Shen L., Ji H.F. The pharmacology of curcumin: is it the degradation products?. Trends Mol. Med. 2012, 18:138-144.
31. Stewart D., Killeen E., Naquin R., Alam S., Alam J. Degradation of transcription factor Nrf2 via the ubiquitin-proteasome pathway and stabilization by cadmium. J. Biol. Chem. 2003, 278:2396-2402.
32. Tapia E., Soto V., Ortiz-Vega K.M., Zarco-Marquez G., Molina-Jijon E., Cristobal-Garcia M., Santamaria J., Garcia-Nino W.R., Correa F., Zazueta C., Pedraza-Chaverri J. Curcumin induces Nrf2 nuclear translocation and prevents glomerular hypertension, hyperfiltration, oxidant stress, and the decrease in antioxidant enzymes in 5/6 nephrectomized rats. Oxidative Med. Cell. Longev. 2012, 2012:269039.
33. Tian H., Zhang B., Di J., Jiang G., Chen F., Li H., Li L., Pei D., Zheng J. Keap1: one stone kills three birds Nrf2, IKKbeta and Bcl-2/Bcl-xL. Cancer Lett. 2012, 325:26-34.
34. Tipoe G.L., Leung T.M., Hung M.W., Fung M.L. Green tea polyphenols as an anti-oxidant and anti-inflammatory agent for cardiovascular protection. Cardiovasc. Hematol. Disord. Drug Targets 2007, 7:135-144.
35. Yang Y., Duan W., Lin Y., Yi W., Liang Z., Yan J., Wang N., Deng C., Zhang S., Li Y., Chen W., Yu S., Yi D., Jin Z. SIRT1 activation by curcumin pretreatment attenuates mitochondrial oxidative damage induced by myocardial ischemia reperfusion injury. Free Radic. Biol. Med. 2013, 65:667-679.
36. Yellon D.M., Hausenloy D.J. Myocardial reperfusion injury. N. Engl. J. Med. 2007, 357:1121-1135.