O-Alkylated derivatives of quercetin induce apoptosis of MCF-7 cells via a caspase-independent mitochondrial pathway

Chemico-Biological Interactions

Volumn 242, Issue , 2015, Pages 91-98

  Liao, Han ^a   Bao, Xinran ^a   Zhu, Jie ^a   Qu, Jiao ^a   Sun, Yong ^a   Ma, Xiaodong ^a   Wang, Enxia ^a   Guo, Xin ^a   Kang, Qi ^a   Zhen, Yuhong ^a  

^a DALIAN MEDICAL UNIVERSITY   (China)

Author keywords

Alkylated quercetin derivatives; Apoptosis; Apoptosis inducing factor; Breast cancer; Endonuclease G

Indexed keywords

7 O BUTYLQUERCETIN; 7 O GERANYLQUERCETIN; ACETYLCYSTEINE; BENZYLOXYCARBONYLVALYLALANYLASPARTYL FLUOROMETHYL KETONE; CASPASE; ENDONUCLEASE G; QUERCETIN; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; 7-O-BUTYLQUERCETIN; 7-O-GERANYLQUERCETIN; AIFM1 PROTEIN, HUMAN; APOPTOSIS INDUCING FACTOR; DEOXYRIBONUCLEASE;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENDOPLASMIC RETICULUM; HUMAN; HUMAN CELL; MCF 7 CELL LINE; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRION; WESTERN BLOTTING; ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; METABOLISM; PROCEDURES;

APOPTOSIS; APOPTOSIS INDUCING FACTOR; CASPASES; DRUG SCREENING ASSAYS, ANTITUMOR; ENDODEOXYRIBONUCLEASES; ENDOPLASMIC RETICULUM; HUMANS; MCF-7 CELLS; MITOCHONDRIA; QUERCETIN; REACTIVE OXYGEN SPECIES;

EID: 84943245576     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2015.09.022     Document Type: Article

References (34)

1. E. Altobelli, and A. Lattanzi Breast cancer in European Union: an update of screening programmes as of March 2014 (review) Int. J. Oncol. 45 2014 1785 1792
2. J.S. Choi, Y.J. Piao, and K.W. Kang Effects of quercetin on the bioavailability of doxorubicin in rats: role of CYP3A4 and p-gp inhibition by quercetin Arch. Pharm. Res. 34 2011 607 613
3. K.V. Hirpara, P. Aggarwal, A.J. Mukherjee, N. Joshi, and A.C. Burman Quercetin and is derivatives: synthesis, pharmacological uses with special emphasis on anti-tumor properties and prodrug with enhanced bio-availability Anti Cancer Agent. Me 9 2009 138 161
4. S. Jaramillo, S. Lopez, L.M. Varela, R. Rodriguez-Arcos, A. Jimenez, R. Abia, R. Guillen, and F.J.G. Muriana The flavonol isorhamnetin exhibits cytotoxic effects on human colon cancer cells J. Agric. Food Chem. 58 2010 10869 10875
5. Y.K. Lee, J.T. Hwang, D.Y. Kwon, Y.J. Surh, and O.J. Park Induction of apoptosis by quercetin is mediated through AMPKa1/ASK1/p38 pathway Cancer Lett. 292 2010 228 236
6. P.J. Mulholland, D.R. Ferry, D. Anderson, S.A. Hussain, A.M. Young, J.E. Cook, E. Hodgkin, L.W. Seymour, and D.R. Kerr Pre-clinical and clinical study of QC12, a water-soluble, prodrug of quercetin Ann. Oncol. 12 2001 245 248
7. L. Zhang, E. Angst, J.L. Park, A. Moro, D.W. Dawson, H.A. Reber, G. Eibl, O.J. Hines, V.L. Go, and Q.Y. Lu Quercetin aglycone is bioavailable in murine pancreas and pancreatic xenografts J. Agric. Food Chem. 58 2010 7252 7257
8. X. Wen, and T. Walle Methylated flavonoids have greatly improved intestinal absorption and metabolic stability Drug Metab. Dispos. 34 2006 1786 1792
9. T. Walle Methylation of dietary flavones greatly improves their hepatic metabolic stability and intestinal absorption Mol. Pharm. 4 2007 826 832
10. M.H. Pan, C.L. Lin, J.H. Tsai, C.T. Ho, and W.J. Chen 3,5,3′,4',5'-Pentamethoxystilbene (MR-5), a synthetically methoxylated analogue of resveratrol, inhibits growth and induces G1 cell cycle arrest of human breast carcinoma MCF-7 cells J. Agric. Food Chem. 58 2010 226 234
11. Y. Zheng, Y. Xin, X. Shi, and Y. Guo Cytotoxicity of monascus pigments and their derivatives to human cancer cells J. Agric. Food Chem. 58 2010 9523 9528
12. M. Fiorani, A. Guidarelli, M. Blasa, C. Azzolini, M. Candiracci, E. Piatti, and O. Cantoni Mitochondria accumulate large amounts of quercetin: prevention of mitochondrial damage and release upon oxidation of the extramitochondrial fraction of the flavonoid J. Nutr. Biochem. 21 2010 397 404
13. F. Kugawa, K. Matsumoto, and M. Aoki Apoptosis-like cell death of human breast cancer cell line MCF-7 induced by buprenorphine hydrochloride Life Sci. 75 2004 287 299
14. X. Liu, H. Zou, P. Widlak, W. Garrard, and X. Wang Activation of the apoptotic endonuclease DFF40 (caspase-activated DNase or nuclease) J. Biol. Chem. 274 1999 13836 13840
15. S. Orrenius Mitochondrial regulation of apoptotic cell death Toxicol. Lett. 149 2004 19 23
16. J.D. Ly, D.R. Grubb, and A. Lawen The mitochondrial membrane potential (Δψ m) in apoptosis; an update Apoptosis 8 2003 115 128
17. J.C. Martinou, and R.J. Oule Mitochondria in apoptosis: Bcl-2 family members and mitochondrial dynamics Dev. Cell. 21 2011 92 101
18. S. Oyadomari, and M. Mori Roles of CHOP/GADD153 in endoplasmic reticulum stress Cell Death Differ. 11 2004 381 389
19. J. Wu, and R.J. Kaufman From acute ER stress to physiological roles of the unfolded protein response Cell Death Differ. 13 2006 374 384
20. H.P. Harding, Y. Zhang, A. Bertolotti, H. Zeng, and D. Ron Perk is essential for translational regulation and cell survival during the unfolded protein response Mol. Cell. 5 2000 897 904
21. H. Otera, S. Ohsakaya, Z.I. Nagaura, N. Ishihara, and K. Mihara Export of mitochondrial AIF in response to proapoptotic stimuli depends on processing at the intermembrane space Embo J. 24 2005 1375 1386
22. E. Norberg, S. Orrenius, and B. Zhivotovsky Mitochondrial regulation of cell death: processing of apoptosis-inducing factor (AIF) Biochem. Bioph. Res. Co. 396 2010 95 100
23. G. Notas, A.P. Nifli, M. Kampa, V. Pelekanou, V.I. Alexaki, P. Theodoropoulos, J. Vercauteren, and E. Castanas Quercetin accumulates in nuclear structures and triggers specific gene expression in epithelial cells J. Nutr. Biochem. 23 2012 656 666
24. K. Mandery, K. Bujok, I. Schmidt, M. Keiser, W. Siegmund, B. Balk, J. König, M.F. Fromm, and H. Glaeser Influence of the flavonoids apigenin, kaempferol and quercetin on the function of organic anion transporting polypeptides 1A2 and 2B1 Biochem. Pharm. 80 2010 1746 1753
25. S. Kitagawa Inhibitory effects of polyphenols on P-glycoprotein-mediated transport Biol. Pharm. Bull. 29 2006 1 6
26. X. Wang, A.W. Wolkoff, and M.E. Morris Flavonoids as a novel class of human organic anion-transporting polypeptide OATP1B1 (OATP-C) modulators Drug Metab. Dispos. 33 2005 1666 1672
27. J. Yuan, I.L.K. Wong, T. Jiang, S.W. Wang, T. Liu, B.J. Wen, L.M.C. Chow, and B.W. Sheng Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells Eur. J. Med. Chem. 54 2012 413 422
28. D. Metodiewa, A.K. Jaiswal, N. Cenas, E. Dickancaité, and J. Segura-Aguilar Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product Free Radic. Bio. Med. 26 1999 107 116
29. R.U. Jänicke MCF-7 breast carcinoma cells do not express caspase-3 Breast Cancer Res. Tr. 117 2009 219 221
30. W.C. Earnshaw, L.M. Martins, and S.H. Kaufmann Mammalian caspases: structure, activation, substrates, and functions during apoptosis Annu. Rev. Biochem. 68 1999 383 424
31. B.B. Wolf, M. Schuler, F. Echeverri, and D.R. Green Caspase-3 is the primary activator of apoptotic DNA fragmentation via DNA fragmentation factor-45/inhibitor of caspase-activated DNase inactivation J. Biol. Chem. 274 1999 30651 30656
32. R.L. Low Mitochondrial endonuclease G function in apoptosis and mtDNA metabolism: a historical perspective Mitochondrion 2 2003 225 236
33. P. Widlak, L.Y. Li, X. Wang, and W.T. Garrard Action of recombinant human apoptotic endonuclease G on naked DNA and chromatin substrates: cooperation with exonuclease and Dnase J. Biol. Chem. 276 2001 48404 48409
34. K.W. Kinnally, P.M. Peixoto, S.Y. Ryu, and L.M. Dejean Is mPTP the gatekeeper for necrosis, apoptosis, or both? Biochim. Biophys. Acta 1831 2011 616 622