메뉴 건너뛰기




Volumn 30, Issue 2, 2012, Pages 558-567

The curcuminoid CLEFMA selectively induces cell death in H441 lung adenocarcinoma cells via oxidative stress

Author keywords

Cancer; CLEFMA; Curcumin; Oxidative stress; Reactive oxygen species

Indexed keywords

4 [3,5 BIS(2 CHLOROBENZYLIDENE 4 OXO PIPERIDINE 1 YL) 4 OXO 2 BUTENOIC ACID]; ACETYLCYSTEINE; ANTINEOPLASTIC AGENT; CATALASE; CURCUMIN; DOXORUBICIN; GEMCITABINE; GLUTAMIC ACID; GLUTATHIONE; GLUTATHIONE DISULFIDE; PACLITAXEL; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG; 4 (3,5 BIS(2 CHLOROBENZYLIDENE) 4 OXOPIPERIDINE 1 YL) 4 OXO 2 BUTENOIC ACID; 4-(3,5-BIS(2-CHLOROBENZYLIDENE)-4-OXOPIPERIDINE-1-YL)-4-OXO-2-BUTENOIC ACID; ANTIOXIDANT; BENZYLIDENE DERIVATIVE; NFE2L2 PROTEIN, HUMAN; PIPERIDONE DERIVATIVE;

EID: 84862273568     PISSN: 01676997     EISSN: 15730646     Source Type: Journal    
DOI: 10.1007/s10637-010-9610-4     Document Type: Article
Times cited : (23)

References (48)
  • 1
    • 70349138396 scopus 로고    scopus 로고
    • Synthesis and structural determination of 3, 5-bis(2-fluorobenzylidene)- 4-piperidone analogs of curcumin
    • Lagisetty P, Powell DR, Awasthi V (2009) Synthesis and structural determination of 3, 5-bis(2-fluorobenzylidene)-4-piperidone analogs of curcumin. J Mol Str 936:23-28
    • (2009) J Mol Str , vol.936 , pp. 23-28
    • Lagisetty, P.1    Powell, D.R.2    Awasthi, V.3
  • 4
    • 33744815937 scopus 로고    scopus 로고
    • Synthesis of EF24-tripeptide chloromethyl ketone: A novel curcumin-related anticancer drug delivery system
    • Sun A, Shoji M, Lu YJ, Liotta DC, Snyder JP (2006) Synthesis of EF24-tripeptide chloromethyl ketone: a novel curcumin-related anticancer drug delivery system. J Med Chem 49:3153-3158
    • (2006) J Med Chem , vol.49 , pp. 3153-3158
    • Sun, A.1    Shoji, M.2    Lu, Y.J.3    Liotta, D.C.4    Snyder, J.P.5
  • 5
    • 35348930988 scopus 로고    scopus 로고
    • EF24 induces G2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by increasing PTEN expression
    • Selvendiran K, Tong L, Vishwanath S, Bratasz A, Trigg NJ, Kutala VK, Hideg K, Kuppusamy P (2007) EF24 induces G2/M arrest and apoptosis in cisplatin-resistant human ovarian cancer cells by increasing PTEN expression. J Biol Chem 282:28609-28618
    • (2007) J Biol Chem , vol.282 , pp. 28609-28618
    • Selvendiran, K.1    Tong, L.2    Vishwanath, S.3    Bratasz, A.4    Trigg, N.J.5    Kutala, V.K.6    Hideg, K.7    Kuppusamy, P.8
  • 6
    • 77955471499 scopus 로고    scopus 로고
    • CLEFMA-an anti-proliferative curcuminoid from structure-activity relationship studies on 3, 5-bis(benzylidene)-4-piperidones
    • Lagisetty P, Vilekar P, Sahoo K, Anant S, Awasthi V (2010) CLEFMA-an anti-proliferative curcuminoid from structure-activity relationship studies on 3, 5-bis(benzylidene)-4-piperidones. Bioorg Med Chem 18:6109-6120
    • (2010) Bioorg Med Chem , vol.18 , pp. 6109-6120
    • Lagisetty, P.1    Vilekar, P.2    Sahoo, K.3    Anant, S.4    Awasthi, V.5
  • 8
    • 0032855959 scopus 로고    scopus 로고
    • K-ras oncogene mutation as a prognostic marker in non-small cell lung cancer: A combined analysis of 881 cases
    • Huncharek M, Muscat J, Geschwind JF (1999) K-ras oncogene mutation as a prognostic marker in non-small cell lung cancer: a combined analysis of 881 cases. Carcinogenesis 20:1507-1510
    • (1999) Carcinogenesis , vol.20 , pp. 1507-1510
    • Huncharek, M.1    Muscat, J.2    Geschwind, J.F.3
  • 9
    • 2542628931 scopus 로고    scopus 로고
    • Ras is involved in the negative control of autophagy through the class i PI3-kinase
    • Furuta S, Hidaka E, Ogata A, Yokota S, Kamata T (2004) Ras is involved in the negative control of autophagy through the class I PI3-kinase. Oncogene 23:3898-3904
    • (2004) Oncogene , vol.23 , pp. 3898-3904
    • Furuta, S.1    Hidaka, E.2    Ogata, A.3    Yokota, S.4    Kamata, T.5
  • 12
    • 33847047830 scopus 로고    scopus 로고
    • Clinical significance of the p53 pathway and associated gene therapy in non-small cell lung cancers
    • Huang CL, Yokomise H, Miyatake A (2007) Clinical significance of the p53 pathway and associated gene therapy in non-small cell lung cancers. Future Oncol (London, England) 3:83-93
    • (2007) Future Oncol (London, England) , vol.3 , pp. 83-93
    • Huang, C.L.1    Yokomise, H.2    Miyatake, A.3
  • 14
    • 37349067228 scopus 로고    scopus 로고
    • Oxidative stress induces autophagic cell death independent of apoptosis in transformed and cancer cells
    • Chen Y, McMillan-Ward E, Kong J, Israels SJ, Gibson SB (2008) Oxidative stress induces autophagic cell death independent of apoptosis in transformed and cancer cells. Cell Death Differ 15:171-182
    • (2008) Cell Death Differ , vol.15 , pp. 171-182
    • Chen, Y.1    McMillan-Ward, E.2    Kong, J.3    Israels, S.J.4    Gibson, S.B.5
  • 15
    • 67650071137 scopus 로고    scopus 로고
    • Targeting cancer cells by ROS-mediated mechanisms: A radical therapeutic approach?
    • Trachootham D, Alexandre J, Huang P (2009) Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nat Rev 8:579-591
    • (2009) Nat Rev , vol.8 , pp. 579-591
    • Trachootham, D.1    Alexandre, J.2    Huang, P.3
  • 16
    • 34247186472 scopus 로고    scopus 로고
    • Reactive oxygen species are essential for autophagy and specifically regulate the activity of Atg4
    • Scherz-Shouval R, Shvets E, Fass E, Shorer H, Gil L, Elazar Z (2007) Reactive oxygen species are essential for autophagy and specifically regulate the activity of Atg4. EMBO J 26:1749-1760
    • (2007) EMBO J , vol.26 , pp. 1749-1760
    • Scherz-Shouval, R.1    Shvets, E.2    Fass, E.3    Shorer, H.4    Gil, L.5    Elazar, Z.6
  • 17
    • 0021343351 scopus 로고
    • Measurement of cell numbers by means of the endogenous enzyme hexosaminidase. Applications to detection of lymphokines and cell surface antigens
    • Landegren U (1984) Measurement of cell numbers by means of the endogenous enzyme hexosaminidase. Applications to detection of lymphokines and cell surface antigens. J Immunol Methods 67:379-388
    • (1984) J Immunol Methods , vol.67 , pp. 379-388
    • Landegren, U.1
  • 19
    • 71049170436 scopus 로고    scopus 로고
    • Internal standard-based analysis of microarray data. Part 1: Analysis of differential gene expressions
    • Dozmorov I, Lefkovits I (2009) Internal standard-based analysis of microarray data. Part 1: analysis of differential gene expressions. Nucleic Acids Res 37:6323-6339
    • (2009) Nucleic Acids Res , vol.37 , pp. 6323-6339
    • Dozmorov, I.1    Lefkovits, I.2
  • 22
    • 0025732732 scopus 로고
    • Dose-dependent induction of apoptosis in human tumour cell lines by widely diverging stimuli
    • Lennon SV, Martin SJ, Cotter TG (1991) Dose-dependent induction of apoptosis in human tumour cell lines by widely diverging stimuli. Cell Prolif 24:203-214
    • (1991) Cell Prolif , vol.24 , pp. 203-214
    • Lennon, S.V.1    Martin, S.J.2    Cotter, T.G.3
  • 24
    • 70449107252 scopus 로고    scopus 로고
    • Redox-directed cancer therapeutics: Molecular mechanisms and opportunities
    • Wondrak GT (2009) Redox-directed cancer therapeutics: molecular mechanisms and opportunities. Antioxid Redox Signal 11:3013-3069
    • (2009) Antioxid Redox Signal , vol.11 , pp. 3013-3069
    • Wondrak, G.T.1
  • 25
    • 1442360000 scopus 로고    scopus 로고
    • Intrinsic oxidative stress in cancer cells: A biochemical basis for therapeutic selectivity
    • Hileman EO, Liu J, Albitar M, Keating MJ, Huang P (2004) Intrinsic oxidative stress in cancer cells: a biochemical basis for therapeutic selectivity. Cancer Chemother Pharmacol 53:209-219
    • (2004) Cancer Chemother Pharmacol , vol.53 , pp. 209-219
    • Hileman, E.O.1    Liu, J.2    Albitar, M.3    Keating, M.J.4    Huang, P.5
  • 26
    • 34547670578 scopus 로고    scopus 로고
    • Tumor-targeted induction of oxystress for cancer therapy
    • Fang J, Nakamura H, Iyer AK (2007) Tumor-targeted induction of oxystress for cancer therapy. J Drug Target 15:475-486
    • (2007) J Drug Target , vol.15 , pp. 475-486
    • Fang, J.1    Nakamura, H.2    Iyer, A.K.3
  • 27
    • 0032694302 scopus 로고    scopus 로고
    • The broad spectrum of responses to oxidants in proliferating cells: A new paradigm for oxidative stress
    • Davies KJ (1999) The broad spectrum of responses to oxidants in proliferating cells: a new paradigm for oxidative stress. IUBMB Life 48:41-47
    • (1999) IUBMB Life , vol.48 , pp. 41-47
    • Davies, K.J.1
  • 28
    • 0034456207 scopus 로고    scopus 로고
    • Oxidative stress, antioxidant defenses, and damage removal, repair, and replacement systems
    • Davies KJ (2000) Oxidative stress, antioxidant defenses, and damage removal, repair, and replacement systems. IUBMB Life 50:279-289
    • (2000) IUBMB Life , vol.50 , pp. 279-289
    • Davies, K.J.1
  • 29
    • 34648813720 scopus 로고    scopus 로고
    • ROS as signalling molecules: Mechanisms that generate specificity in ROS homeostasis
    • D'Autreaux B, Toledano MB (2007) ROS as signalling molecules: mechanisms that generate specificity in ROS homeostasis. Nat Rev Mol Cell Biol 8:813-824
    • (2007) Nat Rev Mol Cell Biol , vol.8 , pp. 813-824
    • D'Autreaux, B.1    Toledano, M.B.2
  • 30
    • 1942520367 scopus 로고    scopus 로고
    • Nrf2 signaling in coordinated activation of antioxidant gene expression
    • Jaiswal AK (2004) Nrf2 signaling in coordinated activation of antioxidant gene expression. Free Radic Biol Med 36:1199-1207
    • (2004) Free Radic Biol Med , vol.36 , pp. 1199-1207
    • Jaiswal, A.K.1
  • 32
    • 0033800922 scopus 로고    scopus 로고
    • Regulation of genes encoding NAD(P)H: Quinone oxidoreductases
    • Jaiswal AK (2000) Regulation of genes encoding NAD(P)H: quinone oxidoreductases. Free Radic Biol Med 29:254-262
    • (2000) Free Radic Biol Med , vol.29 , pp. 254-262
    • Jaiswal, A.K.1
  • 33
    • 0025368036 scopus 로고
    • Regulation of glutathione S-transferase Ya subunit gene expression: Identification of a unique xenobiotic-responsive element controlling inducible expression by planar aromatic compounds
    • Rushmore TH, King RG, Paulson KE, Pickett CB (1990) Regulation of glutathione S-transferase Ya subunit gene expression: identification of a unique xenobiotic-responsive element controlling inducible expression by planar aromatic compounds. Proc Natl Acad Sci USA 87:3826-3830
    • (1990) Proc Natl Acad Sci USA , vol.87 , pp. 3826-3830
    • Rushmore, T.H.1    King, R.G.2    Paulson, K.E.3    Pickett, C.B.4
  • 34
    • 0028914295 scopus 로고
    • Identification of a putative antioxidant response element in the 5κ-flanking region of the human gamma-glutamylcysteine synthetase heavy subunit gene
    • Mulcahy RT, Gipp JJ (1995) Identification of a putative antioxidant response element in the 5κ-flanking region of the human gamma-glutamylcysteine synthetase heavy subunit gene. Biochem Biophys Res Commun 209:227-233
    • (1995) Biochem Biophys Res Commun , vol.209 , pp. 227-233
    • Mulcahy, R.T.1    Gipp, J.J.2
  • 35
    • 0033083205 scopus 로고    scopus 로고
    • Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: Implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase
    • Burczynski ME, Lin HK, Penning TM (1999) Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res 59:607-614
    • (1999) Cancer Res , vol.59 , pp. 607-614
    • Burczynski, M.E.1    Lin, H.K.2    Penning, T.M.3
  • 36
    • 34547692874 scopus 로고    scopus 로고
    • Human aldo-keto reductases: Function, gene regulation, and single nucleotide polymorphisms
    • Penning TM, Drury JE (2007) Human aldo-keto reductases: function, gene regulation, and single nucleotide polymorphisms. Arch Biochem Biophys 464:241-250
    • (2007) Arch Biochem Biophys , vol.464 , pp. 241-250
    • Penning, T.M.1    Drury, J.E.2
  • 38
    • 0035879035 scopus 로고    scopus 로고
    • Cloning and characterization of the 5κ-flanking region of the rat glutamatecysteine ligase catalytic subunit
    • Yang H, Wang J, Huang ZZ, Ou X, Lu SC (2001) Cloning and characterization of the 5κ-flanking region of the rat glutamatecysteine ligase catalytic subunit. Biochem J 357:447-455
    • (2001) Biochem J , vol.357 , pp. 447-455
    • Yang, H.1    Wang, J.2    Huang, Z.Z.3    Ou, X.4    Lu, S.C.5
  • 39
    • 0034816638 scopus 로고    scopus 로고
    • Cloning and analysis of the rat glutamate-cysteine ligase modifier subunit promoter
    • Yang H, Wang J, Ou X, Huang ZZ, Lu SC (2001) Cloning and analysis of the rat glutamate-cysteine ligase modifier subunit promoter. Biochem Biophys Res Commun 285:476-482
    • (2001) Biochem Biophys Res Commun , vol.285 , pp. 476-482
    • Yang, H.1    Wang, J.2    Ou, X.3    Huang, Z.Z.4    Lu, S.C.5
  • 40
    • 0035951825 scopus 로고    scopus 로고
    • The reactive oxygen species-and Michael acceptor-inducible human aldo-keto reductase AKR1C1 reduces the alpha, beta-unsaturated aldehyde 4-hydroxy-2-nonenal to 1, 4-dihydroxy-2-nonene
    • Burczynski ME, Sridhar GR, Palackal NT, Penning TM (2001) The reactive oxygen species-and Michael acceptor-inducible human aldo-keto reductase AKR1C1 reduces the alpha, beta-unsaturated aldehyde 4-hydroxy-2-nonenal to 1, 4-dihydroxy-2-nonene. J Biol Chem 276:2890-2897
    • (2001) J Biol Chem , vol.276 , pp. 2890-2897
    • Burczynski, M.E.1    Sridhar, G.R.2    Palackal, N.T.3    Penning, T.M.4
  • 41
    • 0034662467 scopus 로고    scopus 로고
    • Role of NAD(P)H:quinone oxidoreductase 1 (DT diaphorase) in protection against quinone toxicity
    • Joseph P, Long DJ 2nd, Klein-Szanto AJ, Jaiswal AK (2000) Role of NAD(P)H:quinone oxidoreductase 1 (DT diaphorase) in protection against quinone toxicity. Biochem Pharmacol 60:207-214
    • (2000) Biochem Pharmacol , vol.60 , pp. 207-214
    • Joseph, P.1    Long II, D.J.2    Klein-Szanto, A.J.3    Jaiswal, A.K.4
  • 42
    • 0034009970 scopus 로고    scopus 로고
    • NAD(P)H:Quinone oxidoreductase activity is the principal determinant of beta-lapachone cytotoxicity
    • Pink JJ, Planchon SM, Tagliarino C, Varnes ME, Siegel D, Boothman DA (2000) NAD(P)H:Quinone oxidoreductase activity is the principal determinant of beta-lapachone cytotoxicity. J Biol Chem 275:5416-5424
    • (2000) J Biol Chem , vol.275 , pp. 5416-5424
    • Pink, J.J.1    Planchon, S.M.2    Tagliarino, C.3    Varnes, M.E.4    Siegel, D.5    Boothman, D.A.6
  • 44
    • 0035834304 scopus 로고    scopus 로고
    • Modulation of heme oxygenase in tissue injury and its implication in protection against gastrointestinal diseases
    • Guo X, Shin VY, Cho CH (2001) Modulation of heme oxygenase in tissue injury and its implication in protection against gastrointestinal diseases. Life Sci 69:3113-3119
    • (2001) Life Sci , vol.69 , pp. 3113-3119
    • Guo, X.1    Shin, V.Y.2    Cho, C.H.3
  • 45
    • 0030973242 scopus 로고    scopus 로고
    • Alteration of transcriptional and post-transcriptional expression of gamma-glutamylcysteine synthetase by diethyl maleate
    • Sekhar KR, Long M, Long J, Xu ZQ, Summar ML, Freeman ML (1997) Alteration of transcriptional and post-transcriptional expression of gamma- glutamylcysteine synthetase by diethyl maleate. Radiat Res 147:592-597
    • (1997) Radiat Res , vol.147 , pp. 592-597
    • Sekhar, K.R.1    Long, M.2    Long, J.3    Xu, Z.Q.4    Summar, M.L.5    Freeman, M.L.6
  • 46
    • 0031735363 scopus 로고    scopus 로고
    • Gamma-glutamylcysteine synthetase: MRNA stabilization and independent subunit transcription by 4-hydroxy-2-nonenal
    • Liu RM, Gao L, Choi J, Forman HJ (1998) Gamma-glutamylcysteine synthetase: mRNA stabilization and independent subunit transcription by 4-hydroxy-2-nonenal. Am J Physiol 275:L861-L869
    • (1998) Am J Physiol , vol.275
    • Liu, R.M.1    Gao, L.2    Choi, J.3    Forman, H.J.4
  • 47
    • 77951529058 scopus 로고    scopus 로고
    • Kleinjans JC Global gene expression analysis reveals differences in cellular responses to hydroxyland superoxide anion radical-induced oxidative stress in caco-2 cells
    • Briede JJ, van Delft JM, de Kok TM, van Herwijnen MH, Maas LM, Gottschalk RW, Kleinjans JC Global gene expression analysis reveals differences in cellular responses to hydroxyland superoxide anion radical-induced oxidative stress in caco-2 cells. Toxicol Sci 114:193-203
    • Toxicol Sci , vol.114 , pp. 193-203
    • Briede, J.J.1    Van Delft, J.M.2    De Kok, T.M.3    Van Herwijnen, M.H.4    Maas, L.M.5    Gottschalk, R.W.6
  • 48
    • 0029032154 scopus 로고
    • Low-level oxidative stress causes cell-cycle specific arrest in cultured cells
    • Clopton DA, Saltman P (1995) Low-level oxidative stress causes cell-cycle specific arrest in cultured cells. Biochem Biophys Res Commun 210:189-196
    • (1995) Biochem Biophys Res Commun , vol.210 , pp. 189-196
    • Clopton, D.A.1    Saltman, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.