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Volumn 2, Issue 5, 2011, Pages 353-357

Indomethacin analogues that enhance doxorubicin cytotoxicity in multidrug resistant cells without cox inhibitory activity

Author keywords

Cancer; conformation analysis; cytotoxicity; drug design; nitrogen heterocycles

Indexed keywords

CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DOXORUBICIN; INDOLE; INDOMETACIN; MULTIDRUG RESISTANCE PROTEIN 1; NONSTEROID ANTIINFLAMMATORY AGENT;

EID: 79956090533     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml100292y     Document Type: Article
Times cited : (26)

References (21)
  • 1
    • 42449161959 scopus 로고    scopus 로고
    • Recent advances on the molecular mechanisms involved in the drug resistance of cancer cells and novel targeting therapies
    • DOI 10.1038/sj.clpt.6100296, PII 6100296
    • Mineault, M.; Hauke, R.; Batra, S. K. Recent Advances on the Molecular Mechanisms Involved in the Drug Resistance of Cancer Cells and Novel Targeting Therapies Clin. Pharmacol. Ther. 2008, 83, 673-691 (Pubitemid 351559599)
    • (2008) Clinical Pharmacology and Therapeutics , vol.83 , Issue.5 , pp. 673-691
    • Mimeault, M.1    Hauke, R.2    Batra, S.K.3
  • 2
    • 13744254574 scopus 로고    scopus 로고
    • Cyclooxygenase-2 and epidermal growth factor receptor: Pharmacologic targets for chemoprevention
    • DOI 10.1200/JCO.2005.09.112
    • Dannenberg, A. J.; Lippman, S. M.; Mann, J. R.; Subbaramaiah, K.; Dubois, R. N. Cyclooxygenase-2 and Epidermal Growth Factor Receptor: Pharmacologic Targets for Chemoprevention J. Clin. Oncol. 2005, 23, 254-266 (Pubitemid 46206877)
    • (2005) Journal of Clinical Oncology , vol.23 , Issue.2 , pp. 254-266
    • Dannenberg, A.J.1    Lippman, S.M.2    Mann, J.R.3    Subbaramaiah, K.4    DuBois, R.N.5
  • 3
    • 33744462862 scopus 로고    scopus 로고
    • Indomethacin overcomes doxorubicin resistance with inhibiting multi-drug resistance protein 1 (MRP1)
    • DOI 10.1007/s00280-005-0162-9
    • Matsunaga, S.; Asano, T.; Asano, A. T.; Fukunaga, Y. Indomethacin Overcomes Doxorubicin Resistance with Inhibiting Multi-drug Resistance Protein 1 (MRP1) Cancer Chemother. Pharmacol. 2006, 58, 348-353 (Pubitemid 43800738)
    • (2006) Cancer Chemotherapy and Pharmacology , vol.58 , Issue.3 , pp. 348-353
    • Matsunaga, S.1    Asano, T.2    Tsutsuda-Asano, A.3    Fukunaga, Y.4
  • 4
    • 77649184903 scopus 로고    scopus 로고
    • Celecoxib Inhibits MDR1 Expression through COX-2-dependent Mechanism in Human Hepatocellular Carcinoma (HepG2) Cell Line
    • Roy, K. R.; Reddy, G. V.; Maitreyi, L.; Agarwal, S.; Achari, C.; Vali, S.; Reddanna, P. Celecoxib Inhibits MDR1 Expression through COX-2-dependent Mechanism in Human Hepatocellular Carcinoma (HepG2) Cell Line Cancer Chemother. Pharmacol. 2010, 65, 903-911
    • (2010) Cancer Chemother. Pharmacol. , vol.65 , pp. 903-911
    • Roy, K.R.1    Reddy, G.V.2    Maitreyi, L.3    Agarwal, S.4    Achari, C.5    Vali, S.6    Reddanna, P.7
  • 5
    • 0036208533 scopus 로고    scopus 로고
    • The MDR phenotype is associated with the expression of COX-2 and iNOS in a human hepatocellular carcinoma cell line
    • DOI 10.1053/jhep.2002.32469
    • Fantappie, O.; Masini, E.; Sardi, I.; Raimondi, L.; Bani, D.; Solazzo, M.; Cannacci, A.; Mazzanti, R. The MDR Phenotype is Associated with the Expression of COX-2 and iNOS in a Human Hepatocellular Carcinoma Cell Line Hepatology 2002, 35, 843-852 (Pubitemid 34258378)
    • (2002) Hepatology , vol.35 , Issue.4 , pp. 843-852
    • Fantappie, O.1    Masini, E.2    Sardi, I.3    Raimondi, L.4    Bani, D.5    Solazzo, M.6    Vannacci, A.7    Mazzanti, R.8
  • 6
    • 66849101753 scopus 로고    scopus 로고
    • Enhancement of Doxorubicin Cytotoxicity on Human Esophageal Squamous Cell Carcinoma Cells by Indomethacin and 4-[5-(4-Chlorophenyl)-3-(trifluoromethyl)-1 H -pyrazol-1-yl]benzenesulfonamide (SC236) via Inhibiting P-Glycoprotein Activity
    • Yu, L.; Wu, W. K. K.; Li, Z. J.; Liu, Q. C.; Li, H. T.; Wu, Y. C.; Cho, C. H. Enhancement of Doxorubicin Cytotoxicity on Human Esophageal Squamous Cell Carcinoma Cells by Indomethacin and 4-[5-(4-Chlorophenyl)-3-(trifluoromethyl)-1 H -pyrazol-1-yl]benzenesulfonamide (SC236) via Inhibiting P-Glycoprotein Activity Mol. Pharmacol. 2009, 75, 1364-1373
    • (2009) Mol. Pharmacol. , vol.75 , pp. 1364-1373
    • Yu, L.1    Wu, W.K.K.2    Li, Z.J.3    Liu, Q.C.4    Li, H.T.5    Wu, Y.C.6    Cho, C.H.7
  • 7
    • 0030010696 scopus 로고    scopus 로고
    • 2 synthase cyclooxygenase active site
    • DOI 10.1021/bi952776w
    • Loll, P. J.; Picot, D.; Ekabo, O.; Garavito, R. M. Synthesis and Use of Iodinated Nonsteroidal Antiinflammatory Drug Analogs as Crystallographic Probes of the Prostaglandin H2 Synthase Cyclooxygenase Active Site Biochemistry 1996, 35, 7330-7340 (Pubitemid 26191283)
    • (1996) Biochemistry , vol.35 , Issue.23 , pp. 7330-7340
    • Loll, P.J.1    Picot, D.2    Ekabo, O.3    Garavito, R.M.4
  • 9
    • 33646946173 scopus 로고    scopus 로고
    • Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles
    • DOI 10.1021/jo060308u
    • Arisawa, M.; Terada, Y.; Takahashi, K.; Nishida, A. Development of Isomerization and Cycloisomerization with Use of a Ruthenium Hydride with N -Heterocyclic Carbene and Its Application to the Synthesis of Heterocycles J. Org. Chem. 2006, 71, 4255-4261 (Pubitemid 43794633)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.11 , pp. 4255-4261
    • Arisawa, M.1    Terada, Y.2    Takahashi, K.3    Nakagawa, M.4    Nishida, A.5
  • 10
    • 70349224179 scopus 로고    scopus 로고
    • Aromatic Enamide/Ene Metathesis toward Substituted Indoles and Its Application to the Synthesis of Indomethacins
    • Kasaya, Y.; Hoshi, K.; Terada, Y.; Nishida, A.; Shuto, S.; Arisawa, M. Aromatic Enamide/Ene Metathesis toward Substituted Indoles and Its Application to the Synthesis of Indomethacins Eur. J. Org. Chem. 2009, 4606-4613
    • (2009) Eur. J. Org. Chem. , pp. 4606-4613
    • Kasaya, Y.1    Hoshi, K.2    Terada, Y.3    Nishida, A.4    Shuto, S.5    Arisawa, M.6
  • 11
    • 79956138030 scopus 로고    scopus 로고
    • Demethoxy indomethacine 1b would provide some information concerning an effect of the methoxy group.
    • Demethoxy indomethacine 1b would provide some information concerning an effect of the methoxy group.
  • 12
    • 79956081470 scopus 로고    scopus 로고
    • Energy difference of 1d is lower than those of 1a - c, which is enough to restrict the conformation. Energy difference of 1c is higher than that of 1b, probably due to the influence of the steric bulk of the ethyl.
    • Energy difference of 1d is lower than those of 1a - c, which is enough to restrict the conformation. Energy difference of 1c is higher than that of 1b, probably due to the influence of the steric bulk of the ethyl.
  • 14
    • 0014228967 scopus 로고
    • 1-Acyl-indoles. II. A New Syntheses of 1-(p-chlorobenzoyl)-5-methoxy-3- indolylacetic Acid and Its Polymorphism
    • Yamamoto, H. 1-Acyl-indoles. II. A New Syntheses of 1-(p-chlorobenzoyl)- 5-methoxy-3-indolylacetic Acid and Its Polymorphism Chem. Pharm. Bull. 1968, 16, 17-21
    • (1968) Chem. Pharm. Bull. , vol.16 , pp. 17-21
    • Yamamoto, H.1
  • 15
    • 30144432668 scopus 로고    scopus 로고
    • A new entry to the synthesis of 2,3-disubstituted indoles
    • DOI 10.1021/ol052179u
    • Mukai, C.; Takahashi, Y. A. New Entry to the Synthesis of 2,3-Disubstituted Indoles Org. Lett. 2005, 7, 5793-5796 (Pubitemid 43052854)
    • (2005) Organic Letters , vol.7 , Issue.26 , pp. 5793-5796
    • Mukai, C.1    Takahashi, Y.2
  • 16
    • 79956062380 scopus 로고    scopus 로고
    • Compound 1b is a known.
    • Compound 1b is a known.
  • 17
    • 79956074749 scopus 로고    scopus 로고
    • An NOE experiment of 1d could not performed, since the aromatic proton signals of the 4-chlorobenzoyl and the 2-phenyl groups were overlapped and could not be assigned.
    • An NOE experiment of 1d could not performed, since the aromatic proton signals of the 4-chlorobenzoyl and the 2-phenyl groups were overlapped and could not be assigned.
  • 18
    • 79956071730 scopus 로고    scopus 로고
    • CCDC 814524 and CCDC 814525 contain the supplementary crystallographic data for 1a and 1d, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 814524 and CCDC 814525 contain the supplementary crystallographic data for 1a and 1d, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif.
  • 19
    • 41549115914 scopus 로고    scopus 로고
    • Rayleigh Scattering, Long-time Tails, and the Harmonic Spectrum of Topologically Disordered Systems
    • Hédoux, A.; Guinet, Y.; Capet, F.; Paccou, L.; Descamps, M. Rayleigh Scattering, Long-time Tails, and the Harmonic Spectrum of Topologically Disordered Systems Phys. Rev. B 2008, 77, 094205
    • (2008) Phys. Rev. B , vol.77 , pp. 094205
    • Hédoux, A.1    Guinet, Y.2    Capet, F.3    Paccou, L.4    Descamps, M.5
  • 20
    • 0036347536 scopus 로고    scopus 로고
    • Structure-activity Relationship of Indomethacin Analogues for MRP-1, COX-1 and COX-2 Inhibition
    • Touhey, S.; O'Connor, R.; Plunkett, S.; Maguire, A.; Clynes, M. Structure-activity Relationship of Indomethacin Analogues for MRP-1, COX-1 and COX-2 Inhibition Eur. J. Cancer 2002, 38, 1661-1670
    • (2002) Eur. J. Cancer , vol.38 , pp. 1661-1670
    • Touhey, S.1    O'Connor, R.2    Plunkett, S.3    Maguire, A.4    Clynes, M.5
  • 21
    • 13944277046 scopus 로고    scopus 로고
    • Modulation of MRP-1-mediated multidrug resistance by indomethacin analogues
    • DOI 10.1021/jm0499099
    • Rosenbaum, C.; Röhrs, S.; Müller, O.; Waldmann, H. Modulation of MRP-1-Mediated Multidrug Resistance by Indomethacin Analogues J. Med. Chem. 2005, 48, 1179-1187 (Pubitemid 40270460)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.4 , pp. 1179-1187
    • Rosenbaum, C.1    Rohrs, S.2    Muller, O.3    Waldmann, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.