메뉴 건너뛰기




Volumn 55, Issue 18, 2012, Pages 8152-8163

Design and synthesis of indomethacin analogues that inhibit P-glycoprotein and/or multidrug resistant protein without Cox inhibitory activity

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 CHLOROBENZOYL) 7 ETHYL 2 METHYLINDOLE 3 YL ACETIC ACID; 1 (4 CHLOROBENZOYL) 7 METHOXY 2 METHYLINDOLE 3 YL ACETIC ACID; 2 [1 (4 CHLOROBENZOYL) 2 ETHYLINDOL 3 YL]ACETIC ACID; 2 [1 (4 CHLOROBENZOYL) 2 METHYLINDOL 3 YL]ACETIC ACID; 2 [1 (4 CHLOROBENZOYL) 2 PHENYLINDOLE 3 YL]ACETIC ACID; 2 [1 (4 CHLOROBENZOYL) 2,7 DIMETHYLINDOLE 3 YL]ACETIC ACID; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DOXORUBICIN; INDOMETACIN; MULTIDRUG RESISTANCE PROTEIN; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG;

EID: 84866852586     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301084z     Document Type: Article
Times cited : (30)

References (38)
  • 1
    • 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)- 1H-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)- 1H-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
  • 2
    • 13944277046 scopus 로고    scopus 로고
    • Modulation of MRP-1-mediated Multidrug Resistance by Indomethacin Analogues
    • 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
    • (2005) J. Med. Chem. , vol.48 , pp. 1179-1187
    • Rosenbaum, C.1    Röhrs, S.2    Müller, O.3    Waldmann, H.4
  • 3
    • 13744254574 scopus 로고    scopus 로고
    • Cyclooxygenase-2 and Epidermal Growth Factor Receptor: Pharmacologic Targets for Chemoprevention
    • Dannenberg, A. J.; Lippman, S. M.; Mann, J. R.; Subbaramaiah, K.; Dubois, R. N. J. Cyclooxygenase-2 and Epidermal Growth Factor Receptor: Pharmacologic Targets for Chemoprevention Clin. Oncol. 2005, 23, 254-266
    • (2005) Clin. Oncol. , vol.23 , pp. 254-266
    • Dannenberg, A.J.1    Lippman, S.M.2    Mann, J.R.3    Subbaramaiah, K.4    Dubois, R.N.J.5
  • 4
    • 0030010696 scopus 로고    scopus 로고
    • Synthesis and Use of Iodinated Nonsteroidal Antiinflammatory Drug Analogues as Crystallographic Probes of the Prostaglandin H2 Synthase Cyclooxygenase Active Site
    • Loll, P. J.; Picot, D.; Ekabo, O.; Garavito, R. M. Synthesis and Use of Iodinated Nonsteroidal Antiinflammatory Drug Analogues as Crystallographic Probes of the Prostaglandin H2 Synthase Cyclooxygenase Active Site Biochemistry 1996, 35, 7330-7340
    • (1996) Biochemistry , vol.35 , pp. 7330-7340
    • Loll, P.J.1    Picot, D.2    Ekabo, O.3    Garavito, R.M.4
  • 6
    • 79951653586 scopus 로고    scopus 로고
    • Atropisomerism Observed in Indometacin Derivatives
    • Takahashi and Natsugari introduced atropisomerism to the N -benzoylated indole moiety of indomethacin to elucidate the active conformation of indomethacin that differentiates cyclooxygenase-1 (COX-1) from COX-2 by varying the substituents at the 2′- and 6′-positions of indomethacin (twisted conformation). Takahashi, H.; Wakamatsu, S.; Tabata, H.; Oshitari, T.; Harada, A.; Inoue, K.; Natsugari, H. Atropisomerism Observed in Indometacin Derivatives Org. Lett. 2011, 13, 760-763
    • (2011) Org. Lett. , vol.13 , pp. 760-763
    • Takahashi, H.1    Wakamatsu, S.2    Tabata, H.3    Oshitari, T.4    Harada, A.5    Inoue, K.6    Natsugari, H.7
  • 7
    • 79956090533 scopus 로고    scopus 로고
    • Indomethacin Analogues that Enhance Doxorubicin Cytotoxicity in Multidrug Resistant Cells without Cox Inhibitory Activity
    • Preliminary results of this work were reported as a communication. Arisawa, M.; Kasaya, Y.; Obata, T.; Sasaki, T.; Ito, M.; Abe, H.; Ito, Y.; Yamano, A.; Shuto, S. Indomethacin Analogues that Enhance Doxorubicin Cytotoxicity in Multidrug Resistant Cells without Cox Inhibitory Activity ACS Med. Chem. Lett 2011, 2, 353-357
    • (2011) ACS Med. Chem. Lett , vol.2 , pp. 353-357
    • Arisawa, M.1    Kasaya, Y.2    Obata, T.3    Sasaki, T.4    Ito, M.5    Abe, H.6    Ito, Y.7    Yamano, A.8    Shuto, S.9
  • 8
    • 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
  • 10
    • 0014228967 scopus 로고
    • A New Syntheses of 1-(p -Chlorobenzoyl)-5-methoxy-3-indolylacetic Acid and Its Polymorphism
    • Yamamoto, H. 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
  • 11
    • 30144432668 scopus 로고    scopus 로고
    • New Entry to the Synthesis of 2,3-Disubstituted Indoles
    • Mukai, C.; Takahashi, Y. New Entry to the Synthesis of 2,3-Disubstituted Indoles Org. Lett. 2005, 7, 5793-5796
    • (2005) Org. Lett. , vol.7 , pp. 5793-5796
    • Mukai, C.1    Takahashi, Y.2
  • 12
    • 0014516863 scopus 로고
    • Preparation and Antiinflammatory Properties of Some 1-Substituted 3-(5-tetrazolylmethyl)indoles and Homologues
    • Juby, P. F.; Hudyma, T. W. Preparation and Antiinflammatory Properties of Some 1-Substituted 3-(5-tetrazolylmethyl)indoles and Homologues J. Med. Chem. 1969, 12, 396-401
    • (1969) J. Med. Chem. , vol.12 , pp. 396-401
    • Juby, P.F.1    Hudyma, T.W.2
  • 13
    • 0037132622 scopus 로고    scopus 로고
    • Reactivity Differences of Indomethacin Solid Forms with Ammonia Gas
    • Chen, X.; Morris, K. R.; Griesser, U. J.; Byrn, S. R.; Stowell, J. G. Reactivity Differences of Indomethacin Solid Forms with Ammonia Gas J. Am. Chem. Soc. 2002, 124, 15012-15019
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 15012-15019
    • Chen, X.1    Morris, K.R.2    Griesser, U.J.3    Byrn, S.R.4    Stowell, J.G.5
  • 14
    • 41549115914 scopus 로고    scopus 로고
    • Phonon-defect Scattering in Doped Silicon by Molecular Dynamics Simulation
    • Hédoux, A.; Guinet, Y.; Capet, F.; Paccou, L.; Descamps, M. Phonon-defect Scattering in Doped Silicon by Molecular Dynamics Simulation 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
  • 15
    • 0036347536 scopus 로고    scopus 로고
    • Structure-activity Relationship of Indomethacin Analogues for MRP-1, COX-1 and COX-2 Inhibition - Identification of Novel Chemotherapeutic Drug Resistance Modulators
    • 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-identification of Novel Chemotherapeutic Drug Resistance Modulators 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
  • 16
    • 0037064039 scopus 로고    scopus 로고
    • Regulation of MDR-1 (P-glycoprotein) by Cyclooxygenase-2
    • Patel, V. A.; Dunn, M. J.; Sorokin, A. Regulation of MDR-1 (P-glycoprotein) by Cyclooxygenase-2 J. Biol. Chem. 2002, 277, 38915-38920
    • (2002) J. Biol. Chem. , vol.277 , pp. 38915-38920
    • Patel, V.A.1    Dunn, M.J.2    Sorokin, A.3
  • 18
    • 42449149172 scopus 로고    scopus 로고
    • Seizure-Induced Up-Regulation of P-Glycoprotein at the Blood-Brain Barrier through Glutamate and Cyclooxygenase-2 Signaling
    • Bauer, B.; Hartz, A. M.; Pekcec, A.; Toellner, K.; Miller, D. S.; Potschka, H. Seizure-Induced Up-Regulation of P-Glycoprotein at the Blood-Brain Barrier through Glutamate and Cyclooxygenase-2 Signaling Mol. Pharmacol. 2008, 73, 1444-1453
    • (2008) Mol. Pharmacol. , vol.73 , pp. 1444-1453
    • Bauer, B.1    Hartz, A.M.2    Pekcec, A.3    Toellner, K.4    Miller, D.S.5    Potschka, H.6
  • 19
    • 0031053478 scopus 로고    scopus 로고
    • Indomethacin-mediated Reversal of Multidrug Resistance and Drug Efflux in Human and Murine Cell Lines Overexpressing MRP, but Not P-Glycoprotein
    • Draper, M. P.; Martell, R. L.; Levy, S. B. Indomethacin-mediated Reversal of Multidrug Resistance and Drug Efflux in Human and Murine Cell Lines Overexpressing MRP, but Not P-Glycoprotein Br. J. Cancer 1997, 75, 810-815
    • (1997) Br. J. Cancer , vol.75 , pp. 810-815
    • Draper, M.P.1    Martell, R.L.2    Levy, S.B.3
  • 20
    • 0029124936 scopus 로고
    • Difloxacin Reverses Multidrug Resistance in HL-60/AR Cells That Overexpress the Multidrug Resistance-Related Protein (MRP) Gene
    • Gollapudi, S.; Thadepalli, F.; Kim, C. H.; Gupta, S. Difloxacin Reverses Multidrug Resistance in HL-60/AR Cells That Overexpress the Multidrug Resistance-Related Protein (MRP) Gene Oncol. Res. 1995, 7, 213-225
    • (1995) Oncol. Res. , vol.7 , pp. 213-225
    • Gollapudi, S.1    Thadepalli, F.2    Kim, C.H.3    Gupta, S.4
  • 21
    • 13744254574 scopus 로고    scopus 로고
    • Cyclooxygenase-2 and Epidermal Growth Factor Receptor: Pharmacologic Targets for Chemoprevention
    • 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
    • (2005) J. Clin. Oncol. , vol.23 , pp. 254-266
    • Dannenberg, A.J.1    Lippman, S.M.2    Mann, J.R.3    Subbaramaiah, K.4    Dubois, R.N.5
  • 22
    • 84986437005 scopus 로고
    • MacroModel- An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics
    • MacroModel 7.2, Schrödinger, Portland, OR
    • Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel- An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics J. Comput. Chem. 1990, 11, 440-467. MacroModel 7.2, Schrödinger, Portland, OR.
    • (1990) J. Comput. Chem. , vol.11 , pp. 440-467
    • Mohamadi, F.1    Richards, N.G.J.2    Guida, W.C.3    Liskamp, R.4    Lipton, M.5    Caufield, C.6    Chang, G.7    Hendrickson, T.8    Still, W.C.9
  • 23
    • 5544242529 scopus 로고    scopus 로고
    • MMFF VI. MMFF94s Option for Energy Minimization Studies
    • Halgren, T. A. MMFF VI. MMFF94s Option for Energy Minimization Studies J. Comput. Chem. 1999, 20, 720-729
    • (1999) J. Comput. Chem. , vol.20 , pp. 720-729
    • Halgren, T.A.1
  • 24
    • 0344778061 scopus 로고
    • Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics J. Am. Chem. Soc. 1990, 112, 6127-6129
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 25
    • 0000408363 scopus 로고    scopus 로고
    • Approximate Atomic Surfaces from Linear Combinations of Pairwise Overlaps (LCPO)
    • Weiser, J.; Shenkin, P. S.; Still, W. C. Approximate Atomic Surfaces from Linear Combinations of Pairwise Overlaps (LCPO) J. Comput. Chem. 1999, 20, 217-230
    • (1999) J. Comput. Chem. , vol.20 , pp. 217-230
    • Weiser, J.1    Shenkin, P.S.2    Still, W.C.3
  • 26
    • 0001229337 scopus 로고    scopus 로고
    • Neighbor-List Reduction: Optimization for Computation of Molecular van der Waals and Solvent-Accessible Surface Areas
    • Weiser, J.; Weiser, A. A.; Shenkin, P. S.; Still, W. C. Neighbor-List Reduction: Optimization for Computation of Molecular van der Waals and Solvent-Accessible Surface Areas J. Comput. Chem. 1998, 19, 797-808
    • (1998) J. Comput. Chem. , vol.19 , pp. 797-808
    • Weiser, J.1    Weiser, A.A.2    Shenkin, P.S.3    Still, W.C.4
  • 27
    • 0000860122 scopus 로고    scopus 로고
    • Fast, Approximate Algorithm for Detection of Solvent-Inaccessible Atoms
    • Weiser, J.; Shenkin, P. S.; Still, W. C. Fast, Approximate Algorithm for Detection of Solvent-Inaccessible Atoms J. Comput. Chem. 1999, 20, 586-596
    • (1999) J. Comput. Chem. , vol.20 , pp. 586-596
    • Weiser, J.1    Shenkin, P.S.2    Still, W.C.3
  • 28
    • 84988112508 scopus 로고
    • An Efficient Newton-like Method for Molecular Mechanics Energy Minimization of Large Molecules
    • Ponder, J. W.; Richards, F. M. An Efficient Newton-like Method for Molecular Mechanics Energy Minimization of Large Molecules J. Comput. Chem. 1987, 8, 1016-1024
    • (1987) J. Comput. Chem. , vol.8 , pp. 1016-1024
    • Ponder, J.W.1    Richards, F.M.2
  • 29
    • 0043162336 scopus 로고
    • An Internal-Coordinate Monte Carlo Method for Searching Conformational Space
    • Chang, G.; Guida, W. C.; Still, W. C. An Internal-Coordinate Monte Carlo Method for Searching Conformational Space J. Am. Chem. Soc. 1989, 111, 4379-4386
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4379-4386
    • Chang, G.1    Guida, W.C.2    Still, W.C.3
  • 30
    • 0142236572 scopus 로고    scopus 로고
    • Low Mode Search. An Efficient, Automated Computational Method for Conformational Analysis: Application to Cyclic and Acyclic Alkanes and Cyclic Peptides
    • Kolossvary, I.; Guida, W. C. Low Mode Search. An Efficient, Automated Computational Method for Conformational Analysis: Application to Cyclic and Acyclic Alkanes and Cyclic Peptides J. Am. Chem. Soc. 1996, 118, 5011-5019
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5011-5019
    • Kolossvary, I.1    Guida, W.C.2
  • 31
    • 0001362247 scopus 로고
    • Unit-Cell Refinement from Powder Diffraction Scans
    • Pawley, G. S. Unit-Cell Refinement from Powder Diffraction Scans J. Appl. Crystallogr. 1981, 14, 357-361
    • (1981) J. Appl. Crystallogr. , vol.14 , pp. 357-361
    • Pawley, G.S.1
  • 33
    • 70349324514 scopus 로고    scopus 로고
    • 3-(o -Trifluoroacetamidoaryl)-1-propargylic Esters: Common Intermediates for the Palladium-Catalyzed Synthesis of 2-Aminomethyl-, 2-Vinylic, and 2-Alkylindoles
    • Ambrogio, I.; Cacchi, S.; Fabriza, G.; Prastaro, A. 3-(o -Trifluoroacetamidoaryl)-1-propargylic Esters: Common Intermediates for the Palladium-Catalyzed Synthesis of 2-Aminomethyl-, 2-Vinylic, and 2-Alkylindoles Tetrahedron 2009, 65, 8916-8929
    • (2009) Tetrahedron , vol.65 , pp. 8916-8929
    • Ambrogio, I.1    Cacchi, S.2    Fabriza, G.3    Prastaro, A.4
  • 34
    • 39849083252 scopus 로고    scopus 로고
    • Palladium-Catalyzed Direct Arylation of (Hetero)arenes with Aryl Boronic Acids
    • Yang, S. -D.; Sun, C. -L.; Fang, S.; Li, B. -J.; Li, Y. -Z.; Shi, Z. -J. Palladium-Catalyzed Direct Arylation of (Hetero)arenes with Aryl Boronic Acids Angew. Chem., Int. Ed. 2008, 47, 1473-1476
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1473-1476
    • Yang, S.-D.1    Sun, C.-L.2    Fang, S.3    Li, B.-J.4    Li, Y.-Z.5    Shi, Z.-J.6
  • 35
    • 0035799162 scopus 로고    scopus 로고
    • Reactions of Substituted 2,3-Dihydro-1H-indol-3-ones and Pyrrolo[2,3-b]pyridin-3-ones with Wittig and Horner-Emmons Reagents: Synthesis of 7-Azatryptamine
    • Mérour, J. Y.; Gadonneix, P.; Malapel-Andrieu, B.; Desarbre, E. Reactions of Substituted 2,3-Dihydro-1H-indol-3-ones and Pyrrolo[2,3-b]pyridin- 3-ones with Wittig and Horner-Emmons Reagents: Synthesis of 7-Azatryptamine Tetrahedron 2001, 57, 1995-2002
    • (2001) Tetrahedron , vol.57 , pp. 1995-2002
    • Mérour, J.Y.1    Gadonneix, P.2    Malapel-Andrieu, B.3    Desarbre, E.4
  • 36
    • 2342573386 scopus 로고
    • Application of Reformatsky and Grignard Reagents to 1,2-Disubstituted Indoxylyls
    • Pretka, J. E.; Lindwall, H. G. Application of Reformatsky and Grignard Reagents to 1,2-Disubstituted Indoxylyls J. Org. Chem. 1954, 19, 1080-1088
    • (1954) J. Org. Chem. , vol.19 , pp. 1080-1088
    • Pretka, J.E.1    Lindwall, H.G.2
  • 37
    • 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
    • Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; 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
    • (2006) J. Org. Chem. , vol.71 , pp. 4255-4261
    • Arisawa, M.1    Terada, Y.2    Takahashi, K.3    Nakagawa, M.4    Nishida, A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.