메뉴 건너뛰기




Volumn 52, Issue 15, 2009, Pages 4586-4595

Aromatic 2-(thio)ureidocarboxylic acids as a new family of modulators of multidrug resistance-associated protein 1: Synthesis, biological evaluation, and structure - Activity relationships

Author keywords

[No Author keywords available]

Indexed keywords

2 (3,3 DIETHYLTHIOUREIDO)BENZO[B]THIOPHENE 3 CARBOXYLIC ACID; BENZOTHIOPHENE DERIVATIVE; BREAST CANCER RESISTANCE PROTEIN; CALCEIN; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN 1; UNCLASSIFIED DRUG;

EID: 68549126957     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900688v     Document Type: Article
Times cited : (26)

References (79)
  • 2
    • 0032744001 scopus 로고    scopus 로고
    • Structural, mechanistic and clinical aspects of MRP1
    • Hipfner, D. R.; Deeley, R. G.; Cole, S. P. C. Structural, mechanistic and clinical aspects of MRP1. Biochim. Biophys. Acta 1999, 1461, 359-376.
    • (1999) Biochim. Biophys. Acta , vol.1461 , pp. 359-376
    • Hipfner, D.R.1    Deeley, R.G.2    Cole, S.P.C.3
  • 3
    • 33745736603 scopus 로고    scopus 로고
    • Multidrug resistance: Retrospect and prospects in anti-cancer treatment
    • Pérez-Tomás, R. Multidrug resistance: Retrospect and prospects in anti-cancer treatment. Curr. Med. Chem. 2006, 13, 1859-1876.
    • (2006) Curr. Med. Chem , vol.13 , pp. 1859-1876
    • Pérez-Tomás, R.1
  • 4
    • 33745831231 scopus 로고    scopus 로고
    • Structure, function, expression, genomic organization, and single nucleotide polymorphisms of human ABCB1 (MDR1), ABCC (MRP), and ABCG2 (BCRP) efflux transporters
    • Choudhuri, S.; Klaassen, C. D. Structure, function, expression, genomic organization, and single nucleotide polymorphisms of human ABCB1 (MDR1), ABCC (MRP), and ABCG2 (BCRP) efflux transporters. Int. J. Toxicol. 2006, 25, 231-259.
    • (2006) Int. J. Toxicol , vol.25 , pp. 231-259
    • Choudhuri, S.1    Klaassen, C.D.2
  • 5
    • 67650685020 scopus 로고    scopus 로고
    • Eckford, P. D. W.; Sharom, F. J. ABC Efflux Pump-Based Resistance to Chemotherapy Drugs. Chem. Rev. 2009, DOI 10.1021/cr9000226. (accessed May 13, 2009).
    • Eckford, P. D. W.; Sharom, F. J. ABC Efflux Pump-Based Resistance to Chemotherapy Drugs. Chem. Rev. 2009, DOI 10.1021/cr9000226. (accessed May 13, 2009).
  • 7
    • 0033799839 scopus 로고    scopus 로고
    • Multidrug resistance (MDR) in cancer. Mechanisms, reversal using modulators of MDR and the role of MDR modulators in influencing the pharmacokinetics of anticancer drugs
    • Krishna, R.; Mayer, L. D. Multidrug resistance (MDR) in cancer. Mechanisms, reversal using modulators of MDR and the role of MDR modulators in influencing the pharmacokinetics of anticancer drugs. Eur. J. Pharm. Sci. 2000, 11, 265-283.
    • (2000) Eur. J. Pharm. Sci , vol.11 , pp. 265-283
    • Krishna, R.1    Mayer, L.D.2
  • 8
    • 34548378642 scopus 로고    scopus 로고
    • Concise review: Clinical relevance of drug-drug and herb-drug interactions mediated by the ABC transporter ABCB1 (MDR1, Pglycoprotein)
    • Marchetti, S.; Mazzanti, R.; Beijnen, J. H.; Schellens, J. H. M. Concise review: Clinical relevance of drug-drug and herb-drug interactions mediated by the ABC transporter ABCB1 (MDR1, Pglycoprotein). Oncologist 2007, 12, 927-941.
    • (2007) Oncologist , vol.12 , pp. 927-941
    • Marchetti, S.1    Mazzanti, R.2    Beijnen, J.H.3    Schellens, J.H.M.4
  • 10
    • 57349084070 scopus 로고    scopus 로고
    • 2-[(3-Methoxyphenylethyl)-phenoxy]-Based ABCB1 Inhibitors: Effect of Different Basic Side Chains on Their Biological Properties
    • Colabufo, N. A.; Berardi, F.; Perrone, R.; Rapposelli, S.; Digiacomo, M.; Vanni, M.; Balsamo, A. 2-[(3-Methoxyphenylethyl)-phenoxy]-Based ABCB1 Inhibitors: Effect of Different Basic Side Chains on Their Biological Properties. J. Med. Chem. 2008, 51, 7602-7613.
    • (2008) J. Med. Chem , vol.51 , pp. 7602-7613
    • Colabufo, N.A.1    Berardi, F.2    Perrone, R.3    Rapposelli, S.4    Digiacomo, M.5    Vanni, M.6    Balsamo, A.7
  • 14
    • 62149110091 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of a small molecule library of 3rd generation multidrug resistance modulators
    • Klinkhammer, W.; Müller, H.; Globisch, C.; Pajeva, I. K.; Wiese, M. Synthesis and biological evaluation of a small molecule library of 3rd generation multidrug resistance modulators. Bioorg. Med. Chem. 2009, 17, 2524-2535.
    • (2009) Bioorg. Med. Chem , vol.17 , pp. 2524-2535
    • Klinkhammer, W.1    Müller, H.2    Globisch, C.3    Pajeva, I.K.4    Wiese, M.5
  • 15
    • 0032554868 scopus 로고    scopus 로고
    • Molecular modeling of phenothiazines and related drugs as multidrug resistance modifiers: A comparative molecular field analysis study
    • Pajeva, I.; Wiese, M. Molecular modeling of phenothiazines and related drugs as multidrug resistance modifiers: a comparative molecular field analysis study. J. Med. Chem. 1998, 41, 1815-1826.
    • (1998) J. Med. Chem , vol.41 , pp. 1815-1826
    • Pajeva, I.1    Wiese, M.2
  • 16
    • 2342533129 scopus 로고    scopus 로고
    • Structure-function relationships of multidrug resistance P-glycoprotein
    • Pajeva, I. K.; Globisch, C.; Wiese, M. Structure-function relationships of multidrug resistance P-glycoprotein. J. Med. Chem. 2004, 47, 2523-2533.
    • (2004) J. Med. Chem , vol.47 , pp. 2523-2533
    • Pajeva, I.K.1    Globisch, C.2    Wiese, M.3
  • 17
    • 14544287387 scopus 로고    scopus 로고
    • Inhibitors of P-gp;lead identification and optimisation
    • Pleban, K.; Ecker, G. F. Inhibitors of P-gp;lead identification and optimisation. Mini Rev. Med. Chem. 2005, 5, 153-163.
    • (2005) Mini Rev. Med. Chem , vol.5 , pp. 153-163
    • Pleban, K.1    Ecker, G.F.2
  • 18
    • 33751301012 scopus 로고    scopus 로고
    • Pharmacophore-based discovery of ligands for drug transporters
    • Chang, C.; Ekins, S.; Bahadduri, P.; Swaan, P. W. Pharmacophore-based discovery of ligands for drug transporters. Adv. Drug Delivery Rev. 2006, 58, 1431-1450.
    • (2006) Adv. Drug Delivery Rev , vol.58 , pp. 1431-1450
    • Chang, C.1    Ekins, S.2    Bahadduri, P.3    Swaan, P.W.4
  • 19
    • 66249134216 scopus 로고    scopus 로고
    • Synthesis, Activity, and Pharmacophore Development for Isatin-β-thiosemicarbazones with Selective Activity toward Multidrug-Resistant Cells
    • Hall, M. D.; Salam, N. K.; Hellawell, J. L.; Fales, H. M.; Kensler, C. B.; Ludwig, J. A.; Szakács, G.; Hibbs, D. E.; Gottesman, M. M. Synthesis, Activity, and Pharmacophore Development for Isatin-β-thiosemicarbazones with Selective Activity toward Multidrug-Resistant Cells. J. Med. Chem. 2009, 52, 3191-3204.
    • (2009) J. Med. Chem , vol.52 , pp. 3191-3204
    • Hall, M.D.1    Salam, N.K.2    Hellawell, J.L.3    Fales, H.M.4    Kensler, C.B.5    Ludwig, J.A.6    Szakács, G.7    Hibbs, D.E.8    Gottesman, M.M.9
  • 20
    • 64349122714 scopus 로고    scopus 로고
    • Potent and Selective Inhibitors of Breast Cancer Resistance Protein (ABCG2) Derived from the p-Glycoprotein (ABCB1) Modulator Tariquidar
    • Kühnle, M.; Egger, M.; Müller, C.; Mahringer, A.; Bernhardt, G.; Fricker, G.; König, B.; Buschauer, A. Potent and Selective Inhibitors of Breast Cancer Resistance Protein (ABCG2) Derived from the p-Glycoprotein (ABCB1) Modulator Tariquidar. J. Med. Chem. 2009, 52, 1190-1197.
    • (2009) J. Med. Chem , vol.52 , pp. 1190-1197
    • Kühnle, M.1    Egger, M.2    Müller, C.3    Mahringer, A.4    Bernhardt, G.5    Fricker, G.6    König, B.7    Buschauer, A.8
  • 22
    • 33745897902 scopus 로고    scopus 로고
    • Transport of glutathione and glutathione conjugates by MRP1
    • Cole, S. P.; Deeley, R. G. Transport of glutathione and glutathione conjugates by MRP1. Trends Pharmacol. Sci. 2006, 27, 438-446.
    • (2006) Trends Pharmacol. Sci , vol.27 , pp. 438-446
    • Cole, S.P.1    Deeley, R.G.2
  • 23
    • 33745748312 scopus 로고    scopus 로고
    • The functions and structure of ABC transporters: Implications for the design of new inhibitors of Pgp and MRP1 to control multidrug resistance (MDR)
    • Teodori, E.; Dei, S.; Martelli, C.; Scapecchi, S.; Gualtieri, F. The functions and structure of ABC transporters: implications for the design of new inhibitors of Pgp and MRP1 to control multidrug resistance (MDR). Curr. Drug Targets 2006, 7, 893-909.
    • (2006) Curr. Drug Targets , vol.7 , pp. 893-909
    • Teodori, E.1    Dei, S.2    Martelli, C.3    Scapecchi, S.4    Gualtieri, F.5
  • 24
    • 33846703691 scopus 로고    scopus 로고
    • Portrait of multifaceted transporter, the multidrug resistance-associated protein 1 (MRP1/ABCC1)
    • Bakos, É.; Homolya, L. Portrait of multifaceted transporter, the multidrug resistance-associated protein 1 (MRP1/ABCC1). Pflugers Arch. 2007, 453, 621-641.
    • (2007) Pflugers Arch , vol.453 , pp. 621-641
    • Bakos, E.1    Homolya, L.2
  • 25
    • 2142799057 scopus 로고    scopus 로고
    • Pharmacogenetics of ATP-binding cassette transporters in cancer and chemotherapy
    • Lockhart, A. C.; Tirona, R. G.; Kim, R. B. Pharmacogenetics of ATP-binding cassette transporters in cancer and chemotherapy. Mol. Cancer Ther. 2003, 2, 685-698.
    • (2003) Mol. Cancer Ther , vol.2 , pp. 685-698
    • Lockhart, A.C.1    Tirona, R.G.2    Kim, R.B.3
  • 28
    • 0029157072 scopus 로고
    • Expression pattern ofMRPin human tissues and adult solid tumor cell lines
    • Kruh, G. D.; Gaughan, K. T.; Godwin, A.; Chan, A. Expression pattern ofMRPin human tissues and adult solid tumor cell lines. J. Natl. Cancer Inst. 1995, 87, 1256-1258.
    • (1995) J. Natl. Cancer Inst , vol.87 , pp. 1256-1258
    • Kruh, G.D.1    Gaughan, K.T.2    Godwin, A.3    Chan, A.4
  • 30
    • 0030063480 scopus 로고    scopus 로고
    • Transport of glutathione, glucuronate, and sulfate conjugates by the MRP gene-encoded conjugate export pump
    • Jedlitschky, G.; Leier, I.; Buchholz, U.; Barnouin, K.; Kurz, G.; Keppler, D. Transport of glutathione, glucuronate, and sulfate conjugates by the MRP gene-encoded conjugate export pump. Cancer Res. 1996, 56, 988-994.
    • (1996) Cancer Res , vol.56 , pp. 988-994
    • Jedlitschky, G.1    Leier, I.2    Buchholz, U.3    Barnouin, K.4    Kurz, G.5    Keppler, D.6
  • 31
    • 17144465167 scopus 로고    scopus 로고
    • ATP-dependent transport of glutathione S-conjugates by the multidrug resistance protein MRP1 and its apical isoform MRP2
    • Keppler, D.; Leier, I.; Jedlitschky, G.; König, J. ATP-dependent transport of glutathione S-conjugates by the multidrug resistance protein MRP1 and its apical isoform MRP2. Chem. Biol. Interact. 1998, 111-112, 153-161.
    • (1998) Chem. Biol. Interact , vol.111-112 , pp. 153-161
    • Keppler, D.1    Leier, I.2    Jedlitschky, G.3    König, J.4
  • 32
    • 21744447836 scopus 로고    scopus 로고
    • Anticancer multidrug resistance mediated by MRP1: Recent advances in the discovery of reversal agents
    • Boumendjel, A.; Baubichon-Cortay, H.; Trompier, D.; Perrotton, T.; Di Pietro, A. Anticancer multidrug resistance mediated by MRP1: recent advances in the discovery of reversal agents. Med. Res. Rev. 2005, 25, 453-472.
    • (2005) Med. Res. Rev , vol.25 , pp. 453-472
    • Boumendjel, A.1    Baubichon-Cortay, H.2    Trompier, D.3    Perrotton, T.4    Di Pietro, A.5
  • 33
    • 53349117254 scopus 로고    scopus 로고
    • Substrates and inhibitors of human multidrug resistance associated proteins and the implications in drug development
    • Zhou, S. F.; Wang, L. L.; Di, Y. M.; Xue, C. C.; Duan, W.; Li, C. G.; Li, Y. Substrates and inhibitors of human multidrug resistance associated proteins and the implications in drug development. Curr. Med. Chem. 2008, 15, 1981-2039.
    • (2008) Curr. Med. Chem , vol.15 , pp. 1981-2039
    • Zhou, S.F.1    Wang, L.L.2    Di, Y.M.3    Xue, C.C.4    Duan, W.5    Li, C.G.6    Li, Y.7
  • 34
    • 0027984511 scopus 로고
    • The MRP gene encodes an ATP-dependent export pump for leukotriene C4 and structurally related conjugates
    • Leier, I.; Jedlitschky, G.; Buchholz, U.; Cole, S. P.; Deeley, R. G.; Keppler, D. The MRP gene encodes an ATP-dependent export pump for leukotriene C4 and structurally related conjugates. J. Biol. Chem. 1994, 269, 27807-27810.
    • (1994) J. Biol. Chem , vol.269 , pp. 27807-27810
    • Leier, I.1    Jedlitschky, G.2    Buchholz, U.3    Cole, S.P.4    Deeley, R.G.5    Keppler, D.6
  • 35
    • 0028986245 scopus 로고
    • The leukotriene LTD4 receptor antagonist MK571 specifically modulatesMRPassociated multidrug resistance
    • Gekeler, V.; Ise, W.; Sanders, K. H.; Ulrich, W. R.; Beck, J. The leukotriene LTD4 receptor antagonist MK571 specifically modulatesMRPassociated multidrug resistance. Biochem. Biophys. Res. Commun. 1995, 208, 345-352.
    • (1995) Biochem. Biophys. Res. Commun , vol.208 , pp. 345-352
    • Gekeler, V.1    Ise, W.2    Sanders, K.H.3    Ulrich, W.R.4    Beck, J.5
  • 36
    • 33646732642 scopus 로고    scopus 로고
    • Nitrogen monoxide (NO)-mediated iron release from cells is linked to NOinduced glutathione efflux via multidrug resistance-associated protein 1
    • Watts, R. N.; Hawkins, C.; Ponka, P.; Richardson, D. R. Nitrogen monoxide (NO)-mediated iron release from cells is linked to NOinduced glutathione efflux via multidrug resistance-associated protein 1. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 7670-7675.
    • (2006) Proc. Natl. Acad. Sci. U.S.A , vol.103 , pp. 7670-7675
    • Watts, R.N.1    Hawkins, C.2    Ponka, P.3    Richardson, D.R.4
  • 37
    • 33644777840 scopus 로고    scopus 로고
    • Multidrug resistance protein 1 (MRP1, ABCC1) mediates resistance to mitoxantrone via glutathione-dependent drug efflux
    • Morrow, C. S.; Peklak-Scott, C.; Bishwokarma, B.; Kute, T. E.; Smitherman, P. K.; Townsend, A. J. Multidrug resistance protein 1 (MRP1, ABCC1) mediates resistance to mitoxantrone via glutathione-dependent drug efflux. Mol. Pharmacol. 2006, 69, 1499-1505.
    • (2006) Mol. Pharmacol , vol.69 , pp. 1499-1505
    • Morrow, C.S.1    Peklak-Scott, C.2    Bishwokarma, B.3    Kute, T.E.4    Smitherman, P.K.5    Townsend, A.J.6
  • 38
    • 33645038097 scopus 로고    scopus 로고
    • The PI3K inhibitor LY294002 blocks drug export from resistant colon carcinoma cells overexpressing MRP1
    • Abdul-Ghani, R.; Serra, V.; Györffy, B.; Jürchott, K.; Solf, A.; Dietel, M.; Schäfer, R. The PI3K inhibitor LY294002 blocks drug export from resistant colon carcinoma cells overexpressing MRP1. Oncogene 2006, 25, 1743-1752.
    • (2006) Oncogene , vol.25 , pp. 1743-1752
    • Abdul-Ghani, R.1    Serra, V.2    Györffy, B.3    Jürchott, K.4    Solf, A.5    Dietel, M.6    Schäfer, R.7
  • 39
    • 33750832270 scopus 로고    scopus 로고
    • Mitra, P; Oskeritzian, C. A.; Payne, S. G.; Beaven, M. A.; Milstien, S.; Spiegel, S. Role of ABCC1 in export of sphingosine-1-phosphate from mast cells. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 16394-16399.
    • Mitra, P; Oskeritzian, C. A.; Payne, S. G.; Beaven, M. A.; Milstien, S.; Spiegel, S. Role of ABCC1 in export of sphingosine-1-phosphate from mast cells. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 16394-16399.
  • 40
    • 34347230130 scopus 로고    scopus 로고
    • Glutathione export during apoptosis requires functional multidrug resistance-associated proteins
    • Hammond, C. L.; Marchan, R.; Krance, S. M.; Ballatori, N. Glutathione export during apoptosis requires functional multidrug resistance-associated proteins. J. Biol. Chem. 2007, 282, 14337-14347.
    • (2007) J. Biol. Chem , vol.282 , pp. 14337-14347
    • Hammond, C.L.1    Marchan, R.2    Krance, S.M.3    Ballatori, N.4
  • 41
    • 44649168284 scopus 로고    scopus 로고
    • Multidrug resistance protein-1 affects oxidative stress, endothelial dysfunction, and atherogenesis via leukotriene C4 export
    • Mueller, C. F.; Wassmann, K.; Widder, J. D.; Wassmann, S.; Chen, C. H.; Keuler, B.; Kudin, A.; Kunz, W. S.; Nickenig, G. Multidrug resistance protein-1 affects oxidative stress, endothelial dysfunction, and atherogenesis via leukotriene C4 export. Circulation 2008, 117, 2912-2918.
    • (2008) Circulation , vol.117 , pp. 2912-2918
    • Mueller, C.F.1    Wassmann, K.2    Widder, J.D.3    Wassmann, S.4    Chen, C.H.5    Keuler, B.6    Kudin, A.7    Kunz, W.S.8    Nickenig, G.9
  • 42
    • 54049129967 scopus 로고    scopus 로고
    • Emtricitabine: Inhibitor and substrate of multidrug resistance associated protein
    • Bousquet, L.; Pruvost, A.; Didier, N.; Farinotti, R.; Mabondzo, A. Emtricitabine: inhibitor and substrate of multidrug resistance associated protein. Eur. J. Pharm. Sci. 2008, 35, 247-256.
    • (2008) Eur. J. Pharm. Sci , vol.35 , pp. 247-256
    • Bousquet, L.1    Pruvost, A.2    Didier, N.3    Farinotti, R.4    Mabondzo, A.5
  • 43
    • 58149383084 scopus 로고    scopus 로고
    • The pH sensitive probe 5-(and-6)-carboxyl seminaphthorhodafluor is a substrate for the multidrug resistancerelated protein MRP1
    • Jin, J.; Jones, A. T. The pH sensitive probe 5-(and-6)-carboxyl seminaphthorhodafluor is a substrate for the multidrug resistancerelated protein MRP1. Int. J. Cancer 2009, 124, 233-238.
    • (2009) Int. J. Cancer , vol.124 , pp. 233-238
    • Jin, J.1    Jones, A.T.2
  • 44
    • 0034083906 scopus 로고    scopus 로고
    • ATP-dependent para-aminohippurate transport by apical multidrug resistance protein MRP2
    • Leier, I.; Hummel-Eisenbeiss, J.; Cui, Y.; Keppler, D. ATP-dependent para-aminohippurate transport by apical multidrug resistance protein MRP2. Kidney Int. 2000, 57, 1636-1642.
    • (2000) Kidney Int , vol.57 , pp. 1636-1642
    • Leier, I.1    Hummel-Eisenbeiss, J.2    Cui, Y.3    Keppler, D.4
  • 45
    • 49949092310 scopus 로고    scopus 로고
    • A 4-Aminobenzoic acid derivative as novel lead for selective inhibitors of multidrug resistance-associated proteins
    • Leyers, S.; Häcker, H.-G.; Wiendlocha, J.; Gütschow, M.; Wiese, M. A 4-Aminobenzoic acid derivative as novel lead for selective inhibitors of multidrug resistance-associated proteins. Bioorg. Med. Chem. Lett. 2008, 18, 4761-4763.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 4761-4763
    • Leyers, S.1    Häcker, H.-G.2    Wiendlocha, J.3    Gütschow, M.4    Wiese, M.5
  • 50
    • 0037704286 scopus 로고    scopus 로고
    • Identification and characterization of the canine multidrug resistance-associated protein
    • Ma, L.; Pratt, S. E.; Cao, J.; Dantzig, A. H.; Moore, R. E.; Slapak, C. A. Identification and characterization of the canine multidrug resistance-associated protein. Mol. Cancer Ther. 2002, 1, 1335-1342.
    • (2002) Mol. Cancer Ther , vol.1 , pp. 1335-1342
    • Ma, L.1    Pratt, S.E.2    Cao, J.3    Dantzig, A.H.4    Moore, R.E.5    Slapak, C.A.6
  • 52
    • 12144290723 scopus 로고    scopus 로고
    • Wang, S.; Wan, N. C.; Harrison, J.; Miller, W.; Chuckowree, I.; Sohal, S.; Hancox, T. C.; Baker, S.; Folkes, A.; Wilson, F.; Thompson, D.; Cocks, S.; Farmer, H.; Boyce, A.; Freathy, C.; Broadbridge, J.; Scott, J.; Depledge, P; Faint, R.; Mistry, P.; Charlton, P. Design and synthesis of new templates derived from pyrrolopyrimidine as selective multidrug-resistance-associated protein inhibitors in multidrug resistance. J. Med. Chem. 2004, 47, 1339-1350.
    • Wang, S.; Wan, N. C.; Harrison, J.; Miller, W.; Chuckowree, I.; Sohal, S.; Hancox, T. C.; Baker, S.; Folkes, A.; Wilson, F.; Thompson, D.; Cocks, S.; Farmer, H.; Boyce, A.; Freathy, C.; Broadbridge, J.; Scott, J.; Depledge, P; Faint, R.; Mistry, P.; Charlton, P. Design and synthesis of new templates derived from pyrrolopyrimidine as selective multidrug-resistance-associated protein inhibitors in multidrug resistance. J. Med. Chem. 2004, 47, 1339-1350.
  • 53
    • 0035870580 scopus 로고    scopus 로고
    • Detection of MRP functional activity: Calcein AM but not BCECF AM as a multidrug resistance-related protein (MRP1) substrate
    • Olson, D. P.; Taylor, B. J.; Ivy, S. P. Detection of MRP functional activity: Calcein AM but not BCECF AM as a multidrug resistance-related protein (MRP1) substrate. Cytometry 2001, 46, 105-113.
    • (2001) Cytometry , vol.46 , pp. 105-113
    • Olson, D.P.1    Taylor, B.J.2    Ivy, S.P.3
  • 54
    • 33947569039 scopus 로고    scopus 로고
    • Staiger, R. P.; Wagner, E. C. Isatoic anhydride. III. Reactions with primary and secondary amines. J. Org. Chem. 1953, 18, 1427-1439.
    • Staiger, R. P.; Wagner, E. C. Isatoic anhydride. III. Reactions with primary and secondary amines. J. Org. Chem. 1953, 18, 1427-1439.
  • 55
    • 0038761764 scopus 로고    scopus 로고
    • One-pot reactions of N-(mesyloxy)phthalimides with secondary amines to 2-ureidobenzamides, 2-ureidobenzoic acids, ethyl 2-ureidobenzoates, or isatoic anhydrides
    • Gütschow, M. One-pot reactions of N-(mesyloxy)phthalimides with secondary amines to 2-ureidobenzamides, 2-ureidobenzoic acids, ethyl 2-ureidobenzoates, or isatoic anhydrides. J. Org. Chem. 1999, 64, 5109-5115.
    • (1999) J. Org. Chem , vol.64 , pp. 5109-5115
    • Gütschow, M.1
  • 56
    • 33846044053 scopus 로고    scopus 로고
    • Carpenter, R. D.; Lam, K. S.; Kurth, M. J. Microwave-mediated heterocyclization to benzimidazo[2,1-b]quinazolin-12(5H)-ones. J. Org. Chem. 2007, 72, 284-287.
    • Carpenter, R. D.; Lam, K. S.; Kurth, M. J. Microwave-mediated heterocyclization to benzimidazo[2,1-b]quinazolin-12(5H)-ones. J. Org. Chem. 2007, 72, 284-287.
  • 57
    • 84860875380 scopus 로고
    • 2-Aminothiophenes from methylene-active nitriles, carbonyl compounds and sulfur
    • Gewald, K.; Schinke, E.; Böttcher, H. 2-Aminothiophenes from methylene-active nitriles, carbonyl compounds and sulfur. Chem. Ber. 1966, 99, 94-100.
    • (1966) Chem. Ber , vol.99 , pp. 94-100
    • Gewald, K.1    Schinke, E.2    Böttcher, H.3
  • 59
    • 0038400425 scopus 로고    scopus 로고
    • 2-(Diethylamino)thieno[1,3]oxazin-4-ones as stable inhibitors of human leukocyte elastase
    • Gütschow, M.; Kuerschner, L.; Neumann, U.; Pietsch, M.; Löser, R.; Koglin, N.; Eger, K. 2-(Diethylamino)thieno[1,3]oxazin-4-ones as stable inhibitors of human leukocyte elastase. J. Med. Chem. 1999, 42, 5437-5447.
    • (1999) J. Med. Chem , vol.42 , pp. 5437-5447
    • Gütschow, M.1    Kuerschner, L.2    Neumann, U.3    Pietsch, M.4    Löser, R.5    Koglin, N.6    Eger, K.7
  • 61
    • 33751270193 scopus 로고    scopus 로고
    • Novel tetrahydroisoquinolin-ethyl-phenylamine based multidrug resistance inhibitors with broad-spectrum modulating properties
    • Jekerle, V.; Klinkhammer, W.; Reilly, R. M.; Piquette-Miller, M.; Wiese, M. Novel tetrahydroisoquinolin-ethyl-phenylamine based multidrug resistance inhibitors with broad-spectrum modulating properties. Cancer Chemother. Pharmacol. 2007, 59, 61-69.
    • (2007) Cancer Chemother. Pharmacol , vol.59 , pp. 61-69
    • Jekerle, V.1    Klinkhammer, W.2    Reilly, R.M.3    Piquette-Miller, M.4    Wiese, M.5
  • 62
    • 50349103259 scopus 로고    scopus 로고
    • Structure-activity relationships of new inhibitors of breast cancer resistance protein (ABCG2)
    • Pick, A.; Mueller, H.; Wiese, M. Structure-activity relationships of new inhibitors of breast cancer resistance protein (ABCG2). Bioorg. Med. Chem. 2008, 16, 8224-8236.
    • (2008) Bioorg. Med. Chem , vol.16 , pp. 8224-8236
    • Pick, A.1    Mueller, H.2    Wiese, M.3
  • 63
    • 16644386336 scopus 로고    scopus 로고
    • Comparison of the usefulness of the MTT, ATP, and calcein assays to predict the potency of cytotoxic agents in various human cancer cell lines
    • Mueller, H.; Kassack, M. U.; Wiese, M. Comparison of the usefulness of the MTT, ATP, and calcein assays to predict the potency of cytotoxic agents in various human cancer cell lines. J. Biomol. Screening 2004, 9, 506-515.
    • (2004) J. Biomol. Screening , vol.9 , pp. 506-515
    • Mueller, H.1    Kassack, M.U.2    Wiese, M.3
  • 65
    • 33645967769 scopus 로고    scopus 로고
    • Tetrazole compounds: The effect of structure and pH on Caco-2 cell permeability
    • Young, A. M.; Audus, K. L.; Proudfoot, J.; Yazdanian, M. Tetrazole compounds: The effect of structure and pH on Caco-2 cell permeability. J. Pharm. Sci. 2006, 95, 717-725.
    • (2006) J. Pharm. Sci , vol.95 , pp. 717-725
    • Young, A.M.1    Audus, K.L.2    Proudfoot, J.3    Yazdanian, M.4
  • 66
    • 64349101278 scopus 로고    scopus 로고
    • Topological Polar Surface Area Defines Substrate Transport by Multidrug Resistance Associated Protein 1 (MRP1/ABCC1)
    • Fernandes, J.; Gattass, C. R. Topological Polar Surface Area Defines Substrate Transport by Multidrug Resistance Associated Protein 1 (MRP1/ABCC1). J. Med. Chem. 2009, 52, 1214-1218.
    • (2009) J. Med. Chem , vol.52 , pp. 1214-1218
    • Fernandes, J.1    Gattass, C.R.2
  • 67
    • 35748956867 scopus 로고    scopus 로고
    • Perrotton, T.; Trompier, D.; Chang, X.-B.; Di Pietro, A.; Baubichon-Cortay, H. (R)- and (S)-Verapamil Differentially Modulate the Multidrug-resistant Protein MRP1. J. Biol. Chem. 2007, 282, 31542-31548.
    • Perrotton, T.; Trompier, D.; Chang, X.-B.; Di Pietro, A.; Baubichon-Cortay, H. (R)- and (S)-Verapamil Differentially Modulate the Multidrug-resistant Protein MRP1. J. Biol. Chem. 2007, 282, 31542-31548.
  • 68
    • 0027960078 scopus 로고
    • Pharmacological Characterization of Multidrug Resistant MRP-Transfected Human Tumor Cells
    • Cole, S. P. C.; Sparks, K. E.; Fraser, K.; Loe, D. W.; Grant, C. E.; Wilson, G. M.; Deeley, R. G. Pharmacological Characterization of Multidrug Resistant MRP-Transfected Human Tumor Cells. Cancer Res. 1994, 54, 5902-5910.
    • (1994) Cancer Res , vol.54 , pp. 5902-5910
    • Cole, S.P.C.1    Sparks, K.E.2    Fraser, K.3    Loe, D.W.4    Grant, C.E.5    Wilson, G.M.6    Deeley, R.G.7
  • 69
    • 0035882764 scopus 로고    scopus 로고
    • Verapamil-stimulated glutathione transport by the multidrug resistance associated protein (MRP1) in leukaemia cells
    • Cullen, K. V.; Davey, R. A.; Davey, M. W. Verapamil-stimulated glutathione transport by the multidrug resistance associated protein (MRP1) in leukaemia cells. Biochem. Pharmacol. 2001, 62, 417-424.
    • (2001) Biochem. Pharmacol , vol.62 , pp. 417-424
    • Cullen, K.V.1    Davey, R.A.2    Davey, M.W.3
  • 70
    • 59049102086 scopus 로고    scopus 로고
    • Robey, R. W.; To, K. K. K.; Polgar, O.; Dohse, M.; Fetsch, P.; Dean, M.; Bates, S: E. ABCG2: A perspective. Adv. Drug Delivery Rev. 2009, 61, 3-13.
    • Robey, R. W.; To, K. K. K.; Polgar, O.; Dohse, M.; Fetsch, P.; Dean, M.; Bates, S: E. ABCG2: A perspective. Adv. Drug Delivery Rev. 2009, 61, 3-13.
  • 71
    • 67650084777 scopus 로고    scopus 로고
    • Matsson, P.; Pedersen, J. M.; Norinder, U.; Bergström, C. A. S.; Artursson, P. Identification of Novel Specific and General Inhibitors of the Three Major Human ATP-Binding Cassette Transporters P-gp, BCRP and MRP2 Among Registered Drugs. Pharm. Res. 2009, DOI 10.1007/s11095-009-9896-0, (accessed May 19, 2009).
    • Matsson, P.; Pedersen, J. M.; Norinder, U.; Bergström, C. A. S.; Artursson, P. Identification of Novel Specific and General Inhibitors of the Three Major Human ATP-Binding Cassette Transporters P-gp, BCRP and MRP2 Among Registered Drugs. Pharm. Res. 2009, DOI 10.1007/s11095-009-9896-0, (accessed May 19, 2009).
  • 72
    • 60849085184 scopus 로고    scopus 로고
    • Multi-Drug-Resistance-Reverting Agents: 2-Aryloxazole and 2-Arylthiazole Derivatives as Potent BCRP or MRP1 Inhibitors
    • Colabufo, N. A.; Berardi, F.; Perrone, M G.; Cantore, M.; Contino, M.; Inglese, C.; Niso, M.; Perrone, R. Multi-Drug-Resistance-Reverting Agents: 2-Aryloxazole and 2-Arylthiazole Derivatives as Potent BCRP or MRP1 Inhibitors. ChemMedChem 2009, 4, 188-195.
    • (2009) ChemMedChem , vol.4 , pp. 188-195
    • Colabufo, N.A.1    Berardi, F.2    Perrone, M.G.3    Cantore, M.4    Contino, M.5    Inglese, C.6    Niso, M.7    Perrone, R.8
  • 74
    • 59349100048 scopus 로고    scopus 로고
    • 2-Amino- and 2-alkylthio-4H-3,1- benzothiazin-4-ones: Synthesis, interconversion and enzyme inhibitory activities
    • Häcker, H.-G.; Grundmann, F.; Lohr, F.; Ottersbach, P. A.; Zhou, J.; Schnakenburg, G.; Gütschow, M. 2-Amino- and 2-alkylthio-4H-3,1- benzothiazin-4-ones: Synthesis, interconversion and enzyme inhibitory activities. Molecules 2009, 14, 378-402.
    • (2009) Molecules , vol.14 , pp. 378-402
    • Häcker, H.-G.1    Grundmann, F.2    Lohr, F.3    Ottersbach, P.A.4    Zhou, J.5    Schnakenburg, G.6    Gütschow, M.7
  • 75
    • 0037025293 scopus 로고    scopus 로고
    • Alternate substrate inhibition of cholesterol esterase by thieno[2,3-d][1,3]oxazin-4-ones
    • Pietsch, M.; Gütschow, M. Alternate substrate inhibition of cholesterol esterase by thieno[2,3-d][1,3]oxazin-4-ones. J. Biol. Chem. 2002, 277, 24006-24013.
    • (2002) J. Biol. Chem , vol.277 , pp. 24006-24013
    • Pietsch, M.1    Gütschow, M.2
  • 78
    • 0027432409 scopus 로고
    • Fluorescent Cellular Indicators Are Extruded by the Multidrug Resistance Protein
    • Homolya, L.; Holló, Z.; Germann, U. A.; Pastan, I.; Gottesman, M. M.; Sarkadi, B. Fluorescent Cellular Indicators Are Extruded by the Multidrug Resistance Protein. J. Biol. Chem. 1993, 268, 21493-21496.
    • (1993) J. Biol. Chem , vol.268 , pp. 21493-21496
    • Homolya, L.1    Holló, Z.2    Germann, U.A.3    Pastan, I.4    Gottesman, M.M.5    Sarkadi, B.6
  • 79
    • 0343306779 scopus 로고    scopus 로고
    • Kinetic Analysis of Calcein and Calcein-Acetoxymethylester Efflux Mediated by the Multidrug Resistance Protein and P-Glycoprotein
    • Essodaïgui, M.; Broxterman, H. J.; Garnier-Suillerot, A. Kinetic Analysis of Calcein and Calcein-Acetoxymethylester Efflux Mediated by the Multidrug Resistance Protein and P-Glycoprotein. Biochemistry 1998, 37, 2243-2250.
    • (1998) Biochemistry , vol.37 , pp. 2243-2250
    • Essodaïgui, M.1    Broxterman, H.J.2    Garnier-Suillerot, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.