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Volumn 53, Issue 4, 2010, Pages 1755-1762

Structure-activity relationships studies in a series of N,N-bis(alkanol)amine aryl esters as P-glycoprotein (Pgp) dependent multidrug resistance (MDR) inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; DOXORUBICIN; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; PIRARUBICIN;

EID: 77649203312     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9016174     Document Type: Article
Times cited : (25)

References (50)
  • 1
    • 25144450046 scopus 로고    scopus 로고
    • Apical/basolateral surface expression of drug transporters and its role in vectorial drug transport
    • Ito, K.; Suzuki, H.; Horie, T.; Sugiyama, Y. Apical/basolateral surface expression of drug transporters and its role in vectorial drug transport. Pharm. Res. 2005, 22, 1559-1577.
    • (2005) Pharm. Res. , vol.22 , pp. 1559-1577
    • Ito, K.1    Suzuki, H.2    Horie, T.3    Sugiyama, Y.4
  • 2
    • 34247123807 scopus 로고    scopus 로고
    • Structure and function of ABC transporters
    • Linton, K. J. Structure and function of ABC transporters. Physiology 2007, 22, 122-130.
    • (2007) Physiology , vol.22 , pp. 122-130
    • Linton, K.J.1
  • 4
    • 0033958086 scopus 로고    scopus 로고
    • Multiple physiological functions for multidrug transporter P-glycoprotein?
    • Johnstone, R. W.; Ruefli, A. A.; Smyth, M. J. Multiple physiological functions for multidrug transporter P-glycoprotein? Trends Biochem. Sci. 2000, 25, 1-6.
    • (2000) Trends Biochem. Sci. , vol.25 , pp. 1-6
    • Johnstone, R.W.1    Ruefli, A.A.2    Smyth, M.J.3
  • 6
    • 0030390492 scopus 로고    scopus 로고
    • Resistance mechanisms and their regulation in lung cancer
    • Volm, M.; Mattern, J. Resistance mechanisms and their regulation in lung cancer. Crit. Rev. Oncog. 1996, 7, 227-244.
    • (1996) Crit. Rev. Oncog. , vol.7 , pp. 227-244
    • Volm, M.1    Mattern, J.2
  • 7
    • 0031839225 scopus 로고    scopus 로고
    • Biochemical and clinical aspects of efflux pump related resistance to anti-cancer drugs
    • Aszalos, A.; Ross, D. D. Biochemical and clinical aspects of efflux pump related resistance to anti-cancer drugs. Anticancer Res. 1998, 18, 2937-2944.
    • (1998) Anticancer Res. , vol.18 , pp. 2937-2944
    • Aszalos, A.1    Ross, D.D.2
  • 8
    • 62549108159 scopus 로고    scopus 로고
    • ABC transporters, drug resistance, and cancer stem cells
    • Dean, M. ABC Transporters, Drug Resistance, and Cancer Stem cells. J. Mammary Gland Biol. Neoplasia 2009, 14, 3-9.
    • (2009) J. Mammary Gland Biol. Neoplasia , vol.14 , pp. 3-9
    • Dean, M.1
  • 9
    • 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
  • 10
    • 11844292588 scopus 로고    scopus 로고
    • Recent advances in multidrug resistance modulators
    • Avendano, C.; Menendez, J. C. Recent advances in multidrug resistance modulators. Med. Chem. Rev.-Online 2004, 1, 419-444.
    • (2004) Med. Chem. Rev.-Online , vol.1 , pp. 419-444
    • Avendano, C.1    Menendez, J.C.2
  • 11
    • 0242331085 scopus 로고    scopus 로고
    • Multidrug resistance reversal agents
    • Robert, J.; Jarry, C. Multidrug resistance reversal agents. J. Med. Chem. 2003, 46, 4805-4817.
    • (2003) J. Med. Chem. , vol.46 , pp. 4805-4817
    • Robert, J.1    Jarry, C.2
  • 12
    • 33745746815 scopus 로고    scopus 로고
    • Pharmacological strategies for overcoming multidrug resistance
    • Nobili, S.; Landini, I.; Giglioni, B.; Mini, E. Pharmacological strategies for overcoming multidrug resistance. Curr. Drug Targets 2006, 7, 861-879.
    • (2006) Curr. Drug Targets , vol.7 , pp. 861-879
    • Nobili, S.1    Landini, I.2    Giglioni, B.3    Mini, E.4
  • 13
    • 33747197446 scopus 로고    scopus 로고
    • Cancer cell permeability-glycoprotein as a target of MDR reverters: Possible role of novel dihydropyridine derivatives
    • DOI 10.2174/138945006778019336
    • Fusi, F.; Saponara, S.; Valoti, M.; Dragoni, S.; D'Elia, P.; Sgaragli, T.; Alderighi, D.; Kawase, M.; Shah, A.; Motohashi, N.; Sgaragli, G. Cancer cell permeability-glycoprotein as a target of MDR reverters: possible role of novel dihydropyridine derivatives. Curr. Drug Targets 2006, 8, 949-959. (Pubitemid 44227579)
    • (2006) Current Drug Targets , vol.7 , Issue.8 , pp. 949-959
    • Fusi, F.1    Saponara, S.2    Valoti, M.3    Dragoni, S.4    D'Elia, P.5    Sgaragli, T.6    Alderighi, D.7    Sgaragli, G.8
  • 15
    • 0034456656 scopus 로고    scopus 로고
    • Multidrug resistance transporters and modulation
    • Tan, B.; Piwnica-Worms, D.; Ratner, L. Multidrug resistance transporters and modulation. Curr. Opin. Oncol. 2000, 12, 450-458.
    • (2000) Curr. Opin. Oncol. , vol.12 , pp. 450-458
    • Tan, B.1    Piwnica-Worms, D.2    Ratner, L.3
  • 16
    • 42449134059 scopus 로고    scopus 로고
    • P-Glycoprotein - A clinical target in drug-refractory epilepsy?
    • Robey, R. W.; Lazarowski, A.; bates, S. E. P-Glycoprotein - a clinical target in drug-refractory epilepsy? Mol. Pharmacol. 2008, 73, 1343-1346.
    • (2008) Mol. Pharmacol. , vol.73 , pp. 1343-1346
    • Robey, R.W.1    Lazarowski, A.2    Bates, S.E.3
  • 17
    • 20044362282 scopus 로고    scopus 로고
    • The implications of Pglycoprotein in HIV: Friend or foe?
    • Owen, A.; Chandler, B.; Back, D. J. The implications of Pglycoprotein in HIV: friend or foe? Fund. Clin. Pharmacol. 2005, 19, 283-296.
    • (2005) Fund. Clin. Pharmacol. , vol.19 , pp. 283-296
    • Owen, A.1    Chandler, B.2    Back, D.J.3
  • 18
    • 0037424343 scopus 로고    scopus 로고
    • Three dimensional structures of the mammalian multidrug-resistant P-glycoprotein demonstrate major conformational changes in the transmembrane domain upon nucleotide binding
    • Rosenberg, M. F.; Kamis, A. B.; Callaghan, R.; Higgins, C. F.; Ford, R. C. Three dimensional structures of the mammalian multidrug-resistant P-glycoprotein demonstrate major conformational changes in the transmembrane domain upon nucleotide binding. J. Biol. Chem. 2003, 278, 8294-8299.
    • (2003) J. Biol. Chem. , vol.278 , pp. 8294-8299
    • Rosenberg, M.F.1    Kamis, A.B.2    Callaghan, R.3    Higgins, C.F.4    Ford, R.C.5
  • 20
    • 37649004412 scopus 로고    scopus 로고
    • Flexibility in the ABC transporter MsbA: Alternating access with a twist
    • Ward, A.; Reyes, C. L.; Yu, J.; Roth, C. B.; Chang, G. Flexibility in the ABC transporter MsbA: alternating access with a twist. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 19005-19010.
    • (2007) Proc. Natl. Acad. Sci. U.S.A. , vol.104 , pp. 19005-19010
    • Ward, A.1    Reyes, C.L.2    Yu, J.3    Roth, C.B.4    Chang, G.5
  • 21
    • 33847134349 scopus 로고    scopus 로고
    • Structure of the multidrug ABC transporter Sav1866 from Staphylococcus aureus in complex with AMP-PNP
    • Dawson, R. J. P.; Locher, K. P. Structure of the multidrug ABC transporter Sav1866 from Staphylococcus aureus in complex with AMP-PNP. FEBS Lett. 2007, 581, 935-938.
    • (2007) FEBS Lett. , vol.581 , pp. 935-938
    • Dawson, R.J.P.1    Locher, K.P.2
  • 22
    • 36849079744 scopus 로고    scopus 로고
    • Evidence for a Sav1866-like architecture for the human multidrug transporter Pglycoprotein
    • Zolnerciks, J. K.; Wooding, C.; Linton, K. J. Evidence for a Sav1866-like architecture for the human multidrug transporter Pglycoprotein. FASEB J. 2007, 21, 3937-3948.
    • (2007) FASEB J. , vol.21 , pp. 3937-3948
    • Zolnerciks, J.K.1    Wooding, C.2    Linton, K.J.3
  • 23
    • 34548133239 scopus 로고    scopus 로고
    • P-Glycoprotein models of the apo and ATP-bound states based on homology with Sav1866 and Ma1K
    • O'Mara, M. L.; Tieleman, D. P. P-Glycoprotein models of the apo and ATP-bound states based on homology with Sav1866 and Ma1K. FEBS Lett. 2007, 581, 4217-4222.
    • (2007) FEBS Lett. , vol.581 , pp. 4217-4222
    • O'Mara, M.L.1    Tieleman, D.P.2
  • 24
    • 47049126229 scopus 로고    scopus 로고
    • Identification of putative binding sits of P-glycoprotein based on its homology models
    • Globish, C.; Pajeva, I. K.; Wiese, M. Identification of putative binding sits of P-glycoprotein based on its homology models. ChemMedChem 2008, 3, 280-295.
    • (2008) ChemMedChem , vol.3 , pp. 280-295
    • Globish, C.1    Pajeva, I.K.2    Wiese, M.3
  • 25
    • 0036364467 scopus 로고    scopus 로고
    • Multidrug resistance in cancer: Role of ATP-dependent transporters
    • Gottesman, M. M.; Fojo, T.; Bates, S. E. Multidrug resistance in cancer: role of ATP-dependent transporters. Nature Rev. Cancer 2002, 2, 48-58. (Pubitemid 37328807)
    • (2002) Nature Reviews Cancer , vol.2 , Issue.1 , pp. 48-58
    • Gottesman, M.M.1    Fojo, T.2    Bates, S.E.3
  • 26
    • 1842740025 scopus 로고    scopus 로고
    • Crystal structure of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization
    • Murray, D. S.; Schumacher, M. A.; Brennan, R. G. Crystal structure of QacR-diamidine complexes reveal additional multidrug-binding modes and a novel mechanism of drug charge neutralization. J. Biol. Chem. 2004, 279, 14365-14371.
    • (2004) J. Biol. Chem. , vol.279 , pp. 14365-14371
    • Murray, D.S.1    Schumacher, M.A.2    Brennan, R.G.3
  • 27
    • 4143103793 scopus 로고    scopus 로고
    • Structural mechanism of the simultaneous binding of two drugs to a multidrug binding protein
    • Schumacher, M. A.; Miller, M. C.; Brennan, R. G. Structural mechanism of the simultaneous binding of two drugs to a multidrug binding protein. EMBO J. 2004, 23, 2923-2930.
    • (2004) EMBO J. , vol.23 , pp. 2923-2930
    • Schumacher, M.A.1    Miller, M.C.2    Brennan, R.G.3
  • 31
    • 0033587112 scopus 로고    scopus 로고
    • Design, synthesis, and in vitro activity of catamphiphilic reverters of multidrug resistance: Discovery of a selective, highly efficacious chemosensitizer with potency in the nanomolar range
    • Teodori, E.; Dei, S.; Quidu, P.; Budriesi, R.; Chiarini, A.; Garnier-Suillerot, A.; Gualtieri, F.; Manetti, D.; Romanelli, M. N.; Scapecchi, S. Design, synthesis, and in vitro activity of catamphiphilic reverters of multidrug resistance: discovery of a selective, highly efficacious chemosensitizer with potency in the nanomolar range. J. Med. Chem. 1999, 42, 1687-1697.
    • (1999) J. Med. Chem. , vol.42 , pp. 1687-1697
    • Teodori, E.1    Dei, S.2    Quidu, P.3    Budriesi, R.4    Chiarini, A.5    Garnier-Suillerot, A.6    Gualtieri, F.7    Manetti, D.8    Romanelli, M.N.9    Scapecchi, S.10
  • 32
    • 0034846645 scopus 로고    scopus 로고
    • Structure-activity relationships and optimization of the selective MDR modulator 2-(3,4-dimethoxyphenyl)-5-(9-fluorenylamino)-2-(methylethyl) pentanenitrile (SC11) and its N-methyl derivative (SC17)
    • Dei, S.; Teodori, E.; Garnier-Suillerot, A.; Gualtieri, F.; Scapecchi, S.; Budriesi, R.; Chiarini, A. Structure-activity relationships and optimization of the selective MDR modulator 2-(3,4-dimethoxyphenyl)-5-(9-fluorenylamino)-2- (methylethyl) pentanenitrile (SC11) and its N-methyl derivative (SC17). Bioorg. Med. Chem. 2001, 9, 2673-2682.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 2673-2682
    • Dei, S.1    Teodori, E.2    Garnier-Suillerot, A.3    Gualtieri, F.4    Scapecchi, S.5    Budriesi, R.6    Chiarini, A.7
  • 36
    • 0029011403 scopus 로고
    • Synthesis and activity against Multidrug resistance in chinese hamster ovary cells of new acridone-4-carboxamides
    • Dodic, N.; Dumaitre, B.; Daugan, A.; Pianetti, P. Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides. J. Med. Chem. 1995, 38, 2418-2426.
    • (1995) J. Med. Chem. , vol.38 , pp. 2418-2426
    • Dodic, N.1    Dumaitre, B.2    Daugan, A.3    Pianetti, P.4
  • 38
    • 0012047732 scopus 로고
    • Yntheses of selected ε-(2- Or 9-anthryl)alkanoic acids and certain esters-carbon-13 spin-lattice relaxation time measurements of methyl 5-(2-anthryl)pentanoate and methyl 7-(2-anthryl)-heptanoate
    • Arjunan, P.; Shymasundar, N.; Berlin, K. D.; Najjar, D.; Rockley, M. G. Syntheses of selected ε-(2- or 9-anthryl)alkanoic acids and certain esters-carbon-13 spin-lattice relaxation time measurements of methyl 5-(2-anthryl)pentanoate and methyl 7-(2-anthryl)-heptanoate. J. Org. Chem. 1981, 46, 626-629.
    • (1981) J. Org. Chem. , vol.46 , pp. 626-629
    • Arjunan, P.1    Shymasundar, N.2    Berlin, K.D.3    Najjar, D.4    Rockley, M.G.S.5
  • 39
    • 0030605908 scopus 로고    scopus 로고
    • Chemoselectivity in the rhodium(II) acetate catalysed decomposition of α-diazo-β-keto-γ,δ-alkenyl-δ-aryl compounds: Aromatic C-H insertion reaction or Wolff rearrangement-electrocyclization
    • DOI 10.1016/0040-4020(96)00581-9
    • Collomb, D.; Chantegrel, B.; Deshayes, C. Chemoselectivity in the Rhodium(ll) Acetate Catalysed Decomposition of α-Diazo-β-keto- γ,δ-alkenyl-δ-aryl Compounds: Aromatic C-H Insertion Reaction or Wolff Rearrangement-Electrocydization. Tetrahedron 1996, 52, 10455-10472. (Pubitemid 26244736)
    • (1996) Tetrahedron , vol.52 , Issue.31 , pp. 10455-10472
    • Collomb, D.1    Chantegrel, B.2    Deshayes, C.3
  • 40
    • 2942608090 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of 20-O-linked nitrogen-based camptothecin ester derivatives
    • Wang, C.; Pan, X.; Liu, H.; Fu, Z.; Wei, X.; Yang, L. X. Synthesis and antitumor activity of 20-O-linked nitrogen-based camptothecin ester derivatives. Bioorg. Med. Chem. 2004, 12, 3657-3662.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 3657-3662
    • Wang, C.1    Pan, X.2    Liu, H.3    Fu, Z.4    Wei, X.5    Yang, L.X.6
  • 41
    • 0040821520 scopus 로고
    • The chemistry of some methoxychlor derivatives
    • Baarschers, W. H.; Vukmanich, J. P. The chemistry of some methoxychlor derivatives. Can. J. Chem. 1986, 64, 932-935.
    • (1986) Can. J. Chem. , vol.64 , pp. 932-935
    • Baarschers, W.H.1    Vukmanich, J.P.2
  • 42
    • 0001114499 scopus 로고
    • Modular design of hosts involving a rigid succinimide framework and N-bonded lateral groups. Crystalline inclusion properties and crystal structures of inclusion compounds with dioxane, MeOH, and DMF
    • Weber, E.; Finge, S.; Csoeregh, I. Modular Design of Hosts Involving a Rigid Succinimide Framework and N-Bonded Lateral Groups. Crystalline Inclusion Properties and Crystal Structures of Inclusion Compounds with Dioxane, MeOH, and DMF. J. Org. Chem. 1991, 56, 7281-7287.
    • (1991) J. Org. Chem. , vol.56 , pp. 7281-7287
    • Weber, E.1    Finge, S.2    Csoeregh, I.3
  • 43
    • 0032519555 scopus 로고    scopus 로고
    • 99mTc-MIBI in cells with P-glycoprotein-mediated and multidrug-resistance proteinassociated multidrug-resistance phenothype
    • 99mTc-MIBI in cells with P-glycoprotein-mediated and multidrug-resistance proteinassociated multidrug-resistance phenothype. Eur. J. Biochem. 1998, 252, 140-146.
    • (1998) Eur. J. Biochem. , vol.252 , pp. 140-146
    • Vergote, J.1    Moretti, J.L.2    De Vries, E.G.E.3    Garnier-Suillerot, A.4
  • 44
    • 13844266481 scopus 로고    scopus 로고
    • Decrease of P-glycoprotein activity in K562/ADR cells by MβCD and filipin and lack of effect induced by cholesterol oxidase indicate that this transporter is not located in rafts
    • Reungpatthanaphong, P.; Marbeuf-Gueye, C.; Le Moyec, L.; Salerno, M.; Garnier-Suillerot, A. Decrease of P-glycoprotein activity in K562/ADR cells by MβCD and filipin and lack of effect induced by cholesterol oxidase indicate that this transporter is not located in rafts. J. Bioenerg. Biomembr. 2004, 36, 533-543.
    • (2004) J. Bioenerg. Biomembr. , vol.36 , pp. 533-543
    • Reungpatthanaphong, P.1    Marbeuf-Gueye, C.2    Le Moyec, L.3    Salerno, M.4    Garnier-Suillerot, A.5
  • 45
    • 0016640079 scopus 로고
    • Human chronic myelogenous leukemia cell line positive philadelphia chromosome
    • Lozzio, C. B.; Lozzio, B. B. Human chronic myelogenous leukemia cell line positive philadelphia chromosome. Blood 1975, 45, 321-334.
    • (1975) Blood , vol.45 , pp. 321-334
    • Lozzio, C.B.1    Lozzio, B.B.2
  • 46
    • 0022475690 scopus 로고
    • Characteristics of resistance to adriamycin in human myelogeneous leukemia K562 resistant to adriamycin and in isolated clones
    • Tsuruo, T.; Ida, H.; Kawataba, H.; Oh-Hara, T.; Hamada, H.; Utakoji, T. Characteristics of resistance to adriamycin in human myelogeneous leukemia K562 resistant to adriamycin and in isolated clones. Jpn. J. Cancer Res. 1986, 77, 682-687.
    • (1986) Jpn. J. Cancer Res. , vol.77 , pp. 682-687
    • Tsuruo, T.1    Ida, H.2    Kawataba, H.3    Oh-Hara, T.4    Hamada, H.5    Utakoji, T.6
  • 48
    • 0028236174 scopus 로고
    • Correlation between the shortterm measurements of drug accumulation in living cells and the long-term growth inhibition
    • Pereira, E.; Garnier-Suillerot, A. Correlation between the shortterm measurements of drug accumulation in living cells and the long-term growth inhibition. Biochem. Pharmacol. 1994, 47, 1851-1857.
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 1851-1857
    • Pereira, E.1    Garnier-Suillerot, A.2
  • 50
    • 0032545989 scopus 로고    scopus 로고
    • The ability of verapamil to restore intracellular accumulation of anthracyclines in multidrug resistant cells depends on the kinetics of their uptake
    • Mankehetkorn, S.; Garnier-Suillerot, A. The ability of verapamil to restore intracellular accumulation of anthracyclines in multidrug resistant cells depends on the kinetics of their uptake. Eur. J. Pharmacol. 1998, 343, 313-321.
    • (1998) Eur. J. Pharmacol. , vol.343 , pp. 313-321
    • Mankehetkorn, S.1    Garnier-Suillerot, A.2


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