메뉴 건너뛰기




Volumn 47, Issue 22, 2004, Pages 5555-5566

Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring

Author keywords

[No Author keywords available]

Indexed keywords

5 METHOXY 6,7 DIPROPYLOXYFLAVONE; BAICALEIN; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; UNCLASSIFIED DRUG; VINBLASTINE;

EID: 6044224896     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049949c     Document Type: Article
Times cited : (50)

References (39)
  • 1
    • 0029954843 scopus 로고    scopus 로고
    • P-glycoprotein - A mediator of multidrug resistance in tumour cells
    • Germann, U. A. P-glycoprotein - a mediator of multidrug resistance in tumour cells. Eur. J. Cancer 1996, 32A, 927-944.
    • (1996) Eur. J. Cancer , vol.32 A , pp. 927-944
    • Germann, U.A.1
  • 2
    • 0027218689 scopus 로고
    • Biochemistry of multidrug resistance mediated by the multidrug transporter
    • Gottesman, M. M.; Pastan, I. Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu. Rev. Biochem. 1993, 62, 385-427.
    • (1993) Annu. Rev. Biochem. , vol.62 , pp. 385-427
    • Gottesman, M.M.1    Pastan, I.2
  • 3
    • 0023447098 scopus 로고
    • Cellular localization of the multidrug-resistance gene product P-glycoprotein in normal human tissues
    • Thiebaut, F.; Tsuruo, T.; Hamada, H.; Gottesman, M. M.; Pastan, I. et al. Cellular localization of the multidrug-resistance gene product P-glycoprotein in normal human tissues. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 7735-7738.
    • (1987) Proc. Natl. Acad. Sci. U.S.A. , vol.84 , pp. 7735-7738
    • Thiebaut, F.1    Tsuruo, T.2    Hamada, H.3    Gottesman, M.M.4    Pastan, I.5
  • 4
    • 0029945113 scopus 로고    scopus 로고
    • What have we learnt thus far from mice with disrupted P-glycoprotein genes?
    • Borst, P.; Schinkel, A. H. What have we learnt thus far from mice with disrupted P-glycoprotein genes? Eur. J. Cancer 1996, 32A, 985-990.
    • (1996) Eur. J. Cancer , vol.32 A , pp. 985-990
    • Borst, P.1    Schinkel, A.H.2
  • 5
    • 0033548572 scopus 로고    scopus 로고
    • Multidrug resistance (MDR1) P-glycoprotein enhances esterification of plasma membrane cholesterol
    • Luker, G. D.; Nilsson, K. R.; Covey, D. F.; Piwnica-Worms, D. Multidrug resistance (MDR1) P-glycoprotein enhances esterification of plasma membrane cholesterol. J. Biol. Chem. 1999, 274, 6979-6991.
    • (1999) J. Biol. Chem. , vol.274 , pp. 6979-6991
    • Luker, G.D.1    Nilsson, K.R.2    Covey, D.F.3    Piwnica-Worms, D.4
  • 6
    • 0024506222 scopus 로고
    • Drug-resistance in multiple myeloma and non-Hodgkin's lymphoma: Detection of P-glycoprotein and potential circumvention by addition of verapamil to chemotherapy
    • Dalton, W. S.; Grogan, T. M.; Meltzer, P. S.; Scheper, R. J.; Durie, B. G. et al. Drug-resistance in multiple myeloma and non-Hodgkin's lymphoma: detection of P-glycoprotein and potential circumvention by addition of verapamil to chemotherapy. J. Clin. Oncol. 1989, 7, 415-424.
    • (1989) J. Clin. Oncol. , vol.7 , pp. 415-424
    • Dalton, W.S.1    Grogan, T.M.2    Meltzer, P.S.3    Scheper, R.J.4    Durie, B.G.5
  • 7
    • 0026051296 scopus 로고
    • P-glycoprotein expression in malignant lymphoma and reversal of clinical drug resistance with chemotherapy plus high-dose verapamil
    • Miller, T. P.; Grogan, T. M.; Dalton, W. S.; Spier, C. M.; Scheper, R. J. et al. P-glycoprotein expression in malignant lymphoma and reversal of clinical drug resistance with chemotherapy plus high-dose verapamil. J. Clin. Oncol. 1991, 9, 17-24.
    • (1991) J. Clin. Oncol. , vol.9 , pp. 17-24
    • Miller, T.P.1    Grogan, T.M.2    Dalton, W.S.3    Spier, C.M.4    Scheper, R.J.5
  • 8
    • 0031581672 scopus 로고    scopus 로고
    • Phase I and pharmacokinetic study of the P-glycoprotein modulator dexniguldipine-HCL
    • Nuessler, V.; Scheulen, M. E.; Oberneder, R.; Kriegmair, M.; Goebel, K. J. et al. Phase I and pharmacokinetic study of the P-glycoprotein modulator dexniguldipine-HCL. Eur. J. Med. Res. 1997, 2, 55-61.
    • (1997) Eur. J. Med. Res. , vol.2 , pp. 55-61
    • Nuessler, V.1    Scheulen, M.E.2    Oberneder, R.3    Kriegmair, M.4    Goebel, K.J.5
  • 9
    • 0029025957 scopus 로고
    • Phase I and pharmacokinetic study of the multidrug resistance modulator dexverapamil with EPOCH chemotherapy
    • Wilson, W. H.; Jamis-Dow, C.; Bryant, G.; Balis, F. M.; Klecker, R. W. et al. Phase I and pharmacokinetic study of the multidrug resistance modulator dexverapamil with EPOCH chemotherapy. J. Clin. Oncol. 1995, 13, 1985-1994.
    • (1995) J. Clin. Oncol. , vol.13 , pp. 1985-1994
    • Wilson, W.H.1    Jamis-Dow, C.2    Bryant, G.3    Balis, F.M.4    Klecker, R.W.5
  • 10
    • 0027524642 scopus 로고
    • In vitro and in vivo reversal of multidrug resistance by GF120918, an acridonecarboxamide derivative
    • Hyafil, F.; Vergely, C.; Du Vignaud, P.; Grand-Perret, T. In vitro and in vivo reversal of multidrug resistance by GF120918, an acridonecarboxamide derivative. Cancer Res. 1993, 53, 4595-4602.
    • (1993) Cancer Res. , vol.53 , pp. 4595-4602
    • Hyafil, F.1    Vergely, C.2    Du Vignaud, P.3    Grand-Perret, T.4
  • 11
    • 0026014503 scopus 로고
    • In vivo circumvention of P-glycoprotein-mediated multidrug resistance of tumor cells with SDZ PSC 833
    • Boesch, D.; Gaveriaux, C.; Jachez, B.; Pourtier-Manzanedo, A.; Bollinger, P. et al. In vivo circumvention of P-glycoprotein-mediated multidrug resistance of tumor cells with SDZ PSC 833. Cancer Res. 1991, 51, 4226-4233.
    • (1991) Cancer Res. , vol.51 , pp. 4226-4233
    • Boesch, D.1    Gaveriaux, C.2    Jachez, B.3    Pourtier-Manzanedo, A.4    Bollinger, P.5
  • 12
    • 0021149466 scopus 로고
    • Restoration of doxorubicin responsiveness in doxorubicin-resistant P388 murine leukaemia cells
    • Ramu, A.; Spanier, R.; Rahamimoff, H.; Fuks, Z. Restoration of doxorubicin responsiveness in doxorubicin-resistant P388 murine leukaemia cells. Br. J. Cancer 1984, 50, 501-507.
    • (1984) Br. J. Cancer , vol.50 , pp. 501-507
    • Ramu, A.1    Spanier, R.2    Rahamimoff, H.3    Fuks, Z.4
  • 13
    • 0033637140 scopus 로고    scopus 로고
    • The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer
    • Middleton, E., Jr.; Kandaswami, C.; Theoharides, T. C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 2000, 52, 673-751.
    • (2000) Pharmacol. Rev. , vol.52 , pp. 673-751
    • Middleton Jr., E.1    Kandaswami, C.2    Theoharides, T.C.3
  • 15
    • 0029055363 scopus 로고
    • Disposition of intravenous and oral cyclosporine after administration with grapefruit juice
    • Ducharme, M. P.; Warbasse, L. H.; Edwards, D. J. Disposition of intravenous and oral cyclosporine after administration with grapefruit juice. Clin. Pharmacol. Ther. 1995, 57, 485-491.
    • (1995) Clin. Pharmacol. Ther. , vol.57 , pp. 485-491
    • Ducharme, M.P.1    Warbasse, L.H.2    Edwards, D.J.3
  • 16
    • 0028886499 scopus 로고
    • Effect of synthetic and naturally occurring chalcones on ovarian cancer cell growth: Structure-activity relationships
    • De Vincenzo, R.; Scambia, G.; Benedetti Panici, P.; Ranelletti, F. O.; Bonanno, G. et al. Effect of synthetic and naturally occurring chalcones on ovarian cancer cell growth: structure-activity relationships. Anticancer Drug Des. 1995, 10, 481-490.
    • (1995) Anticancer Drug Des. , vol.10 , pp. 481-490
    • De Vincenzo, R.1    Scambia, G.2    Benedetti Panici, P.3    Ranelletti, F.O.4    Bonanno, G.5
  • 17
    • 0033017670 scopus 로고    scopus 로고
    • Inhibition of gastric H+, K(+)-ATPase by flavonoids: A structure-activity study
    • Murakami, S.; Muramatsu, M.; Tomisawa, K. Inhibition of gastric H+, K(+)-ATPase by flavonoids: a structure-activity study. J. Enzyme Inhib. 1999, 14, 151-166.
    • (1999) J. Enzyme Inhib. , vol.14 , pp. 151-166
    • Murakami, S.1    Muramatsu, M.2    Tomisawa, K.3
  • 18
    • 0023664272 scopus 로고
    • Genistein, a specific inhibitor of tyrosine-specific protein kinases
    • Akiyama, T.; Ishida, J.; Nakagawa, S.; Ogawara, H.; Watanabe, S. et al. Genistein, a specific inhibitor of tyrosine-specific protein kinases. J. Biol. Chem. 1987, 262, 5592-5595.
    • (1987) J. Biol. Chem. , vol.262 , pp. 5592-5595
    • Akiyama, T.1    Ishida, J.2    Nakagawa, S.3    Ogawara, H.4    Watanabe, S.5
  • 20
    • 0036720280 scopus 로고    scopus 로고
    • Recent advances in the discovery of flavonoids and analogues with high-affinity binding to P-glycoprotein responsible for cancer cell multidrug resistance
    • Boumendjel, A.; Di Pietro, A.; Dumontet, C.; Barron, D. Recent advances in the discovery of flavonoids and analogues with high-affinity binding to P-glycoprotein responsible for cancer cell multidrug resistance. Med. Res. Rev. 2002, 22, 512-529.
    • (2002) Med. Res. Rev. , vol.22 , pp. 512-529
    • Boumendjel, A.1    Di Pietro, A.2    Dumontet, C.3    Barron, D.4
  • 21
    • 0036304314 scopus 로고    scopus 로고
    • Activity of drugs from traditional Chinese medicine toward sensitive and MDR1- or MRP1-overexpressing multidrug-resistant human CCRF-CEM leukemia cells
    • Efferth, T.; Davey, M.; Olbrich, A.; Rucker, G.; Gebhart, E. et al. Activity of drugs from traditional Chinese medicine toward sensitive and MDR1- or MRP1-overexpressing multidrug-resistant human CCRF-CEM leukemia cells. Blood Cells Mol. Dis. 2002, 28, 160-168.
    • (2002) Blood Cells Mol. Dis. , vol.28 , pp. 160-168
    • Efferth, T.1    Davey, M.2    Olbrich, A.3    Rucker, G.4    Gebhart, E.5
  • 22
    • 0032544087 scopus 로고    scopus 로고
    • Flavonoids: A class of modulators with bifunctional interactions at vicinal ATP- and steroid-binding sites on mouse P-glycoprotein
    • Conseil, G.; Baubichon-Cortay, H.; Dayan, G.; Jault, J. M.; Barron, D. et al. Flavonoids: a class of modulators with bifunctional interactions at vicinal ATP- and steroid-binding sites on mouse P-glycoprotein. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 9831-9836.
    • (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 9831-9836
    • Conseil, G.1    Baubichon-Cortay, H.2    Dayan, G.3    Jault, J.M.4    Barron, D.5
  • 23
    • 0035139550 scopus 로고    scopus 로고
    • High-affinity binding of silybin derivatives to the nucleotide-binding domain of a Leishmania tropica P-glycoprotein-like transporter and chemosensitization of a multidrug-resistant parasite to daunomycin
    • Perez-Victoria, J. M.; Perez-Victoria, F. J.; Conseil, G.; Maitre-jean, M.; Comte, G. et al. High-affinity binding of silybin derivatives to the nucleotide-binding domain of a Leishmania tropica P-glycoprotein-like transporter and chemosensitization of a multidrug-resistant parasite to daunomycin. Antimicrob Agents Chemother 2001, 45, 439-446.
    • (2001) Antimicrob Agents Chemother. , vol.45 , pp. 439-446
    • Perez-Victoria, J.M.1    Perez-Victoria, F.J.2    Conseil, G.3    Maitre-Jean, M.4    Comte, G.5
  • 24
    • 0026034414 scopus 로고
    • Effect of myricetin and other flavonoids on the liver plasma membrane Ca2+ pump. Kinetics and structure-function relationships
    • Thiyagarajah, P.; Kuttan, S. C.; Lim, S. C.; Teo, T. S.; Das, N. P. Effect of myricetin and other flavonoids on the liver plasma membrane Ca2+ pump. Kinetics and structure-function relationships. Biochem. Pharmacol. 1991, 41, 669-675.
    • (1991) Biochem. Pharmacol. , vol.41 , pp. 669-675
    • Thiyagarajah, P.1    Kuttan, S.C.2    Lim, S.C.3    Teo, T.S.4    Das, N.P.5
  • 25
    • 0024431825 scopus 로고
    • Effects of synthetic and naturally occurring flavonoids on Na+, K+-ATPase: Aspects of the structure-activity relationship and action mechanism
    • Hirano, T.; Oka, K.; Akiba, M. Effects of synthetic and naturally occurring flavonoids on Na+, K+-ATPase: aspects of the structure-activity relationship and action mechanism. Life Sci. 1989, 45, 1111-1117.
    • (1989) Life Sci. , vol.45 , pp. 1111-1117
    • Hirano, T.1    Oka, K.2    Akiba, M.3
  • 26
    • 0026845466 scopus 로고
    • Inhibition of rat liver cyclic AMP-dependent protein kinase by flavonoids
    • Jinsart, W.; Ternai, B.; Polya, G. M. Inhibition of rat liver cyclic AMP-dependent protein kinase by flavonoids. Biol. Chem. Hoppe Seyler 1992, 373, 205-211.
    • (1992) Biol. Chem. Hoppe Seyler. , vol.373 , pp. 205-211
    • Jinsart, W.1    Ternai, B.2    Polya, G.M.3
  • 27
    • 0024550507 scopus 로고
    • Protein kinase C inhibition by plant flavonoids. Kinetic mechanisms and structure-activity relationships
    • Ferriola, P. C.; Cody, V.; Middleton, E., Jr. Protein kinase C inhibition by plant flavonoids. Kinetic mechanisms and structure-activity relationships. Biochem. Pharmacol. 1989, 38, 1617-1624.
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 1617-1624
    • Ferriola, P.C.1    Cody, V.2    Middleton Jr., E.3
  • 28
    • 0023897154 scopus 로고
    • Differential effects of flavonoids as inhibitors of tyrosine protein kinases and serine/threonine protein kinases
    • Hagiwara, M.; Inoue, S.; Tanaka, T.; Nunoki, K.; Ito, M. et al. Differential effects of flavonoids as inhibitors of tyrosine protein kinases and serine/threonine protein kinases. Biochem. Pharmacol. 1988, 37, 2987-2992.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 2987-2992
    • Hagiwara, M.1    Inoue, S.2    Tanaka, T.3    Nunoki, K.4    Ito, M.5
  • 29
    • 0039552151 scopus 로고    scopus 로고
    • Correlation between the affinity of flavonoids binding to the cytosolic site of Leishmania tropica multidrug transporter and their efficiency to revert parasite resistance to daunomycin
    • Perez-Victoria, J. M.; Chiquero, M. J.; Conseil, G.; Dayan, G.; Di Pietro, A. et al. Correlation between the affinity of flavonoids binding to the cytosolic site of Leishmania tropica multidrug transporter and their efficiency to revert parasite resistance to daunomycin. Biochemistry 1999, 38, 1736-1743.
    • (1999) Biochemistry , vol.38 , pp. 1736-1743
    • Perez-Victoria, J.M.1    Chiquero, M.J.2    Conseil, G.3    Dayan, G.4    Di Pietro, A.5
  • 30
    • 0033326585 scopus 로고    scopus 로고
    • P-glycoprotein and drug therapy in organ transplantation
    • Lo, A.; Burckart, G. J. P-glycoprotein and drug therapy in organ transplantation. J. Clin. Pharmacol. 1999, 39, 995-1005.
    • (1999) J. Clin. Pharmacol. , vol.39 , pp. 995-1005
    • Lo, A.1    Burckart, G.J.2
  • 31
    • 0038480045 scopus 로고    scopus 로고
    • Structure-activity relationship: Analyses of p-glycoprotein substrates and inhibitors
    • Wang, R. B.; Kuo, C. L.; Lien, L. L.; Lien, E. J. Structure-activity relationship: analyses of p-glycoprotein substrates and inhibitors. J. Clin. Pharm. Ther. 2003, 28, 203-228.
    • (2003) J. Clin. Pharm. Ther. , vol.28 , pp. 203-228
    • Wang, R.B.1    Kuo, C.L.2    Lien, L.L.3    Lien, E.J.4
  • 32
    • 18244376403 scopus 로고    scopus 로고
    • Modulation by flavonoids of cell multidrug resistance mediated by P-glycoprotein and related ABC transporters
    • Di Pietro, A.; Conseil, G.; Perez-Victoria, J. M.; Dayan, G.; Baubichon-Cortay, H. et al. Modulation by flavonoids of cell multidrug resistance mediated by P-glycoprotein and related ABC transporters. Cell Mol. Life Sci. 2002, 59, 307-322.
    • (2002) Cell Mol. Life Sci. , vol.59 , pp. 307-322
    • Di Pietro, A.1    Conseil, G.2    Perez-Victoria, J.M.3    Dayan, G.4    Baubichon-Cortay, H.5
  • 33
    • 0027460274 scopus 로고
    • Identification of specific sites in human P-glycoprotein phosphorylated by protein kinase C
    • Chambers, T. C.; Pohl, J.; Raynor, R. L.; Kuo, J. F. Identification of specific sites in human P-glycoprotein phosphorylated by protein kinase C. J. Biol. Chem. 1993, 268, 4592-4595.
    • (1993) J. Biol. Chem. , vol.268 , pp. 4592-4595
    • Chambers, T.C.1    Pohl, J.2    Raynor, R.L.3    Kuo, J.F.4
  • 34
    • 0028881514 scopus 로고
    • Interaction of tamoxifen with the multidrug resistance P-glycoprotein
    • Callaghan, R.; Higgins, C. F. Interaction of tamoxifen with the multidrug resistance P-glycoprotein. Br. J. Cancer 1995, 71, 294-299.
    • (1995) Br. J. Cancer , vol.71 , pp. 294-299
    • Callaghan, R.1    Higgins, C.F.2
  • 35
    • 0028818853 scopus 로고
    • Circumvention of P-glycoprotein-mediated multiple drug resistance by phosphorylation modulators is independent of protein kinases
    • Smith, C. D.; Zilfou, J. T. Circumvention of P-glycoprotein-mediated multiple drug resistance by phosphorylation modulators is independent of protein kinases. J. Biol. Chem. 1995, 270, 28145-28152.
    • (1995) J. Biol. Chem. , vol.270 , pp. 28145-28152
    • Smith, C.D.1    Zilfou, J.T.2
  • 36
    • 0035957082 scopus 로고    scopus 로고
    • Protein kinase C effectors bind to multidrug ABC transporters and inhibit their activity
    • Conseil, G.; Perez-Victoria, J. M.; Jault, J. M.; Gamarro, F.; Goffeau, A. et al. Protein kinase C effectors bind to multidrug ABC transporters and inhibit their activity. Biochemistry 2001, 40, 2564-2571.
    • (2001) Biochemistry , vol.40 , pp. 2564-2571
    • Conseil, G.1    Perez-Victoria, J.M.2    Jault, J.M.3    Gamarro, F.4    Goffeau, A.5
  • 37
    • 0030663804 scopus 로고    scopus 로고
    • Binding of steroid modulators to recombinant cytosolic domain from mouse P-glycoprotein in close proximity to the ATP site
    • Dayan, G.; Jault, J. M.; Baubichon-Cortay, H.; Baggetto, L. G.; Renoir, J. M. et al. Binding of steroid modulators to recombinant cytosolic domain from mouse P-glycoprotein in close proximity to the ATP site. Biochemistry 1997, 36, 15208-15215.
    • (1997) Biochemistry , vol.36 , pp. 15208-15215
    • Dayan, G.1    Jault, J.M.2    Baubichon-Cortay, H.3    Baggetto, L.G.4    Renoir, J.M.5
  • 38
    • 0027175126 scopus 로고
    • BIBW 22, a dipyridamole analogue, acts as a bifunctional modulator on tumor cells by influencing both P-glycoprotein and nucleoside transport
    • Chen, H. X.; Bamberger, U.; Heckel, A.; Guo, X.; Cheng, Y. C. BIBW 22, a dipyridamole analogue, acts as a bifunctional modulator on tumor cells by influencing both P-glycoprotein and nucleoside transport. Cancer Res. 1993, 53, 1974-1977.
    • (1993) Cancer Res. , vol.53 , pp. 1974-1977
    • Chen, H.X.1    Bamberger, U.2    Heckel, A.3    Guo, X.4    Cheng, Y.C.5
  • 39
    • 0037081269 scopus 로고    scopus 로고
    • X-ray repair cross-complementing gene I protein plays an important role in camptothecin resistance
    • Park, S. Y.; Lam, W.; Cheng, Y. C. X-ray repair cross-complementing gene I protein plays an important role in camptothecin resistance. Cancer Res. 2002, 62, 459-465.
    • (2002) Cancer Res. , vol.62 , pp. 459-465
    • Park, S.Y.1    Lam, W.2    Cheng, Y.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.