메뉴 건너뛰기




Volumn 58, Issue 4, 2015, Pages 1832-1845

Synthesis of new steroidal inhibitors of P-glycoprotein-mediated multidrug resistance and biological evaluation on K562/R7 erythroleukemia cells

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOSPORIN A; DAUNORUBICIN; DOXORUBICIN; GLYCOPROTEIN; HYDROXYL GROUP; MIFEPRISTONE; MULTIDRUG RESISTANCE PROTEIN; OXYGEN; PROGESTERONE DERIVATIVE; TETRAHYDROPYRANYL ETHER; VERAPAMIL; PROGESTERONE;

EID: 84923914311     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501676v     Document Type: Article
Times cited : (13)

References (78)
  • 1
    • 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 Nat. Rev. Cancer 2002, 21, 48-58
    • (2002) Nat. Rev. Cancer , vol.21 , pp. 48-58
    • Gottesman, M.M.1    Fojo, T.2    Bates, S.E.3
  • 2
    • 33745748312 scopus 로고    scopus 로고
    • The functions and structures of ABC transporters: Implications for the design of new inhibitors of Pgp and MRP1 to control the multidrug resistance (MDR)
    • Teodori, E.; Dei, S.; Martelli, C.; Scapecchi, S.; Gualtieri, F. The functions and structures of ABC transporters: implications for the design of new inhibitors of Pgp and MRP1 to control the multidrug resistance (MDR) Curr. Drug Targets 2006, 7, 896-909
    • (2006) Curr. Drug Targets , vol.7 , pp. 896-909
    • Teodori, E.1    Dei, S.2    Martelli, C.3    Scapecchi, S.4    Gualtieri, F.5
  • 3
    • 0035038919 scopus 로고    scopus 로고
    • The orphan nuclear receptor SXR coordinately regulates drug metabolism and efflux
    • Synold, T. W.; Dussault, I.; Forman, B. M. The orphan nuclear receptor SXR coordinately regulates drug metabolism and efflux Nat. Med. 2001, 7, 584-590
    • (2001) Nat. Med. , vol.7 , pp. 584-590
    • Synold, T.W.1    Dussault, I.2    Forman, B.M.3
  • 4
    • 77949371041 scopus 로고    scopus 로고
    • Perspectives of P-glycoprotein modulating agents in oncology and neurodegenerative diseases: Pharmaceutical, biological, and diagnostic potentials
    • Colabufo, N. A.; Berardi, F.; Cantore, M.; Contino, M.; Inglese, C.; Niso, M.; Perrone, R. Perspectives of P-glycoprotein modulating agents in oncology and neurodegenerative diseases: Pharmaceutical, biological, and diagnostic potentials J. Med. Chem. 2010, 53, 1883-1897
    • (2010) J. Med. Chem. , vol.53 , pp. 1883-1897
    • Colabufo, N.A.1    Berardi, F.2    Cantore, M.3    Contino, M.4    Inglese, C.5    Niso, M.6    Perrone, R.7
  • 5
    • 84894649947 scopus 로고    scopus 로고
    • Homology modeling and structural analysis of human P-glycoprotein
    • Yamaguchi, H.; Kidachi, Y.; Kamiie, K.; Noshita, T.; Umetsu, H. Homology modeling and structural analysis of human P-glycoprotein Bioinformation 2012, 22, 1066-1074
    • (2012) Bioinformation , vol.22 , pp. 1066-1074
    • Yamaguchi, H.1    Kidachi, Y.2    Kamiie, K.3    Noshita, T.4    Umetsu, H.5
  • 7
    • 0344761958 scopus 로고    scopus 로고
    • The importance of a nitrogen atom in modulators of multidrug resistance
    • Ecker, G.; Huber, M.; Schmid, D.; Chiba, P. The importance of a nitrogen atom in modulators of multidrug resistance Mol. Pharmacol. 1999, 56, 791-796
    • (1999) Mol. Pharmacol. , vol.56 , pp. 791-796
    • Ecker, G.1    Huber, M.2    Schmid, D.3    Chiba, P.4
  • 9
    • 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
  • 10
    • 33645991819 scopus 로고    scopus 로고
    • Role of transmembrane domain/transmembrane domain interfaces of P-glycoprotein (ABCB1) in solute transport. Convergent information from photoaffinity labeling, site directed mutagenesis and in silico importance prediction
    • Chiba, P.; Mihalek, I.; Ecker, G. F.; Kopp, S.; Lichtarge, O. Role of transmembrane domain/transmembrane domain interfaces of P-glycoprotein (ABCB1) in solute transport. Convergent information from photoaffinity labeling, site directed mutagenesis and in silico importance prediction Curr. Med. Chem. 2006, 13, 793-805
    • (2006) Curr. Med. Chem. , vol.13 , pp. 793-805
    • Chiba, P.1    Mihalek, I.2    Ecker, G.F.3    Kopp, S.4    Lichtarge, O.5
  • 11
    • 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
  • 13
    • 73949155491 scopus 로고    scopus 로고
    • Overcoming multidrug resistance in cancer: Clinical studies of P-glycoprotein inhibitors
    • Coley, H. M. Overcoming multidrug resistance in cancer: Clinical studies of P-glycoprotein inhibitors Methods Mol. Biol. 2010, 596, 341-358
    • (2010) Methods Mol. Biol. , vol.596 , pp. 341-358
    • Coley, H.M.1
  • 14
    • 0024501045 scopus 로고
    • Progesterone interacts with P-glycoprotein in multidrug-resistant cells and in the endometrium of gravid uterus
    • Yang, C. P.; DePinho, S. G.; Greenberger, L. M.; Arceci, R. J.; Horwitz, S. B. Progesterone interacts with P-glycoprotein in multidrug-resistant cells and in the endometrium of gravid uterus J. Biol. Chem. 1989, 264, 782-788
    • (1989) J. Biol. Chem. , vol.264 , pp. 782-788
    • Yang, C.P.1    Depinho, S.G.2    Greenberger, L.M.3    Arceci, R.J.4    Horwitz, S.B.5
  • 16
    • 0030589989 scopus 로고    scopus 로고
    • Steroid transport, accumulation, and antagonism of P-glycoprotein in multidrug-resistant cells
    • Barnes, K. M.; Dickstein, B.; Cutler, G. B.; Fojo, T.; Bates, S. E. Steroid transport, accumulation, and antagonism of P-glycoprotein in multidrug-resistant cells Biochemistry 1996, 35, 4820-4827
    • (1996) Biochemistry , vol.35 , pp. 4820-4827
    • Barnes, K.M.1    Dickstein, B.2    Cutler, G.B.3    Fojo, T.4    Bates, S.E.5
  • 17
    • 0033575293 scopus 로고    scopus 로고
    • Identification of P-glycoprotein mutations causing a loss of steroid recognition and transport
    • Vo, Q. D.; Gruol, D. J. Identification of P-glycoprotein mutations causing a loss of steroid recognition and transport J. Biol. Chem. 1999, 274, 20318-20327
    • (1999) J. Biol. Chem. , vol.274 , pp. 20318-20327
    • Vo, Q.D.1    Gruol, D.J.2
  • 19
    • 0027299488 scopus 로고
    • Non-glucocorticoid steroid analogues (21-aminosteroids) sensitize multidrug resistant cells to vinblastine
    • Abraham, I.; Wolf, C. L.; Sampson, K. E. Non-glucocorticoid steroid analogues (21-aminosteroids) sensitize multidrug resistant cells to vinblastine Cancer Chemother. Pharmacol. 1993, 32, 116-122
    • (1993) Cancer Chemother. Pharmacol. , vol.32 , pp. 116-122
    • Abraham, I.1    Wolf, C.L.2    Sampson, K.E.3
  • 20
    • 77954763228 scopus 로고    scopus 로고
    • Novel steroid carbamates reverse multidrug-resistance in cancer therapy and show linkage among efficacy, loci of drug action and P-glycoproteins cellular localization
    • Argov, M.; Bod, T.; Batra, S.; Margalit, R. Novel steroid carbamates reverse multidrug-resistance in cancer therapy and show linkage among efficacy, loci of drug action and P-glycoproteins cellular localization Eur. J. Pharm. Sci. 2010, 41, 53-59
    • (2010) Eur. J. Pharm. Sci. , vol.41 , pp. 53-59
    • Argov, M.1    Bod, T.2    Batra, S.3    Margalit, R.4
  • 21
    • 0034945212 scopus 로고    scopus 로고
    • Reversal effects of nomegestrol acetate on multidrug resistance in adriamycin-resistant MCF7 breast cancer cell line
    • Li, J.; Xu, L. Z.; He, K. L.; Guo, W. J.; Zheng, Y. H.; Xia, P.; Chen, Y. Reversal effects of nomegestrol acetate on multidrug resistance in adriamycin-resistant MCF7 breast cancer cell line Breast Cancer Res. 2001, 3, 253-263
    • (2001) Breast Cancer Res. , vol.3 , pp. 253-263
    • Li, J.1    Xu, L.Z.2    He, K.L.3    Guo, W.J.4    Zheng, Y.H.5    Xia, P.6    Chen, Y.7
  • 23
    • 40849083469 scopus 로고    scopus 로고
    • Effects of plant sterols on human multidrug transporters ABCB1 and ABCC1
    • Nabekura, T.; Yamaki, T.; Ueno, K.; Kitagawa, S. Effects of plant sterols on human multidrug transporters ABCB1 and ABCC1 Biochem. Biophys. Res. Commun. 2008, 369, 363-368
    • (2008) Biochem. Biophys. Res. Commun. , vol.369 , pp. 363-368
    • Nabekura, T.1    Yamaki, T.2    Ueno, K.3    Kitagawa, S.4
  • 24
    • 74949111437 scopus 로고    scopus 로고
    • Reversal of P-glycoprotein-mediated multidrug resistance by guggulsterone in doxorubicin-resistant human myelogenous leukemia (K562/DOX) cells
    • Xu, H. B.; Li, L.; Liu, G. Q. Reversal of P-glycoprotein-mediated multidrug resistance by guggulsterone in doxorubicin-resistant human myelogenous leukemia (K562/DOX) cells Pharmazie 2009, 64, 660-665
    • (2009) Pharmazie , vol.64 , pp. 660-665
    • Xu, H.B.1    Li, L.2    Liu, G.Q.3
  • 25
    • 47549086990 scopus 로고    scopus 로고
    • Tenacigenin B derivatives reverse P-glycoprotein-mediated multidrug resistance in HepG2/Dox cells
    • Hu, Y. J.; Shen, X. L.; Lu, H. L.; Zhang, Y. H.; Huang, X. A.; Fu, L. C.; Fong, W. F. Tenacigenin B derivatives reverse P-glycoprotein-mediated multidrug resistance in HepG2/Dox cells J. Nat. Prod. 2008, 71, 1049-1051
    • (2008) J. Nat. Prod. , vol.71 , pp. 1049-1051
    • Hu, Y.J.1    Shen, X.L.2    Lu, H.L.3    Zhang, Y.H.4    Huang, X.A.5    Fu, L.C.6    Fong, W.F.7
  • 26
    • 0031058658 scopus 로고    scopus 로고
    • Chemosensitizing steroids: Glucocorticoid receptor agonists capable of inhibiting P-glycoprotein function
    • Gruol, D. J.; Bourgeois, S. Chemosensitizing steroids: Glucocorticoid receptor agonists capable of inhibiting P-glycoprotein function Cancer Res. 1997, 57, 720-727
    • (1997) Cancer Res. , vol.57 , pp. 720-727
    • Gruol, D.J.1    Bourgeois, S.2
  • 27
    • 32044437970 scopus 로고    scopus 로고
    • Modulation of p-glycoprotein and breast cancer resistance protein by some prescribed corticosteroids
    • Cooray, H. C.; Shahi, S.; Cahn, A. P.; Van Veen, H. W.; Hladky, S. B.; Barrand, M. A. Modulation of p-glycoprotein and breast cancer resistance protein by some prescribed corticosteroids Eur. J. Pharmacol. 2006, 531, 25-33
    • (2006) Eur. J. Pharmacol. , vol.531 , pp. 25-33
    • Cooray, H.C.1    Shahi, S.2    Cahn, A.P.3    Van Veen, H.W.4    Hladky, S.B.5    Barrand, M.A.6
  • 32
  • 33
    • 48849098124 scopus 로고    scopus 로고
    • Inhibit multidrug resistance and induce apoptosis by using glycocholic acid and epirubicin
    • Lo, Y. L.; Ho, C. T.; Tsai, F. L. Inhibit multidrug resistance and induce apoptosis by using glycocholic acid and epirubicin Eur. J. Pharm. Sci. 2008, 35, 52-67
    • (2008) Eur. J. Pharm. Sci. , vol.35 , pp. 52-67
    • Lo, Y.L.1    Ho, C.T.2    Tsai, F.L.3
  • 34
    • 0026079367 scopus 로고
    • Transient enhancement of multidrug resistance by the bile acid deoxycholate in murine fibrosarcoma cells in vitro
    • OBrian, C. A.; Fan, D.; Ward, N. E.; Dong, Z.; Iwamoto, L.; Gupta, K. P.; Earnest, L. E.; Fidler, I. J. Transient enhancement of multidrug resistance by the bile acid deoxycholate in murine fibrosarcoma cells in vitro Biochem. Pharmacol. 1991, 41, 797-806
    • (1991) Biochem. Pharmacol. , vol.41 , pp. 797-806
    • Obrian, C.A.1    Fan, D.2    Ward, N.E.3    Dong, Z.4    Iwamoto, L.5    Gupta, K.P.6    Earnest, L.E.7    Fidler, I.J.8
  • 35
    • 0033963413 scopus 로고    scopus 로고
    • Effects of sodium deoxycholate and sodium caprate on the transport of epirubicin in human intestinal epithelial Caco-2 cell layers and everted gut sacs of rats
    • Lo, Y. L.; Huang, J. D. Effects of sodium deoxycholate and sodium caprate on the transport of epirubicin in human intestinal epithelial Caco-2 cell layers and everted gut sacs of rats Biochem. Pharmacol. 2000, 59, 665-672
    • (2000) Biochem. Pharmacol. , vol.59 , pp. 665-672
    • Lo, Y.L.1    Huang, J.D.2
  • 36
    • 0028235746 scopus 로고
    • Bile acid inhibition of P-glycoprotein-mediated transport in multidrug-resistant cells and rat liver canalicular membrane vesicles
    • Mazzanti, R.; Fantappié, O.; Kamimoto, Y.; Gatmaitan, Z.; Gentilini, P.; Arias, I. M. Bile acid inhibition of P-glycoprotein-mediated transport in multidrug-resistant cells and rat liver canalicular membrane vesicles Hepatology 1994, 20, 170-176
    • (1994) Hepatology , vol.20 , pp. 170-176
    • Mazzanti, R.1    Fantappié, O.2    Kamimoto, Y.3    Gatmaitan, Z.4    Gentilini, P.5    Arias, I.M.6
  • 37
    • 0035091515 scopus 로고    scopus 로고
    • Reversal of multidrug resistance and increase in plasma membrane fluidity in CHO cells with R-verapamil and bile salts
    • Schuldes, H.; Dolderer, J. H.; Zimmer, G.; Knobloch, J.; Bickeböller, R.; Jonas, D.; Woodcock, B. G. Reversal of multidrug resistance and increase in plasma membrane fluidity in CHO cells with R-verapamil and bile salts Eur. J. Cancer 2001, 37, 660-667
    • (2001) Eur. J. Cancer , vol.37 , pp. 660-667
    • Schuldes, H.1    Dolderer, J.H.2    Zimmer, G.3    Knobloch, J.4    Bickeböller, R.5    Jonas, D.6    Woodcock, B.G.7
  • 38
    • 0036839818 scopus 로고    scopus 로고
    • Evidence for the locations of distinct steroid and Vinca alkaloid interaction domains within the murine mdr1b P-glycoprotein
    • Gruol, D. J.; King, M. N.; Kuehne, M. E. Evidence for the locations of distinct steroid and Vinca alkaloid interaction domains within the murine mdr1b P-glycoprotein Mol. Pharmacol. 2002, 62, 1238-1248
    • (2002) Mol. Pharmacol. , vol.62 , pp. 1238-1248
    • Gruol, D.J.1    King, M.N.2    Kuehne, M.E.3
  • 40
    • 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.; Baulieu, E. E.; Gros, P.; Di Pietro, A. 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    Baulieu, E.E.6    Gros, P.7    Di Pietro, A.8
  • 41
    • 8144230162 scopus 로고    scopus 로고
    • Comparison of steroid substrates and inhibitors of P-glycoprotein by 3D-QSAR analysis
    • Li, Y.; Wang, Y. H.; Yang, L.; Zhang, S. W.; Liu, C. H.; Yang, S. L. Comparison of steroid substrates and inhibitors of P-glycoprotein by 3D-QSAR analysis J. Mol. Struct. 2005, 733, 111-118
    • (2005) J. Mol. Struct. , vol.733 , pp. 111-118
    • Li, Y.1    Wang, Y.H.2    Yang, L.3    Zhang, S.W.4    Liu, C.H.5    Yang, S.L.6
  • 42
    • 67650448010 scopus 로고    scopus 로고
    • Identification of putative steroid-binding sites in human ABCB1 and ABCG2
    • Mares-Samano, S.; Badhan, R.; Penny, J. Identification of putative steroid-binding sites in human ABCB1 and ABCG2 Eur. J. Med. Chem. 2009, 44, 3601-3611
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 3601-3611
    • Mares-Samano, S.1    Badhan, R.2    Penny, J.3
  • 43
    • 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.; Di Pietro, A. 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    Di Pietro, A.6
  • 44
    • 0032578434 scopus 로고    scopus 로고
    • Structural flexibility of the linker region of human P-glycoprotein permits ATP hydrolysis and drug transport
    • Hrycyna, C. A.; Airan, L. E.; Germann, U. A.; Ambudkar, S. V.; Pastan, I.; Gottesman, M. M. Structural flexibility of the linker region of human P-glycoprotein permits ATP hydrolysis and drug transport Biochemistry 1998, 37, 13660-13673
    • (1998) Biochemistry , vol.37 , pp. 13660-13673
    • Hrycyna, C.A.1    Airan, L.E.2    Germann, U.A.3    Ambudkar, S.V.4    Pastan, I.5    Gottesman, M.M.6
  • 46
    • 1442300944 scopus 로고    scopus 로고
    • Biochemical basis of polyvalency as a strategy for enhancing the efficacy of P-glycoprotein (ABCB1) modulators: Stipiamide homodimers separated with defined-length spacers reverse drug efflux with greater efficacy
    • Sauna, Z. E.; Andrus, M. B.; Turner, T. M.; Ambudkar, S. V. Biochemical basis of polyvalency as a strategy for enhancing the efficacy of P-glycoprotein (ABCB1) modulators: stipiamide homodimers separated with defined-length spacers reverse drug efflux with greater efficacy Biochemistry 2004, 43, 2262-2271
    • (2004) Biochemistry , vol.43 , pp. 2262-2271
    • Sauna, Z.E.1    Andrus, M.B.2    Turner, T.M.3    Ambudkar, S.V.4
  • 47
    • 65549092069 scopus 로고    scopus 로고
    • Flavonoid dimers as bivalent modulators for P-glycoprotein-based multidrug resistance: Structure-activity relationships
    • Chan, K. F.; Zhao, Y.; Chow, T. W.; Yan, C. S.; Ma, D. L.; Burkett, B. A.; Wong, I. L.; Chow, L. M.; Chan, T. H. Flavonoid dimers as bivalent modulators for P-glycoprotein-based multidrug resistance: Structure-activity relationships ChemMedChem 2009, 4, 594-614
    • (2009) ChemMedChem , vol.4 , pp. 594-614
    • Chan, K.F.1    Zhao, Y.2    Chow, T.W.3    Yan, C.S.4    Ma, D.L.5    Burkett, B.A.6    Wong, I.L.7    Chow, L.M.8    Chan, T.H.9
  • 48
    • 77952322979 scopus 로고    scopus 로고
    • Design, synthesis and evaluation of progesterone-adenine hybrids as bivalent inhibitors of P-glycoprotein-mediated multidrug efflux
    • Zeinyeh, W.; Alameh, G.; Radix, S.; Grenot, C.; Dumontet, C.; Walchshofer, N. Design, synthesis and evaluation of progesterone-adenine hybrids as bivalent inhibitors of P-glycoprotein-mediated multidrug efflux Bioorg. Med. Chem. Lett. 2010, 20, 3165-3168
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3165-3168
    • Zeinyeh, W.1    Alameh, G.2    Radix, S.3    Grenot, C.4    Dumontet, C.5    Walchshofer, N.6
  • 49
    • 0033083015 scopus 로고    scopus 로고
    • Stimulation of P-glycoprotein-mediated drug transport by prazosin and progesterone. Evidence for a third drug-binding site
    • Shapiro, A. B.; Fox, K.; Lam, P.; Ling, V. Stimulation of P-glycoprotein-mediated drug transport by prazosin and progesterone. Evidence for a third drug-binding site Eur. J. Biochem. 1999, 259, 841-850
    • (1999) Eur. J. Biochem. , vol.259 , pp. 841-850
    • Shapiro, A.B.1    Fox, K.2    Lam, P.3    Ling, V.4
  • 50
    • 0031039693 scopus 로고    scopus 로고
    • Competitive and non-competitive inhibition of the multidrug-resistance-associated P-glycoprotein ATPase further experimental evidence for a multisite model
    • Garrigos, M.; Mir, L. M.; Orlowski, S. Competitive and non-competitive inhibition of the multidrug-resistance-associated P-glycoprotein ATPase further experimental evidence for a multisite model Eur. J. Biochem. 1997, 244, 664-673
    • (1997) Eur. J. Biochem. , vol.244 , pp. 664-673
    • Garrigos, M.1    Mir, L.M.2    Orlowski, S.3
  • 51
    • 0033404139 scopus 로고    scopus 로고
    • Multiple recognition of various amphiphilic molecules by the multidrug resistance P-glycoprotein: Molecular mechanisms and pharmacological consequences coming from functional interactions between various drugs
    • Orlowski, S.; Garrigos, M. Multiple recognition of various amphiphilic molecules by the multidrug resistance P-glycoprotein: molecular mechanisms and pharmacological consequences coming from functional interactions between various drugs Anticancer Res. 1999, 19, 3109-3123
    • (1999) Anticancer Res. , vol.19 , pp. 3109-3123
    • Orlowski, S.1    Garrigos, M.2
  • 52
    • 0020992924 scopus 로고
    • Synthesis of 3α,7α-dihydroxy-5β-androstan-17-one
    • Lai, C. K.; Byon, C. Y.; Gut, M. Synthesis of 3α,7α-dihydroxy-5β-androstan-17-one Steroids 1983, 42, 707-711
    • (1983) Steroids , vol.42 , pp. 707-711
    • Lai, C.K.1    Byon, C.Y.2    Gut, M.3
  • 53
    • 84855895182 scopus 로고    scopus 로고
    • Synthesis of deuterium labeled NMDA receptor inhibitor - 20-oxo-5β-[9,12,12-2H3]pregnan-3α-yl-L-glutamyl 1-ester
    • Kapras, V.; Slavickova, A.; Stastna, E.; Vyklicky, L., Jr.; Vales, K.; Chodounska, H. Synthesis of deuterium labeled NMDA receptor inhibitor-20-oxo-5β-[9,12,12-2H3]pregnan-3α-yl-L-glutamyl 1-ester Steroids 2012, 77, 282-287
    • (2012) Steroids , vol.77 , pp. 282-287
    • Kapras, V.1    Slavickova, A.2    Stastna, E.3    Vyklicky, Jr.L.4    Vales, K.5    Chodounska, H.6
  • 54
    • 84914576588 scopus 로고
    • Preparation of Δ5-7-oxo-steroids by allylic oxidation of Δ5-steroids: A study of the reactivity of the chromium trioxide-pyridine 1:1 and 1:2 complexes prepared in situ
    • Mappus, E.; Cuilleron, C. Y. Preparation of Δ5-7-oxo-steroids by allylic oxidation of Δ5-steroids: a study of the reactivity of the chromium trioxide-pyridine 1:1 and 1:2 complexes prepared in situ J. Chem. Res. 1979, 42, 501-535
    • (1979) J. Chem. Res. , vol.42 , pp. 501-535
    • Mappus, E.1    Cuilleron, C.Y.2
  • 55
    • 0018366161 scopus 로고
    • Synthesis and stereochemistry of C-3 and C-7-linked (O-carboxymethyl)-oxyimino)- and hemisuccinamido derivatives of 5α-dihydrotestosterone
    • Mappus, E.; Cuilleron, C. Y. Synthesis and stereochemistry of C-3 and C-7-linked (O-carboxymethyl)-oxyimino)- and hemisuccinamido derivatives of 5α-dihydrotestosterone Steroids 1979, 33, 693-718
    • (1979) Steroids , vol.33 , pp. 693-718
    • Mappus, E.1    Cuilleron, C.Y.2
  • 56
    • 84959971999 scopus 로고
    • Stereospecific syntheses of 7β- and 7α-hydroxycholesterols
    • Kumar, V.; Amann, A.; Ourisson, G.; Lulu, B. Stereospecific syntheses of 7β- and 7α-hydroxycholesterols Synth. Commun. 1987, 17, 1279-1286
    • (1987) Synth. Commun. , vol.17 , pp. 1279-1286
    • Kumar, V.1    Amann, A.2    Ourisson, G.3    Lulu, B.4
  • 57
    • 0014322443 scopus 로고
    • A one-step procedure for the preparation of tertiary α-ketols from the corresponding ketones
    • Gardner, J. N.; Carlon, F. E.; Gnoj, O. A one-step procedure for the preparation of tertiary α-ketols from the corresponding ketones J. Org. Chem. 1968, 33, 3294-3297
    • (1968) J. Org. Chem. , vol.33 , pp. 3294-3297
    • Gardner, J.N.1    Carlon, F.E.2    Gnoj, O.3
  • 58
    • 0017889714 scopus 로고
    • A convenient synthesis of 3-keto bile acids by selective oxidation of bile acids with silver carbonate-Celite
    • Tserng, K. Y. A convenient synthesis of 3-keto bile acids by selective oxidation of bile acids with silver carbonate-Celite J. Lipid Res. 1978, 19, 501-504
    • (1978) J. Lipid Res. , vol.19 , pp. 501-504
    • Tserng, K.Y.1
  • 59
    • 0001449676 scopus 로고
    • A symmetrical alternative to the tetrahydropyranyl protecting group
    • Reese, C. B.; Saffhill, R.; Suiston, J. E. A symmetrical alternative to the tetrahydropyranyl protecting group J. Am. Chem. Soc. 1967, 89, 3366-3368
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3366-3368
    • Reese, C.B.1    Saffhill, R.2    Suiston, J.E.3
  • 60
    • 37049123067 scopus 로고
    • X-ray crystal structure determination of the more laevorotatory diastereoisomer of 2′-O-terahydropyranyladenosine. Correlation of physical properties of tetrahydropyranyl ethers with absolute configuration
    • Kennard, O.; Motherwell, W. D. S.; Coppola, J. C.; Griffin, B. E.; Reese, C. B.; Larson, A. C. X-ray crystal structure determination of the more laevorotatory diastereoisomer of 2′-O-terahydropyranyladenosine. Correlation of physical properties of tetrahydropyranyl ethers with absolute configuration J. Chem. Soc. B 1971, 1940-1946
    • (1971) J. Chem. Soc. B , pp. 1940-1946
    • Kennard, O.1    Motherwell, W.D.S.2    Coppola, J.C.3    Griffin, B.E.4    Reese, C.B.5    Larson, A.C.6
  • 61
    • 0010626560 scopus 로고
    • Structure of an enantiomerically pure tetrahydropyranyl ether
    • Mash, E. A.; Fryling, J. A.; Wexler, P. A. Structure of an enantiomerically pure tetrahydropyranyl ether Acta Crystallogr. 1991, C47, 2708-2709
    • (1991) Acta Crystallogr. , vol.47 , pp. 2708-2709
    • Mash, E.A.1    Fryling, J.A.2    Wexler, P.A.3
  • 63
    • 0001381021 scopus 로고
    • Anomeric effect in 2-alkoxytetrahydropyrans studied by 13C and 17O NMR chemical shifts
    • McKelvey, R. D.; Kawada, Y.; Sugawara, T.; Iwamura, H. Anomeric effect in 2-alkoxytetrahydropyrans studied by 13C and 17O NMR chemical shifts J. Org. Chem. 1981, 46, 4948-4952
    • (1981) J. Org. Chem. , vol.46 , pp. 4948-4952
    • McKelvey, R.D.1    Kawada, Y.2    Sugawara, T.3    Iwamura, H.4
  • 64
    • 84986738357 scopus 로고
    • 13C N.M.R spectra of steroids-A survey and commentary
    • Blunt, J. W.; Stothers, J. B. 13C N.M.R spectra of steroids-A survey and commentary Org. Magn. Reson. 1977, 9, 439-464
    • (1977) Org. Magn. Reson. , vol.9 , pp. 439-464
    • Blunt, J.W.1    Stothers, J.B.2
  • 65
    • 0021691235 scopus 로고
    • Homonuclear decoupling in heteronuclear chemical shift correlation spectroscopy. 1. Study of progesterone
    • Wong, T. C.; Rutar, V. Homonuclear decoupling in heteronuclear chemical shift correlation spectroscopy. 1. Study of progesterone J. Am. Chem. Soc. 1984, 106, 7380-7384
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 7380-7384
    • Wong, T.C.1    Rutar, V.2
  • 66
    • 0017301888 scopus 로고
    • Carbon-13 nuclear magnetic resonance spectra of hydroxy steroids
    • Eggert, H.; VanAntwerp, C. L.; Bhacca, N. S.; Djerassi, C. Carbon-13 nuclear magnetic resonance spectra of hydroxy steroids J. Org. Chem. 1976, 41, 71-78
    • (1976) J. Org. Chem. , vol.41 , pp. 71-78
    • Eggert, H.1    Vanantwerp, C.L.2    Bhacca, N.S.3    Djerassi, C.4
  • 67
    • 70349637956 scopus 로고    scopus 로고
    • Development and screening of water-soluble analogues of progesterone and allopregnanolone in models of brain injury
    • MacNevin, C. J.; Atif, F.; Sayeed, I.; Stein, D. G.; Liotta, D. C. Development and screening of water-soluble analogues of progesterone and allopregnanolone in models of brain injury J. Med. Chem. 2009, 52, 6012-6023
    • (2009) J. Med. Chem. , vol.52 , pp. 6012-6023
    • Macnevin, C.J.1    Atif, F.2    Sayeed, I.3    Stein, D.G.4    Liotta, D.C.5
  • 68
    • 84989111485 scopus 로고
    • Preparation and carbon-13 NMR study of 3- and 20-methylene analogues of steroid hormones
    • Gonzales, M. D.; Burton, G. Preparation and carbon-13 NMR study of 3- and 20-methylene analogues of steroid hormones Magn. Reson. Chem. 1988, 26, 963-966
    • (1988) Magn. Reson. Chem. , vol.26 , pp. 963-966
    • Gonzales, M.D.1    Burton, G.2
  • 69
    • 0022245636 scopus 로고
    • Nuclear magnetic resonance spectroscopy of bile acids. Development of two-dimensional NMR methods for the elucidation of proton resonance assignments for five common hydroxylated bile acids, and their parent bile acid, 5β-cholanoic acid
    • Waterhous, D. V.; Barnes, S.; Muccio, D. D. Nuclear magnetic resonance spectroscopy of bile acids. Development of two-dimensional NMR methods for the elucidation of proton resonance assignments for five common hydroxylated bile acids, and their parent bile acid, 5β-cholanoic acid J. Lipid Res. 1985, 26, 1068-1078
    • (1985) J. Lipid Res. , vol.26 , pp. 1068-1078
    • Waterhous, D.V.1    Barnes, S.2    Muccio, D.D.3
  • 70
    • 84989625499 scopus 로고
    • Studies on the conformations in solution of 5β-steroids having different side chains by 13C NMR spectroscopy
    • Seldes, A. M.; DeLuca, M. E.; Gros, E. G. Studies on the conformations in solution of 5β-steroids having different side chains by 13C NMR spectroscopy Magn. Reson. Chem. 1986, 24, 185-189
    • (1986) Magn. Reson. Chem. , vol.24 , pp. 185-189
    • Seldes, A.M.1    Deluca, M.E.2    Gros, E.G.3
  • 71
    • 0025210432 scopus 로고
    • Proton and carbon-13 nuclear magnetic resonance spectroscopy of diastereoisomeric 3- and 17β-tetrahydropyranyl ether derivatives of estrone and estradiol
    • Boucheau, V.; Renaud, M.; Rolland de Ravel, M.; Mappus, E.; Cuilleron, C. Y. Proton and carbon-13 nuclear magnetic resonance spectroscopy of diastereoisomeric 3- and 17β-tetrahydropyranyl ether derivatives of estrone and estradiol Steroids 1990, 55, 209-221
    • (1990) Steroids , vol.55 , pp. 209-221
    • Boucheau, V.1    Renaud, M.2    Rolland De Ravel, M.3    Mappus, E.4    Cuilleron, C.Y.5
  • 72
    • 0033930859 scopus 로고    scopus 로고
    • High-field NMR studies of 3β-tetrahydropyranyloxy steroids
    • Szendi, Z.; Forgo, P.; Kover, K. E.; Sweet, F. High-field NMR studies of 3β-tetrahydropyranyloxy steroids Steroids 2000, 65, 415-422
    • (2000) Steroids , vol.65 , pp. 415-422
    • Szendi, Z.1    Forgo, P.2    Kover, K.E.3    Sweet, F.4
  • 73
    • 0032528254 scopus 로고    scopus 로고
    • Multidrug resistance transporter P-glycoprotein has distinct but interacting binding sites for cytotoxic drugs and reversing agents
    • Pascaud, C.; Garrigos, M.; Orlowski, S. Multidrug resistance transporter P-glycoprotein has distinct but interacting binding sites for cytotoxic drugs and reversing agents Biochem. J. 1998, 333, 351-358
    • (1998) Biochem. J. , vol.333 , pp. 351-358
    • Pascaud, C.1    Garrigos, M.2    Orlowski, S.3
  • 74
  • 75
    • 23744464363 scopus 로고    scopus 로고
    • Expression of the drug transporters MDR1/ABCB1, MRP1/ABCC1, MRP2/ABCC2, BCRP/ABCG2, and PXR in peripheral blood mononuclear cells and their relationship with the expression in intestine and liver
    • Albermann, N.; Schmitz-Winnenthal, F. H.; ZGraggen, K.; Volk, C.; Hoffmann, M. M.; Haefeli, W. E.; Weiss, J. Expression of the drug transporters MDR1/ABCB1, MRP1/ABCC1, MRP2/ABCC2, BCRP/ABCG2, and PXR in peripheral blood mononuclear cells and their relationship with the expression in intestine and liver Biochem. Pharmacol. 2005, 70, 949-958
    • (2005) Biochem. Pharmacol. , vol.70 , pp. 949-958
    • Albermann, N.1    Schmitz-Winnenthal, F.H.2    Zgraggen, K.3    Volk, C.4    Hoffmann, M.M.5    Haefeli, W.E.6    Weiss, J.7
  • 76
    • 2942622680 scopus 로고    scopus 로고
    • Expression of key genes of fatty acid oxidation, including adiponectin receptors, in skeletal muscle of Type 2 diabetic patients
    • Debard, C.; Laville, M.; Berbe, V.; Loizon, E.; Guillet, C.; Morio-Liondore, B.; Boirie, Y.; Vidal, H. Expression of key genes of fatty acid oxidation, including adiponectin receptors, in skeletal muscle of Type 2 diabetic patients Diabetologia 2004, 47, 917-925
    • (2004) Diabetologia , vol.47 , pp. 917-925
    • Debard, C.1    Laville, M.2    Berbe, V.3    Loizon, E.4    Guillet, C.5    Morio-Liondore, B.6    Boirie, Y.7    Vidal, H.8
  • 77
    • 33748101221 scopus 로고    scopus 로고
    • Structure-activity relationship of natural and synthetic coumarins inhibiting the multidrug transporter P-glycoprotein
    • Raad, I.; Terreux, R.; Richomme, P.; Matera, E. L.; Dumontet, C.; Raynaud, J.; Guilet, D. Structure-activity relationship of natural and synthetic coumarins inhibiting the multidrug transporter P-glycoprotein Bioorg. Med. Chem. 2006, 14, 6979-6987
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 6979-6987
    • Raad, I.1    Terreux, R.2    Richomme, P.3    Matera, E.L.4    Dumontet, C.5    Raynaud, J.6    Guilet, D.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.