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Volumn 54, Issue 1-3, 2002, Pages 71-84

Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods

Author keywords

Affinity chromatography; Chiral separation; Immobilized protein; Stereoselective binding

Indexed keywords

ACENOCOUMAROL; BENZODIAZEPINE DERIVATIVE; BOVINE SERUM ALBUMIN; COUMARIN ANTICOAGULANT; HUMAN SERUM ALBUMIN; SERUM ALBUMIN; TOFISOPAM; WARFARIN;

EID: 0037207250     PISSN: 0165022X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0165-022X(02)00131-8     Document Type: Article
Times cited : (45)

References (30)
  • 1
    • 0022596032 scopus 로고
    • Chirality of bioactive agents in protein binding, storage and transport processes
    • Simonyi M., Fitos I., Visy J. Chirality of bioactive agents in protein binding, storage and transport processes. Trends Pharmacol. Sci. 7:1986;112-116.
    • (1986) Trends Pharmacol. Sci. , vol.7 , pp. 112-116
    • Simonyi, M.1    Fitos, I.2    Visy, J.3
  • 2
    • 0020484492 scopus 로고
    • Application of ultrafiltration and CD spectroscopy for studying stereoselective binding of racemic ligands
    • Simonyi M., Fitos I., Kajtár J., Kajtár M. Application of ultrafiltration and CD spectroscopy for studying stereoselective binding of racemic ligands. Biochem. Biophys. Res. Comm. 109:1982;851-857.
    • (1982) Biochem. Biophys. Res. Comm. , vol.109 , pp. 851-857
    • Simonyi, M.1    Fitos, I.2    Kajtár, J.3    Kajtár, M.4
  • 4
    • 0027257878 scopus 로고
    • Stereoselective distribution of acenocoumarol enantiomers in human plasma: Chiral chromatographic analysis of the ultrafiltrates
    • Fitos I., Visy J., Simonyi M., Hermansson J. Stereoselective distribution of acenocoumarol enantiomers in human plasma: chiral chromatographic analysis of the ultrafiltrates. Chirality. 5:1993;346-349.
    • (1993) Chirality , vol.5 , pp. 346-349
    • Fitos, I.1    Visy, J.2    Simonyi, M.3    Hermansson, J.4
  • 6
    • 0018639333 scopus 로고
    • Binding of some fatty acids and drugs to immobilized bovine serum albumin studied by column affinity chromatography
    • Lagercrantz C., Larsson T., Karlsson H. Binding of some fatty acids and drugs to immobilized bovine serum albumin studied by column affinity chromatography. Anal. Biochem. 99:1979;352-364.
    • (1979) Anal. Biochem. , vol.99 , pp. 352-364
    • Lagercrantz, C.1    Larsson, T.2    Karlsson, H.3
  • 7
    • 0019468518 scopus 로고
    • Stereoselective binding of the enantiomers of warfarin and tryptophan to serum albumin from some different species studied by affinity chromatography on columns of immobilized serum albumin
    • Lagercrantz C., Larsson T., Denfors I. Stereoselective binding of the enantiomers of warfarin and tryptophan to serum albumin from some different species studied by affinity chromatography on columns of immobilized serum albumin. Comp. Biochem. Physiol. 69C:1981;375-378.
    • (1981) Comp. Biochem. Physiol. , vol.69 C , pp. 375-378
    • Lagercrantz, C.1    Larsson, T.2    Denfors, I.3
  • 8
    • 0020965261 scopus 로고
    • Optical resolution of a series of N-aroyl D,L-amino acids by high performance liquid chromatography on bovine serum albumin covalently bound to silica
    • Allenmark S., Bomgren B., Borén H. Optical resolution of a series of N-aroyl D,L-amino acids by high performance liquid chromatography on bovine serum albumin covalently bound to silica. J. Chromatogr. 264:1983;63-68.
    • (1983) J. Chromatogr. , vol.264 , pp. 63-68
    • Allenmark, S.1    Bomgren, B.2    Borén, H.3
  • 9
    • 0025663317 scopus 로고
    • Immobilized serum albumin: Rapid HPLC probe of stereoselective protein-binding interactions
    • Domenici E., Bertucci C., Salvadori P., Motellier S., Wainer I.W. Immobilized serum albumin: rapid HPLC probe of stereoselective protein-binding interactions. Chirality. 2:1990;263-268.
    • (1990) Chirality , vol.2 , pp. 263-268
    • Domenici, E.1    Bertucci, C.2    Salvadori, P.3    Motellier, S.4    Wainer, I.W.5
  • 10
    • 0027371531 scopus 로고
    • Determination of the magnitude and enantioselectivity of ligand binding to rat and rabbit serum albumins using immobilized-protein high performance liquid chromatography stationary phases
    • Massolini G., Aubry A.-F., McGann A., Wainer I.W. Determination of the magnitude and enantioselectivity of ligand binding to rat and rabbit serum albumins using immobilized-protein high performance liquid chromatography stationary phases. Biochem. Pharmacol. 46:1993;1285-1293.
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 1285-1293
    • Massolini, G.1    Aubry, A.-F.2    McGann, A.3    Wainer, I.W.4
  • 11
    • 0021090901 scopus 로고
    • 1-acid glycoprotein as the chiral stationary phase
    • 1-acid glycoprotein as the chiral stationary phase. J. Chromatogr. 269:1983;71-80.
    • (1983) J. Chromatogr. , vol.269 , pp. 71-80
    • Hermansson, J.1
  • 12
    • 0028231454 scopus 로고
    • Enantioselective high-performance liquid affinity chromatography as a probe of ligand-biopolymer interactions: An overview of a different use for high-performance liquid chromatographic chiral stationary phases
    • Wainer I.W. Enantioselective high-performance liquid affinity chromatography as a probe of ligand-biopolymer interactions: an overview of a different use for high-performance liquid chromatographic chiral stationary phases. J. Chromatogr., A. 666:1994;221-234.
    • (1994) J. Chromatogr., A , vol.666 , pp. 221-234
    • Wainer, I.W.1
  • 13
    • 0035847290 scopus 로고    scopus 로고
    • Chromatographic and electrophoretic studies of protein binding to chiral solutes
    • Hage D.S. Chromatographic and electrophoretic studies of protein binding to chiral solutes. J. Chromatogr., A. 906:2001;459-481.
    • (2001) J. Chromatogr., A , vol.906 , pp. 459-481
    • Hage, D.S.1
  • 14
    • 0035847245 scopus 로고    scopus 로고
    • Protein-based chiral stationary phases for high-performance liquid chromatography enantioseparations
    • Haginaka J. Protein-based chiral stationary phases for high-performance liquid chromatography enantioseparations. J. Chromatogr., A. 906:2001;253-273.
    • (2001) J. Chromatogr., A , vol.906 , pp. 253-273
    • Haginaka, J.1
  • 15
    • 0026664548 scopus 로고
    • Atomic structure and chemistry of human serum albumin
    • He X.-M., Carter D.C. Atomic structure and chemistry of human serum albumin. Nature. 358:1992;209-215.
    • (1992) Nature , vol.358 , pp. 209-215
    • He, X.-M.1    Carter, D.C.2
  • 16
    • 0027219371 scopus 로고
    • X-ray and primary structure of horse serum albumin (Equus caballus) at 0.27 nm resolution
    • Ho J.X., Holowachuk E.W., Norton E.J., Twigg P.D., Carter D.C. X-ray and primary structure of horse serum albumin (Equus caballus) at 0.27 nm resolution. Eur. J. Biochem. 215:1993;205-212.
    • (1993) Eur. J. Biochem. , vol.215 , pp. 205-212
    • Ho, J.X.1    Holowachuk, E.W.2    Norton, E.J.3    Twigg, P.D.4    Carter, D.C.5
  • 18
    • 0031472928 scopus 로고    scopus 로고
    • Species differences of serum albumins: I. Drug binding sites
    • Kosa T., Maruyama T., Otagiri M. Species differences of serum albumins: I. Drug binding sites. Pharm. Res. 14:1997;1607-1612.
    • (1997) Pharm. Res. , vol.14 , pp. 1607-1612
    • Kosa, T.1    Maruyama, T.2    Otagiri, M.3
  • 19
    • 0018069149 scopus 로고
    • Species-dependent stereospecific serum protein binding of the oral anticoagulant drug phenprocoumon
    • Schmidt W., Jähnchen E. Species-dependent stereospecific serum protein binding of the oral anticoagulant drug phenprocoumon. Experientia. 34:1978;1323-1325.
    • (1978) Experientia , vol.34 , pp. 1323-1325
    • Schmidt, W.1    Jähnchen, E.2
  • 20
    • 0020600516 scopus 로고
    • Resolution by affinity chromatography: Stereoselective binding of racemic oxazepam esters to human serum albumin
    • Fitos I., Simonyi M., Tegyey Zs., Ötvös L., Kajtár J., Kajtár M. Resolution by affinity chromatography: stereoselective binding of racemic oxazepam esters to human serum albumin. J. Chromatogr. 259:1983;494-498.
    • (1983) J. Chromatogr. , vol.259 , pp. 494-498
    • Fitos, I.1    Simonyi, M.2    Tegyey, Zs.3    Ötvös, L.4    Kajtár, J.5    Kajtár, M.6
  • 21
    • 0022483033 scopus 로고
    • Stereoselective binding of 3-acetoxy-, and 3-hydroxy-1,4-benzodiazepine-2-ones to human serum albumin. Selective allosteric interaction with warfarin enantiomers
    • Fitos I., Tegyey Zs., Simonyi M., Sjöholm I., Larsson T., Lagercrantz C. Stereoselective binding of 3-acetoxy-, and 3-hydroxy-1,4-benzodiazepine-2-ones to human serum albumin. Selective allosteric interaction with warfarin enantiomers. Biochem. Pharmacol. 35:1986;263-269.
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 263-269
    • Fitos, I.1    Tegyey, Zs.2    Simonyi, M.3    Sjöholm, I.4    Larsson, T.5    Lagercrantz, C.6
  • 22
    • 0027340469 scopus 로고
    • Binding studies with recombinant human serum albumin obtained by expression of a synthetic gene in yeast
    • Fitos I., Visy J., Simoncsits A. Binding studies with recombinant human serum albumin obtained by expression of a synthetic gene in yeast. Biochem. Pharmacol. 46:1993;1159-1163.
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 1159-1163
    • Fitos, I.1    Visy, J.2    Simoncsits, A.3
  • 23
    • 0020606434 scopus 로고
    • Stereoselective binding of a 2,3-benzodiazepine to human serum albumin: Effect of conformation on tofizopam binding
    • Simonyi M., Fitos I. Stereoselective binding of a 2,3-benzodiazepine to human serum albumin: effect of conformation on tofizopam binding. Biochem. Pharmacol. 32:1983;1917-1920.
    • (1983) Biochem. Pharmacol. , vol.32 , pp. 1917-1920
    • Simonyi, M.1    Fitos, I.2
  • 24
    • 0026725572 scopus 로고
    • Stereoselective effect of phenprocoumon enantiomers on the binding of benzodiazepines to human serum albumin
    • Fitos I., Simonyi M. Stereoselective effect of phenprocoumon enantiomers on the binding of benzodiazepines to human serum albumin. Chirality. 4:1992;21-23.
    • (1992) Chirality , vol.4 , pp. 21-23
    • Fitos, I.1    Simonyi, M.2
  • 25
    • 84986426633 scopus 로고
    • Racematspaltung von (±)-5-Äthyl-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-methyl-5H-2, 3-benzodiazepin und anomales chiroptisches Verhalten der Enantiomeren
    • Tóth G., Fogassy E., Ács M., Toke L., Láng T. Racematspaltung von (±)-5-Äthyl-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-methyl-5H-2, 3-benzodiazepin und anomales chiroptisches Verhalten der Enantiomeren. J. Heterocycl. Chem. 20:1983;709-713.
    • (1983) J. Heterocycl. Chem. , vol.20 , pp. 709-713
    • Tóth, G.1    Fogassy, E.2    Ács, M.3    Toke, L.4    Láng, T.5
  • 26
    • 0029082915 scopus 로고
    • Separation of enantiomers of benzodiazepines on the Chiral-AGP column
    • Fitos I., Visy J., Simonyi M., Hermansson J. Separation of enantiomers of benzodiazepines on the Chiral-AGP column. J. Chromatogr., A. 709:1995;265-273.
    • (1995) J. Chromatogr., A , vol.709 , pp. 265-273
    • Fitos, I.1    Visy, J.2    Simonyi, M.3    Hermansson, J.4
  • 27
    • 0018636458 scopus 로고
    • General approach to chiroptical characterization of binding of prochiral and chiral 1,4-benzodiazepin-2-ones to human serum albumin
    • Konowal A., Snatzke G., Alebić-Kolbah T., Kajfež F., Rendić S., Šunjić V. General approach to chiroptical characterization of binding of prochiral and chiral 1,4-benzodiazepin-2-ones to human serum albumin. Biochem. Pharmacol. 28:1979;3109-3113.
    • (1979) Biochem. Pharmacol. , vol.28 , pp. 3109-3113
    • Konowal, A.1    Snatzke, G.2    Alebić-Kolbah, T.3    Kajfež, F.4    Rendić, S.5    Šunjić, V.6
  • 28
    • 0016631551 scopus 로고
    • High stereospecificity of the benzodiazepine binding site on human serum albumin. Studies with D- and L-oxazepam hemisuccinate
    • Müller W.E., Wollert U. High stereospecificity of the benzodiazepine binding site on human serum albumin. Studies with D- and L-oxazepam hemisuccinate. Mol. Pharmacol. 11:1975;52-60.
    • (1975) Mol. Pharmacol. , vol.11 , pp. 52-60
    • Müller, W.E.1    Wollert, U.2
  • 29
    • 0024740704 scopus 로고
    • Racemization kinetics of enantiomeric oxazepams and stereoselective hydrolysis of enantiomeric oxazepam 3-acetates in rat liver microsomes and brain homogenate
    • Yang S.K., Lu X.L. Racemization kinetics of enantiomeric oxazepams and stereoselective hydrolysis of enantiomeric oxazepam 3-acetates in rat liver microsomes and brain homogenate. J. Pharm. Sci. 78:1989;789-795.
    • (1989) J. Pharm. Sci. , vol.78 , pp. 789-795
    • Yang, S.K.1    Lu, X.L.2
  • 30
    • 0026512036 scopus 로고
    • Direct liquid chromatographic separation of enantiomers on immobilized protein stationary phases. IX. Influence of the cross-linking reagent on the retentive and enantio-selective properties of chiral sorbents based on bovine serum albumin
    • Andersson S., Thompson R.A., Allenmark S.G. Direct liquid chromatographic separation of enantiomers on immobilized protein stationary phases. IX. Influence of the cross-linking reagent on the retentive and enantio-selective properties of chiral sorbents based on bovine serum albumin. J. Chromatogr. 591:1992;65-73.
    • (1992) J. Chromatogr. , vol.591 , pp. 65-73
    • Andersson, S.1    Thompson, R.A.2    Allenmark, S.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.