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Volumn 23, Issue 3, 2009, Pages 225-238

Microseparation techniques for the study of the enantioselectivity of drug-plasma protein binding

Author keywords

Allosteric effects; Enantiomer enantiomer interactions; Interspecies effect; Separation techniques; Stereoselective drug plasma protein binding

Indexed keywords

BIOCHEMISTRY; DRUG INTERACTIONS; ENANTIOSELECTIVITY; PROTEINS; STEREOSELECTIVITY;

EID: 65249166083     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1134     Document Type: Review
Times cited : (15)

References (68)
  • 1
    • 33748766072 scopus 로고    scopus 로고
    • Drug binding to human serum albumin: Abridged review of results obtained with high-performance liquid chromatography and circular dichroism
    • Ascoli GA, Domenici E and Bertucci C. Drug binding to human serum albumin: abridged review of results obtained with high-performance liquid chromatography and circular dichroism. Chirality 2006; 18: 667-679.
    • (2006) Chirality , vol.18 , pp. 667-679
    • Ascoli, G.A.1    Domenici, E.2    Bertucci, C.3
  • 3
    • 0030802874 scopus 로고    scopus 로고
    • Comparison of five methods for the study of drug protein binding in affinity capillary electrophoresis
    • Busch MHA, Carells LB, Boelens HFM, Kraak JC and Poe H. Comparison of five methods for the study of drug protein binding in affinity capillary electrophoresis. Journal of Chromatography A 1997; 777: 311-328.
    • (1997) Journal of Chromatography A , vol.777 , pp. 311-328
    • Busch, M.H.A.1    Carells, L.B.2    Boelens, H.F.M.3    Kraak, J.C.4    Poe, H.5
  • 4
    • 0025105217 scopus 로고
    • Metabolic stereoisomeric inversion of 2-arylpropionic acids. On the mechanism of ibuprofen epimerization in rats
    • Chen CS, Chen TL and Shieh W-R. Metabolic stereoisomeric inversion of 2-arylpropionic acids. On the mechanism of ibuprofen epimerization in rats. Biochimica et Biophysica Acta 1990; 1033: 1-6.
    • (1990) Biochimica et Biophysica Acta , vol.1033 , pp. 1-6
    • Chen, C.S.1    Chen, T.L.2    Shieh, W.-R.3
  • 6
    • 8344226902 scopus 로고    scopus 로고
    • Quantitative analysis of allosteric drug-protein binding by biointeraction chromatography
    • Chen J and Hage DS. Quantitative analysis of allosteric drug-protein binding by biointeraction chromatography. Nature Biotechnology 2004; 22: 1445-1448.
    • (2004) Nature Biotechnology , vol.22 , pp. 1445-1448
    • Chen, J.1    Hage, D.S.2
  • 7
    • 29744448678 scopus 로고    scopus 로고
    • Chromatographic analysis of allosteric effects between ibuprofen and benzodiazepines on human serum albumin
    • Chen J, Fitos I and Hage DS. Chromatographic analysis of allosteric effects between ibuprofen and benzodiazepines on human serum albumin. Chirality 2006; 18: 24-36.
    • (2006) Chirality , vol.18 , pp. 24-36
    • Chen, J.1    Fitos, I.2    Hage, D.S.3
  • 8
    • 33644681693 scopus 로고    scopus 로고
    • Stereoselective binding of human serum albumin
    • Chuang VTG and Otagiri M. Stereoselective binding of human serum albumin. Chirality 2006; 18: 159-166.
    • (2006) Chirality , vol.18 , pp. 159-166
    • Chuang, V.T.G.1    Otagiri, M.2
  • 10
    • 0032873044 scopus 로고    scopus 로고
    • Study of interaction between drug enantiomers and serum albumin by capillary electrophoresis
    • Ding Y, Zhu X and Lin B. Study of interaction between drug enantiomers and serum albumin by capillary electrophoresis. Electrophoresis 1999; 20: 1890-1894.
    • (1999) Electrophoresis , vol.20 , pp. 1890-1894
    • Ding, Y.1    Zhu, X.2    Lin, B.3
  • 13
    • 0032948439 scopus 로고    scopus 로고
    • Stereoselective binding of zopiclone to human plasma proteins
    • Fernandez C, Gimenez F, Thuillier A and Farinotti R. Stereoselective binding of zopiclone to human plasma proteins. Chirality 1999; 11: 129-132.
    • (1999) Chirality , vol.11 , pp. 129-132
    • Fernandez, C.1    Gimenez, F.2    Thuillier, A.3    Farinotti, R.4
  • 15
    • 0027257878 scopus 로고
    • Stereoselective distribution of acenocoumarol enantiomers in human plasma - chiral chromatographic analysis of the ultrafiltrates
    • Fitos I, Visy J, Simonyi M and Hermansson J. Stereoselective distribution of acenocoumarol enantiomers in human plasma - chiral chromatographic analysis of the ultrafiltrates. Chirality 1993; 5: 346-349.
    • (1993) Chirality , vol.5 , pp. 346-349
    • Fitos, I.1    Visy, J.2    Simonyi, M.3    Hermansson, J.4
  • 16
    • 0029082915 scopus 로고
    • Separation of enantiomers of benzodiazepines on the Chiral-AGP column
    • Fitos I, Visy J, Simonyi M and Hermansson J. Separation of enantiomers of benzodiazepines on the Chiral-AGP column. Journal of Chromatography A 1995; 709: 265-273.
    • (1995) Journal of Chromatography A , vol.709 , pp. 265-273
    • Fitos, I.1    Visy, J.2    Simonyi, M.3    Hermansson, J.4
  • 17
    • 0032928205 scopus 로고    scopus 로고
    • Stereoselective allosteric binding interaction on human serum albumin between ibuprofen and lorazepam acetate
    • Fitos I, Visy J, Simonyi M and Hermansson J. Stereoselective allosteric binding interaction on human serum albumin between ibuprofen and lorazepam acetate. Chirality 1999; 11: 115-120.
    • (1999) Chirality , vol.11 , pp. 115-120
    • Fitos, I.1    Visy, J.2    Simonyi, M.3    Hermansson, J.4
  • 18
    • 0037207250 scopus 로고    scopus 로고
    • Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods
    • Fitos I, Visy J and Simonyi M. Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods. Journal Biochemical Biophysical Methods 2002; 54: 71-84.
    • (2002) Journal Biochemical Biophysical Methods , vol.54 , pp. 71-84
    • Fitos, I.1    Visy, J.2    Simonyi, M.3
  • 19
    • 0036381071 scopus 로고    scopus 로고
    • Protein binding of indobufen enantiomers: Pharmacokinetics of free fraction-studies after single or multiple doses of rac-indobufen
    • Glówka FK and Caldwell J. Protein binding of indobufen enantiomers: pharmacokinetics of free fraction-studies after single or multiple doses of rac-indobufen. Chirality 2002; 14: 736-741.
    • (2002) Chirality , vol.14 , pp. 736-741
    • Glówka, F.K.1    Caldwell, J.2
  • 22
    • 0028883311 scopus 로고
    • Characterization of the protein binding of chiral drugs by high-performance affinity chromatography: Interactions of R- and S-ibuprofen with human serum albumin
    • Hage DS, Noctor TAG and Wainer IW. Characterization of the protein binding of chiral drugs by high-performance affinity chromatography: interactions of R- and S-ibuprofen with human serum albumin. Journal of Chromatography A 1995; 693: 23-32.
    • (1995) Journal of Chromatography A , vol.693 , pp. 23-32
    • Hage, D.S.1    Noctor, T.A.G.2    Wainer, I.W.3
  • 24
    • 0030641640 scopus 로고    scopus 로고
    • Protein-binding high-performance frontal analysis of (R)- and (S)-warfarin on HSA with and without phenylbutazone
    • He JY, Shibukawa A, Tokunaga S and Nakagawa T. Protein-binding high-performance frontal analysis of (R)- and (S)-warfarin on HSA with and without phenylbutazone. Journal of Pharmaceutical Sciences 1997; 86: 120-125.
    • (1997) Journal of Pharmaceutical Sciences , vol.86 , pp. 120-125
    • He, J.Y.1    Shibukawa, A.2    Tokunaga, S.3    Nakagawa, T.4
  • 27
    • 0036088138 scopus 로고    scopus 로고
    • Stereoselective protein binding of alprenolol in the renal diseased state
    • Imamura H, Komori T, Ismail A, Suenaga A and Otagiri M. Stereoselective protein binding of alprenolol in the renal diseased state. Chirality 2002; 14: 599-603.
    • (2002) Chirality , vol.14 , pp. 599-603
    • Imamura, H.1    Komori, T.2    Ismail, A.3    Suenaga, A.4    Otagiri, M.5
  • 28
    • 0029971601 scopus 로고    scopus 로고
    • Stereoselective binding of carbenicillin epimers to human serum albumin
    • Itoh T, Nakashima K, Tsuda Y and Yamada H. Stereoselective binding of carbenicillin epimers to human serum albumin. Chirality 1996; 8: 201-206.
    • (1996) Chirality , vol.8 , pp. 201-206
    • Itoh, T.1    Nakashima, K.2    Tsuda, Y.3    Yamada, H.4
  • 29
    • 0030751537 scopus 로고    scopus 로고
    • Stereoselective pharmacokinetics of ibuprofen in rats: Effect of enantiomer-enantiomer interaction in plasma protein binding
    • Itoh T, Maruyama J, Tsuda Y and Yamada H. Stereoselective pharmacokinetics of ibuprofen in rats: effect of enantiomer-enantiomer interaction in plasma protein binding. Chirality 1997; 9: 354-361.
    • (1997) Chirality , vol.9 , pp. 354-361
    • Itoh, T.1    Maruyama, J.2    Tsuda, Y.3    Yamada, H.4
  • 30
    • 40849092423 scopus 로고    scopus 로고
    • Analysis of flurbiprofen, ketoprofen and etodolac enantiomers by pre-column derivatization RP-HPLC and application to drug-protein binding in human plasma
    • Jin Y-X, Tang Y-H and Zeng S. Analysis of flurbiprofen, ketoprofen and etodolac enantiomers by pre-column derivatization RP-HPLC and application to drug-protein binding in human plasma. Journal of Pharmaceutical and Biomedical Analysis 2008; 46: 953-958.
    • (2008) Journal of Pharmaceutical and Biomedical Analysis , vol.46 , pp. 953-958
    • Jin, Y.-X.1    Tang, Y.-H.2    Zeng, S.3
  • 32
    • 33646891086 scopus 로고    scopus 로고
    • 1-acid glycoprotein control the enantioselectivity and binding affinity of oxybutynin
    • 1-acid glycoprotein control the enantioselectivity and binding affinity of oxybutynin. Pharmaceutical Research 2006; 23: 1038-1042.
    • (2006) Pharmaceutical Research , vol.23 , pp. 1038-1042
    • Kimura, T.1    Shibukawa, A.2    Matsuzaki, K.3
  • 33
    • 0022371924 scopus 로고
    • Free drug measurements: Methodology and clinical significance
    • Kwong TC. Free drug measurements: methodology and clinical significance. Clinica Chimica Acta 1985; 151: 193-216.
    • (1985) Clinica Chimica Acta , vol.151 , pp. 193-216
    • Kwong, T.C.1
  • 36
    • 0019851928 scopus 로고
    • Disopyramide binding to serum protein in man and animals
    • Lima JJ and Haughey DB. Disopyramide binding to serum protein in man and animals. Drug Metabolism and Disposition 1981; 9: 582-583.
    • (1981) Drug Metabolism and Disposition , vol.9 , pp. 582-583
    • Lima, J.J.1    Haughey, D.B.2
  • 42
    • 0028892458 scopus 로고
    • Capillary electrophoresis/frontal analysis for microanalysis of enantioselective protein binding of a basic drug
    • Ohara T, Shibukawa A and Nakagawa T. Capillary electrophoresis/frontal analysis for microanalysis of enantioselective protein binding of a basic drug Analytical Chemistry 1995; 67: 3520-3525.
    • (1995) Analytical Chemistry , vol.67 , pp. 3520-3525
    • Ohara, T.1    Shibukawa, A.2    Nakagawa, T.3
  • 44
    • 0029922030 scopus 로고    scopus 로고
    • Drug-protein binding studies. New trends in analytical and experimental methodology
    • Oravcová J, Böhs B and Lindner W. Drug-protein binding studies. New trends in analytical and experimental methodology. Journal of Chromatography B 1996; 677: 1-28.
    • (1996) Journal of Chromatography B , vol.677 , pp. 1-28
    • Oravcová, J.1    Böhs, B.2    Lindner, W.3
  • 46
    • 0032824437 scopus 로고    scopus 로고
    • Simultaneous determination of enantioselective plasma protein binding of aminohydantoins by ultrafiltration and chiral high-performance liquid chromatography
    • Peng SX, Henson C and Wilson LJ. Simultaneous determination of enantioselective plasma protein binding of aminohydantoins by ultrafiltration and chiral high-performance liquid chromatography. Journal of Chromatography B 1999; 732: 31-37.
    • (1999) Journal of Chromatography B , vol.732 , pp. 31-37
    • Peng, S.X.1    Henson, C.2    Wilson, L.J.3
  • 47
    • 0015593637 scopus 로고
    • Circular dichroic investigation of binding of fenoprofen, 2(3-phenoxyphenyl)-propionic acid, to human-serum albumin
    • Perrin JH. Circular dichroic investigation of binding of fenoprofen, 2(3-phenoxyphenyl)-propionic acid, to human-serum albumin. Journal of Pharmacy and Pharmacology 1973; 25: 208-212.
    • (1973) Journal of Pharmacy and Pharmacology , vol.25 , pp. 208-212
    • Perrin, J.H.1
  • 48
    • 39749188802 scopus 로고    scopus 로고
    • Species-dependent stereoselective drug binding to albumin: A circular dichroism study
    • Pistolozzi M and Bertucci C. Species-dependent stereoselective drug binding to albumin: a circular dichroism study. Chirality 2008; 20: 552-558.
    • (2008) Chirality , vol.20 , pp. 552-558
    • Pistolozzi, M.1    Bertucci, C.2
  • 49
    • 0034257094 scopus 로고    scopus 로고
    • Optimization of the enantiomeric separation of tryptophan analogs by membrane processes
    • Randon J, Garnier F, Rocca JL and Maïsterrena B. Optimization of the enantiomeric separation of tryptophan analogs by membrane processes. Journal of Membrane Science 2000; 175: 111-117.
    • (2000) Journal of Membrane Science , vol.175 , pp. 111-117
    • Randon, J.1    Garnier, F.2    Rocca, J.L.3    Maïsterrena, B.4
  • 52
    • 0033372227 scopus 로고    scopus 로고
    • Binding study of semotiadil and levosemotiadil with human serum albumin using high-performance frontal analysis
    • Rodriguez Rosas ME, Shibukawa A, Yoshikawa Y, Kuroda Y and Nakagawa T. Binding study of semotiadil and levosemotiadil with human serum albumin using high-performance frontal analysis. Analytical Sciences 1999b; 15: 217-222.
    • (1999) Analytical Sciences , vol.15 , pp. 217-222
    • Rodriguez Rosas, M.E.1    Shibukawa, A.2    Yoshikawa, Y.3    Kuroda, Y.4    Nakagawa, T.5
  • 54
    • 0027062906 scopus 로고
    • High-performance frontal analysis high-performance liquid-chromatographic system for stereoselective determination of unbound ketoprofen enantiomers in plasma after direct sample injection
    • Shibukawa A, Terakita A, He JY and Nakagawa T. High-performance frontal analysis high-performance liquid-chromatographic system for stereoselective determination of unbound ketoprofen enantiomers in plasma after direct sample injection. Journal of Pharmaceutical Sciences 1992; 81: 710-715.
    • (1992) Journal of Pharmaceutical Sciences , vol.81 , pp. 710-715
    • Shibukawa, A.1    Terakita, A.2    He, J.Y.3    Nakagawa, T.4
  • 55
    • 0027419859 scopus 로고
    • High-performance frontal analysis high-performance liquid-chromatographic system for the enantioselective determination of unbound fenoprofen concentration in protein-binding equilibrium
    • Shibukawa A, Nagao M, Terakita A, He JY and Nakagawa T. High-performance frontal analysis high-performance liquid-chromatographic system for the enantioselective determination of unbound fenoprofen concentration in protein-binding equilibrium. Journal of Liquid Chromatography 1993; 16: 903-914.
    • (1993) Journal of Liquid Chromatography , vol.16 , pp. 903-914
    • Shibukawa, A.1    Nagao, M.2    Terakita, A.3    He, J.Y.4    Nakagawa, T.5
  • 56
    • 0027932264 scopus 로고
    • Determination of the unbound concentration of hydrophobic drugs in albumin solutions by high-performance frontal analysis using a diol-silica column
    • Shibukawa A, Nakao C, Sawada T, Terakita A, Morokoshi N and Nakagawa T. Determination of the unbound concentration of hydrophobic drugs in albumin solutions by high-performance frontal analysis using a diol-silica column. Journal of Pharmaceutical Sciences 1994; 83: 868-873.
    • (1994) Journal of Pharmaceutical Sciences , vol.83 , pp. 868-873
    • Shibukawa, A.1    Nakao, C.2    Sawada, T.3    Terakita, A.4    Morokoshi, N.5    Nakagawa, T.6
  • 57
    • 0028929901 scopus 로고
    • Study of the enantioselective binding between BOF-4272 and serum albumins by means of high-performance frontal analysis
    • Shibukawa A, Kadohara M, He J-y, Nishimura M, Naito S and Nakagawa T. Study of the enantioselective binding between BOF-4272 and serum albumins by means of high-performance frontal analysis. Journal of Chromatography A 1995; 694: 81-89.
    • (1995) Journal of Chromatography A , vol.694 , pp. 81-89
    • Shibukawa, A.1    Kadohara, M.2    He, J.-Y.3    Nishimura, M.4    Naito, S.5    Nakagawa, T.6
  • 59
    • 0032806797 scopus 로고    scopus 로고
    • Development of high-performance frontal analysis and the application to the study of drug-plasma protein binding
    • Shibukawa A, Kuroda Y and Nakagawa T. Development of high-performance frontal analysis and the application to the study of drug-plasma protein binding. TrAC-Trends in Analytical Chemistry 1999b; 18: 549-556.
    • (1999) TrAC-Trends in Analytical Chemistry , vol.18 , pp. 549-556
    • Shibukawa, A.1    Kuroda, Y.2    Nakagawa, T.3
  • 63
    • 0035033024 scopus 로고    scopus 로고
    • Stereoselective binding and degradation of sulbenicillin in the presence of human serum albumin
    • Tsuda Y, Tsunoi T, Watanabe N, Ishida M, Yamada H and Itoh T. Stereoselective binding and degradation of sulbenicillin in the presence of human serum albumin. Chirality 2001; 13: 236-243.
    • (2001) Chirality , vol.13 , pp. 236-243
    • Tsuda, Y.1    Tsunoi, T.2    Watanabe, N.3    Ishida, M.4    Yamada, H.5    Itoh, T.6
  • 64
    • 0347632978 scopus 로고
    • Tillement JP, Lindenlaub E eds, Schattauer: Stuttgart
    • Urien S. In: ProteinBinding and Drug Transport, Tillement JP, Lindenlaub E (eds). Schattauer: Stuttgart, 1986; 63-75.
    • (1986) ProteinBinding and Drug Transport , pp. 63-75
    • Urien, S.1
  • 66
    • 0037080864 scopus 로고    scopus 로고
    • Study of competitive binding of entantiomers to protein by affinity capillary electrochromatograpy
    • Ye M, Zou H, Liu Z, Wu R, Lei Z and Ni J. Study of competitive binding of entantiomers to protein by affinity capillary electrochromatograpy. Journal of Pharmaceutical and Biomedical Analysis 2002; 27: 651-660.
    • (2002) Journal of Pharmaceutical and Biomedical Analysis , vol.27 , pp. 651-660
    • Ye, M.1    Zou, H.2    Liu, Z.3    Wu, R.4    Lei, Z.5    Ni, J.6
  • 67
    • 0031058095 scopus 로고    scopus 로고
    • Human orosomucoid polymorphism: Molecular basis of the three common ORM1 alleles, ORM1*F1, ORM1*F2, and ORM1*S
    • Yuasa I, Umetsu K, Vogt U, Nakamura H, Nanba E, Tamaki N and Irizawa Y. Human orosomucoid polymorphism: molecular basis of the three common ORM1 alleles, ORM1*F1, ORM1*F2, and ORM1*S. Human Genetics 1997; 99: 393-398.
    • (1997) Human Genetics , vol.99 , pp. 393-398
    • Yuasa, I.1    Umetsu, K.2    Vogt, U.3    Nakamura, H.4    Nanba, E.5    Tamaki, N.6    Irizawa, Y.7


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