High-performance affinity chromatography: a powerful tool for studying serum protein binding.

High-performance affinity chromatography (HPAC) is a method in which a biologically-related ligand is used as a stationary phase in an HPLC system. This approach is a powerful means for selectively isolating or quantitating agents in complex samples, but it can also be employed to study the interactions of biological systems. In recent years there have been numerous reports in which HPAC has been used to examine the interactions of drugs, hormones and other substances with serum proteins. This review discusses how HPAC has been used in such work. Particular attention is given to the techniques of zonal elution and frontal analysis. Various applications are provided for these techniques, along with a list of factors that need to be considered in their optimization and use. New approaches based on band-broadening studies and rapid immunoextraction are also discussed.

[1]  I. Wainer,et al.  Use of a human serum albumin-based stationary phase for high-performance liquid chromatography as a tool for the rapid determination of drug-plasma protein binding. , 1993, Journal of pharmaceutical sciences.

[2]  R. Kaliszan,et al.  Binding site for basic drugs on alpha 1-acid glycoprotein as revealed by chemometric analysis of biochromatographic data. , 1995, Biomedical chromatography : BMC.

[3]  J. Bojarşki,et al.  Direct liquid chromatographic separation of enantiomers on immobilized protein stationary phases. VI. Optical resolution of a series of racemic barbiturates: studies of substituent and mobile phase effects. , 1988, Journal of chromatography.

[4]  J. Hansen,et al.  Resolution and binding site determination of D,L-thyronine by high-performance liquid chromatography using immobilized albumin as chiral stationary phase. Determination of the optical purity of thyroxine in tablets. , 1989, Journal of pharmaceutical and biomedical analysis.

[5]  D C Carter,et al.  Structure of serum albumin. , 1994, Advances in protein chemistry.

[6]  H. Zou,et al.  Comparative separation of biologically active components inRhizoma chuanxiong by affinity chromatography with α1-acid glycoprotein and human serum albumin as stationary phasesglycoprotein and human serum albumin as stationary phases , 2000 .

[7]  Y. Guillaume,et al.  Retention behavior of D,L-dansyl-amino acids on a human serum albumin chiral stationary phase: effect of a mobile phase modifier. , 1998, Journal of chromatography. A.

[8]  J. Haginaka,et al.  Enantioselectivity of bovine serum albumin-bonded columns produced with isolated protein fragments. , 1997, Journal of chromatography. A.

[9]  D. S. Hage,et al.  Recent advances in chromatographic and electrophoretic methods for the study of drug-protein interactions. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[10]  P Salvadori,et al.  Use of a human serum albumin-based high-performance liquid chromatography chiral stationary phase for the investigation of protein binding: detection of the allosteric interaction between warfarin and benzodiazepine binding sites. , 1991, Journal of pharmaceutical sciences.

[11]  Z. Zhivkova,et al.  Stereoselective binding of ketoprofen enantiomers to human serum albumin studied by high-performance liquid affinity chromatography. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[12]  D. S. Hage,et al.  Characterization of thyroxine-albumin binding using high-performance affinity chromatography. I. Interactions at the warfarin and indole sites of albumin. , 1992, Journal of chromatography.

[13]  R. Kaliszan.  Chromatography and capillary electrophoresis in modelling the basic processes of drug action , 1999 .

[14]  Y. Guillaume,et al.  Characterization of solute binding at human serum albumin site II and its geometry using a biochromatographic approach. , 1999, Biophysical journal.

[15]  K. Mosbach,et al.  High performance liquid affinity chromatography (HPLAC) and its application to the separation of enzymes and antigens , 1978, FEBS letters.

[16]  R. Nation,et al.  Influence of octanoic acid on the reversible protein binding of ketorolac enantiomers to human serum albumin (HSA): comparative liquid chromatographic studies using a HSA chiral stationary phase. , 1994, Journal of chromatography. B, Biomedical applications.

[17]  R. R. Walters,et al.  Effect of Baseline Errors on the Calculation of Statistical Moments of Tailed Chromatographic Peaks , 1984 .

[18]  M. Jaroniec,et al.  Synthesis and Characterization of Silica-Immobilized Serum Albumin Stationary Phases for HPLC , 1996 .

[19]  R. Gilpin,et al.  Species dependency of the liquid chromatographic properties of silica-immobilized serum albumins. , 1995, Analytical chemistry.

[20]  B. Dunn,et al.  Quantitative affinity chromatography. Determination of binding constants by elution with competitive inhibitors. , 1974, Proceedings of the National Academy of Sciences of the United States of America.

[21]  Y. Guillaume,et al.  HSA-solute interactions, enantioselectivity, and binding site geometrical characteristics. , 1998, Analytical chemistry.

[22]  I. Wainer,et al.  Chiral separations of cationic and anionic drugs on an α1-acid glycoprotein-bonded stationary phase (enantiopac®) , 1986 .

[23]  Y. Fujimoto,et al.  Study of drug-protein binding by affinity chromatography: interaction of bovine serum albumin and salicylic acid. , 1978, Journal of pharmaceutical sciences.

[24]  D. S. Hage,et al.  Analysis of free drug fractions by ultrafast immunoaffinity chromatography. , 2001, Analytical chemistry.

[25]  D. S. Hage,et al.  Allosteric and competitive displacement of drugs from human serum albumin by octanoic acid, as revealed by high-performance liquid affinity chromatography, on a human serum albumin-based stationary phase. , 1992, Journal of chromatography.

[26]  C. Beddell,et al.  Quantitative structure-retention relationships of acyclovir esters using immobilised albumin high-performance liquid chromatography and reversed-phase high-performance liquid chromatography , 1995 .

[27]  Y. Guillaume,et al.  Interactions between dansyl amino acids and human serum albumin using high-performance liquid chromatography: mobile-phase pH and temperature considerations. , 1997, Analytical chemistry.

[28]  C. S. Gilpin,et al.  Liquid chromatographic studies of memory effects of silica Immobilized Bovine serum Albumin: I. Influence of Methanol on Solute Retention , 1996 .

[29]  I. Chaiken.  Analytical Affinity Chromatography , 1987 .

[30]  C. Bertucci,et al.  Improved chromatographic performance of a modified human albumin based stationary phase. , 1997, Chirality.

[31]  Z. Zhivkova,et al.  Albumin binding sites studied by high-performance liquid affinity chromatography , 1998 .

[32]  D. S. Hage,et al.  Development of tryptophan-modified human serum albumin columns for site-specific studies of drug-protein interactions by high-performance affinity chromatography. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[33]  S. Allenmark.  Chiral discrimination by albumin: a mechanistic study of liquid chromatographic optical resolution of nonaromatic carboxylic acids. , 1993, Chirality.

[34]  R. Gilpin,et al.  Liquid chromatographic studies of the effect of temperature on the chiral recognition of tryptophan by silica-immobilized bovine albumin , 1991 .

[35]  R. Kaliszan,et al.  Chromatographic modelling of interactions between melanin and phenothiazine and dibenzazepine drugs. , 1995, Biomedical chromatography : BMC.

[36]  Z. Zhivkova,et al.  Protein Binding of Piroxicam Studied by Means of Affinity Chromatography and Circular Dichroism , 1999, The Journal of pharmacy and pharmacology.

[37]  D. S. Hage,et al.  Characterization of the protein binding of chiral drugs by high-performance affinity chromatography. Interactions of R- and S-ibuprofen with human serum albumin. , 1995, Journal of chromatography. A.

[38]  D. S. Hage,et al.  Characterization of minor site probes for human serum albumin by high-performance affinity chromatography. , 1999, Analytical chemistry.

[39]  D. S. Hage,et al.  Effects of ligand heterogeneity in the characterization of affinity columns by frontal analysis. , 1997, Analytical chemistry.

[40]  D. S. Hage,et al.  Characterisation of the binding of digitoxin and acetyldigitoxin to human serum albumin by high-performance affinity chromatography. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[41]  P Salvadori,et al.  Immobilized serum albumin: rapid HPLC probe of stereoselective protein-binding interactions. , 1990, Chirality.

[42]  R. Kaliszan,et al.  Quantitative structure-retention relationships in the examination of the topography of the binding site of antihistamine drugs on alpha 1-acid glycoprotein. , 1996, Journal of chromatography. A.

[43]  I. Wainer,et al.  Evaluation of a chiral stationary phase based on mixed immobilized proteins , 1994 .

[44]  J. Hermansson,et al.  Chiral high-performance liquid chromatographic separations of vinca alkaloid analogues on alpha 1-acid glycoprotein and human serum albumin columns. , 1992, Journal of chromatography.

[45]  C. Beddell,et al.  Binding measurements of indolocarbazole derivatives to immobilised human serum albumin by high-performance liquid chromatography. , 1996, Journal of chromatography. B, Biomedical applications.

[46]  D. S. Hage,et al.  Characterization of the binding and chiral separation of D- and L-tryptophan on a high-performance immobilized human serum albumin column. , 1993, Journal of chromatography.

[47]  D. S. Hage,et al.  Effect of mobile phase composition on the binding kinetics of chiral solutes on a protein-based high-performance liquid chromatography column: interactions of D- and L-tryptophan with immobilized human serum albumin. , 1997, Journal of chromatography. A.

[48]  B. Sébille,et al.  Determination of binding equilibrium constants by numerical simulation in zonal high-performance affinity chromatography , 1988 .

[49]  R. Kaliszan.  Retention data from affinity high-performance liquid chromatography in view of chemometrics. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[50]  T. Peters,et al.  All About Albumin: Biochemistry, Genetics, and Medical Applications , 1995 .

[51]  Y. Guillaume,et al.  Chromatographic study of magnesium and calcium binding to immobilized human serum albumin. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[52]  J. Haginaka,et al.  Enantioselectivity of bovine serum albumin-bonded columns produced with isolated protein fragments. II. Characterization of protein fragments and chiral binding sites. , 1997, Journal of chromatography. A.

[53]  C. Bevan,et al.  Immobilized human serum albumin: liquid chromatography/mass spectrometry as a method of determining drug-protein binding. , 1995, Rapid communications in mass spectrometry : RCM.

[54]  T. Kwong.  Free drug measurements: methodology and clinical significance. , 1985, Clinica chimica acta; international journal of clinical chemistry.

[55]  I. Wainer,et al.  Stereochemical aspects of benzodiazepine binding to human serum albumin. II. Quantitative relationships between structure and enantioselective retention in high performance liquid affinity chromatography. , 1992, Molecular pharmacology.

[56]  Z. Zhivkova,et al.  New mathematical approach for the evaluation of drug binding to human serum albumin by high-performance liquid affinity chromatography. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[57]  Y. Guillaume,et al.  Peculiarities of dansyl amino acid enantioselectivity using human serum albumin as a chiral selector. , 1998, Journal of chromatographic science.

[58]  D. S. Hage,et al.  Role of binding capacity versus binding strength in the separation of chiral compounds on protein-based high-performance liquid chromatography columns. Interactions of D- and L-tryptophan with human serum albumin. , 1996, Journal of chromatography. A.

[59]  I. Wainer.  The impact of new liquid chromatography chiral stationary phase technology on the study of stereoselective pharmacokinetics , 1993 .

[60]  Y. Guillaume,et al.  Effect of tetrabutylammonium chloride as eluent modifier on the retention and enantioselectivity of d,l-dansyl amino acids using immobilized human serum albumin. , 1999, Talanta.

[61]  D Sixsmith,et al.  The effect of compression on some physical properties of microcrystalline cellulose powders , 1977, The Journal of pharmacy and pharmacology.

[62]  H. Borén,et al.  Direct liquid chromatographic separation of enantiomers on immobilized protein stationary phases : III. 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 , 1983 .

[63]  Yukui Zhang,et al.  Stereoselective binding of warfarin and ketoprofen to human serum albumin determined by microdialysis combined with HPLC , 1998 .

[64]  F. Arnold,et al.  Analytical affinity chromatography : I. Local equilibrium theory and the measurement of association and inhibition constants , 1986 .

[65]  M. Nakayama,et al.  Effects of organic modifiers on the chiral recognition by different types of silica-immobilized bovine serum albumin. , 1996, Journal of chromatography. A.

[66]  John G. Dorsey,et al.  A Review of the Exponentially Modified Gaussian (EMG) Function: Evaluation and Subsequent Calculation of Universal Data , 1984 .

[67]  E. Domenici,et al.  Synthesis and chromatographic properties of an HPLC chiral stationary phase based upon human serum albumin , 1990 .

[68]  A. Karlsson,et al.  Enantiomeric resolution on Chiral-AGP with the aid of experimental design Unusual effects of mobile phase pH and column temperature , 1997 .

[69]  N. Nakano,et al.  Mutual displacement interactions in the binding of two drugs to human serum albumin by frontal affinity chromatography. , 1980, Journal of chromatography.

[70]  I. Wainer,et al.  Stereochemical aspects of benzodiazepine binding to human serum albumin. I. Enantioselective high performance liquid affinity chromatographic examination of chiral and achiral binding interactions between 1,4-benzodiazepines and human serum albumin. , 1992, Molecular pharmacology.

[71]  D. Corradini.  Handbook of HPLC , 1998 .

[72]  M. Woodruff,et al.  Free Drug Concentration Monitoring in Clinical Practice , 1986 .

[73]  H. Borén,et al.  Direct liquid chromatographic separation of enantiomers on immobilized protein stationary phases. IV. Molecular interaction forces and retention behaviour in chromatography on bovine serum albumin as a stationary phase. , 1984, Journal of chromatography.

[74]  D. S. Hage,et al.  Studies of protein binding to nonpolar solutes by using zonal elution and high-performance affinity chromatography: interactions of cis- and trans-clomiphene with human serum albumin in the presence of beta-cyclodextrin. , 1998, Analytical chemistry.

[75]  A. Cavalli,et al.  Stereoselective binding of 2,3-substituted 3-hydroxypropionic acids on an immobilised human serum albumin chiral stationary phase: stereochemical characterisation and quantitative structure-retention relationship study. , 2000, Journal of chromatography. A.

[76]  H. Karlsson,et al.  Binding of some fatty acids and drugs to immobilized bovine serum albumin studied by column affinity chromatography. , 1979, Analytical biochemistry.

[77]  G. Guiochon,et al.  Estimation of the number of enantioselective sites of bovine serum albumin using frontal chromatography. , 1993, Chirality.

[78]  Y. Guillaume,et al.  Chiral discrimination ofN-(dansyl)-dl-amino acids on human serum albumin stationary phase: Effect of a mobile phase modifier , 1998 .

[79]  D. S. Hage,et al.  Chiral separation mechanisms in protein-based HPLC columns. 2. Kinetic studies of (R)- and (S)-warfarin binding to immobilized human serum albumin. , 1994, Analytical chemistry.

[80]  B. Sébille,et al.  Enantiomeric properties of human albumin immobilized on porous silica supports coated with polymethacryloyl chloride. , 1997, Journal of chromatography. A.

[81]  I. Wainer,et al.  The in Situ Acetylation of an Immobilized Human Serum Albumin Chiral Stationary Phase for High-Performance Liquid Chromatography in the Examination of Drug–Protein Binding Phenomena , 1992, Pharmaceutical Research.

[82]  M. Turowski,et al.  Collagen immobilised on silica derivatives as a new stationary phase for HPLC. , 1998, Biomedical chromatography : BMC.

[83]  John D. Green,et al.  Chromatographic Enantioseparation: Methods and Applications , 1988 .

[84]  R. Kaliszan,et al.  Quantitative structure-retention relationships with model analytes as a means of an objective evaluation of chromatographic columns. , 2001, Journal of chromatographic science.

[85]  D. S. Hage,et al.  Characterization of thyroxine-albumin binding using high-performance affinity chromatography. II. Comparison of the binding of thyroxine, triiodothyronines and related compounds at the warfarin and indole sites of human serum albumin. , 1995, Journal of chromatography. B, Biomedical applications.

[86]  K. Kasai,et al.  Affinity chromatography of trypsin and related enzymes. I. Preparation and characteristics of an affinity adsorbent containing tryptic peptides from protamine as ligands. , 1975, Journal of biochemistry.

[87]  B. Sébille,et al.  Enantioselectivity properties of human serum albumin immobilized on anion-exchangers based on polyvinylimidazole-coated silica. Effect of protein loading on separation properties. , 1997, Journal of chromatography. A.

[88]  F. Beaudry,et al.  Determination of drug-plasma protein binding using human serum albumin chromatographic column and multiple linear regression model. , 1999, Biomedical chromatography : BMC.

[89]  D. S. Hage,et al.  Affinity chromatography: a review of clinical applications. , 1999, Clinical chemistry.

[90]  Y. Guillaume,et al.  Sucrose dependence of solute retention on human serum albumin stationary phase: hydrophobic effect and surface tension considerations. , 1998, Analytical chemistry.

[91]  Z. Zhivkova,et al.  Protein binding of some nonsteroidal anti-inflammatory drugs studied by high-performance liquid affinity chromatography. , 1999, International journal of pharmaceutics.

[92]  D. S. Hage.  Chromatographic and electrophoretic studies of protein binding to chiral solutes. , 2001, Journal of chromatography. A.

[93]  K. Netter.  Progress in drug metabolism , 1985 .

[94]  D. S. Hage,et al.  High-performance affinity chromatography and immobilized serum albumin as probes for drug- and hormone-protein binding. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[95]  D. S. Hage,et al.  Development of sandwich HPLC microcolumns for analyte adsorption on the millisecond time scale. , 2001, Analytical chemistry.

[96]  Irving W. Wainer,et al.  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 , 1994 .

[97]  N. Nakano,et al.  Binding capacities of human serum albumin monomer and dimer by continuous frontal affinity chromatography. , 1982, Journal of chromatography.

[98]  P. McNamara,et al.  Alpha 1-acid glycoprotein high-performance liquid chromatography column (EnantioPAC) as a screening tool for protein binding. , 1989, Journal of chromatography.

[99]  C. Bertucci,et al.  Ligand binding to a human serum albumin stationary phase: use of same-drug competition to discriminate pharmacologically relevant interactions. , 1998, Biomedical chromatography : BMC.

[100]  Y. Guillaume,et al.  Reanalysis of solute retention on immobilized human serum albumin using fractal geometry. , 1999, Analytical chemistry.