Affinity chromatography: a review of clinical applications.

Affinity chromatography is a type of liquid chromatography that makes use of biological-like interactions for the separation and specific analysis of sample components. This review describes the basic principles of affinity chromatography and examines its use in the testing of clinical samples, with an emphasis on HPLC-based methods. Some traditional applications of this approach include the use of boronate, lectin, protein A or protein G, and immunoaffinity supports for the direct quantification of solutes. Newer techniques that use antibody-based columns for on- or off-line sample extraction are examined in detail, as are methods that use affinity chromatography in combination with other analytical methods, such as reversed-phase liquid chromatography, gas chromatography, and capillary electrophoresis. Indirect analyte detection methods are also described in which immunoaffinity chromatography is used to perform flow-based immunoassays. Other applications that are reviewed include affinity-based chiral separations and the use of affinity chromatography for the study of drug or hormone interactions with binding proteins. Some areas of possible future developments are then considered, such as tandem affinity methods and the use of synthetic dyes, immobilized metal ions, molecular imprints, or aptamers as affinity ligands for clinical analytes.

[1]  H. Weightman,et al.  High-performance liquid chromatographic determination of alkylamidopropyl-N,N-dimethyl-N-(2,3-dihydroxypropyl)ammonium chlorides in aqueous solutions and cosmetic formulations , 1989 .

[2]  D. Seligson,et al.  Clinical Chemistry , 1965, Bulletin de la Societe de chimie biologique.

[3]  L. Björck,et al.  A physicochemical study of protein G, a molecule with unique immunoglobulin G-binding properties. , 1986, The Journal of biological chemistry.

[4]  D. Westerlund,et al.  Direct injection of plasma and urine in automated analysis of catecholamines by coupled-column liquid chromatography with post-column derivatization. , 1984, Journal of pharmaceutical and biomedical analysis.

[5]  J. T. Stewart,et al.  High-performance liquid chromatography determination of praziquantel enantiomers in human serum using a reversed-phase cellulose-based chiral stationary phase and disc solid-phase extraction. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[6]  G. S. Wilson,et al.  Rapid heterogeneous competitive electrochemical immunoassay for IgG in the picomole range. , 1987, Analytical chemistry.

[7]  R H Levy,et al.  Rationale for Monitoring Free Drug Levels , 1984, Clinical pharmacokinetics.

[8]  C. Gay,et al.  Characterization of calcium efflux by osteoblasts derived from long bone periosteum. , 1995, Comparative biochemistry and physiology. Part A, Physiology.

[9]  P. Berna,et al.  How to use immobilized metal ion affinity chromatography , 1992 .

[10]  B. Johansson Simplified quantitative determination of plasma phenytoin: on-line pre-column high-performance liquid immunoaffinity chromatography with sample pre-purification. , 1986, Journal of chromatography.

[11]  H. Echizen,et al.  Determination of unbound warfarin enantiomers in human plasma and 7-hydroxywarfarin in human urine by chiral stationary-phase liquid chromatography with ultraviolet or fluorescence and on-line circular dichroism detection. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

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

[13]  R. Farinotti,et al.  Determination of the enantiomers of zopiclone and its two chiral metabolites in urine using an automated coupled achiral-chiral chromatographic system. , 1993, Journal of chromatography.

[14]  F. Regnier,et al.  Immunological-chromatographic analysis. , 1988, Journal of chromatography.

[15]  R. Farinotti,et al.  Determination of zopiclone enantiomers in plasma by liquid chromatography using a chiral cellulose carbamate column. , 1991, Journal of chromatography.

[16]  G. S. Wilson,et al.  Rapid sub-picomole electrochemical enzyme immunoassay for immunoglobulin G. , 1985, Analytical chemistry.

[17]  H. Parlar,et al.  Determination of Δ9-tetrahydrocannabinol from human saliva by tandem immunoaffinity chromatography-high-performance liquid chromatography , 1996 .

[18]  L. V. van Ginkel,et al.  Assay for trenbolone and its metabolite 17 alpha-trenbolone in bovine urine based on immunoaffinity chromatographic clean-up and off-line high-performance liquid chromatography-thin-layer chromatography. , 1988, Journal of chromatography.

[19]  J. Haginaka,et al.  Beta-cyclodextrin bonded silica for direct injection analysis of drug enantiomers in serum by liquid chromatography. , 1990, Analytical chemistry.

[20]  B. Mattiasson,et al.  Flow-ELISA: Binding assays for process control , 1990 .

[21]  T. Phillips,et al.  Recycling immunoaffinity chromatography for multiple analyte analysis in biological samples. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[22]  N. Kitagawa,et al.  CHROMATOGRAPHIC STUDY OF IMMOBILIZED BORONATE STATIONARY PHASE , 1991 .

[23]  S. Ohlson HIGH PERFORMANCE LIQUID AFFINITY CHROMATOGRAPHY (HPLAC) WITH PROTEIN A-SILICA , 1983 .

[24]  M. Castagnola,et al.  Human platelet glycocalicin purification by phenyl boronate affinity chromatography coupled to anion-exchange high-performance liquid chromatography. , 1988, Journal of chromatography.

[25]  S. Ohlson,et al.  High-performance liquid affinity chromatography: rapid immunoanalysis of transferrin in serum. , 1988, Clinical chemistry.

[26]  G. Geisslinger,et al.  Stereoselective high-performance liquid chromatographic determination of flurbiprofen in human plasma. , 1992, Journal of chromatography.

[27]  J. Rogalski,et al.  The preparation of sorbents for the analysis of human antithrombin III by means of high performance affinity chromatography , 1993 .

[28]  Rolf Schmid,et al.  Flow injection analysis (FIA) based on enzymes or antibodies , 1990 .

[29]  D. S. Hage,et al.  Intact parathyroid hormone: performance and clinical utility of an automated assay based on high-performance immunoaffinity chromatography and chemiluminescence detection. , 1992, Clinical chemistry.

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

[31]  R Chesler,et al.  Liposome-based flow-injection immunoassay for determining theophylline in serum. , 1993, Clinical chemistry.

[32]  D. S. Hage,et al.  Chiral separation mechanisms in protein-based HPLC columns. 1. Thermodynamic studies of (R)- and (S)-warfarin binding to immobilized human serum albumin. , 1994, Analytical chemistry.

[33]  G. Blaschke,et al.  Direct determination of the enantiomeric ratio of verapamil, its major metabolite norverapamil and gallopamil in plasma by chiral high-performance liquid chromatography. , 1992, Journal of chromatography.

[34]  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.

[35]  S. Ohlson Affinity Chromatography and Biological Recognition , 1983 .

[36]  M. Mizugaki,et al.  Novel derivatization and immunoextraction to improve microanalysis of 11-dehydrothromboxane B2 in human urine. , 1991, Journal of chromatography.

[37]  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.

[38]  C. Swift,et al.  Stereospecific analysis of the major metabolites of ibuprofen in urine by sequential achiral-chiral high-performance liquid chromatography. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[39]  J. Greef,et al.  On-line immunochemical detection in liquid chromatography using fluorescein-labelled antibodies , 1993 .

[40]  E. Schlimme,et al.  Synthesis and application of a boronic acid-substituted silica for high-performance liquid affinity chromatography , 1983 .

[41]  A. Preiss,et al.  Determination of chloramphenicol in muscle, liver, kidney and urine of pigs by means of immunoaffinity chromatography and gas chromatography with electron-capture detection. , 1995, Journal of chromatography. B, Biomedical applications.

[42]  J. Mcconnell,et al.  Determination of fibrinogen in plasma by high-performance immunoaffinity chromatography. , 1993, Journal of chromatography.

[43]  James N. Miller,et al.  A Model On-line Flow Injection Fluorescence Immunoassay Using a Protein a Immunoreactor and Lucifer Yellow , 1993 .

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

[45]  R. Krohn,et al.  Preparation and Use of a Boronic Acid Affinity Support for Separation and Quantitation of Glycosylated Hemoglobins , 1981 .

[46]  T. Miyakawa,et al.  Application of an ovomucoid-conjugated column for the optical resolution of some pharmaceutically important compounds. , 1987, Journal of chromatography.

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

[48]  D. Armstrong Optical isomer separation by liquid chromatography. , 1987, Analytical chemistry.

[49]  K. Shima,et al.  High-performance affinity chromatography system for the rapid, efficient assay of glycated albumin. , 1992, Journal of chromatography.

[50]  Fred E. Regnier,et al.  Tandem Chromatographic-Immunological Analyses , 1993 .

[51]  T. Phillips High-performance immunoaffinity chromatography. , 1989, Advances in chromatography.

[52]  R. Flückiger,et al.  Quantitation of Glycosylated Hemoglobin by Boronate Affinity Chromatography , 1984, Diabetes.

[53]  L. Gold,et al.  Systematic evolution of ligands by exponential enrichment: RNA ligands to bacteriophage T4 DNA polymerase. , 1990, Science.

[54]  Olof Ramström,et al.  Peer Reviewed: Molecular Imprinting: New Possibilities for Sensor Technology , 1997 .

[55]  T. Hayashi,et al.  HPLC analysis of human epidermal growth factor using immunoaffinity precolumn. II. Determination of hEGFs in biological fluids , 1989 .

[56]  L. Bowers,et al.  Immunoaffinity trapping of urinary human chorionic gonadotropin and its high-performance liquid chromatographic-mass spectrometric confirmation. , 1996, Journal of chromatography. B, Biomedical applications.

[57]  D. S. Hage Chromatographic approaches to immunoassays , 1997 .

[58]  L. Hansson,et al.  Boronic acid—silica: a new tool for the purification of catecholic compounds on-line with reversed-phase high-performance liquid chromatography , 1983 .

[59]  J. T. Stewart,et al.  HPLC separation of pentazocine enantiomers in serum using an ovomucoid chiral stationary phase. , 1994, Biomedical chromatography : BMC.

[60]  R. Pacifici,et al.  Stereoselective determination of fluoxetine and norfluoxetine enantiomers in plasma samples by high-performance liquid chromatography , 1996 .

[61]  W. Scouten,et al.  Boronate affinity chromatography. , 2015, Methods in molecular biology.

[62]  R Fanelli,et al.  Quantitative profiling of 6-ketoprostaglandin F1 alpha, 2,3-dinor-6-ketoprostaglandin F1 alpha, thromboxane B2 and 2,3-dinor-thromboxane B2 in human and rat urine by immunoaffinity extraction with gas chromatography-mass spectrometry. , 1989, Journal of chromatography.

[63]  E. Mutschler,et al.  Simultaneous determination of (R)- and (S)-celiprolol in human plasma and urine: high-performance liquid chromatographic assay on a chiral stationary phase with fluorimetric detection. , 1989, Journal of chromatography.

[64]  N. Madry,et al.  Measures to overcome HAMA interferences in immunoassays. , 1997, Anticancer research.

[65]  A. Aubry,et al.  Comparison of drug binding interactions on human, rat and rabbit serum albumin using high-performance displacement chromatography. , 1995, Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology.

[66]  J. T. Stewart,et al.  Stereoselective determination of mepivacaine in human serum using a brush-type chiral stationary phase and solid-phase extraction. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[67]  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.

[68]  B. Kågedal,et al.  Determination of 5-S-cysteinyldopa in human urine by direct injection in coupled-column high-performance liquid chromatography. , 1987, Journal of chromatography.

[69]  K. Jones A review of biotechnology and large scale affinity chromatography , 1991 .

[70]  G Geisslinger,et al.  Stereoselective high-performance liquid chromatographic determination of the enantiomers of ketamine and norketamine in plasma. , 1991, Journal of chromatography.

[71]  C. Pham-Huy,et al.  High-performance liquid chromatographic determination of (S)- and (R)-propranolol in human plasma and urine with a chiral beta-cyclodextrin bonded phase. , 1995, Journal of chromatography. B, Biomedical applications.

[72]  F. Regnier,et al.  Enzyme-linked immunosorbent assays in a chromatographic format. , 1996, Journal of chromatography. A.

[73]  M. Wikström,et al.  Determination of vanilmandelic acid in urine by coupled-column liquid chromatography combining affinity to boronate and separation by anion exchange. , 1991, Journal of chromatography.

[74]  J. Hermansson Direct liquid chromatographic resolution of racemic drugs using α1-acid glycoprotein as the chiral stationary phase , 1983 .

[75]  C. Shellum,et al.  Flow-injection immunoassays , 1993 .

[76]  D. S. Hage,et al.  Determination of urinary albumin using high-performance immunoaffinity chromatography and flow injection analysis. , 1994, Analytical chemistry.

[77]  R. Fanelli,et al.  Determination of O6-butylguanine in DNA by immunoaffinity extraction/gas chromatography-mass spectrometry. , 1990, Cancer research.

[78]  D. Rutledge,et al.  Rapid high-performance liquid chromatographic method for the measurement of the enantiomers of metoprolol in serum using a chiral stationary phase. , 1989, Journal of chromatography.

[79]  L. Björck,et al.  Purification and some properties of streptococcal protein G, a novel IgG-binding reagent. , 1984, Journal of immunology.

[80]  K. Chiba,et al.  Simultaneous determination of disopyramide and mono-N-dealkyldisopyramide enantiomers in plasma and urine by use of a chiral cellulose-derivative column. , 1990, Clinical chemistry.

[81]  H. Aboul‐Enein,et al.  Direct enantiomeric high performance liquid chromatographic separation of propafenone and its major metabolite in serum on a cellulose tris-3,5-dimethylphenyl carbamate chiral stationary phase. , 1993, Biomedical chromatography : BMC.

[82]  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.

[83]  D. S. Hage,et al.  Survey of recent advances in analytical applications of immunoaffinity chromatography. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[84]  J. T. Stewart,et al.  A High Performance Liquid Chromatographic Method for the Determination of Albuterol Enantiomers in Human Serum Using Solid Phase Extraction and a Sumichiral-OA Chiral Stationary Phase , 1993 .

[85]  T. Phillips Immunoaffinity measurement of recombinant granulocyte colony stimulating factor in patients with chemotherapy-induced neutropenia. , 1994, Journal of chromatography. B, Biomedical applications.

[86]  H. Irth,et al.  Bioanalysis of digoxin and its metabolites using direct serum injection combined with liquid chromatography and on-line immunochemical detection. , 1994, Journal of chromatography. B, Biomedical applications.

[87]  J. Baker,et al.  Inaccuracy in measuring glycated albumin concentration by thiobarbituric acid colorimetry and by boronate chromatography. , 1988, Clinical chemistry.

[88]  V. Agarwal Analysis of Antibiotic/Drug Residues in Food Products of Animal Origin , 2012, Springer US.

[89]  J. Henion,et al.  On-line immunoaffinity extraction-coupled column capillary liquid chromatography/tandem mass spectrometry: trace analysis of LSD analogs and metabolites in human urine. , 1996, Analytical chemistry.

[90]  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.

[91]  S. Takagaki,et al.  Determination of the R,R- and S,S-enantiomers of vamicamide in human serum and urine by high-performance liquid chromatography on a Chiral-AGP column. , 1993, Journal of chromatography.

[92]  D. Boulton,et al.  Determination of salbutamol enantiomers in human plasma and urine by chiral high-performance liquid chromatography. , 1995, Journal of chromatography. B, Biomedical applications.

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

[94]  H. Lingeman,et al.  Immunoaffinity precolumn for selective sample pretreatment in column liquid chromatography: Immunoselective desorption , 1991 .

[95]  L. Ettre,et al.  Nomenclature for chromatography (IUPAC Recommendations 1993) , 1993 .

[96]  L. V. Ginkel Immunoaffinity chromatography, its applicability and limitations in multi-residue analysis of anabolizing and doping agents. , 1991 .

[97]  T. Phillips Measurement of recombinant interferon levels by high performance immunoaffinity chromatography in body fluids of cancer patients on interferon therapy. , 1992, Biomedical chromatography : BMC.

[98]  R. Lindmark,et al.  Quantitation of Specific IgG Antibodies in Rabbits by a Solid‐phase Radioimmunoassay with 125I‐Protein A from Staphylococcus aureus , 1981, Scandinavian journal of immunology.

[99]  R. Fanelli,et al.  Analysis of diethylstilbestrol, dienestrol and hexestrol in biological samples by immunoaffinity extraction and gas chromatography-negative-ion chemical ionization mass spectrometry. , 1990, Journal of chromatography.

[100]  G. Geisslinger,et al.  Stereoselective determination of the enantiomers of methadone in plasma using high-performance liquid chromatography. , 1992, Journal of chromatography.

[101]  U. Brinkman,et al.  Direct introduction of large-volume urine samples into an on-line immunoaffinity sample pretreatment-capillary gas chromatography system. , 1991, Analytical chemistry.

[102]  E. Schlimme,et al.  Development and performance of an automated HPLC-analyzer for catecholamines , 1987 .

[103]  A. Lundblad,et al.  Analysis and purification of oligosaccharides by high-performance liquid affinity chromatography. , 1989, Methods in enzymology.

[104]  E. Schlimme,et al.  On-line high-performance liquid affinity chromatography-high-performance liquid chromatography analysis of monomeric ribonucleoside compounds in biological fluids. , 1983, Journal of Chromatography A.

[105]  P. Edlund Determination of dihydroxyphenylalanine and dihydroxyphenylacetic acid in biological samples by coupled-column liquid chromatography with dual coulometric-amperometric detection. , 1986, Journal of pharmaceutical and biomedical analysis.

[106]  F. Regnier,et al.  Immunological-chromatographic analysis of lysozyme variants. , 1989, Journal of chromatography.

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

[108]  Ulrich Westphal,et al.  Steroid-Protein Interactions , 1971, Monographs on Endocrinology.

[109]  Leslie S. Ettre,et al.  Nomenclature for Chromatography. , 1993 .

[110]  I. Wainer,et al.  The Use of Displacement Chromatography to Alter Retention and Enantioselectivity on a Human Serum Albumin-Based HPLC Chiral Stationary Phase: A Mini-Review , 1993 .

[111]  B. Rochat,et al.  Analysis of Enantiomers of Citalopram and Its Demethylated Metabolites in Plasma of Depressive Patients Using Chiral Reverse‐Phase Liquid Chromatography , 1995, Therapeutic drug monitoring.

[112]  C. Haux,et al.  Isolation of turbot (Scophthalmus maximus) vitellogenin by high-performance anion-exchange chromatography. , 1989, Journal of chromatography.

[113]  S. Jortani,et al.  Determination of thioridazine enantiomers in human serum by sequential achiral and chiral high-performance liquid chromatography. , 1993, Journal of analytical toxicology.

[114]  A. Silver,et al.  Investigation and validation of the affinity chromatography method for measuring glycated albumin in serum and urine. , 1991, Clinica chimica acta; international journal of clinical chemistry.

[115]  V. Debari,et al.  Ligand affinity chromatographic separation of serum IgG on recombinant protein G-silica. , 1991, Clinical chemistry.

[116]  J. Rogalski,et al.  High Performance Affinity Chromatography for Analysis of Human Antithrombin III , 1994 .

[117]  Z. Freedman,et al.  Protein glycosylation in diabetes mellitus: a review of laboratory measurements and of their clinical utility. , 1983, Clinica chimica acta; international journal of clinical chemistry.

[118]  R. R. Walters,et al.  Determination of immunoglobulins in blood serum by high-performance affinity chromatography. , 1983, Journal of chromatography.

[119]  S. Pond,et al.  First-Pass Elimination Basic Concepts and Clinical Consequences , 1984, Clinical pharmacokinetics.

[120]  U. Brinkman,et al.  On-line immunoaffinity sample pre-treatment for column liquid chromatography: evaluation of desorption techniques and operating conditions using an anti-estrogen immuno-precolumn as a model system. , 1991, The Analyst.

[121]  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.

[122]  T. Phillips,et al.  High-performance affinity chromatography: a rapid technique for the isolation and quantitation of IgG from cerebral spinal fluid. , 1984, Journal of chromatography.

[123]  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 .

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

[125]  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.

[126]  Phillips Tm,et al.  High-performance immunoaffinity chromatography. , 1989 .

[127]  T. Phillips,et al.  Isolation and quantitation of serum IgE levels by high-performance immunoaffinity chromatography. , 1985, Journal of chromatography.

[128]  D. S. Hage,et al.  Dual-column determination of albumin and immunoglobulin G in serum by high-performance affinity chromatography. , 1987, Journal of chromatography.

[129]  D. S. Hage,et al.  High-performance immunoaffinity chromatography and chemiluminescent detection in the automation of a parathyroid hormone sandwich immunoassay. , 1991, Analytical chemistry.

[130]  B. Sébille,et al.  Separation procedures used to reveal and follow drug-protein binding. , 1990, Journal of chromatography.

[131]  G. S. Wilson,et al.  Noncompetitive flow injection immunoassay for a hapten, alpha-(difluoromethyl)ornithine. , 1993, Analytical chemistry.

[132]  C. Brunner,et al.  Enantiomeric analysis of phenylpropanolamine in plasma via resolution of dinitrophenylurea derivatives on a high performance liquid chromatographic chiral stationary phase. , 1991, Biomedical chromatography : BMC.

[133]  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.

[134]  J. O'brien,et al.  Alkaline phosphatase isoenzymes of liver and bone origin are incompletely resolved by wheat-germ-lectin affinity chromatography. , 1989, Clinical chemistry.

[135]  O. Beck,et al.  Chiral analysis of methadone in plasma by high-performance liquid chromatography. , 1991, Journal of chromatography.

[136]  A. Lundblad,et al.  Analysis of a glucose-containing tetrasaccharide by high-performance liquid affinity chromatography. , 1989, Analytical biochemistry.

[137]  G. Blaschke,et al.  Achiral and chiral high-performance liquid chromatographic determination of tramadol and its major metabolites in urine after oral administration of racemic tramadol. , 1993, Journal of chromatography.

[138]  T. Inoue,et al.  Microheterogeneity with concanavalin A affinity of serum transferrin in patients with alcoholic liver disease. , 1996, Alcoholism, clinical and experimental research.

[139]  C. Cooney,et al.  Mathematical modelling of the continuous affinity-recycle extraction purification technique , 1989 .

[140]  J. Turková,et al.  Affinity chromatography. , 1974, Journal of chromatography.

[141]  B Guss,et al.  Chimeric IgG-binding receptors engineered from staphylococcal protein A and streptococcal protein G. , 1988, The Journal of biological chemistry.

[142]  N. Haagsma,et al.  Immunochemical Methods in the Analysis of Veterinary Drug Residues , 1992 .

[143]  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.

[144]  G. Schinella,et al.  Separation of ApoA- and ApoB-containing lipoproteins of human plasma by affinity chromatography on concanavalin A. , 1991, Progress in lipid research.

[145]  M. Baraldi,et al.  Measurement of urinary 8-Epi-prostaglandin F2alpha, a novel index of lipid peroxidation in vivo, by immunoaffinity extraction/gas chromatography-mass spectrometry. Basal levels in smokers and nonsmokers. , 1996, Free radical biology & medicine.

[146]  G. Hermanson,et al.  Immobilized Affinity Ligand Techniques , 1992 .

[147]  K. Stoschitzky,et al.  Stereoselective HPLC bioanalysis of atenolol enantiomers in plasma: application to a comparative human pharmacokinetic study. , 1993, Chirality.

[148]  I. Krull,et al.  Immunochromatographic analysis of bovine growth hormone releasing factor involving reversed-phase high-performance liquid chromatography-immunodetection. , 1996, Journal of chromatography. A.

[149]  J. T. Stewart,et al.  High-performance liquid chromatographic analysis of pindolol enantiomers in human serum and urine using a reversed-phase cellulose-based chiral column. , 1995, Journal of chromatography. B, Biomedical applications.

[150]  F. Regnier,et al.  Kinetic chromatographic sequential addition immunoassays using protein A affinity chromatography. , 1992, Analytical chemistry.

[151]  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.

[152]  D. Musson,et al.  Stereoselective determination of R-(+)- and S-(-)-remoxipride, a dopamine D2-receptor antagonist, in human plasma by chiral high-performance liquid chromatography. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[153]  J. Greef,et al.  Strategies for on-line coupling of immunoassays to high-performance liquid chromatography , 1995 .

[154]  F. Regnier,et al.  Immunochromatographic analysis of proteins. Identification, characterization and purity determination. , 1993, Journal of chromatography.

[155]  Gary D. Christian,et al.  Flow-injection immunoassays: Present and future , 1992 .

[156]  K. Kasai,et al.  Immobilized urokinase column as part of a specific detection system for plasminogen species separated by high-performance affinity chromatography. , 1991, Journal of chromatography.

[157]  P. Chiap,et al.  Automated determination of tramadol enantiomers in human plasma using solid-phase extraction in combination with chiral liquid chromatography. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[158]  C. Ayotte,et al.  Determination of the enantiomers of bunolol in human urine by high-performance liquid chromatography on a chiral AGP stationary phase and identification of their metabolites by gas chromatography-mass spectrometry. , 1994, Journal of chromatography. B, Biomedical applications.

[159]  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.

[160]  D. Shuker,et al.  Isolation of urinary 3-methyladenine using immunoaffinity columns prior to determination by low-resolution gas chromatography-mass spectrometry. , 1991, Chemical research in toxicology.

[161]  C. Cámara,et al.  Development of a flow fluoroimmunosensor for determination of theophylline , 1995 .

[162]  T. Phillips Measurement of total and bioactive interleukin-2 in tissue samples by immunoaffinity-receptor affinity chromatography. , 1997, Biomedical chromatography : BMC.

[163]  T. Phillips,et al.  High-performance immunoaffinity chromatographic detection of immunoregulatory anti-idiotypic antibodies in cancer patients receiving immunotherapy. , 1988, Clinical chemistry.

[164]  C. Jenkin,et al.  Isolation of pure IgG1, IgG2a and IgG2b immunoglobulins from mouse serum using protein A-sepharose. , 1978, Immunochemistry.

[165]  L. V. van Ginkel,et al.  Effective monitoring of residues of nortestosterone and its major metabolite in bovine urine and bile. , 1989, Journal of chromatography.

[166]  J. Montali,et al.  Examination of glutathione S-transferase isoenzyme profiles in human liver using high-performance affinity chromatography. , 1994, Journal of chromatography. A.

[167]  H. Bartsch,et al.  Immunoaffinity purification and gas chromatography-mass spectrometric quantification of 3-alkyladenines in urine: metabolism studies and basal excretion levels in man. , 1993, Carcinogenesis.

[168]  J. Montali,et al.  Coupled affinity-reversed-phase high-performance liquid chromatography systems for the measurement of glutathione S-transferases in human tissues. , 1994, Journal of chromatography. A.

[169]  I. Wainer,et al.  Chiral separations of cationic and anionic drugs on an alpha 1-acid glycoprotein-bonded stationary phase (EnantioPac). II. Influence of mobile phase additives and pH on chiral resolution and retention. , 1986, Journal of chromatography.

[170]  T. Yasaka,et al.  Reversed-phase liquid chromatographic investigation of nucleosides and bases in mucosa and modified nucleosides in urines from patients with gastrointestinal cancer. , 1985, Journal of chromatography.

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

[172]  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.

[173]  James N. Miller,et al.  Rapid fluorescence flow injection immunoassay using a novel perfusion chromatographic material , 1994 .

[174]  M. Reinke,et al.  Simultaneous determination of the primary prostanoids prostaglandin E2, prostaglandin F2 alpha and 6-oxoprostaglandin F1 alpha by immunoaffinity chromatography in combination with negative ion chemical ionization gas chromatography-tandem mass spectrometry. , 1989, Journal of chromatography.

[175]  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 .

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

[177]  D. Haupt Determination of citalopram enantiomers in human plasma by liquid chromatographic separation on a Chiral-AGP column. , 1996, Journal of chromatography. B, Biomedical applications.

[178]  K. Pettersson,et al.  Concanavalin A affinity chromatography of human serum gonadotropins: evidence for changes of carbohydrate structure in different clinical conditions. , 1993, The Journal of clinical endocrinology and metabolism.

[179]  I. Wainer,et al.  Determination of metyrapone and the enantiomers of its chiral metabolite metyrapol in human plasma and urine using coupled achiral-chiral liquid chromatography. , 1995, Journal of chromatography. B, Biomedical applications.

[180]  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.

[181]  D. Breimer,et al.  Enantioselective determination of felodipine and other chiral dihydropyridine calcium entry blockers in human plasma. , 1990, Journal of chromatography.

[182]  L. McGown,et al.  The nucleic acid ligand. A new tool for molecular recognition. , 1995, Analytical chemistry.

[183]  R. Kennedy,et al.  Selective preconcentration for capillary zone electrophoresis using protein G immunoaffinity capillary chromatography , 1995, Electrophoresis.

[184]  R. Straka,et al.  Analysis of metoprolol enantiomers in human serum by liquid chromatography on a cellulose-based chiral stationary phase. , 1990, Journal of chromatography.

[185]  I. Wainer,et al.  Determination of the enantiomers of verapamil and norverapamil in serum using coupled achiral-chiral high-performance liquid chromatography. , 1989, Journal of chromatography.

[186]  D. S. Hage,et al.  Theory of a sequential addition competitive binding immunoassay based on high-performance immunoaffinity chromatography. , 1993, Analytical chemistry.

[187]  T. E. Edmonds,et al.  Flow Injection Immunosensor for Theophylline , 1993 .

[188]  C. Creaser,et al.  On-line immunoaffinity chromatography—high-performance liquid chromatography—mass spectrometry for the determination of dexamethasone , 1996 .

[189]  F. Regnier,et al.  Tandem chromatographic-immunological analyses. , 1993, Analytical chemistry.

[190]  B. Wilhelmi,et al.  Comparison of immunoaffinity chromatography combined with gas chromatography-negative ion chemical ionisation mass spectrometry and radioimmunoassay for screening dexamethasone in equine urine. , 1993, Journal of chromatography.

[191]  M. Novotny,et al.  Dual microcolumn immunoaffinity liquid chromatography: an analytical application to human plasma proteins. , 1993, Analytical chemistry.

[192]  S. Mori,et al.  Separation of prepolymers of phenol-formaldehyde resins by supercritical-fluid chromatography , 1989 .

[193]  P. Larsson High-performance liquid affinity chromatography. , 1984, Methods in enzymology.

[194]  A. J. Oosterkamp,et al.  Online Coupling of Liquid Chromatography to Biochemical Assays Based on Fluorescent-Labeled Ligands , 1994 .

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

[196]  E. Vérette,et al.  On-line column-switching high-performance liquid chromatography analysis of cardiovascular drugs in serum with automated sample clean-up and zone-cutting technique to perform chiral separation. , 1997, Journal of chromatography. A.

[197]  P. K. Smith,et al.  Determination of glycosylated hemoglobin by affinity chromatography: comparison with colorimetric and ion-exchange methods, and effects of common interferences. , 1982, Clinical chemistry.

[198]  B. Gould,et al.  Measurement of glycosylated haemoglobins using an affinity chromatography method. , 1982, Clinica chimica acta; international journal of clinical chemistry.

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

[200]  H. Ogata,et al.  Determination of propranolol enantiomers in human plasma and urine and in rat tissues using chiral stationary-phase liquid chromatography. , 1988, Journal of pharmaceutical sciences.

[201]  J. Henion,et al.  Determination of drugs from urine by on-line immunoaffinity chromatography-high-performance liquid chromatography-mass spectrometry. , 1992, Journal of chromatography.

[202]  R. Heinig,et al.  Determination of the enantiomers of nisoldipine in human plasma using high-performance liquid chromatography on a chiral stationary phase and gas chromatography with mass-selective detection. , 1994, Journal of chromatography. B, Biomedical applications.

[203]  M. Vanderlaan,et al.  Perfusion immunoassay for acetylcholinesterase: analyte detection based on intrinsic activity. , 1995, Journal of chromatography. A.

[204]  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.

[205]  W. Schoeppe,et al.  Isolation and partial characterization of angiotensinase A and aminopeptidase M from urine and human kidney by lectin affinity chromatography and high-performance liquid chromatography. , 1990, Journal of chromatography.

[206]  M. Woodruff,et al.  Free drug concentration monitoring in clinical practice. Rationale and current status. , 1986, Clinical pharmacokinetics.

[207]  A. Olsson,et al.  Liquid chromatographic determination of the enantiomers of ibuprofen in plasma using a chiral AGP column. , 1991, Journal of chromatography.

[208]  B. Wilhelmi,et al.  Immunoaffinity chromatography combined with gas chromatography-negative ion chemical ionisation mass spectrometry for the confirmation of flumethasone abuse in the equine. , 1993, Journal of chromatography.

[209]  B. Nilsson Extraction and quantitation of cortisol by use of high-performance liquid affinity chromatography. , 1983, Journal of chromatography.

[210]  F. Regnier,et al.  Dual-column immunoassays using protein G affinity chromatography. , 1989, Analytical chemistry.

[211]  P. Haddad Foreword to the Proceedings of International Ion Chromatography Symposium, San Diego, CA 1990 , 1991 .

[212]  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.

[213]  S. Kitahara,et al.  Serial lectin affinity chromatography with concavalin A and wheat germ agglutinin demonstrates altered asparagine-linked sugar-chain structures of prostatic acid phosphatase in human prostate carcinoma. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[214]  J. Szostak,et al.  In vitro selection of RNA molecules that bind specific ligands , 1990, Nature.

[215]  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.

[216]  S. Hjertén,et al.  High-performance liquid chromatography of proteins on deformed non-porous agarose beads. Fast boronate affinity chromatography of haemoglobin at neutral pH. , 1990, Journal of chromatography.

[217]  H. Aboul‐Enein,et al.  Enantiomeric separation of ketamine hydrochloride in pharmaceutical formulation and human serum by chiral liquid chromatography , 1992 .

[218]  N. Guzman Biomedical Applications of On-Line Preconcentration-Capillary Electrophoresis Using an Analyte Concentrator: Investigation of Design Options , 1995 .

[219]  T. Nagatsu,et al.  Selective removal of beta 2-microglobulin from human plasma by high-performance immunoaffinity chromatography. , 1989, Journal of chromatography.

[220]  G. Geisslinger,et al.  Stereoselective high-performance liquid chromatographic determination of ketoprofen, ibuprofen and fenoprofen in plasma using a chiral alpha 1-acid glycoprotein column. , 1990, Journal of chromatography.

[221]  T. Blemmer,et al.  Enantioselective high-performance liquid chromatographic method for the determination of methadone in serum using an AGP and a CN column as chiral and analytical column, respectively. , 1994, Journal of chromatography. A.

[222]  Nathan Sharon,et al.  The Lectins: Properties, Functions and Applications in Biology and Medicine , 1986 .

[223]  B Zimmerli,et al.  Determination of ochratoxin A at the ppt level in human blood, serum, milk and some foodstuffs by high-performance liquid chromatography with enhanced fluorescence detection and immunoaffinity column cleanup: methodology and Swiss data. , 1995, Journal of chromatography. B, Biomedical applications.

[224]  P. Wilding,et al.  Macroenzymes: biochemical characterization, clinical significance, and laboratory detection. , 1989, Clinical chemistry.

[225]  M. Panteghini,et al.  Determination of Glycated Apolipoprotein B in Serum by a Combination of Affinity Chromatography and Immunonephelometry , 1994, Annals of clinical biochemistry.

[226]  M. Siewierski,et al.  Drug residue analysis using immunoaffinity chromatography. , 1992, Journal of chromatography.

[227]  A. Bernareggi,et al.  Assay of moguisteine metabolites in human plasma and urine: conventional and chiral high-performance liquid chromatographic methods. , 1994, Journal of chromatography. B, Biomedical applications.

[228]  R Fanelli,et al.  Determination of zeranol and beta-zearalanol in calf urine by immunoaffinity extraction and gas chromatography-mass spectrometry after repeated administration of zeranol. , 1991, Journal of chromatography.

[229]  T. Phillips,et al.  Immunoaffinity capillary electrophoretic analysis of cyclosporin in tears. , 1994, Biomedical chromatography : BMC.

[230]  B. Riggs,et al.  Clinical evaluation of high-performance affinity chromatography for the separation of bone and liver alkaline phosphatase isoenzymes. , 1991, Clinica chimica acta; international journal of clinical chemistry.

[231]  U Kragh-Hansen,et al.  Molecular aspects of ligand binding to serum albumin. , 1981, Pharmacological reviews.

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

[233]  I. Wainer,et al.  Simultaneous direct determination of the enantiomers of verapamil and norverapamil in plasma using a derivatized amylose high-performance liquid chromatographic chiral stationary phase. , 1992, Journal of chromatography.

[234]  D. Anderson,et al.  Liver- and bone-derived isoenzymes of alkaline phosphatase in serum as determined by high-performance affinity chromatography. , 1990, Clinical chemistry.

[235]  Börje Sellergren,et al.  Noncovalent molecular imprinting: antibody-like molecular recognition in polymeric network materials , 1997 .

[236]  R A Durst,et al.  Liposome flow injection immunoassay: model calculations of competitive immunoreactions involving univalent and multivalent ligands. , 1991, Analytical chemistry.

[237]  C. Anfinsen,et al.  [31] Affinity chromatography , 1971 .

[238]  G. Guiochon,et al.  Experimental and theoretical study of the adsorption behavior and mass transfer kinetics of propranolol enantiomers on cellulase protein as the selector. , 1996, Analytical chemistry.

[239]  C. Shellum,et al.  Development of an automated flow injection chemiluminescence immunoassay for human immunoglobulin G , 1995 .