Pharmaceutical and biomedical applications of affinity chromatography: Recent trends and developments

Journal of Pharmaceutical and Biomedical Analysis

Volumn 69, Issue , 2012, Pages 93-105

  Hage, David S ^a   Anguizola, Jeanethe A ^a   Bi, Cong ^a   Li, Rong ^a   Matsuda, Ryan ^a   Papastavros, Efthimia ^a   Pfaunmiller, Erika ^a   Vargas, John ^a   Zheng, Xiwei ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

Affinity chromatography; Boronate affinity chromatography; Immobilized metal ion affinity chromatography; Immunoaffinity chromatography; Lectin affinity chromatography

Indexed keywords

BORONIC ACID DERIVATIVE; CONCANAVALIN A; JACALIN; LECTIN; SAMBUCUS NIGRA EXTRACT; WHEAT GERM AGGLUTININ;

AFFINITY CHROMATOGRAPHY; ANALYTIC METHOD; BORONATE AFFINITY CHROMATOGRAPHY; EQUILIBRIUM CONSTANT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMOBILIZED ENZYME REACTOR; IMMOBILIZED METAL AFFINITY CHROMATOGRAPHY; IMMUNOAFFINITY CHROMATOGRAPHY; LECTIN AFFINITY CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; REVIEW; SEPARATION TECHNIQUE;

BORON; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, AFFINITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; IMMUNOASSAY; IONS; LECTINS; LIGANDS; MASS SPECTROMETRY; METALS; PHARMACEUTICAL PREPARATIONS; POLYMERS; SURFACE PROPERTIES; TECHNOLOGY, PHARMACEUTICAL;

EID: 84865075245     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.01.004     Document Type: Review

References (199)

1. Separation Techniques in Clinical Chemistry 2003, Marcel Dekker, New York. H.Y. Aboul-Enein (Ed.).
2. Handbook of HPLC 2011, CRC Press, Boca Raton. 2nd ed. D. Corradini, T.M. Phillips (Eds.).
3. Handbook of Affinity Chromatography 2005, CRC Press, Boca Raton, FL. D.S. Hage (Ed.).
4. Hage D.S., Ruhn P.F. An introduction to affinity chromatography. Handbook of Affinity Chromatography 2005, 3-13. CRC Press, Boca Raton, FL. D.S. Hage (Ed.).
5. Walters R.R. Affinity chromatography. Anal. Chem. 1985, 57:1099A-1114A.
6. Cuatrecasas P., Wilchek M., Anfinsen C.B. Selective enzyme purification by affinity chromatography. Proc. Natl. Acad. Sci. U.S.A. 1968, 68:636-643.
7. Turkova J. Affinity Chromatography 1978, Elsevier, Amsterdam.
8. Hermanson G.T., Mallia A.K., Smith P.K. Immobilized Affinity Ligand Techniques 1992, Academic Press, New York.
9. Larsson P.O. High-performance liquid affinity chromatography. Methods Enzymol. 1987, 104:212-223.
10. Gustavsson P.E., Larsson P.O. Support materials for affinity chromatography. Handbook of Affinity Chromatography 2005, 15-33. CRC Press, Boca Raton, FL. D.S. Hage (Ed.).
11. Schiel J.E., Mallik R., Soman S., Joseph K.S., Hage D.S. Applications of silica supports in affinity chromatography. J. Sep. Sci. 2006, 29:719-737.
12. Mallik R., Hage D.S. Affinity monolith chromatography. J. Sep. Sci. 2006, 29:1686-1704.
13. Yoo M.J., Hage D.S. Affinity monolith chromatography: principles and recent developments. Monolithic Chromatography and its Modern Applications 2010, ILM Publications, UK, (Chapter 1). P. Wang (Ed.).
14. Uzun L., Yavuz H., Say R., Ersoez A., Denizli A. Poly(ethylene dimethacrylate-glycidyl methacrylate) monolith as a stationary phase in dye-affinity chromatography. Ind. Eng. Chem. Res. 2004, 43:6507-6513.
15. Jiang T., Mallik R., Hage D.S. Affinity monoliths for ultrafast immunoextraction. Anal. Chem. 2005, 77:2362-2372.
16. Okanda F.M., El Rassi Z. Affinity monolithic capillary columns for glycomics/proteomics: 1. Polymethacrylate monoliths with immobilized lectins for glycoprotein separation by affinity capillary electrochromatography and affinity nano-liquid chromatography in either a single column or columns coupled in series. Electrophoresis 2006, 27:1020-1030.
17. 1-acid glycoprotein for chiral separations. J. Chromatogr. A 2007, 1149:294-304.
18. Hage D.S. A survey of recent advances in analytical applications of immunoaffinity chromatography. J. Chromatogr. 1998, 715:3-28.
19. Hage D.S., Xuan H., Nelson M.A. Application and elution in affinity chromatography. Handbook of Affinity Chromatography 2005, 79-97. CRC Press, Boca Raton, FL. 2nd ed. D.S. Hage (Ed.).
20. Kool J., Giera M., Irth H., Niessen W.M.A. Advances in mass spectrometry-based post-column bioaffinity profiling of mixtures. Anal. Bional. Chem. 2011, 399:2655-2668.
21. Nuwaysir L.M., Stults J.T. Electrospray ionization mass spectrometry of phosphopeptides isolated by on-line immobilized metal-ion affinity chromatography. J. Am. Soc. Mass Spectrom. 1993, 4:662-669.
22. de Frutos M M., Regnier F.E. Tandem chromatographic-immunological analyses. Anal. Chem. 1993, 65:17A-25A.
23. Ohlson S., Lundblad A., Zopf D. Novel approach to affinity chromatography using weak monoclonal antibodies. Anal. Biochem. 1988, 169:204-208.
24. Wikstroem M., Ohlson S. Computer simulation of weak affinity chromatography. J. Chromatogr. 1992, 597:83-92.
25. Ohlson S., Bergstroem M., Pahlsson P., Lundblad A. Use of monoclonal antibodies for weak affinity chromatography. J. Chromatogr. A 1997, 758:199-208.
26. Strandh M., Andersson H.S., Ohlson S. Weak affinity chromatography. Methods Mol. Biol. 2000, 147:7-23.
27. Vosseller K., Trinidad J.C., Chalkley R.J., Specht C.G., Thalhammer A., Lynn A.J., et al. O-Linked N-acetylglucosamine proteomics of postsynaptic density preparations using lectin weak affinity chromatography and mass spectrometry. Mol. Cell. Proteomics 2006, 5:923-934.
28. Patel S., Wainer I.W., Lough J.W. Affinity-based chiral stationary phases. Handbook of Affinity Chromatography 2006, 571-592. CRC Press, Boca Raton. 2nd ed. D.S. Hage (Ed.).
29. Allenmark S. Chromatographic Enantioseparation: Methods and Applications 1991, Ellis Horwood, New York. 2nd ed.
30. Duong-Thi M.-D., Meiby E., Bergstroem M., Fex T., Isaksson R., Ohlson S. Weak affinity chromatography as a new approach for fragment screening in drug discovery. Anal. Biochem. 2011, 414:138-146.
31. Cheshev P., Morelli L., Marchesi M., Podlipnik C., Bergstrom M., Bernadi A. Synthesis and affinity evaluation of a small library of bidentate cholera toxin ligands: towards nonhydrolyzable ganglioside mimics. Chemistry 2010, 16:1951-1967.
32. Bergstrom M., Liu S., Kiick K., Ohlson S. Cholera toxin inhibitors studied with high-performance liquid affinity chromatography: a robust method to evaluate receptor-ligand interactions. Chem. Biol. Drug Des. 2009, 73:132-141.
33. Yoo M.J., Hage D.S. Evaluation of silica monoliths in affinity microcolumns for high-throughput analysis of drug-protein interactions. J. Sep. Sci. 2009, 32:2776-2785.
34. Yoo M.J., Schiel J.S., Hage D.S. Evaluation of affinity microcolumns containing human serum albumin for rapid analysis of drug-protein binding. J. Chromatogr. B 2010, 878:1707-1713.
35. Moser A.C., Hage D.S. Immunoaffinity chromatography. Bioanalysis 2010, 2:769-790.
36. del Castillo E., Montes-Batyón M., Anón E., Sanz'Medel A. Quantitative targeted biomarker assay for glycated haemoglobin by multidimensional LC using mass spectrometric detection. J. Proteomics 2011, 74:35-43.
37. Kullolli M., Hancock W.S., Hincapie M. Automated platform for fractionation of human plasma glycoproteome in clinical proteomics. Anal. Chem. 2010, 82:115-120.
38. Clarke W., Roy Choudhuri A., Hage D.S. Analysis of free drug fractions by ultra-fast immunoaffinity chromatography. Anal. Chem. 2001, 73:2157-2164.
39. Clarke W., Schiel J.E., Moser A., Hage D.S. Analysis of free hormone fractions by an ultrafast immunoextraction/displacement immunoassay: studies using free thyroxine as a model system. Anal. Chem. 2005, 77:1859-1866.
40. Ohnmacht C.M., Schiel J.E., Hage D.S. Analysis of free drug fractions using near-infrared fluorescent labels and an ultrafast immunoextraction/displacement assay. Anal. Chem. 2006, 78:7547-7556.
41. Mallik R., Yoo M.J., Briscoe C.J., Hage D.S. Analysis of drug-protein binding by ultrafast affinity chromatography using immobilized human serum albumin. J. Chromatogr. A 2010, 1217:2796-2803.
42. Cellar N.A., Karnoup A.S., Albers D.R., Langhorst M.L., Young S.A. Immunodepletion of high abundance proteins coupled on-line with reversed-phase liquid chromatography: a two-dimensional LC sample enrichment and fractionation technique for mammalian proteomics. J. Chromatogr. B 2009, 877:79-85.
43. Hage D.S., Bian M., Burks R., Karle E., Ohnmacht C., Wa C. Bioaffinity chromatography. Handbook of Affinity Chromatography 2005, 107-135. CRC Press, Boca Raton, FL. 2nd ed. D.S. Hage (Ed.).
44. The Lectins: Properties, Functions and Applications in Biology and Medicine 1986, Academic Press, Waltham, MS. I.E. Liener, N. Sharon, I.J. Goldstein IJ (Eds.).
45. Yamamoto K., Tsuji T., Osawa T. Affinity chromatography of oligosaccharides and glycopeptides with immobilized lectins. The Protein Protocols Handbook 2002, 917-931. Humana Press, Totowa, NJ. J. Walker (Ed.).
46. Hauri H.P., Appenzeller C., Kuhn F., Nufer O. Lectins and traffic in the secretory pathway. FEBS Lett. 2000, 476:32-37.
47. Sing R.S., Bhari R., Kaur H.P. Current trends of lectins from microfungi. Crit. Rev. Biotechnol. 2011, 31:193-210.
48. Alexandre K.B., Gray E.S., Lambson B.E., Moore P.L., Choge I.A., Mlisana K., Abdool K., Salim S., McMahon J., O'Keefe B., Chikwamba R., Morris L. Mannose-rich glycosylation patterns on HIV-1 subtype C gp120 and sensitivity to the lectins Griffithsin, Cyanovirin-N and Scytovirin. Virology 2010, 402:187-196.
49. Bourne Y., Astoul C.H., Zamboni V., Peumans W.J., Menu-Bouaouiche L., Van Damme E.J.M., Barre A., Rouge P. Structural basis for the unusual carbohydrate-binding specificity of jacalin towards galactose and mannose. J. Biochem. 2002, 364:173-180.
50. de Paula E., de Melo R., Sartim M.A., Callejon D.R., Paiva H.H., Antonucci G.A., Rosa J.C., Oliveira A.C., Franco J.J., Candiani E., Dias-Baruffi M., Vilela S. Isolation, functional, and partial biochemical characterization of galactrox, an acidic lectin from Bothrops atrox snake venom. Acta Biochim. Biophys. Sin. 2011, 43:181-192.
51. Vivekananda S., Nickens Z., Shah P., Sinnathamby G., Semmes O.J., Philip R. Investigation of sialylation aberration in N-linked glycopeptides by lectin and tandem labeling (LTL) quantitative proteomics. Anal. Chem. 2010, 82:9201-9210.
52. Qiu R., Zhang X., Regnier F.E. A method for the identification of glycoproteins from human serum by a combination of lectin affinity chromatography along with anion exchange and Cu-IMAC selection of tryptic peptides. J. Chromatogr. B 2007, 845:143-150.
53. Plavina T., Wakshull E., Hancock W.S., Hincapie M. Combination of abundant protein depletion and multi-lectin affinity chromatography (MLAC) for plasma protein biomarker discovery. J. Proteome Res. 2007, 6:662-671.
54. Zeng Z., Hincapie M., Haab B.B., Hanash S., Pitteri S.J., Kluck S., Hogan J.M., Kennedy J., Hancock W.S. The development of an integrated platform to identify breast cancer glycoproteome changes in human serum. J. Chromatogr. A 2010, 1217:3307-3315.
55. Zeng Z., Hincapie M., Pitteri S.J., Hanash S., Schalkwijk J., Hogan J.M., Wang H., Hancock W.S. A proteomics platform combining depletion, multi-lectin affinity chromatography (M-LAC), and isoelectric focusing to study the breast cancer proteome. Anal. Chem. 2011, 83:4845-4854.
56. Calvano C.D., Zambonin C.G., Jensen O.N. Assessment of lectin and HILIC based enrichment protocols for characterization of serum glycoproteins by mass spectrometry. J. Proteomics 2008, 71:304-317.
57. Liu X.C, Scouten W. Boronate affinity chromatography. Handbook of Affinity Chromatography 2005, 243-261. CRC Press, Boca Raton, FL. D.S. Hage (Ed.).
58. Mayer T.K., Freedman Z.R. Protein glycosylation in diabetes mellitus: a review of laboratory measurements and of their clinical utility. Clin. Chim. Acta 1983, 127:147-184.
59. Bouriotis V., Stott J., Galloway A., Bellingham A.J., Dean P.D.G. Measurement of glycosylated haemoglobins using affinity chromatography. Diabetologia 1981, 21:579-580.
60. Middle F.A., Bannister A., Bellingham A.J., Dean P.D.G. Separation of glycosylated haemoglobins using immobilized phenylboronic acids. Biochem. J. 1983, 209:771-779.
61. Mallia A.K., Hermanson G.T., Krohn R.I., Fujimoto E.K., Smith P.K. Preparation and use of a boronic acid affinity support for the separation and quantitation of glycosylated hemoglobins. Anal. Lett. 1981, 14:649-661.
62. Hjerten S., Li J.P. High-performance liquid chromatography of proteins on deformed non-porous agarose beads: fast boronate affinity chromatography of haemoglobin at neutral pH. J. Chromatogr. 1990, 500:543-553.
63. Gould B.J., Hall P.M., Cook J.G.H. Measurement of glycosylated haemoglobins using an affinity chromatography method. Clin. Chim. Acta 1982, 125:41-48.
64. Singhal R.P., DeSilva S.S.M Boronate affinity chromatography. Adv. Chromatogr. 1992, 31:293-335.
65. Kitagawa N., Treat-Clemens L.G. Chromatographic study of immobilized boronate stationary phases. Anal. Sci. 1991, 7:195-198.
66. Stevenson T. Glycosal: the first rapid, point-of-care test for the determination of hemoglobin A1c in patients with diabetes. Diabetes Technol. Ther. 1999, 1:425-431.
67. Silver A.C., Lamb E., Cattell W.R., Dawnay A.B.S.J. Investigation and validation of the affinity chromatography method for measuring glycated albumin in serum and urine. Clin. Chim. Acta 1991, 202:11-22.
68. Panteghini M., Bonora R., Pagani F. Determination of glycated apolipoprotein B in serum by a combination of affinity chromatography and immunonephelometry. Ann. Clin. Biochem. 1994, 31:544-549.
69. Peterson K.P., Pavlovich J.G., Goldstein D., Little R., England J., Peterson C.M What is haemoglobin A1c? An analysis of glycated hemoglobin by electrospray ionization mass spectrometry. Clin. Chem. 1998, 44:1951-1958.
70. Little R.R., Roberts W.L. A review of variant hemoglobins interfering with hemoglobin A1c measurement. J. Diabetes Sci. Technol. 2009, 3:446-451.
71. Lee S-C., Wang L-S., Tsai S-M., Fang H-Y., Tsai L-Y Effects of the Hb E, Hb H and Hb G-Taichung variants on HbA1c values by the Bio-Rad variant™ turbo analyzer. Clin. Biochem. 2011, 44:1338-1342.
72. Ren L., Liu Y., Dong M., Liu Z. Synthesis of hydrophilic boronate affinity monolithic capillary for specific capture of glycoproteins by capillary liquid chromatography. J. Chromatogr. A 2009, 1216:8421-8425.
73. Liu Y., Ren L., Liu Z. A unique boronic acid functionalized monolithic capillary for specific capture, separation and immobilization of cis-diol biomolecules. Chem. Commun. 2011, 47:5067-5069.
74. Suksrichavalita T., Yoshimatsua K., Prachayasittikulb V., Bülowa L., Ye L. Clickable affinity ligands for effective separation of glycoproteins. J. Chromatogr. A 2010, 1217:3635-3641.
75. Monzo A., Bonn G., Guttman A. Boronic acid-lectin affinity chromatography. 1. Simultaneous glycoprotein binding with selective or combined elution. Anal. Bioanal. Chem. 2007, 389:2097-2102.
76. Thomas D.H., Taylor J.D., Barnaby O.S., Hage D.S. Determination of free catecholamines in urine by tandem affinity/ion-pair chromatography and flow injection analysis. Clin. Chim. Acta 2008, 398:63-69.
77. Hage D.S., Phillips T.M. Immunoaffinity chromatography. Handbook of Affinity Chromatography 2005, 127-172. CRC Press, Boca Raton, FL. 2nd ed. D.S. Hage (Ed.).
78. Wilchek M., Miron T., Kohn J. Affinity chromatography. Methods Enzymol. 1984, 104:3-55.
79. Hage D.S., Nelson M.A. Chromatographic immunoassays. Anal. Chem. 2001, 73:198A-205A.
80. Moser A.C., Hage D.S. Chromatographic immunoassays. Handbook of Affinity Chromatography 2006, CRC Press, Boca Raton, FL, (Chapter 29). 2nd ed. D.S. Hage (Ed.).
81. Hage D.S., Thomas D.H., Roy Chowdhuri A., Clarke W. Development of a theoretical model for chromatographic-based competitive binding immunoassays with simultaneous injection of sample and label. Anal. Chem. 1999, 71:2965-2975.
82. Nelson M.A., Reiter W.S., Hage D.S. Chromatographic competitive binding immunoassays: a comparison of the sequential and simultaneous injection methods. Biomed. Chromatogr. 2003, 17:188-200.
83. Oates M.R., Clarke W., Zimlich A., Hage D.S. Optimization and development of an HPLC-based one-site immunometric assay with chemiluminescence detection. Anal. Chim. Acta 2002, 470:37-50.
84. Todorova D., Vijayalakshmi M.A. Immobilized metal-ion affinity chromatography. Handbook of Affinity Chromatography 2005, CRC Press, Boca Raton, (Chapter 10). 2nd ed. D.S. Hage (Ed.).
85. Chaga G.S. Twenty-five years of immobilized metal ion affinity chromatography: past, present and future. J. Biochem. Biophys. Methods 2001, 49:313-334.
86. Mrabet N.T., Vijayalakshmi M.A. Immobilized metal-ion affinity chromatography. From phenomenological hallmarks to structure-based molecular insights. Biochromatography-Theory and Practice 2002, 272-294. Taylor & Francis, London. M.A. Vijayalakshmi (Ed.).
87. Porath J., Carlsson J., Olsson I., Belfrage B. Metal chelate affinity chromatography: a new approach to protein fraction. Nature 1975, 258:598-599.
88. Li R., Wang Y., Guo L.C., Shi M., Wang X.G., Chen B., Zheng J.B. A novel silica-based metal chelate stationary phase-l-glutamic acid-copper(II). Sep. Sci. Technol. 2011, 46:309-314.
89. Block H., Maertens B., Spriestersbach A., Brinker N., Kubicek J., Fabis R., Labahn J., Schäfer F. Immobilized-metal affinity chromatography (IMAC): a review. Methods Enzymol. 2009, 463:439-473.
90. Gutiérrez R., Martín del Valle E.M., Galán M.A. Immobilized metal-ion affinity chromatography: status and trends. Sep. Purif. Rev. 2007, 36:71-111.
91. Dong X.Y., Chen L.J., Sun Y. Refolding and purification of histidine-tagged protein by artificial chaperone-assisted metal affinity chromatography. J. Chromatogr. A 2009, 1216:5207-5213.
92. Wang C.Z., Wang L.L., Geng X.D. Optimization of refolding with simultaneous purification of recombinant human granulocyte colony-stimulating factor from Escherichia coli by immobilized metal ion affinity chromatography. Biochem. Eng. J. 2009, 43:197-202.
93. Ye J.Y., Zhang X.M., Young C., Zhao X.L., Hao Q., Cheng L., Jensen O.N. Optimized IMAC protocol for phosphopeptide recovery from complex biological samples. J. Proteome Res. 2010, 9:3561-3573.
94. Lee Y.M., Venkataraman K., Hwang S., Han D.K., Hla T. A novel method to quantify sphingosine 1-phosphate by immobilized metal affinity chromatography (IMAC). Prostaglandins Other Lipid Mediat. 2007, 84:154-162.
95. Takeda N., Matsuoka T., Gotoh M. Potentiality of IMAC as sample pretreatment tool in food analysis for veterinary drugs. Chromatographia 2010, 72:127-131.
96. Felix K., Fakelman F., Hartmann D., Giese N.A., Gaida M.M., Schnoelzer M., Flad T., Buechler M.W., Werner J. Identification of serum proteins involved in pancreatic cancer cachexia. Life Sci. 2011, 88:218-225.
97. Wu C., Wang Z.F., Liu L.J., Zhao P., Wang W.J., Yao D.K., Shi B., Lu J.H., Liao P., Yang Y.N., Zhu L. Surface enhanced laser desorption/ionization profiling: new diagnostic method of HBV-related hepatocellular carcinoma. J. Gastroenterol. Hepatol. 2009, 24:55-62.
98. Liu Z.J., Wang B., Yan Z.Y., Song X.X., Qian D.M., Bai Z.Q. Using the SELDI ProteinChip system to detect changes in protein expression in Vero cells after infection. Virol. Sin. 2007, 22:68-73.
99. QIAGEN Group Mass·Spec·Focus IMAC Chip Handbook 2007, Hilden, Germany. 3rd ed.
100. Victor M.B.G, Owen R.D. Structural analysis and classification of native proteins from commonly co-purified by immobilised metal affinity chromatography. Biochim. Biophys. Acta 2006, 1760:1304-1313.
101. Block H., Kubicek J., Labahn J., Roth U., Schafer F. Production and comprehensive quality control of recombinant human interleukin-1b: a case study for a process development strategy. Protein Expr. Purif. 2008, 27:244-254.
102. Lewinson O., Lee A.T., Douglas C.R. The funnel approach to the precrystallization production of membrane proteins. J. Mol. Biol. 2008, 377:62-73.
103. Garberc-Porekar V., Menart V., Jevsevar S., Vidensek A., Stalc A. Histidines in affinity tags and surface clusters for immobilized metal-ion affinity chromatography of trimeric tumor necrosis factor α. J. Chromatogr. A 1999, 852:117-128.
104. Wang W. Instability, stabilization, and formulation of liquid protein pharmaceuticals. Int. J. Pharm. 1999, 185:129-188.
105. Garberc-Porekar V., Menart V. Perspectives of immobilized-metal affinity chromatography. J. Biochem. Biophys. Methods 2001, 49:335-360.
106. Pedersen J., Lauritzen C., Madsen M.T., Dahl S.W. Removal of N-terminal polyhistidine tags from recombinant proteins using engineered aminopeptidases. Protein Expr. Purif. 1999, 15:389-400.
107. Analytical Affinity Chromatography 1987, CRC Press, Boca Raton, FL. I.M. Chaiken (Ed.).
108. Hage D.S., Chen J. Quantitative affinity chromatography: practical aspects. Handbook of Affinity Chromatography 2006, 595-628. CRC Press, Boca Raton. 2nd ed. D.S. Hage (Ed.).
109. Winzor D.J. Quantitative affinity chromatography: recent theoretical developments. Handbook of Affinity Chromatography 2006, 595-628. CRC Press, Boca Raton. 2nd ed. D.S. Hage (Ed.).
110. Schiel J.E., Joseph K.S., Hage D.S. Biointeraction affinity chromatography. Advances in Chromatography 2009, vol. 48. Taylor & Francis, New York, (Chapter 4).
111. Hage D.S., Anguizola J.A., Jackson A.J., Matsuda R., Papastavros E., Pfaunmiller E., Tong Z., Vargas-Badilla J., Yoo M.J., Zheng X. Chromatographic analysis of drug interactions in the serum proteome. Anal. Methods 2011, 8:1449-1460.
112. Nelson M.A., Moser A.C., Hage D.S. Biointeraction analysis by high-performance affinity chromatography: kinetic studies of immobilized antibodies. J. Chromatogr. B 2010, 878:165-171.
113. Schiel J.E., Hage D.S. Kinetic studies of biological interactions by affinity chromatography. J. Sep. Sci. 2009, 32:1507-1522.
114. Patel S., Wainer I.W., Lough W.J. Chromatographic studies of molecular recognition and solute binding to enzymes and plasma proteins. Handbook of Affinity Chromatography 2006, 663-683. CRC Press, Boca Raton. 2nd ed. D.S. Hage (Ed.).
115. Kim H.S., Wainer I.W. Rapid analysis of the interactions between drugs and human serum albumin (HSA) using high-performance affinity chromatography (HPAC). J. Chromatogr. B 2008, 870:22-26.
116. 1-acid glycoprotein chiral stationary phase: separation of R- and S-propranolol. J. Sep. Sci. 2006, 29:1412-1422.
117. Kalizan R., Noctor T.A.G., Wainer I.W. Stereochemical aspects of benzodiazepine binding to human serum albumin. II. Quantitative relationships between structure and enantioselective retention in high performance liquid affinity chromatography. Mol. Pharmacol. 1992, 42:512-517.
118. 1-acid glycoprotein. J. Chromatogr. A 1996, 722:25-32.
119. Nasal A., Radwanska A., Osmialowski K., Bucinski A., Kaliszan R., Barker G.E., Sun P., Hartwick R.A. Quantitative relationships between the structure of β-adrenolytic and antihistamine drugs and their retention on an α1-acid glycoprotein HPLC column. Biomed. Chromatogr. 1994, 8:125-129.
120. Loun B., Hage D.S. Chiral separation mechanisms in protein-based HPLC columns. I. Thermodynamic studies of R- and S-warfarin binding to immobilized human serum albumin. Anal. Chem. 1994, 66:3814-3822.
121. Matsuda R., Anguizola J.A., Joseph K.S., Hage D.S. High-performance affinity chromatography and the analysis of drug interactions with modified proteins: binding of gliclazide with glycated human serum albumin. Anal. Bioanal. Chem. 2011, 401:2811-2819.
122. Dalgaard L., Hansen J.J., Pedersen J.L. Resolution and binding site determination of d,l-thyronine by high-performance liquid chromatography using immobilized albumin as chiral stationary phase. Determination of optical purity of thyroxine in tablets. J. Pharm. Biomed. Anal. 1989, 7:361-368.
123. Domenici E., Bertucci C., Salvadorri P., Wainer I.W. Use of human serum albumin-based high-performance affinity chromatography chiral stationary phase for the investigation between warfarin and benzodiazepine binding site. J. Pharm. Sci. 1991, 80:164-166.
124. Noctor T.A.G., Wainer I.W., Hage D.S. 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. J. Chromatogr. 1992, 577:305-315.
125. Basiaga S.B.G., Hage D.S. Chromatographic studies of changes in binding of sulfonylurea drugs to human serum albumin due to glycation and fatty acids. J. Chromatogr. B 2010, 878:3193-3197.
126. Joseph K.S., Moser A.C., Basiaga S., Schiel J.E., Hage D.S. Evaluation of alternatives to warfarin as probes for sudlow site I of human serum albumin: characterization by high performance affinity chromatography. J. Chromatogr. A 2009, 1216:3492-3500.
127. Conrad M.L., Moser A.C., Hage D.S. Evaluation of indole-based probes for studying drug binding to human serum albumin in high-performance affinity separations. J. Sep. Sci. 2009, 32:1145-1155.
128. Chen J., Hage D.S. Quantitative analysis of allosteric drug-protein binding by biointeraction chromatography. Nat. Biotechnol. 2004, 22:1445-1448.
129. Chen J., Fitos I., Hage D.S. Chromatographic analysis of allosteric effects between ibuprofen and benzodiazepines on human serum albumin. Chirality 2006, 18:24-36.
130. Chen J., Hage D.S. Quantitative studies of allosteric effects by biointeraction chromatography: analysis of protein binding to low solubility drugs. Anal. Chem. 2006, 78:2672-2683.
131. Noctor T.A.G., Wainer I.W. 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 phenomenon. Pharm. Res. 1992, 9:480-484.
132. Chattopadhyay A., Tian T., Kortum L., Hage D.S. Development of tryptophan-modified human serum albumin columns for site-specific studies of drug-protein interactions by high-performance affinity chromatography. J. Chromatogr. B 1998, 715:183-190.
133. Joseph K.S., Anguizola J.A., Hage D.S. Binding of tolbutamide to glycated human serum albumin. J. Pharm. Biomed. Anal. 2011, 54:426-432.
134. Joseph K.S., Anguizola J.A., Jackson A.J., Hage D.S. Chromatographic analysis of acetohexamide binding to glycated human serum albumin. J. Chromatogr. B 2010, 878:2775-2781.
135. Joseph K.S., Hage D.S. The effects of glycation on the binding of human serum albumin to warfarin and l-tryptophan. J. Pharm. Biomed. Anal. 2010, 53:811-818.
136. Schreimer D.C. Biosensor alternative: frontal affinity chromatography. Anal. Chem. 2004, 76:440-448.
137. Loun B., Hage D.S. Characterization of thyroxine-albumin binding using high-performance affinity chromatography. 1. Interactions at the warfarin and indole sites of albumin. J. Chromatogr. 1992, 579:225-235.
138. Yang J., Hage D.S. Role of binding capacity versus binding strength in the separation of chiral compounds on protein-based high-performance liquid chromatographic columns: interactions of d- and l-tryptophan with human serum albumin. J. Chromatogr. B 1996, 725:273-285.
139. Yang J., Hage D.S. Characterization of the binding and chiral separation of d- and l-tryptophan on a high-performance immobilized human serum albumin column. J. Chromatogr. 1993, 645:241-250.
140. Nakano N.I., Shimamori Y., Yamaguchi S. Binding capacities of human serum albumin monomer and dimer by continuous frontal affinity chromatography. J. Chromatogr. 1982, 237:225-232.
141. Tweed S.A., Loun B., Hage D.S. Effects of ligand heterogeneity in the characterization of affinity columns by frontal analysis. Anal. Chem. 1997, 69:4790-4798.
142. Joseph K.S., Hage D.S. Characterization of the binding of sulfonylurea drugs to HSA by high-performance affinity chromatography. J. Chromatogr. B 2010, 878:1590-1598.
143. Kim H.S., Hage D.S. Chromatographic analysis of carbamazepine binding to human serum albumin. J. Chromatogr. B 2005, 816:57-66.
144. Chen J., Ohnmacht C., Hage D.S. Studies of phenytoin binding to human serum albumin by high-performance affinity chromatography. J. Chromatogr. B 2004, 809:137-145.
145. Soman S., Yoo M.J., Jang Y.J., Hage D.S. Lidocaine interactions with serum proteins using high-performance affinity chromatography. J. Chromatogr. B 2010, 878:705-708.
146. Mallik R., Yoo M.J., Chen S., Hage D.S. Studies of verapamil binding to human serum albumin by high-performance affinity chromatography. J. Chromatogr. B 2008, 876:69-75.
147. Yoo M.J., Smith Q.R., Hage D.S. Studies of imipramine binding to human serum albumin by high-performance affinity chromatography. J. Chromatogr. B 2009, 877:1149-1154.
148. Xuan H., Joseph K.S., Wa C., Hage D.S. Biointeraction analysis of carbamazepine binding to alpha 1-acid glycoprotein by high-performance affinity chromatography. J. Sep. Sci. 2010, 33:2294-2301.
149. Chen S., Sobansky M.R., Hage D.S. Analysis of drug interactions with high-density lipoprotein by high-performance affinity chromatography. Anal. Biochem. 2010, 397:107-114.
150. Tong Z., Joseph K.S., Hage D.S. Detection of heterogeneous drug-protein binding by frontal analysis and high-performance affinity chromatography. J. Chromatogr. A 2011, 1218:8915-8924.
151. Chan N., Lewis D., Kelly M., Ng E.S.M., Schriemer D.C. Frontal affinity chromatography-mass spectrometry for ligand discovery and characterization. Mass Spectrometry in Medicinal Chemistry 2007, 217-246. Wiley, Weinheim, Germany. K.T. Wanner, G. Hofner (Eds.).
152. Slon-Usakiewicz J.J., Dai J.R., Ng W., Foster J.E., Deretey E., Toledo-Sherman L., Redden P.R., Pasternak A., Reid N. Global kinase screening. Applications of frontal affinity chromatography coupled to mass spectrometry in drug discovery. Anal. Chem. 2005, 77:1268-1274.
153. Kovarik P., Hodgson R.J., Covey T., Brook M.A., Brennan J.D. Capillary-scale frontal affinity chromatography MALDI tandem mass spectrometry using protein-doped monolithic silica columns. Anal. Chem. 2005, 77:3340-3350.
154. Iwaki J., Minamisawa T., Tateno H., Kominami J., Suzuki K., Nishi N., Nakamura T., Hirabayashi J. Desulfated galactosaminoglycans are potential ligands for galectins: evidence from frontal affinity chromatography. Biochem. Biophys. Res. Commun. 2008, 373:206-212.
155. Tachibana K., Nakamura, Wang H., Iwasaki H., Tachibana K., Maebara K., Cheng L., Hirabayashi J., Narimatsu H. Elucidation of binding specificity of jacalin toward O-glycosylated peptides: quantitative analysis by frontal affinity chromatography. Glycobiology 2006, 16:46-53.
156. Nakamura-Tsuruta S., Uchiyama N., Hirabayashi J. High-throughput analysis of lectin-oligosaccharide interactions by automated frontal affinity chromatography. Methods Enzymol. 2006, 415:311-325.
157. Ng E.S.M., Yang F., Kameyama A., Palcic M.M., Hindsgaul O., Schriemer D.C. High-throughput screening for enzyme inhibitors using frontal affinity chromatography with liquid chromatography and mass spectrometry. Anal. Chem. 2005, 77:6125-6133.
158. Arata Y., Ishii N., Tamura M., Nonaka T., Kasai K.I. Identification of the amino acid residue in the nematode galectin LEC-1 responsible for Its unique sugar binding property: analysis by combination of site-directed mutagenesis and frontal affinity chromatography. Biol. Pharm. Bull. 2007, 30:2012-2017.
159. Itakura Y., Nakamura-Tsuruta S., Kominami J., Sharon N., Kasai K., Hirabayashi J. Systematic comparison of oligosaccharide specificity of Ricinus communis agglutinin I and erythrina lectins: a search by frontal affinity chromatography. J. Biochem. 2007, 142:459-469.
160. Loun B., Hage D.S. Chiral separation mechanisms in protein based HPLC columns 2. Kinetic studies of (R)- and (S)-warfarin binding to immobilized human serum albumin. Anal. Chem. 1996, 68:1218-1225.
161. Yang J., Hage D.S. 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. J. Chromatogr. B 1997, 766:15-25.
162. Talbert A.M., Tranter G.E., Holmes E., Francis P.L. Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using l-tryptophan and albumin. Anal. Chem. 2002, 74:446-452.
163. Schiel J.E., Ohnmacht C.M., Hage D.S. Measurement of drug-protein dissociation rates by high-performance affinity chromatography and peak profiling. Anal. Chem. 2009, 81:4320-4333.
164. Tong Z., Schiel J.E., Papastavros E., Ohnmacht C.M., Smith Q.R., Hage D.S. Kinetic studies of drug-protein interactions by using peak profiling and high-performance affinity chromatography: examination of multi-site interactions of drugs with human serum albumin columns. J. Chromatogr. A 2011, 1218:2065-2071.
165. Tong Z., Hage D.S. Characterization of interaction kinetics between chiral solutes and human serum albumin by using high-performance affinity chromatography and peak profiling. J. Chromatogr. A 2011, 1218:6892-6897.
166. Chen J., Schiel J.E., Hage D.S. Noncompetitive peak decay analysis of drug-protein dissociation by high-performance affinity chromatography. J. Sep. Sci. 2009, 32:1632-1641.
167. Yoo M.J., Hage D.S. Use of peak decay analysis and affinity microcolumns containing silica monoliths for rapid determination of drug-protein dissociation rates. J. Chromatogr. A 2011, 1218:2072-2078.
168. E. Pfaunmiller, A.C. Moser, D.S. Hage, Biointeraction analysis of immobilized antibodies and related agents by high-performance immunoaffinity chromatography, Methods, in press. doi:10.1016/j.ymeth.2011.08.016.
169. Jozwiak K., Haginaka J., Moaddel R., Wainer I. Displacement and nonlinear chromatographic techniques in the investigation of interaction of noncompetitive inhibitors with an immobilized a3b4 nicotinic acetylcholine receptor liquid chromatographic stationary phase. Anal. Chem. 2002, 74:4618-4624.
170. Jozwiak K., Hernandex S.C., Kellar K.J., Wainer I. Enantioselective interactions of dextromethorphan and levomethorphan with the a3B4-nicotinic acetylcholine receptor: comparison of chromatographic and functional data. J. Chromatogr. B 2003, 797:373-379.
171. Jozwiak K., Ravichandran S., Collins J.R., Moaddel R., Wainer I. Interaction of noncompetitive inhibitors with the a3B2 nicotinic acetylcholine receptor investigated by affinity chromatography and molecular docking. J. Med. Chem. 2007, 50:6279-6283.
172. Jozwiak K., Ravichandran S., Collins J.R., Wainer I. Interaction of noncompetitive inhibitors with an immobilized a3b4 nicotinic acetylcholine receptor investigated by affinity chromatography. Quantitative-structure activity relationship analysis and molecular docking. J. Med. Chem. 2004, 47:4008-4021.
173. Moaddel R., Jozwiak K., Yamaguchi R., Wainer I.W. Direct chromatographic determination of dissociation rate constants of ligand-receptor complexes: assessment of the interaction of noncompetitive inhibitors with an immobilized nicotinic acetylcholine receptor-based Liquid chromatography stationary phase. Anal. Chem. 2005, 77:5421-5426.
174. Moaddel R., Wainer I. Conformational mobility of immobilized proteins. J. Pharm. Biomed. Anal. 2007, 43:399-406.
175. Friedberg F., Rhoads A.R. Affinity chromatography of enzymes. Handbook of Affinity Chromatography 2005, 313-346. CRC Press, Boca Raton, FL. D.S. Hage (Ed.).
176. Bowers-Komro D.M., Yamada Y., McCormick D.B. Substrate specificity and variables affecting efficiency of mammalian flavin adenine dinucleotide synthesis. Biochemistry 1989, 28:8439-8844.
177. Kuester M., Becker G.L., Hardes K., Lindberg I., Steinmetzer T., Than M.E. Purification of the proprotein convertase furin by affinity chromatography based on PC-specific inhibitors. Biol. Chem. 2011, 392:973-981.
178. Bartolini M., Cavrini V., Andrisano V. Characterization of reversible and pseudo-irreversible acetylcholinesterase inhibitors by means of an immobilized enzyme reactor. J. Chromatogr. A 2007, 1144:102-110.
179. Hodgson R.J., Besanger T.R., Brook M.A., Brennan J.D. Inhibitor screening using immobilized enzyme reactor chromatography/mass spectrometry. Anal. Chem. 2005, 77:7512-7519.
180. Kim H.S., Wainer I.W. The covalent immobilization of microsomal uridine diphospho-glucuronosyltransferase (UDPGT): initial synthesis and characterization of an UDPGT immobilized enzyme reactor for the on-line study of glucuronidation. J. Chromatogr. B 2005, 823:158-166.
181. Mancini F., Naldi M., Cavrini W., Andrisano V. Development and characterization of β-secretase monolithic micro-immobilized enzyme reactor for on-line high-performance liquid chromatography studies. J. Chromatogr. A 2007, 1175:217-226.
182. Labrou N.E., Mazitsos K., Clonis Y.D. Dye-ligand and biomimetic affinity chromatography. Handbook of Affinity Chromatography 2005, 231-255. CRC Press, Boca Raton, FL. 2nd ed. D.S. Hage (Ed.).
183. Denizli A., Pikin E. Dye-ligand affinity systems. J. Biochem. Biophys. Methods 2001, 49:391-416.
184. Labrou N.E. Dye-ligand affinity chromatography for protein separation and purification. Methods in Molecular Biology, Affinity Chromatography: Methods and Protocols 2000, 129-139. Humana Press, Totowa, NJ. J.M. Walker (Ed.).
185. Caspi S., Halimi M., Yanai A., Sasson S.B., Taraboulos A., Gabizon R. The anti-prion activity of Congo Red. Putative mechanism. J. Biol. Chem. 1998, 273:3484-3489.
186. Hattori T., Zhang X., Weiss C., Xu Y., Kubo T., Sato Y., Nishikawa S., Sakaida H., Uchiyama T. Triazine dyes inhibit HIV-1 entry by binding to envelope glycoproteins. Microbiol. Immunol. 1997, 41:717-724.
187. Brown R.A., Combridge B.S. Binding of hepatitis virus particles to immobilized Procion Blue-HB and Cibacron Blue 3GA. J. Virol. Methods 1986, 14:267-274.
188. Lowe C.R. Combinatorial approaches to affinity chromatography. Curr. Opin. Chem. Biol. 2001, 5:248-256.
189. Haginaka J. Monodispersed, molecularly imprinted polymers as affinity-based chromatography media. J. Chromatogr. B 2008, 3-13.
190. Haupt K. Molecularly imprinted polymers: artificial receptors for affinity separations. Handbook of Affinity Chromatography 2006, 837-856. Taylor & Francis, Boca Raton, FL. 2nd ed. D.S. Hage (Ed.).
191. Oliveira H.M., Segundo M.A., Lima J.L.F.C., Miro M., Cerda V. Exploiting automatic on-line renewable molecularly imprinted solid-phase extraction in lab-on-valve format as front end to liquid chromatography: application to the determination of riboflavin in foodstuffs. Anal. Bioanal. Chem. 2010, 397:77-86.
192. Boonjob W., Yu Y., Miro M., Segundo M.A., Wang J., Cerda V. Online hyphenation of multimodal microsolid phase extraction involving renewable molecularly imprinted and reversed-phase sorbents to liquid chromatography for automatic multiresidue assays. Anal. Chem. 2010, 82:3052-3060.
193. Romig T.S., Bell C., Drolet D.W. Aptamer affinity chromatography: combinatorial chemistry applied to protein purification. J. Chromatogr. B 1999, 731:275-284.
194. German I., Buchanan D.D., Kennedy R.T. Aptamers as ligands in affinity probe capillary electrophoresis. Anal. Chem. 1998, 70:4540-4545.
195. Potyrailo R.A., Conrad R.C., Ellington A.D., Hieftje G.M. Adapting selected nucleic acid ligands (aptamers) to biosensors. Anal. Chem. 1998, 70:3419-3425.
196. Xu Y., Yang X., Wang E. Review: aptamers in microfluidic chips. Anal. Chim. Acta 2010, 683:12-20.
197. Zhao Q., Li X.-F., Shao Y., Le X.C. Aptamer-based affinity chromatographic assays for thrombin. Anal. Chem. 2008, 80:7586-7593.
198. Zhao Q., Li X.-F., Le X.C. Aptamer-modified monolithic capillary chromatography for protein separation and detection. Anal. Chem. 2008, 80:3915-3920.
199. Mairal T., Oezalp V.C., Sanchez P.L., Mir M., Katakis I., O'Sullivan C.K. Aptamers: molecular tools for analytical applications. Anal. Bioanal. Chem. 2008, 390:989-1007.