Phospholipids and liposomes in liquid chromatographic and capillary electromigration techniques

The structural resemblance of liposomes to natural cell membranes has caused them to be employed in liquid chromatographic and capillary electromigration techniques to study the interactions between analytes and phospholipid membranes. Phospholipids and liposomes are immobilized in stationary phases for liquid chromatography by a variety of techniques, to which we give special attention. We present selected applications to the separation of analytes. Though still few, applications in capillary electromigration are particularly attractive because of the small amounts of liposomes and samples that are required. We demonstrate the promising use of liposomes as carriers and coating materials in capillary electrophoresis with reference to recent applications. We note future directions for the utilization of phospholipids and liposomes in liquid chromatographic and capillary electromigration techniques.

[1]  M. Riekkola,et al.  Phospholipid‐lysozyme coating for chiral separation in capillary electrophoresis , 2004, Electrophoresis.

[2]  C. Pidgeon,et al.  Predicting drug-membrane interactions , 1995 .

[3]  M. Riekkola,et al.  Cholesterol‐containing phosphatidylcholine liposomes: Characterization and use as dispersed phase in electrokinetic capillary chromatography , 2002 .

[4]  M. Khaledi,et al.  Characterization of solvation properties of lipid bilayer membranes in liposome electrokinetic chromatography. , 2002, Journal of chromatography. A.

[5]  D. E. Nichols,et al.  Silica subsurface amine effect on the chemical stability and chromatographic properties of end-capped immobilized artificial membrane surfaces. , 1991, Analytical chemistry.

[6]  C. Jefcoate,et al.  Immobilized artificial membrane chromatography: rapid purification of functional membrane proteins. , 1991, Analytical biochemistry.

[7]  S. Yabushita,et al.  Liposome Immobilization on Polymer Gel Particles by in situ Formation of Covalent Linkages , 2003 .

[8]  Q. Yang,et al.  Immobilized proteoliposome affinity chromatography for quantitative analysis of specific interactions between solutes and membrane proteins. Interaction of cytochalasin B and D-glucose with the glucose transporter Glut1. , 1995, Biochemistry.

[9]  T. Österberg,et al.  Chromatographic retention of drug molecules on immobilised liposomes prepared from egg phospholipids and from chemically pure phospholipids. , 2001, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[10]  E. Brekkan,et al.  Immobilized liposome and biomembrane partitioning chromatography of drugs for prediction of drug transport , 1998 .

[11]  C. Pidgeon,et al.  Membrane partition coefficients chromatographically measured using immobilized artificial membrane surfaces. , 1995, Analytical chemistry.

[12]  B. Bannwarth,et al.  Potential of immobilized artificial membrane chromatography for lipophilicity determination of arylpropionic acid non-steroidal anti-inflammatory drugs. , 2003, Journal of pharmaceutical and biomedical analysis.

[13]  M. Khaledi,et al.  Evaluation of liposomal delivery of antisense oligonucleotide by capillary electrophoresis with laser-induced fluorescence detection. , 2003, Journal of chromatography. A.

[14]  M. Yoshimoto,et al.  Immobilized liposome chromatography for studies of protein-membrane interactions and refolding of denatured bovine carbonic anhydrase. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[15]  R A Durst,et al.  Liposome behavior in capillary electrophoresis. , 1996, Analytical chemistry.

[16]  E. Brekkan,et al.  Immobilized membrane vesicle or proteoliposome affinity chromatography. Frontal analysis of interactions of cytochalasin B and D-glucose with the human red cell glucose transporter. , 1996, Biochemistry.

[17]  C. Pidgeon,et al.  Phospholipid immobilization on solid surfaces. , 1994, Analytical chemistry.

[18]  J. Miyake,et al.  Phospholipase A(2)-catalyzed membrane leakage studied by immobilized liposome chromatography with online fluorescent detection. , 2001, Analytical biochemistry.

[19]  C. Pidgeon,et al.  Thermodynamics of solute partitioning into immobilized artificial membranes. , 1995, Analytical chemistry.

[20]  A. Lundqvist,et al.  Biomembrane affinity chromatographic analysis of inhibitor binding to the human red cell nucleoside transporter in immobilized cells, vesicles and proteoliposomes. , 1998, Biochimica et biophysica acta.

[21]  H. Wunderli-Allenspach,et al.  Immobilized Artificial Membrane (lAM)-HPLC for Partition Studies of Neutral and Ionized Acids and Bases in Comparison with the Liposomal Partition System , 1999, Pharmaceutical Research.

[22]  M. Yoshimoto,et al.  Immobilized liposome chromatography for refolding and purification of protein. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[23]  C. Pidgeon,et al.  Chromatographic surfaces prepared from lyso phosphatidylcholine ligands , 1994 .

[24]  K. Chapman,et al.  Rapid purification of cotton seed membrane-bound N-acylphosphatidylethanolamine synthase by immobilized artificial membrane chromatography. , 1995, Journal of chromatography. A.

[25]  M. Riekkola,et al.  Simple coating of capillaries with anionic liposomes in capillary electrophoresis. , 2003, Journal of chromatography. A.

[26]  M. Yoshimoto,et al.  Covalent immobilization of unilamellar liposomes in gel beads for chromatography. , 1999, Analytical biochemistry.

[27]  Q. Yang,et al.  Steric immobilization of liposomes in chromatographic gel beads and incorporation of integral membrane proteins into their lipid bilayers. , 1994, Analytical biochemistry.

[28]  H. Umakoshi,et al.  Stimuli-responsive separation of proteins using immobilized liposome chromatography. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[29]  A. Lundqvist,et al.  Glucose affinity for the glucose transporter Glut1 in native or reconstituted lipid bilayers. Temperature-dependence study by biomembrane affinity chromatography. , 1997, Journal of chromatography. A.

[30]  A. Lundqvist,et al.  Chromatography on cells and biomolecular assemblies. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[31]  E. Krause,et al.  Noncovalent immobilized artificial membrane chromatography, an improved method for describing peptide-lipid bilayer interactions. , 1999, Journal of chromatography. A.

[32]  G. Caldwell,et al.  Evaluation of the immobilized artificial membrane phosphatidylcholine. Drug discovery column for high-performance liquid chromatographic screening of drug-membrane interactions. , 1998, Journal of chromatography. A.

[33]  M. L. La Rotonda,et al.  Interactions of nonsteroidal antiinflammatory drugs with phospholipids: comparison between octanol/buffer partition coefficients and chromatographic indexes on immobilized artificial membranes. , 1997, Journal of pharmaceutical sciences.

[34]  Q. Yang,et al.  Immobilized-liposome chromatographic analysis of drug partitioning into lipid bilayers. , 1995, Journal of chromatography. A.

[35]  Qing Yang,et al.  Self-assembly and immobilization of liposomes in fused-silica capillary by avidin–biotin binding , 1998 .

[36]  E. Grushka,et al.  Characterization of dynamically prepared phospholipid-modified reversed-phase columns. , 2001, Journal of chromatography. A.

[37]  C. Nakamura,et al.  A novel chromatographic solid support with immobilized unilamellar liposomes for model analysis of solute–membrane interaction: comparison with analysis using immobilized artificial membranes and free liposomal membranes , 2001 .

[38]  P. Camilleri,et al.  Biomembrane lipids as components of chromatographic phases: Comparative chromatography on coated and bonded phases , 2000 .

[39]  Z. Deyl,et al.  Application of capillaries with minimized electroosmotic flow to the electrokinetic study of acidic drug–β-oleoyl-γ-palmitoyl-l-α-phosphatidyl choline liposome interactions , 2003 .

[40]  I. Wainer,et al.  Deactivated hydrocarbonaceous silica and immobilized artificial membrane stationary phases in high-performance liquid chromatographic determination of hydrophobicities of organic bases: relationship to log P and CLOGP. , 1993, Journal of pharmaceutical and biomedical analysis.

[41]  M. Sandberg,et al.  Immobilization of phospholipid vesicles on alkyl derivatives of agarose gel beads , 1987 .

[42]  J. Foley,et al.  Comparison of the retention behavior of beta-blockers using immobilized artificial membrane chromatography and lysophospholipid micellar electrokinetic chromatography. , 1998, Journal of chromatography. A.

[43]  Y. Zhang,et al.  Immobilized liposome chromatography of drugs on capillary continuous beds for model analysis of drug-membrane interactions. , 1996, Journal of chromatography. A.

[44]  K. Markides,et al.  Method for immobilization of liposomes in capillary electrophoresis by electrostatic interaction with derivatized agarose , 2002, Electrophoresis.

[45]  M. Wilchek,et al.  Avidin- and streptavidin-containing probes. , 1990, Methods in enzymology.

[46]  M. Khaledi,et al.  Rapid determination of liposome-water partition coefficients (Klw) using liposome electrokinetic chromatography (LEKC). , 2002, Journal of pharmaceutical sciences.

[47]  Y. Zhang,et al.  Immobilized liposome chromatography for analysis of interactions between lipid bilayers and peptides. , 1995, Analytical biochemistry.

[48]  Q. Yang,et al.  Lipid-vesicle-surface chromatography. , 1990, Journal of chromatography.

[49]  A. Berglund,et al.  Structure-property model for membrane partitioning of oligopeptides. , 2000, Journal of medicinal chemistry.

[50]  P. Haddad,et al.  Creation and characteristics of phosphatidylcholine stationary phases for the chromatographic separation of inorganic anions. , 2003, Journal of chromatography. A.

[51]  Beate I. Escher,et al.  Evaluation of Liposome−Water Partitioning of Organic Acids and Bases. 2. Comparison of Experimental Determination Methods , 2000 .

[52]  C. Pidgeon,et al.  Fourier transform infrared assay of membrane lipids immobilized to silica: leaching and stability of immobilized artificial membrane-bonded phases. , 1989, Analytical biochemistry.

[53]  J. Miyake,et al.  Avidin-biotin immobilization of unilamellar liposomes in gel beads for chromatographic analysis of drug-membrane partitioning. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[54]  C. Lucy,et al.  Phospholipid bilayer coatings for the separation of proteins in capillary electrophoresis. , 2002, Analytical chemistry.

[55]  C. Nakamura,et al.  Avidin-biotin-immobilized liposome column for chromatographic fluorescence on-line analysis of solute-membrane interactions. , 2001, Journal of chromatography. B, Biomedical sciences and applications.

[56]  C. Pidgeon,et al.  Immobilized-artificial-membrane chromatography: measurements of membrane partition coefficient and predicting drug membrane permeability. , 1996, Journal of chromatography. A.

[57]  R. Apkarian,et al.  Study of lipid and apolipoprotein binding interactions using vesicle affinity capillary electrophoresis. , 2003, Analytical Chemistry.

[58]  M. Yoshimoto,et al.  Oxidative Refolding of Denatured/Reduced Lysozyme Utilizing the Chaperone‐like Function of Liposomes and Immobilized Liposome Chromatography , 1999, Biotechnology progress.

[59]  P. Lundahl,et al.  Immobilized liposome chromatography of drugs for model analysis of drug-membrane interactions , 1997 .

[60]  D. Lasič,et al.  The mechanism of vesicle formation. , 1988, The Biochemical journal.

[61]  Z. Deyl,et al.  Affinity electrochromatography of acidic drugs using a liposome-modified capillary. , 2003, Journal of chromatography. A.

[62]  M. Riekkola,et al.  Liposomes as carriers in electrokinetic capillary chromatography , 2000, Electrophoresis.

[63]  M. Riekkola,et al.  Study on liposomes by capillary electrophoresis , 2001, Electrophoresis.

[64]  L. Holland,et al.  Bilayered phospholipid micelles and capillary electrophoresis: A new additive for electrokinetic chromatography , 2003, Electrophoresis.

[65]  Q. Yang,et al.  Liposome chromatography: liposomes immobilized in gel beads as a stationary phase for aqueous column chromatography. , 1991, Journal of chromatography.

[66]  E. Brekkan,et al.  Properties of immobilized-liposome-chromatographic supports for interaction analysis , 1995 .

[67]  C. Pidgeon,et al.  Immobilized Artificial Membranes — screens for drug membrane interactions , 1997 .

[68]  Yukihiro Kuroda,et al.  Role of phospholipids in drug-LDL bindings as studied by high-performance frontal analysis/capillary electrophoresis. , 2003, Journal of pharmaceutical and biomedical analysis.

[69]  Qing Yang,et al.  Binding of lysozyme on the surface of entrapped phosphatidylserine—phosphatidylcholine vesicles and an example of high-performance lipid vesicle surface chromatography , 1990 .

[70]  R. Gennis Protein-lipid interactions. , 1977, Annual review of biophysics and bioengineering.

[71]  Yukihiro Kuroda,et al.  Effect of oxidation of low‐density lipoprotein on drug binding affinity studied by high performance frontal analysis‐capillary electrophoresis , 2001, Electrophoresis.

[72]  J. Miyake,et al.  Partitioning of triphenylalkylphosphonium homologues in gel bead-immobilized liposomes: chromatographic measurement of their membrane partition coefficients. , 1999, Biochimica et biophysica acta.

[73]  L. Prokai,et al.  Integration of mass spectrometry into early-phase discovery and development of central nervous system agents. , 2001, Journal of mass spectrometry : JMS.

[74]  P. Lundahl,et al.  Entrapment of lipid vesicles and membrane protein-lipid vesicles in gel bead pores. , 1989, Biochimica et biophysica acta.

[75]  P. Carrupt,et al.  Molecular Factors Influencing Retention on Immobilized Artificial Membranes (IAM) Compared to Partitioning in Liposomes and n-Octanol , 2002, Pharmaceutical Research.

[76]  L. Prokai,et al.  Immobilized artificial membrane chromatography coupled with atmospheric pressure ionization mass spectrometry. , 2002, Journal of chromatography. A.

[77]  C. Pidgeon,et al.  Immobilized artificial membrane chromatography: supports composed of membrane lipids. , 1989, Analytical biochemistry.

[78]  H. Terada,et al.  Phosphatidylcholine-coated silica as a useful stationary phase for high-performance liquid chromatographic determination of partition coefficients between octanol and water , 1987 .

[79]  G. Carter,et al.  Immobilized artificial membrane chromatography with mass spectrometric detection: a rapid method for screening drug-membrane interactions. , 2001, Rapid communications in mass spectrometry : RCM.

[80]  T. Uchida,et al.  Affinity chromatography of protein kinase C-phorbol ester receptor on polyacrylamide-immobilized phosphatidylserine. , 1984, The Journal of biological chemistry.

[81]  Q. Yang,et al.  Immobilization of phospholipid vesicles and protein-lipid vesicles containing red cell membrane proteins on octyl derivatives of large-pore gels. , 1988, Biochimica et biophysica acta.

[82]  KhalequeMd. Abdul,et al.  Controlled Detachment of Immobilized Liposomes on Polymer Gel Support , 2000 .

[83]  R. Möllby,et al.  Phospholipids immobilized on beaded agarose by hydrophobic interaction as hydrophilic substrates for phospholipase C , 1978, FEBS letters.

[84]  M. L. La Rotonda,et al.  Chromatographic Indexes on Immobilized Artificial Membranes for Local Anesthetics: Relationships with Activity Data on Closed Sodium Channels , 1997, Pharmaceutical Research.

[85]  C. Pidgeon,et al.  Mobile phase effects on membrane protein elution during immobilized artificial membrane chromatography. , 1996, Journal of chromatography. A.

[86]  C. Pidgeon,et al.  Predicting drug-membrane interactions by HPLC: structural requirements of chromatographic surfaces. , 1995, Analytical chemistry.

[87]  Hiroshi Nakamura,et al.  Liposome Electrokinetic Chromatography as a Novel Tool for the Separation of Hydrophobic Compounds , 1996 .

[88]  C. Pidgeon,et al.  IAM chromatography: an in vitro screen for predicting drug membrane permeability. , 1995, Journal of medicinal chemistry.

[89]  J. Miyake,et al.  Effect of liposome type and membrane fluidity on drug-membrane partitioning analyzed by immobilized liposome chromatography. , 2001, Journal of chromatography. A.

[90]  G. R. Bartlett Phosphorus assay in column chromatography. , 1959, The Journal of biological chemistry.

[91]  S. Hjertén,et al.  Liposome capillary electrophoresis for analysis of interactions between lipid bilayers and solutes , 1995, Electrophoresis.

[92]  E. Kaiser,et al.  A method for probing the affinity of peptides for amphiphilic surfaces. , 1985, Analytical biochemistry.