Interactions between chiral drugs and cyclodextrins

Affinity Capillary Electrophoresis in Pharmaceutics and Biopharmaceutics

Volumn , Issue , 2003, Pages 175-209

  Blaschke, Gottfried ^a   Chankvetadze, Bezhan ^b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b Thilisi State University   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244434933     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (80)

1. F Cramer. Einschlussverbindungen der Cyclodextrine. Angew Chem 64: 136, 1952.
2. JC Giddings. Generation of variance theoretical plates, resolution and peak capacity in electrophoresis and sedimentations. Separ Sci 4: 181-189, 1969.
3. B Chankvetadze, G Blaschke. Enantioseparations in capillary electromigration techniques: recent developments and future trends. J Chromatogr A 906: 309-363, 2001.
4. B Chankvetadze. Separation selectivity in chiral capillary electrophoresis with charged selectors. J Chromatogr A 792: 269-295, 1997.
5. B Chankvetadze, N Burjanadze, D Bergenthal, G Blaschke. Potential of flowcounterbalanced capillary electrophoresis for analytical and micropreparative separations. Electrophoresis 20: 2680-2685, 1999.
6. A Tiselius. Moving boundary method of studying the electrophoresis of proteins. Nova Acta Reg Soc Uppsal Ser IV 7: 1-107, 1930.
7. KL Rundlett, DW Armstrong. Examination of the origin, variation, and proper use of expressions for the estimation of association constants by capillary electrophoresis. J Chromatogr A 721: 173-186, 1996.
8. KL Rundlett, DW Armstrong. Methods for the estimation of binding constants by capillary electrophoresis. Electrophoresis 18: 2194-2202, 1997.
9. KL Rundlett, DW Annstrong. Methods for the detennination of binding constants by capillary electrophoresis. Electrophoresis 22: 1419-1427, 2001.
10. A Rizzi. Fundamental aspects of chiral separations by capillary electrophoresis. Electrophoresis 22: 3079-3106, 2001.
11. SG Penn, ET Bergstrom, DM Goodall, JS Loran. Capillary electrophoresis with chiral selectors: optimization of separation and detennination of thennodynamic parameters for binding of tioconazole enantiomers to cyclodextrins. Anal Chem 66: 2866-2873, 1994.
12. S Cladrowa-Runge, A Rizzi. Enantioseparations of 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate derivatized amino acids by capillary zone electrophoresis using native and substituted β-cyclodextrins as chiral additives II. Evaluation of complexation constants. J Chromatogr A 759: 167-175, 1997.
13. a shift-associated effects in enantioseparations by cyclodextrin- mediated capillary zone electrophoresis. Electrophoresis 20: 2715-2722, 1999.
14. S Sabbah, GKE Scriba. Separation of dipeptide and tripeptide enantiomers in capillary electrophoresis using carboxymethyl-β-cyclodextrin and succinyl-f3cyclodextrin: influence of the amino acid sequence, nature of the cyclodextrin and pH. Electrophoresis 22: 1385-1393, 2001.
15. S Sabbah, F Suss, GKE Scriba. pH-Dependence of complexation constants and complex mobility in capillary electrophoresis separation of dipeptide enantiomers. Electrophoresis 22: 3163-3170, 2001.
16. B Chankvetadze, I Kartozia, N Burjanadze, D Bergenthal, H Luftmann, G Blaschke. Enantioseparation of chiral phenothiazine derivatives in capillary electrophoresis using cyclodextrin-type chiral selectors. Chromatographia 53: S290-S296, 2001.
17. B Chankvetadze. Capillary Electrophoresis in Chiral Analysis. Wiley, Chichester, UK, 1997.
18. R Kuhn, F Stoeklin, F Emi. Chiral separations by host-guest complexation with cyclodextrin and crown ether in capillary zone electrophoresis. Chromatographia 33: 32-36, 1992.
19. A Shibukawa, DK Lloyd, IW Wainer. Simultaneous chiral separation of leucovorin and its major metabolite 5-methyl-tetrahydrofolate by capillary electrophoresis using cyclodextrins as chiral selector. Estimation of the formation constants and mobility of the solute-cyclodextrin complexes. Chromatographia 35: 419-429, 1993.
20. SG Penn, DM Goodall, JS Loran. Differential binding of tioconazole enantiomers to hydroxypropyl-β-cyclodextrin studied by capillary electrophoresis. J Chromatogr 636: 149-152, 1993.
21. SG Penn, GY Liu, ET Bergstrom, DM Goodall, JS Loran. Systematic approach to treatment of enantiomeric separations in capillary electrophoresis and liquid chromatography. 1. Initial evaluation using propranolol and dansylated amino acids. J Chromatogr A 680: 147-155, 1994.
22. IE Valko, HA Billiet, J Frank KCHAM Luyben. Factors affecting the separation of mandelic acid enantiomers by capillary electrophoresis. Chromatographia 38: 730-736, 1994.
23. MM Rogan, KD Altria, DM Goodall. Enantiomeric separation of salbutamol and related impurities using capillary electrophoresis. Electrophoresis 15: 808-817, 1994.
24. SAC Wren, RC Rowe, RS Payne. A theoretical approach to chiral capillary electrophoresis with some practical implications. Electrophoresis 15: 774-778, 1994.
25. CL Cooper, JB Davis, RO Cole, M Sepaniak. Separations of derivatized amino acid enantiomers by cyclodextrin-modified cypillary electrophoresis. Mechanistic and molecular modeling studies. Electrophoresis 15: 785-792, 1994.
26. CL Cooper, JB Davis, MJ Sepaniak. Mechanisms of enantiomeric resolution in cyclodextrin-modified capillary electrophoretic separations of binaphthyl compounds. Chirality 7: 401-408, 1995.
27. P Baumy, P Morin, M Dreux, MC Viaud, S Boye, G Guillaumet. Determination of β-cyclodextrin inclusion complex constants for 3,4-dihydro-2-H-1-benzopyran enantiomers by capillary electrophoresis. J Chromatogr A 707: 311-326, 1995.
28. KH Gahm, AM Stalcup. Capillary zone electrophoresis study of napthylethylcarbamoylated β-cyclodextrins. Anal Chem 67: 19-35, 1995.
29. CE Sänger-van de Griend, K Groningsson, D Westerlund. Chiral separation of local anaesthetics with capillary electrophoresis. Evaluation of the inclusion complex of the enantiomers with heptakis(2,6-di-O-methyl)-β-cyclodextrin. Chromatographia 42: 263-268, 1996.
30. EC Rickard, R Bopp, DJ Skanchy, KL Chetwin, B Pahlen, JF Stobaugh. Role of capillary electrophoresis methods in the drug development process. Chirality 8: 108-121, 1996.
31. F Lelievre, P Gareil. Chiral separations of underivatized arylpropionic acids by capillary electrophoresis with various cyclodextrins. Acidity and inclusion constants determinations. J Chromatogr A 735: 311-320, 1996.
32. YY Rawjee, DU Staerk, G Vigh. Capillary electrophoretic chiral separations with cyclodextrin additives. 1. Acids-chiral selectivity as a function of pH and the concentration of β-cyclodextrin for fenoprofen and ibuprofen. J Chromatogr 635: 291-306, 1993.
33. YY Rawjee, RL Williams, G Vigh. Capillary electrophoretic chiral separations using β-cyclodextrin as resolving agent. 2. Bases-chiral selectivity as a function of pH and the concentration of β-cyclodextrin. J Chromatogr A 652: 233-244, 1993.
34. YY Rawjee, RL Williams, G Vigh. Capillary electrophoretic chiral separations using cyclodextrin additives. 3. Peak resolution surfaces for ibuprofen and homatropine as a function of the pH and the concentration of β-cyclodextrin. J Chromatogr A 680: 599-607, 1994.
35. YY Rawjee, RL Williams, LA Buckingham, G Vigh. Effect of pH and hydroxylpropyl β-cyclodextrin concentration on peak resolution in the capillary electrophoretic separation of the enantiomers of weak bases. J Chromatogr A 688: 273-282, 1994.
36. YY Rawjee, G Vigh. A peak resolution model for the capillary electrophoretic separation of the enantiomers of weak acids with hydroxypropyl β-cyclodextrin- containing background electrolytes. Anal Chem 66: 619-627, 1994.
37. R Vespalec, S Fanali, P Bocek. Consequences of a maximum existing in the dependence of separation selectivity on concentration of cyclodextrin added as chiral selector in capillary zone electrophoresis. Electrophoresis 15: 1523-1525, 1994.
38. JJ Li, K Waldron. Estimation of the pH-independent binding constants of alanylphenylalanine and leucylphenylalanine stereoisomers with β-cyclodextrin in the presence of urea. Electrophoresis 20: 171-179, 1999.
39. S Sabah, GKE Scriba. pH-Dependent reversal of the chiral recognition of tripeptide enantiomers by carboxymethyl-β-cyclodextrin. J Chromatogr A 833: 261-266, 1999.
40. R Vespalec, P Bocek. Calculation of constants for the chiral selector-enantiorner interactions from electrophoretic mobilities. J Chromatogr A 875: 431-445, 2000.
41. S Sabah, GKE Scriba. Influence of the structure of cyclodextrins and amino acid sequence of dipeptides and tripeptides on the pH-dependent reversal of the migration order in capillary electrophoresis. J Chromatogr A 894: 267-272, 2000.
42. MT Bowser, DDY Chen. Higher-order equilibria and their effect on analyte migration behavior in capillary electrophoresis. Anal Chem 70: 3261-3270, 1998.
43. MT Bowser, DDY Chen. Monte Carlo simulation of error propagation in the detennination of binding constants from rectangular hyperbolae. 1. Ligand concentration range and binding constants. J. Phys Chem 102: 8063-8071, 1998.
44. MT Bowser, DDY Chen. Monte Carlo simulation of error propagation in the determination of binding constants from rectangular hyperbolae. 2. Effect of the maximum response range. J Phys Chem 103: 197-202, 1999.
45. T Ohara, A Shibukawa, T Nakagawa. Capillary electrophoresis frontal analysis for microanalysis of enantioselective protein binding of a basic drug. Anal Chem 67: 3520-3525, 1995.
46. A Shibukawa, Y Kuroda, T Nakagawa. High-performance frontal analysis for drug-protein binding study. J Pharm Biomed Anal 18: 1047-1055, 1999.
47. NAL Mohamed, Y Kuroda, A Shibukawa, T Nakagawa, ST Elo Gizawy, HF Askal, ME El Kommos. Binding analysis of nilvadipine to plama lipoproteins by capillary electrophoresis-frontal analysis. J Pharm Biomed Anal 21: 1037-1043, 1999.
48. 1 -acid glycoproten in enantioselective binding to basic drugs as studied by capillary electrophoresis. Anal Biochem 268: 9-14, 1999.
49. NAL Mohamed, Y Kuroda, A Shibukawa, T Nakagawa, ST Elo Gizawy, HF Askal, ME EI Kommos. Enantioselective binding analysis of verapamil to plasma lipoproteins by capillary electrophoresis-frontal analysis. J Chromatogr A 875: 447-453, 2000.
50. 1 -acid glycoprotein using highperformance frontal analysis. Anal Biochem 274: 27-33, 1999.
51. 1 -acid glycoprotein in enantioselective binding of basic drugs as studied by high-performance frontal analysis/capillary electrophoresis. Pharm Res 18: 389-393, 2001.
52. J Oravcova, D Sojkova, W Lindner. Comparison of the Humel-Dreyer method in high-performance liquid chromatography and capillary electrophoresis conditions for study of the interactions of (RS)- (R)- and (S)-carvedilol with isolated plasma proteins. J Chromatogr B 682: 349-357, 1996.
53. MHA Busch, LB Carels, HFM Boelens, JC Kraak, H Poppe. Comparison of five methods for the study of drug-protein binding in affinity capillary electrophoresis. J Chromatogr A 777: 311-328, 1997.
54. J Oravcova, B Bohs, W Lindner. Drug-protein binding studies-New trends in analytical and experimental methodology. J Chromatogr B 677: 1-28, 1996.
55. NHH Heegaard. A heparin-binding peptide from human serum amiloid P component characterized by affinity capillary electrophoresis. Electrophoresis 19: 442-447, 1998.
56. A Amini, U Paulsen-Sorman, D Westerlund. Principle and applications of the partial filling techniques in capillary electrophoresis. Chromatographia 50: 497-506, 1999.
57. A Amini, U Paulsen-Sorman, D Westerlund. Dependence of chiral separations on the amount of cyclodextrins as selectors, employing the partial-filling technique in capillary zone electrophoresis. Chromatographia 51: 226-230, 2000.
58. 1 -acid glycopotein by applying a partial-filling technique in affinity capillary electrophoresis. Anal Chem 70: 1425-1430, 1998.
59. A Amini, N Merclin, S Bastami, D Westerlund. Determination of association constants between enantiomers of orciprenaline and methyl-β-cyclodextrin as chiral selector by capillary zone electrophoresis using a partial filling technique. Electrophoresis 20: 180-188, 1999.
60. SAC Wren, RC Rowe. Theoretical aspects of chiral separation in capillary electrophoresis. I. Initial evaluation of a model. J Chromatogr 603: 235-241, 1992.
61. T Schmitt, H Engelhardt. Derivatized cyclodextrins for the separation of enantiomers in capillary electrophoresis. HRC-J High Resol Chromatogr 16: 525-529, 1993.
62. B Chankvetadze, G Endresz, G Blaschke. Charged cyclodextrin derivatives as chiral selecots in capillary electrophoresis. Chem Soc Rev 25: 141-153, 1996.
63. B Chankvetadze, G Blaschke. Selector-selectand interactions in chiral capillary electrophoresis. Electrophoresis 20: 2592-2604, 1999.
64. B Chankvetadze, M Fillet, N Bmjanadze, D Bergenthal, C Bergander, H Luftmann, J Crommen, G Blaschke. Enantioseparation of aminoglutethimide with cyclodextrins in capillary electrophoresis and studies of selector-selectand interactions using NMR spectroscopy and electrospray ionization mass spectrometry. Enantiomer 5: 313-322, 2000.
65. B Chankvetadze, K Lomsadze, D Bergenthal, J Breitkreutz, K Bergander, G Blaschke. Mechanistic study on the opposite migration order of clenbuterol enantiomers in capillary electrophoresis with β-cyclodextrin and single-isomer heptakis(2,3-diacetyl-6-sulfo-)-β-cyclodextrin. Electrophoresis 22: 3178-3184.
66. HJ Schneider, F Hacket, V Riidiger. NMR studies of cyclodextrins and cyclodextrin complexes. Chem Rev 98: 1755-1785, 1998.
67. G Galaverna, R Corradini, A Dossena, R Marcelli. Histamane-modified cationic β-cyclodextrin as chiral selector for the enantiomeric separation of hydroxy acids and carboxylic acids by capillary electrophoresis. Electrophoresis 20: 2619-2629, 1999.
68. U Holzgrabe, H Mallwitz, SK Branch, TM Jefferies, M Wiese. Chiral discrimination by NMR spectroscopy of ephedrine and N-methylephedrine induced by β-cyclodextrin, heptakis(2,3-di-O-acetyl)-β-cyclodextrin and heptakis-(6-O-acetyl)-β-cyclodextrin. Chirality 9: 211-219, 1997.
69. B Chankvetadze, G Pintore, N Burjanadze, D Bergenthal, K Bergander, J Breitkreutz, C Miihlenbrock, G Blaschke. Mechanistic study of opposite migration order of dimethindene enantiomers in capillary electrophoresis in the presence of native β-CD and heptakis-(2,3,6-tri-O-methyl)-β-CD. J Chromatogr A 875: 455-469, 2000.
70. B Chankvetadze, N Burjanadze, G Pintore, D Bergenthal, K Bergander, J Breitkreutz, C Miihlenbrock, G Blaschke. Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV-spectrometry, ESI-MS and Xray crystallography. J Chromatogr A 875: 471-484, 2000.
71. PK Owens, AF Fell, MW Coleman, M Kinns, JC Berridge. Use of H’-NMR spectroscopy to determine the enantioselective mechanism of neutral and anionic cyclodextrins in capillary electrophoresis. J Pharm Biomed Anal 15: 1603-1619, 1997.
72. G Galaverna, MC Paganuzzi, R Corradini, A Dossena, R Marcelli. Enantiomeric separation of hydroxy acids and carboxylic acids by diamino-β-cyclodextrin (AB, AC, AD) in capillary electrophoresis. Electrophoresis 22: 3171-3177,2001.
73. P Cescutti, D Carozzo, R Rizzo. Study of the inclusion complexes of aromatic molecules with cyclodextrins using ionspray mass spectrometry. Carbohydr Res 290: 105-115, 1996.
74. A Hyble, RE Rundle, DE Williams. The crystal and molecular structure of the cyclohexaamylose-potassium acetate complex. J Am Chem Soc 87: 2779-2788, 1965.
75. W Saenger, J Jacob, K Gessler, T Steiner, D Hoffmenn, H Sanabe, K Koizumi, SM Smith, T Takaha. Structure of the common cyclodextrins and their larged analogues-beyond the doughnut. Chem Rev 98: 1787-1802, 1998.
76. K Harata. Structural aspects of stereodifferentiation in the solid state. Chem Rev 98: 1803-1827, 1998.
77. KB Lipkowitz. Atomistic modeling of enantioselection in chromatography. J Chromatogr A 906: 417-442,2001.
78. KB Lipkowitz. Atomistic modeling of enantioselective binding. Acc Chem Res 33: 555-562, 2000.
79. K Kano, Y Tamiya, C Otsuki, T Shimomura, T Ohno, O Hayashida, Y Murakami. Chiral recognition by cyclic oligosaccharides. Enantioselective complexation of binaphthyl derivatives with cyclodextrins. Supramol Chem 2: 137, 1993.
80. K Kano, K Minami, K Horiguchi, T Ishihana, M Kodera. Ability of noncyclic oligosccharides to fonn molecular complexes and its use for chiral separation by capillary zone electrophoresis. J Chromatogr A 694: 307-313, 1995.