Chiral recognition in liquid chromatography utilising chargeable cyclodextrins for resolution of doxazosin enantiomers

Chirality

Volumn 9, Issue 2, 1997, Pages 184-190

  Owens, Paul K ^a   Fell, Anthony F ^a   Coleman, Michael W ^b   Berridge, John C ^b  

^a UNIVERSITY OF BRADFORD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

carboxymethyl cyclodextrin; central composite design; chiral; doxazosin; experimental design; liquid chromatography; mobile phase additive; optimisation; rac doxazosin

Indexed keywords

CYCLODEXTRIN DERIVATIVE; DOXAZOSIN; SODIUM DIHYDROGEN PHOSPHATE;

CAPILLARY ELECTROPHORESIS; CHIRALITY; COMPLEX FORMATION; CONFERENCE PAPER; ENANTIOMER; HYDROGEN BOND; LIQUID CHROMATOGRAPHY; MICELLAR ELECTROKINETIC CHROMATOGRAPHY; MOLECULAR RECOGNITION; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0030998550     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:2<184::AID-CHIR20>3.0.CO;2-I     Document Type: Conference Paper

References (24)

1. Kristulovic, A.M. Chiral Separations by HPLC, Applications to Pharmaceutical Compounds, Cyclodextrin Additives Ellis Horwood Limited. Chichester: Wiley, 1989:147-172.
2. Armstrong, D.W., Yang, X., Han, S.M., Menges, R.A. Direct liquid chromatographic separation of racemates with an α-cyclodextrin bonded phase. Anal. Chem. 59:2594-2596, 1988.
3. Armstrong, D.W., Demond, W. Cyclodextrin bonded phases for the liquid-chromatographic separation of optical, geometrical and structural isomers. J. Chromatogr. Sci. 22(9):411-415, 1984.
4. Furata, R., Nakazawa, H. Optical resolution mechanisms of uniconazole and structurally related compounds on cyclodextrin-bonded columns. Chromatographia 35(9-12):555-559, 1993.
5. Debowski, J., Sybilska, D., Jurczak, J. β-cyclodextrin as a chiral component of the mobile phase for separation of mandelic acid into enantiomers in reversed-phase systems of high-performance liquid chromatography. J. Chromatogr. 237:303-306, 1982.
6. Debowski, J., Sybilska, D., Jurczak, J. Resolution of some chiral mandelic acid derivatives into enantiomers by reversed-phase liquid chromatography via α- and β-cyclodextrin inclusion complexes. J. Chromatogr. 282:83-88, 1983.
7. Fanali, S. Use of cyclodextrins in capillary zone electrophoresis. Resolution of terbutaline and propranolol enantiomers. J. Chromatogr. 545: 437-444, 1991.
8. Stalcup, A.M., Chang, S.C., Armstrong, D.W., Pitha, J. (S)-2-hydroxypropyl-β-cyclodextrin, a new chiral stationary phase for reversed-phase liquid-chromatography. J. Chromatogr. 513:181-194, 1990.
9. Penn, S.G., Goodall, D.M., Loran, J.S. Differential binding of tioconazole enantiomers to hydroxypropyl-β-cyclodextrin studied by capillary electrophoresis. J. Chromatogr. 636(1):149-152, 1993.
10. Tait, R.J., Skanchy, D.J., Thompson, D.P., Chetwyn, N.C., Dunshee, D.A., Rajewski, R.A., Stella, V.J., Stobaugh, J.F. Characterization of sulphoalkyl ether derivatives of β-cyclodextrin by capillary electrophoresis with indirect UV detection. J. Pharm. Biomed. Anal. 10:615-622, 1992.
11. Owens, P.K., Fell, A.F., Coleman, M.W., Berridge, J.C. Method development in liquid chromatography with a charged cyclodextrin additive for chiral resolution utilising a central composite design. Chirality 8:466-476, 1996.
12. Dette, C., Ebel, S., Terabe, S. Neutral and anionic cyclodextrins in capillary zone electrophoresis: Enantiomeric separation of ephedrine and related compounds. Electrophoresis 15:799-803, 1994.
13. Terabe, S., Ozaki, H., Otsuka, K., Ando, T. Electrokinetic chromatography with 2-O-carboxymethyl-β-cyclodextrin as a moving stationary phase. J. Chromatogr. 332:211-217, 1985.
14. Roussel, C., Favrou, A. Cationic β-cyclodextrin: A new versatile chiral additive for separation of drug enantiomers by high-performance liquid chromatography. J. Chromatogr. A, 704:67-74, 1995.
15. Crommen, J., Fillet, M., Bechet, I., Hubert, P. Resolution improvement by use of carboxymethyl-β-cyclodextrin as chiral additive for the enantiomeric separation of basic drugs by capillary electrophoresis. J. Pharm. Biomed. Anal. 14(8-10):1107-1114, 1996.
16. Zukowski, J., Sybilska, D., Bojarski, J. Application of α- and β-cyclodextrin and heptakis(2,6-di-o-methyl)-β-cyclodextrin as mobile phase components for the separation of some chiral barbiturates into enantiomers by reversed-phase high-performance liquid chromatography. J. Chromatogr. 225-232, 1986.
17. Zukowski, J., Sybilska, D., Bojarski, J. Resolution of mephenytoin and some chiral barbiturates into enantiomers by reversed phase high performance liquid chromatography via beta-cyclodextrin inclusion complexes. J. Liq. Chrom. 9(2,3) 364:591-606, 1986.
18. Berridge, J.C. Techniques for the Automated Optimisation of HPLC Separations: The Solvent Selectivity Triangle and Mixture Designs. Chichester: Wiley, 1985:70-84.
19. Box, G.E.P., Wilson, K.B. On the experimental attainment of optimum conditions. J. R. Stat. Soc. B 13:1-45, 1951.
20. Kaiser, R.E. Gas Chromatographie. Leipzig: Geest and Portig, 1960.
21. Hinze, W.L., Riehl, T.E., Armstrong, D.W., Demond, W., Alak, A., Ward, T. Chromatographic separation of enantiomers using a chiral β-cyclodextrin-bonded phase and conventional aqueous organic mobile phases. Anal. Chem. 57(1):237-242, 1985.
22. Zarzycki, P.K., Wierzbowska, M., Lamparczyk, H. The influence of temperature on the high-performance liquid-chromatographic separation of steroids using mobile phases modified with β-cyclodextrin. J. Pharm. Biomed. Anal. 14(8-10):1305-1311, 1996.
23. Crommen, J., Fillet, M., Bechet, I., Hubert, P. Chiral separations of drugs by capillary electrophoresis using neutral and charged cyclodextrin derivatives. Seventh International Symposium on Pharmaceutical and Biomedical Analysis, Osaka, Japan, 1996.
24. Owens, P.K., Fell, A.F., Coleman, M.W., Kinns, M., Berridge, J.C. NMR for studies on the enantioselective mechanism for charged cyclodextrins in capillary electrophoresis. Seventh International Symposium on Pharmaceutical and Biomedical Analysis, Osaka, Japan, 1996.