Comparison of chiral electrophoretic separation methods for phenethylamines and application on impurity analysis

Journal of Pharmaceutical and Biomedical Analysis

Volumn 53, Issue 5, 2010, Pages 1201-1209

  Borst, Claudia ^a   Holzgrabe, Ulrike ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Enantioseparation; Ephedrine derivatives; Impurity analysis; Microemulsion electrokinetic chromatography; Sulfated cyclodextrin

Indexed keywords

2 (DIBUTYLAMINO) 1 PHENYL 1 PROPANOL; 2 PROPANOL; ACETIC ACID ETHYL ESTER; ADRENALIN; BETA CYCLODEXTRIN; BUTANOL; DIETHYLNOREPHEDRINE; DIPIVEFRINE; DODECYL SULFATE SODIUM; EPHEDRINE; HEPTAKIS(2,3 DI O DIACETYL 6 O SULFO)BETA CYCLODEXTRIN; METHYLEPHEDRINE; NORADRENALIN; NOREPHEDRINE; PHENETHYLAMINE DERIVATIVE; PHENYLETHANOLAMINE; PHOSPHATE; PSEUDOEPHEDRINE; UNCLASSIFIED DRUG; WATER OIL CREAM;

ARTICLE; CONTROLLED STUDY; DRUG IMPURITY; ENANTIOMER; MICROEMULSION ELECTROKINETIC CHROMATOGRAPHY; PH; PRIORITY JOURNAL;

CHEMISTRY, PHARMACEUTICAL; DRUG CONTAMINATION; ELECTROPHORESIS, CAPILLARY; PHENETHYLAMINES; STEREOISOMERISM;

EID: 77955925513     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2010.06.025     Document Type: Article

References (39)

1. Mutschler E., Geisslinger G., Kroemer H.K., Ruth P., Schäfer-Korting M. Lehrbuch der Pharmakologie 2008, Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart. 9th edition.
2. Aktories K., Förstermann U., Hofmann F., Starke K. Allgemeine und spezielle Pharmakologie und Toxikologie 2005, Elsevier GmbH, München. 9th edition.
3. Ammon H.P.T., Hunnius C. Hunnius - Pharmazeutisches Wörterbuch 2004, de Gruyter, Berlin/New York. 9th edition.
4. Liu Y.-M., Sheu S.-J. Determination of ephedrine alkaloids by capillary electrophoresis. J. Chromatogr. A 1992, 600:370-372.
5. Okamura N., Miki H., Harada T., Yamashita S., Masaoka Y., Nakamoto Y., Tsuguma M., Yoshitomi H., Yagi A. Simultaneous determination of ephedrine, pseudoephedrine, norephedrine and methylephedrine in kampo medicines by high-performance liquid chromatography. J. Pharm. Biol. Anal. 1999, 20:363-372.
6. Sagara K., Oshima T., Misaki T. A simultaneous determination of norephedrine, pseudoephedrine, ephedrine and methylephedrine in ephedrae herba and oriental pharmaceutical preparations by ion-pair high-performance liquid chromatography. Chem. Pharm. Bull. 1983, 31:2359-2365.
7. Kroemer H.K., Fromm M.F., Eichelbaum M. Stereoselectivity in drug metabolism and action: effects of enzyme inhibition and induction. Therap. Drug Monitor. 1996, 18:388-392.
8. Campo V.L., Bernardes L.S.C., Carvalho I. Stereoselectivity in drug metabolism; molecular mechanisms and analytical methods. Curr. Drug Metalbol. 2009, 10:188-205.
9. Fanali S. Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors. J. Chromatogr. A 2000, 875:89-122.
10. Fanali S. Chiral separations by CE employing CDs. Electrophoresis 2009, 30:S203-210.
11. Watarai H. Microemulsion capillary electrophoresis. Chem. Lett. 1991, 20:391-394.
12. Suntornsuk L. Capillary electrophoresis in pharmaceutical analysis: a survey on recent applications. J. Chromatogr. Sci. 2007, 45:559-577.
13. Huie C.W. Recent applications of microemulsion electrokinetic chromatography. Electrophoresis 2006, 27:60-75.
14. McEvoy E., Marsh A., Altria K., Donegan S., Power J. Recent advances in the development and application of microemulsion EKC. Electrophoresis 2007, 28:193-207.
15. Altria K.D. Background theory and applications of microemulsion electrokinetic chromatography. J. Chromatogr. A 2000, 892:171-186.
16. Miola M.F., Snowden M.J., Altria K.D. The use of microemulsion electrokinetic chromatography in pharmaceutical analysis. J. Pharm. Biomed. Anal. 1998, 18:785-797.
17. Schmitt U., Branch S.K., Holzgrabe U. Chiral separations by cyclodextrin-modified capillary electrophoresis-determination of the enantiomeric excess. J. Sep. Sci. 2002, 25:959-974.
18. Wedig M., Holzgrabe U. Enantioseparation of tropa alkaloids by means of anionic cyclodextrin-modified capillary electrophoresis. Electrophoresis 1999, 20:1555-1560.
19. Mertzman M.D., Foley J.P. Chiral cyclodextrin-modified microemulsion electrokinetic chromatography. Electrophoresis 2004, 25:1188-1200.
20. Zhao H., Xiang X., He J. Enantiomeric separation of cypermethrin with microemulsion electrokinetic chromatography. Chem. J. Internet 2005, 7.
21. Gübitz G., Schmid M.G. Recent advances in chiral separation principles in capillary electrophoresis and capillary electrochromatography. Electrophoresis 2004, 25:3981-3996.
22. Amini A. Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis. Electrophoresis 2001, 22:3107-3313.
23. Chankvetadze B. Chiral compounds: separation by CE and MEKC with cyclodextrins. Encyclopedia Chromatogr. (3rd edition) 2010, 1:419-424.
24. Hammitzsch-Wiedemann M., Scriba G.K.E. Effect of urea on analyte complexation by 2,6-dimethyl-β-CD in peptide enantioseparations by CE. Electrophoresis 2009, 30:3764-3771.
25. Van Eeckhaut A., Michotte Y. Chromatographic Sciences Series, vol. 100, Chiral Separations by Capillary Electrophoresis 2010, CRC Press, Taylor & Francis Group, Boca Raton.
26. Threeprom J. (S)-(+)-2-Octanol as a chiral oil core for the microemulsion electrokinetic chromatographic separation of chiral basic drugs. Anal. Sci. 2007, 23:1071-1075.
27. Threeprom J. Separation of enantiomeric basic drugs by microemulsion electrokinetic chromatography with chiral 2-octanol as the oil core. Chromatographia 2007, 65:569-573.
28. Kahle K.A., Foley J.P. Two-chiral component microemulsion EKC - chiral surfactant and chiral oil. Part 2. Diethyl tartrate. Electrophoresis 2007, 28:2644-2657.
29. Kahle K.A., Foley J.P. Two-chiral-component microemulsion electrokinetic chromatography-chiral surfactant and chiral oil. Part 1. Dibutyl tartrate. Electrophoresis 2007, 28:1723-1734.
30. Kahle K.A., Foley J.P. Chiral microemulsion electrokinetic chromatography with two chiral components: Improved separations via synergies between a chiral surfactant and a chiral cosurfactant. Electrophoresis 2006, 27:896-904.
31. Mertzman M.D., Foley J.P. Effect of surfactant concentration and buffer selection on chromatographic figures of merit in chiral microemulsion electrokinetic chromatography. Electrophoresis 2004, 25:3247-3256.
32. Zhen Z.-X., Lin J.-M., Chan W.-H., Lee A.W.M., Huie C. Separation of enantiomers in microemulsion electrokinetic chromatography using chiral alcohols as cosurfactants. Electrophoresis 2004, 25:3263-3269.
33. Bao Y., Yue D., Cá N.D., Larock R.C., Armstrong D.W. Enantiomeric separation of isochromene derivatives by cyclodextrin-modified micellar capillary electrophoresis. J. Liq. Chromatogr. Relat. Technol. 2008, 31:2035-2052.
34. Borst C., Holzgrabe U. Enantioseparation of dopa and related compounds by cyclodextrin-modified microemulsion electrokinetic chromatography. J. Chromatogr. A 2008, 1204:191-196.
35. Bitar Y., Holzgrabe U. Enantioseparation of chiral tropa alkaloids by means of cyclodextrin-modified microemulsion electrokinetic chromatography. Electrophoresis 2007, 28:2693-2700.
36. Wedig M., Holzgrabe U. Resolution of ephedrine derivatives by means of neutral and sulfated heptakis(2,3-di-O-acetyl)-β-cyclodextrins using capillary electrophoresis and nuclear magnetic resonance spectroscopy. Electrophoresis 1999, 20:2698-2704.
37. Wedig M., Laug S., Christians T., Thunhorst M., Holzgrabe U. Do we know the mechanism of chiral recognition between cyclodextrins and analytes?. J. Pharm. Biomed. Anal. 2002, 27:531-540.
38. Liu L.-B., Zheng Z.-X., Lin J.-M. Application of dimethyl-β-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of ephedrine and related compounds in some drugs. Biomed. Chromatogr. 2005, 19:447-453.
39. Deeb S.E., Hasemann P., Wätzig H. Strategies in method development to quantify enantiomeric impurities using CE. Electrophoresis 2008, 29:3552-3562.