Chiral separation of fluoxetine and its analogs with charged cyclodextrins by capillary electrophoresis

Journal of Liquid Chromatography and Related Technologies

Volumn 26, Issue 14, 2003, Pages 2351-2367

  Inoue, Takayo ^a,b   Chang, Jen P ^a  

^a ELANCO ANIMAL HEALTH   (United States)

^b Synta Pharmaceuticals Corp   (United States)

Author keywords

Capillary electrophoresis; Chiral separation; Cyclodextrins; Fluoxetine

Indexed keywords

ELECTROPHORESIS; IMPURITIES; SEPARATION;

CHIRAL SEPARATION;

CAPILLARITY;

AMINE; CARBOXYL GROUP; CYCLODEXTRIN; FLUOXETINE; LY 270513; LY 280494; LY 507311; NORFLUOXETINE; UNCLASSIFIED DRUG;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHIRALITY; CONCENTRATION RESPONSE; DRUG ANALYSIS; DRUG BINDING; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; STRUCTURE ANALYSIS;

EID: 0042934072     PISSN: 10826076     EISSN: None     Source Type: Journal    
DOI: 10.1081/JLC-120023251     Document Type: Article

References (30)

1. De Camp, W.H. The FDA perspective on the development of stereoisomers. Chirality 1989, 1, 2-6.
2. Wong, D.T.; Bymaster, F.P.; Horng, J.S.; Molloy, B.B. New selective inhibitor for uptake of serotonin into synaptosomes of rat brain. 3-(p-trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine. J. Pharmacol. Exp. Ther. 1975, 193 (3), 804-811.
3. Lemberger, L.; Rowe, H.; Crimichael, R. Pharmacologic effects in man of a specific serotonin-reuptake inhibitor. Science 1978, 199 (4327), 436-437.
4. Lemberger, L.; Rowe, H.; Crimichael, R.; Crabtree, R.; Horng, J.S.; Bymaster, F.; Wong, D. Fluoxetine, a selective serotonin uptake inhibitor. Clin. Pharmacol. Ther. 1978, 23 (4), 421-429.
5. Freeman, C.P.L.; Hampson, M. Fluoxetine as a treatment for bulimia nervosa. Int. J. Obesity 1987, 3, 171-177.
6. Jenike, M.A.; Buttolph, L.; Baer, L.; Ricciardi, J.; Holland, A. Open trial of fluoxetine in obsessive-compulsive disorder. Am. J. Psychiatry 1989, 146 (7), 909-911.
7. Wong, D.T.; Fuller, R.W.; Robertson, D.W. Fluoxetine and its two enantiomers as selective serotonin uptake inhibitors. Acta Pharm. Nord. 1990, 2 (3), 171-180.
8. Fuller, R.W.; Wong, D.T.; Robertson, D.W. Fluoxetine, a selective inhibitor of serotonin uptake. Med. Res. Rev. 1991, 11 (1), 17-34.
9. Soini, H.; Stefansson, M.; Riekkola, M.L.; Novotny, M.V. Maltooligosaccharides as chiral selectors for the separation of pharmaceuticals by capillary electrophoresis. Anal. Chem. 1994, 66 (20), 3477-3484.
10. Gotti, R.; Pomponio, R.; Cavrini, V. Linear, neutral polysaccharides as chiral selectors in enantioresolution of basic drug racemates by capillary electrophoresis. Chromatographia 2000, 52 (5-6), 273-277.
11. Desiderio, C.; Rudaz, S.; Raggi, M.A.; Fanali, S. Enantiomeric separation of fluoxetine and norfluoxetine in plasma and serum samples with high detection sensitivity capillary electrophoresis. Electrophoresis 1999, 20 (17), 3432-3438.
12. D'Hulst, A.; Verbeke, N. Chiral analysis of basic drugs by oligosaccharide-mediated capillary electrophoresis. J. Chromatogr. A 1996, 735 (1-2), 283-293.
13. Piperaki, S.; Penn, S.G.; Goodall, D.M. Systematic approach to treatment of enantiomeric separations in capillary electrophoresis and liquid chromatography II. A study of the enantiomeric separation of fluoxetine and norfluoxetine. J. Chromatogr. A 1995, 700 (1-2), 59-67.
14. Soini, H.; Riekkola, M.L.; Novotny, M.V. Chiral separations of basic drugs and quantitation of bupivacaine enantiomers in serum by capillary electrophoresis with modified cyclodextrin buffers. J. Chromatogr. 1992, 608 (1-2), 265-274.
15. Christians, T.; Holzgrabe, U. New single-isomer chiral selector for capillary electrophoresis: the highly water-soluble heptakis (2-N, N-dimethylcarbamoyl)-β-cyclodextrin. J. Chromatog. A 2001, 911 (2), 249-257.
16. Hongwei, Y.; Ching, C.B.; Ping, F.; Ng, S.C. Liquid chromatographic retention behavior and enantioseparation of fluoxetine on a new β-cyclodextrin bonded-phase column. Do, Duong D., Ed.; World Scientific Publishing Co. Pte. Ltd.: Singapore, Adsorpt. Sci. Technol., Proc. Pac. Basin Conf. 2nd 2000, 144-148.
17. Olsen, B.A.; Wirth, D.D.; Larew, J.S. Determination of fluoxetine hydrochloride enantiomeric excess using high-performance liquid chromatography with chiral stationary phases. J. Pharm. Biomed. Anal. 1998, 17 (4-5), 623-630.
18. Piperaki, S.; Parissi-Poulou, M. Use of cyclodextrins as chiral selectors for direct resolution of the enantiomers of fluoxetine and its metabolite norfluoxetine by HPLC. Chirality 1993, 5 (4), 258-266.
19. Chankvetadze, B. Native and derivatized cyclodextrins as chiral selectors in capillary electrophoresis. In Capillary Electrophoresis in Chiral Analysis; John Wiley & Sons: Chichester, UK, 1997; 141-228.
20. Terabe, S. Electrokinetic chromatography: an interface between electrophoresis and chromatography. Trends Anal. Chem. 1989, 8 (4), 129.
21. Fanali, S. Separation of optical isomers by capillary zone electrophoresis based on host-guest complexation with cyclodextrins. J. Chromatogr. 1989, 474 (2), 441-446.
22. Chankvetadze, B.; Endresz, G.; Blaschke, G. About some aspects of the use of charged cyclodextrins for capillary electrophoresis enantioseparation. Electrophoresis 1994, 15, 804-807.
23. 13C NMR study of the chiral recognition mechanism. J. Chromatogr. A 1995, 717 (1-2), 245-253.
24. Tait, R.J.; Thompson, D.O.; Stobaugh, J.F. Sulfobutyl ether β-cyclodextrin as a chiral discriminator for use with capillary electrophoresis. Anal. Chem. 1994, 66 (22), 4013-4018.
25. Vincent, J.B.; Sokolowski, A.D.; Nguyen, T.V.; Vigh, G. A family of single-isomer chiral resolving agents for capillary electrophoresis. 1. Heptakis(2,3-diacetyl-6-sulfato)-β-cyclodextrin. Anal. Chem. 1997, 69 (20), 4226-4233.
26. Vincent, J.B.; Kirby, D.M.; Nguyen, T.V.; Vigh, G. A family of single-isomer chiral resolving agents for capillary electrophoresis. 2. Hepta-6-sulfato-β-cyclodextrin. Anal. Chem. 1997, 69 (21), 4419-4428.
27. Cai, H.; Nguyen, T.V.; Vigh, G. A family of single-isomer chiral resolving agents for capillary electrophoresis. 3. Heptakis(2,3-dimethyl-6-sulfato)-β-cyclodextrin. Anal. Chem. 1998, 70 (3), 580-589.
28. Zhou, L.; Johnson, B.D.; Miller, C.; Wyvratt, J.M. Chiral capillary electrophoretic analysis of the enantiomeric purity of a pharmaceutical compound using sulfated β-cyclodextrin. J. Chromatogr. A 2000, 875 (1-2), 389-401.
29. Cladrowa-Runge, S.; Hirz, R.; Kenndler, E.; Rizzi, A. Enantiomeric separation of amphetamine related drugs by capillary zone electrophoresis using native and derivatized β-cyclodextrin as chiral additives. 1995, 710 (2), 339-345.
30. Wozniak, T.J.; Bopp, R.J.; Jensen, E.C. Chiral drugs: an industrial analytical perspective. J. Pharm. Biomed. Anal. 1991, 9 (5), 363-382.