Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Resolution of Tocainide and Its Analogues on Liquid Chromatographic Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

  • Hyun, Myung-Ho (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Min, Hye-Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Cho, Yoon-Jae (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
  • Published : 2003.07.20
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Abstract

Two liquid chromatographic chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid were successfully applied in the resolution of racemic tocainide and its analogues. In the resolution of tocainide, especially, the CSP containing N-CH₃ amide tethering groups was quite effective, showing clear baseline resolution (RS: 2.66) with reasonable enantioselectivity ( a: 1.25). Consequently, the CSP containing N-CH₃ amide tethering groups is expected to be useful to monitor the enantiomeric composition of tocainide in clinical samples. In addition, the chromatographic behaviors for the resolution of tocainide and its analogues on the two CSPs were found controllable by varying the content and the type of organic and acidic modifiers in aqueous mobile phase.

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References

  1. Roden, D. M.; Woosley, R. L. New Eng. J. Med. 1986, 315, 41. https://doi.org/10.1056/NEJM198607033150107
  2. Hoffmann, K.-J.; Renberg, L.; Gyllenhaal, O. Biopharm. DrugDispos. 1990, 11, 351. https://doi.org/10.1002/bdd.2510110404
  3. Antonsson, A.-M.; Gyllenhaal, O.; Kylberg-Hanssen, K.; Johansson,L.; Vessman, J. J. Chromatogr. Biomed. Appl. 1984, 308, 181. https://doi.org/10.1016/0378-4347(84)80207-8
  4. Jamali, F.; Mehvar, R.; Pasutto, F. M. J. Pharm. Sci. 1989, 78, 695. https://doi.org/10.1002/jps.2600780902
  5. Chiral Separations by Liquid Chromatography, ACS Symposium Series 471; Ahuja, S., Ed.; American Chemical Society: Washington, DC, 1991.
  6. A Practical Approach to Chiral Separations by Liquid Chromatography; Subramanian, G., Ed.; VCH: Weinheim, 1994.
  7. Beesley, T. E.; Scott, R. P. W. Chiral Chromatography;Wiley: Chichester, 1998.
  8. Ahuja, S. Chiral Separations byChromatography; American Chemical Society, Oxford UniversityPress: Oxford, 2000.
  9. Schill, G.; Wainer, I. W.; Barkan, S. A. J. Liq. Chromatogr. 1986,9, 641. https://doi.org/10.1080/01483918608076658
  10. Andersson, S.; Allenmark, S.; Moller, P.; Persson, B.; Sanchez, D.J. Chomatogr. A 1996, 741, 23. https://doi.org/10.1016/0021-9673(96)00153-7
  11. Hyun, M. H. J. Sep. Sci. 2003, 26, 242. https://doi.org/10.1002/jssc.200390030
  12. Aboul-Enein, H. Y.; Bakr, S. A.; Islam, M. R.; Rothchild, R. J.Liq. Chromatogr. 1991, 14, 3475. https://doi.org/10.1080/01483919108049404
  13. Hyun, M. H.; Jin, J. S.; Lee, W. J. Chromatogr. A 1998, 822, 155. https://doi.org/10.1016/S0021-9673(98)00606-2
  14. Hyun, M. H.; Jin, J. S.; Koo, H. J.; Lee, W. J. Chromatogr. A 1999,837, 75. https://doi.org/10.1016/S0021-9673(99)00100-4
  15. Hyun, M. H.; Han, S. C.; Jin, J. S.; Lee, W. Chromatographia2000, 52, 473. https://doi.org/10.1007/BF02535722
  16. Hyun, M. H.; Cho, Y. J.; Jin, J. S. J. Sep. Sci. 2002, 25, 648. https://doi.org/10.1002/1615-9314(20020701)25:10/11<648::AID-JSSC648>3.0.CO;2-D
  17. Aboul-Enein, H. Y.; Ali, I.; Hyun, M. H.; Cho, Y. J.; Jin, J. S. J.Biochem. Biophys. Methods 2002, 54, 407. https://doi.org/10.1016/S0165-022X(02)00142-2
  18. Hyun, M. H.; Cho, Y. J.; Kim, J. A.; Jin, J. S. J. Chromatogr. A2003, 984, 163. https://doi.org/10.1016/S0021-9673(02)01833-2
  19. Thompson, R. A.; Ge, Z.; Grinberg, N.; Ellison, D.; Tway, P. Anal.Chem. 1995, 67, 1580. https://doi.org/10.1021/ac00105a017

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