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Stereoselective HPLC assay of TJ0711 enantiomers by precolumn derivatization with GITC using UV detection and its application in pharmacokinetics in rats

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Summary

This investigation describes a new precise, sensitive and accurate stereoselective RP-HPLC method for determination of the enantiomers of a novel α- and β-receptor blocking agent, 1-[4-(2-methoxyethyl) phenoxy]-3-[[2-(2- methoxyphenoxy) ethyl]amino]-2-propanol (TJ0711), in rat plasma. GITC was used for precolumn derivatization of TJ0711 enantiomers. Enantiomeric resolution was achieved on a Eurospher-100 C18 column (250 mm×4.6 mm ID, 5-μm particle size), with UV detection at 255 nm, and the mobile phase consisted of acetonitrile and water (58:42, v/v) containing 0.02% glacial acetic acid (v/v). Using the chromatographic conditions described, TJ0711 enantiomers were well resolved with mean retention time of 10.2 and 11.5 min, respectively. Linear response (r>0.999) was observed over the range of 0.125–12.5 μg/mL of TJ0711 hydrochloride enantiomers. The mean relative standard deviation (RSD%) of the results of within-day precision was ⩽ 10%. The proposed method was found to be suitable and accurate for the quantitative determination of TJ0711 enantiomers in rat plasma, and it can be used in pharmacokinetic studies.

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References

  1. Caldwell J. The important of stereochemistry in drug action and disposition. J Clin Pharmacol, 1992,32(10):925–929

    PubMed  CAS  Google Scholar 

  2. Nation RL. Chirality in new drug development: Clinical pharmacokinetic considerations. Clin Pharmacokinet, 1994, 27(4):249–255

    Article  PubMed  CAS  Google Scholar 

  3. Eichelbaum M. Pharmacokinetic and pharmacodynamic consequences of stereoselective drug metabolism in man. Biochem Pharmacol, 1998,37(1):93–96

    Article  Google Scholar 

  4. Jamali F, Mehvar R, Pasutto FM. Enantioselective aspects of drug action and disposition:therapeutic pitfalls. J Pharm Sci, 1989,78(9):695–715

    Article  PubMed  CAS  Google Scholar 

  5. Caldwell J. ’Chiral pharmacology’ and the regulation of new drugs. Chem Ind, 1995(3):176–179

  6. Martens J, Bhushan R. Resolution of enantiomers with achiral phase chromatography. J Liq Chromatogr, 1992, 15(1):1–27

    Article  CAS  Google Scholar 

  7. Kim KH, Heo SY, Hong SP, et al. Enantiomeric purity test of bevantolol by reversed-phase high performance liquid chromatography after derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate. Arch Pharm Res, 2000,23(6):568–573

    Article  PubMed  CAS  Google Scholar 

  8. Kim KH, Kim DS, Hong SP, et al. Reversed-phase high performance liquid chromatographic separation of the enantiomers of terbutaline by derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate. Arch Pharm Res, 2000,23(1):26–30

    Article  PubMed  Google Scholar 

  9. Yang E, Wang S, Kratz J, et al. Stereoselective analysis of carvedilol in human plasma using HPLC/MS/MS after chiral derivatization. J Pharm Biomed Anal, 2004,36(3): 609–615

    Article  PubMed  CAS  Google Scholar 

  10. Tang YH, He Y, Yao TW, et al. Simultaneous determination of the enantiomers of esmolol and its acid metabolite in human plasma by reversed phase liquid chromatography with solid-phase extraction. J Chromatogr B, 2004, 805(2):249–254

    Article  CAS  Google Scholar 

  11. Hess S, Gustafson KR, Milanowski DJ, et al. Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography-electrospray ionization mass spectrometry. J Chromatogr A, 2004,1035(2): 211–219

    Article  PubMed  CAS  Google Scholar 

  12. Braghiroli D, Bella MD. Asymmetric syntheses of (R)-and (S)-2-aminobutanesulfonic acid and their 3, 3-dimethylderivatives. Tetrahedron: Asymmetry, 1996,7(7):2145–2150

    Article  CAS  Google Scholar 

  13. Zhou Q, Yao TW, Zeng S. Chiral reversed phase high-performance liquid chromatography for determining propranolol enantiomers in transgenic Chinese hamster CHL cell lines expressing human cytochrome P450. J Biochem Biophys Meth, 2002,54(1–3):369–376

    Article  PubMed  CAS  Google Scholar 

  14. Jin D, Kumar AP, Song GC, et al. Determination of thyroxine enantiomers in pharmaceutical formulation by high-performance liquid chromatography-mass spectrometry with precolumn derivatization. Microchem J, 2008,88(1):62–66

    Article  CAS  Google Scholar 

  15. Chernobrovkin MG, Shapovalova EN, Guranda DT, et al. Chiral high-performance liquid chromatography analysis of α-amino acid mixtures using a novel SH reagent—N-R-mandelyl-l-cysteine and traditional enantiomeric thiols for precolumn derivatization. J Chromatogr A, 2007,1175(1):89–95

    Article  PubMed  CAS  Google Scholar 

  16. Unceta N, Barrondo S, de Azúa IR, et al. Determination of fluoxetine, norfluoxetine and their enantiomers in rat plasma and brain samples by liquid chromatography with fluorescence detection. J Chromatogr B, 2007,852(1–2): 519–528

    Article  CAS  Google Scholar 

  17. Nimura N, Fujiwara T, Watanabe A, et al. A novel chiral thiol reagent for automated precolumn derivatization and high-performance liquid chromatographic enantioseparation of amino acids and its application to the aspartate racemase assay. Anal Biochem, 2003,315(2):262–269

    Article  PubMed  CAS  Google Scholar 

  18. Hori Y, Fujisawa M, Shimada K, et al. Enantioselective analysis of glufosinate using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase liquid chromatography. J Chromatogr B, 2002,776(2):191–198

    Article  CAS  Google Scholar 

  19. Gunaratna C, Kissinger PT. Investigation of stereoselective metabolism of amphetamine in rat liver microsomes by microdialysis and liquid chromatography with precolumn chiral derivatization. J Chromatogr A, 1998,828(1–2):95–103

    Article  PubMed  CAS  Google Scholar 

  20. Vermeij TAC, Edelbroek PM. High-performance liquid chromatographic analysis of vigabatrin enantiomers in human serum by precolumn derivatization with O-phthaldialdehyde-N-acetyl-L-cysteine and fluorescence detection. J Chromatogr B, 1998,716(1–2):233–238

    CAS  Google Scholar 

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This project was supported by a grant from a science and technology research program of Hubei provincial government (No. 2003AA301B05) and the Wuhan New Drug Development Program (No. 20066002103).

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Sun, S., Si, L., Fan, Z. et al. Stereoselective HPLC assay of TJ0711 enantiomers by precolumn derivatization with GITC using UV detection and its application in pharmacokinetics in rats. J. Huazhong Univ. Sci. Technol. [Med. Sci.] 29, 427–430 (2009). https://doi.org/10.1007/s11596-009-0407-7

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  • DOI: https://doi.org/10.1007/s11596-009-0407-7

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