Enantioseparation of beta-blockers labelled with a chiral fluorescent reagent, R (-)-DBD-PyNCS, by reversed-phase liquid chromatography
| Autor: | Toshimasa Toyo'oka, Yasuko Ishii, Masako Toriumi |
|---|---|
| Rok vydání: | 1997 |
| Předmět: |
Male
Hydrochloride Clinical Biochemistry Adrenergic beta-Antagonists Pharmaceutical Science Administration Oral High-performance liquid chromatography Analytical Chemistry chemistry.chemical_compound Isothiocyanates Drug Discovery Trifluoroacetic acid Animals Rats Wistar Saliva Racemization Spectroscopy Chromatography High Pressure Liquid Fluorescent Dyes Oxadiazoles Chromatography Molecular Structure Chemistry Diastereomer Stereoisomerism Reversed-phase chromatography Propranolol Rats Reagent Enantiomer |
| Zdroj: | Journal of pharmaceutical and biomedical analysis. 15(9-10) |
| ISSN: | 0731-7085 |
| Popis: | A fluorescent chiral tagging reagent, 4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfony l)-2,1, 3-benzoxadiazole [R(-)-DBD-PyNCS], has been used for the liquid chromatographic resolution of racemic pairs of beta-blockers. The reagents reacts with beta-blockers at 65 degrees C for 90 min in aqueous acetonitrile containing 0.05% triethylamine to produce the corresponding pair of diastereomers. No racemization occurs during the tagging reaction under these conditions. From results of the time-course study of oxprenolol the reactivities of the enantiomers of beta-blockers with R(-)-DBD-PyNCS are comparable. The optimum excitation and emission wavelengths of the resulting derivatives were ca. 460 and 550 nm, respectively. The derivatives of beta-blockers were efficiently resolved by a reversed-phase column with water-acetonitrile containing 0.1% trifluoroacetic acid as the eluent. The resolution (Rs) values of the diastereomers derived from 10 beta-blockers were in the range of 1.54-4.80. The Rs value for timolol was 0.643. The detection limits (signal-to-noise ratio of 2) were one or two orders of magnitude lower with beta-blockers having the iso-propylamino structure (15-300 fmol) than with those having the tert-butylamino structure (1.25-8.00 pmol). The proposed procedure was applied to the determination of R(+)- and S(-)-propranolol in rat plasma and saliva after oral administration of R(+)-propranolol hydrochloride or S(-)-propranolol hydrochloride. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect