1. Labeling of alprenolol with fluorescent aryl iodide as a reagent based on Mizoroki–Heck coupling reaction
- Author
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Mizuho Ohkuma, Naotaka Kuroda, Naoya Kishikawa, Rie Ikeda, Kenichiro Nakashima, Mitsuhiro Wada, and Kaname Ohyama
- Subjects
Male ,Fluorophore ,Fluorescent labeling ,Iodobenzene ,Iodide ,Sensitivity and Specificity ,Biochemistry ,Fluorescence spectroscopy ,Analytical Chemistry ,chemistry.chemical_compound ,Heck reaction ,Animals ,Terminal double bond ,Rats, Wistar ,Alprenolol ,Chromatography, High Pressure Liquid ,Fluorescent Dyes ,Mizoroki-Heck coupling reaction ,chemistry.chemical_classification ,Chromatography ,Molecular Structure ,Iodobenzenes ,Organic Chemistry ,Imidazoles ,Reproducibility of Results ,General Medicine ,Fluorescence ,Rats ,Spectrometry, Fluorescence ,chemistry ,Reagent ,Linear Models ,cardiovascular system ,Fluorescent aryl iodide - Abstract
A novel fluorescent labeling method for alprenolol was developed based on Mizoroki-Heck coupling reaction. We designed and synthesized fluorescent aryl iodide, 4-(4,5-diphenyl-1H-imidazol-2-yl)iodobenzene (DIBI) as a labeling reagent. DIBI has a lophine skeleton carrying an iodide atom acting as fluorophore and reactive center, respectively. In order to evaluate the usefulness of DIBI, a high-performance liquid chromatography (HPLC) with fluorescence detection method was developed for the determination of alprenolol as a model compound of terminal double bond. The fluorescent labeling of alprenolol with DIBI was achieved in the presence of palladium acetate as a catalyst, and the labeled alprenolol was detected fluorometrically. In addition, it was found that the fluorescence of DIBI derivative increased and red shifted when compared with that of DIBI. Furthermore, the proposed method could be applied to determine the alprenolol concentration in rat plasma after administration of alprenolol without interferences from biological components. The detection limit (S/N=3) for alprenolol in rat plasma was 0.74 ng/mL (30 fmol on column)., Journal of Chromatography. A, 1218(20), pp.3002-3006; 2011
- Published
- 2011
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