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Chiral separation of beta-blockers by high-performance liquid chromatography and determination of bisoprolol enantiomers in surface waters

Marijana Pocrnić
Marijana Pocrnić
, 
Martin Ansorge
Martin Ansorge
, 
Magda Dovhunová
Magda Dovhunová
, 
Iva Habinovec
Iva Habinovec
, 
Eva Tesařová
Eva Tesařová
 et 
Nives Galić
Nives Galić
   | 09 avr. 2020
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Article Category: Original article
Publié en ligne: 09 avr. 2020
Pages: 56 - 62
Reçu: 01 juil. 2019
Accepté: 01 févr. 2020
DOI: https://doi.org/10.2478/aiht-2020-71-3318
© 2020 Marijana Pocrnić, Martin Ansorge, Magda Dovhunová, Iva Habinovec, Eva Tesařová, Nives Galić, published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Figure 1

Structures of the analysed beta-blockers (chiral centres are marked with an asterisk)
Structures of the analysed beta-blockers (chiral centres are marked with an asterisk)

Figure 2

Chromatographic separation of acebutolol, atenolol, bisoprolol, labetalol, and metoprolol enantiomers on the Chirobiotic V column using the MeOH:HAc:TEA (100:0.2:0.15) mobile phase, flow rate of 0.5 mL/min, and column temperature of 45 °C (detection wavelength 230 nm)
Chromatographic separation of acebutolol, atenolol, bisoprolol, labetalol, and metoprolol enantiomers on the Chirobiotic V column using the MeOH:HAc:TEA (100:0.2:0.15) mobile phase, flow rate of 0.5 mL/min, and column temperature of 45 °C (detection wavelength 230 nm)

Figure 3

Chromatograms of samples from the Kunraticky stream (A) and the Sava River (B), spiked with bisoprolol enantiomers at 12 μg/L after solid-phase extraction
Chromatograms of samples from the Kunraticky stream (A) and the Sava River (B), spiked with bisoprolol enantiomers at 12 μg/L after solid-phase extraction

Chromatographic parameters for beta-blockers separated on the Chirobiotic V column using the MeOH:HAc:TEA (100:0.2:0.15) mobile phase, flow rate of 0.5 mL/min, and column temperature of 45 °C (detection wavelength 230 nm)

Analyte Enantiomer Retention time/min Rs k α
E1 13.19 1.12
Acebutolol E2 13.99 1.43 1.24 1.12
E1 14.53 1.33
Atenolol E2 15.38 1.37 1.46 1.10
Bisoprolol E1 10.85 1.30 0.74 1.12
E2 11.43 0.83
E1 17.49 0.65 1.77 1.03
Labetalol E2 18.11 3.06 1.82 1.26
E3 21.16 2.30
E4 23.67 2.41 2.69 1.17
E1 11.43 0.84
Metoprolol E2 12.04 1.30 0.93 1.12

Expected and calculated concentrations of bisoprolol enantiomers and their recoveries in spiked samples of distilled and surface waters from Zagreb and Prague

Expected γ (μg/L) Calculated γ (μg/L) Recovery (%)
BIS 1 BIS 2 BIS 1 BIS 2 BIS 1 BIS 2
Distilled water 1 12.00 12.00 12.02 11.85 100.2 98.8
Distilled water 2 240.00 240.00 265.71 264.58 110.7 110.2
Prague 1 12.00 12.00 13.18 13.19 109.8 109.9
Prague 2 9.36 9.36 10.08 10.08 107.7 107.7
Prague 3 8.16 8.16 9.44 9.49 115.7 116.3
Sava 1 1.80 1.80 2.27 2.35 126.3 130.3
Sava 2 6.00 6.00 8.14 8.30 135.7 138.3
Sava 3 12.00 12.00 13.90 14.31 115.8 119.3
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Medicine, Basic Medical Science, other
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