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enantioseparation of some potencial β-blockers of aryloxyaminopropanol type by HPLC using macrocyclic antibiotics as chiral selector. Acta Fac Pharm Univ Comen. 2006;53:68-75. Crowter AF, Smith LH. Beta-adrenergic blocking agents II. Propranolol and related 3-amino-1-naphthoxy-2-propanols. J Med Chem. 1968;11:1009-1013. Čižmáriková R, Hroboňová K, Lehotay J, Račanská E, Bruchatá K. Preparation, pharmacological activity and enantioseparation of [3-cyclopentyloxymethyl)-4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]ethanone as potential β-blocker. Acta Fac Pharm Univ Comen. 2005

by LCMS/MS: Application to a clinical pharmacokinetic study. Biomed Chromatogr. 2013,27:1192–1199. 7. Kannappan V, Mannemala SS - Simultaneous enantioseparation and purity determination of chiral switches of amlodipine and atenolol by liquid chromatography. J Pharm Biomed Anal. 2016; 120:221–227. 8. Luksa J, Josíc D, Podobnik B, Furlan B, Kremser M - Semi-preparative chromatographic purification of the enantiomers S-(-)-amlodipine and R-(+)-amlodipine. J Chromatogr B Biomed Sci Appl. 1997;693(2):367-375. 9. Ansari KA, Pagar KP, Vavia PR - Development and validation

;12:614-20. Bhushan R, Arora M. Direct enantiomeric resolution of (±) atenolol, (±) metoprolol, and (±) propranolol by impregnated TLC using L-aspartic acid as chiral selector. Biomed Chrom. 2003;17:226-230. Bhushan R, Tanwar S. Direct TLC resolution of atenolol and propranolol into their enantiomers using different chiral selectors as impregnating reagents. Biomed Chrom. 2008;22:1028-1034. Bruchata K, Čižmarikova R, Polakovičova M, Hroboňova K, Pastirova Z. Synthesis, conformational study and HPLC enantioseparation of nitrophenoxyaminopropanols. Acta Facult Pharm Univ

References [1] Aboul-Enein HY, Ali I. HPLC enantiomeric resolution of nebivolol on normal and reversed amylose based chiral phases. Pharmazie. 2001;56:214-216. [2] Agrawal YK, Patel RN. Chiral chromatographic separation of β-blockers. J Chromatogr B. 2005;820:23-31. [3] Bojarsky J. Stereoselective chromatography of cardiovascular drugs: an update. J Biochem Biophys Methods. 2002;54:197-220. [4] Bojarsky J, Aboul - Enein YH, Ghanem A. What/s new in chromatographic enantioseparations. Curr Anal Chem. 2005;1:59-77. [5] Bruchata K, Čižmarikova R. New derivatives of

.: Optimization of the separation of the enantiomers of basic drugs. Retention mechanism and dinamic modification of the chiral bonding properties on an α- acid glicoprotein column. J. Chromatogr. A, 694, 1995, 57-69. HROBOŇOVÁ, K., LEHOTAY, J., ČIŽMÁRIK, J., ARMSTRONG, D.W.: In vitro study of enzymatic hydrolysis of diperodon enantiomers in blood serum by twodimensional LC. J. Pharm. Biomed. Anal., 30, 2002a, 875-880. HROBOŇOVÁ, K., LEHOTAY, J., ČIŽMÁRIK, J., RENČOVÁ, M., ARMSTRONG, D.W.: Study of mechanism of enantioseparation II. HPLC chiral analysis of alkoxysubstututed

References BERKECZ, R., SZTOJKOV-IVANOV, A., ILISZ, I., FORRÓ, E., FÜLÖP, F., HYUN, M. H., PÉTER, A.: High-performance liquid chromatographic enantioseparation of β-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12- tetracarboxylic acid-based chiral stationary phase. J. Chromatogr. A, 1125, 2006, 138-143. BOESTEN, J.M.M., BERKHEIJ, M., SCHOEMAKER, H.E., HIEMSTRA, H., DUCHATEAU, A.L.L.: Enantioselective high-performance liquid hromatographic separation of N-methyloxycarbonyl unsaturated amino acids on macrocyclic glycopeptide stationary phases. J

;14(22):3533-3536. 20. Bojarski J, Aboun-Enein HY, Ghanem A - What’s new in chromatographic enantioseparations. Curr Anal Chem. 2005;1:59-97. 21. Singh AK, Pedro LG, Gomes FP, et al. - Development and validation of sensitive methods for determination of sibutramine hydrochloride monohydrate and direct enantiomeric separation on a protein-based chiral stationary phase. J. AOAC Int. 2008; 91(3):572-579. 22. Radhakrishna T, Lakshmi-Narayana C, Sreenivas-Rao D, et al. - LC method for the determination of assay and purity of sibutramine hydrochloride and its enantiomers by chiral

Abstract

Beta-blockers are chiral compounds with enantiomers that have different bioactivity, which means that while one is active, the other can be inactive or even harmful. Due to their high consumption and incomplete degradation in waste water, they may reach surface waters and affect aquatic organisms. To address this issue we developed a chromatographic method suitable for determining beta-blocker enantiomers in surface waters. It was tested on five beta-blockers (acebutolol, atenolol, bisoprolol, labetalol and metoprolol) and validated on bisoprolol enantiomers. Good enantioseparation of all analysed beta-blockers was achieved on the Chirobiotic V column with the mobile phase composed of methanol/acetic acid/triethylamine (100/0.20/0.15 v/v/v) at a flow rate of 0.5 mL/min and column temperature of 45 °C. Method proved to be linear in the concentration range from 0.075 µg/mL to 5 µg/mL, and showed good recovery. The limits of bisoprolol enantiomer detection were 0.025 µg/mL and 0.026 µg/mL and of quantification 0.075 µg/mL and 0.075 µg/mL. Despite its limitations, it seems to be a promising method for bisoprolol enantiomer analysis in surface water samples. Further research could focus on waste water analysis, where enantiomer concentrations may be high. Furthermore, transferring the method to a more sensitive one such as liquid chromatography coupled with tandem mass spectrometry and using ammonium acetate as the mobile phase additive instead of acetic acid and triethylamine would perhaps yield much lower limits of detection and quantification.

configuration]. Arch Pharm (Weinheim). 1989; 322(8):499-505. 19. Szabo ZI, Foroughbakhshfasaei M, Gal R, Horvath P, Komjati B, Noszal B, Tóth G. Chiral separation of lenalidomide by liquid chromatography on polysaccharide-type stationary phases and by capillary electrophoresis using cyclodextrin selectors. J Sep Sci. 2018; 41(6):1414-1423. 20. Szabo ZI, Szocs L, Horvath P, Komjati B, Nagy J, Janoska A, Noszal B., Toth G. Liquid chromatography with mass spectrometry enantioseparation of pomalidomide on cyclodextrin-bonded chiral stationary phases and the elucidation of the

References ARMSTRONG, D.W., NAIR, U.B.: Capillary electrophoretic enantioseparations using macrocyclic antibiotics as chiral selectors. Electrophoresis, 18, 1997, 2331-2342. ARMSTRONG, D.W., YOUBANG, L., EKBORGOTT, K.: A covalently bonded teicoplanin chiral stationary phase for HPLC enantioseparations. Chirality, 7, 1995, 474-497. BERTHOD, A., CHEN, Z., KULLMAN, J.P., ARMSTRONG, D.W., GASPARRINI, F., D`ACQUARICA, I., VILLANI, C., CAROTTI, A.: Role of the carbohydrate moieties in chiral recognition on teicoplanin-based LC stationary phases. Anal. Chem., 72, 2000