Rapid chiral separation of atenolol, metoprolol, propranolol and the zwitterionic metoprolol acid using supercritical fluid chromatography–tandem mass spectrometry – Application to wetland microcosms

Svan, Alfred; Hedeland, Mikael; Arvidsson, Torbjörn; Jasper, Justin T.; Sedlak, David L.; Pettersson, Curt

doi:10.1016/j.chroma.2015.07.075

Cited by 31 publications

(22 citation statements)

References 47 publications

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“…The microcosms used for metabolite identification were incubated at UC Berkeley and have previously been described . In summary, fresh material from a pilot‐scale wetland (Discovery Bay, CA, USA) receiving nitrified, non‐disinfected secondary wastewater effluent was used to set up three different microcosm types, from two different kinds of wetlands.…”

Section: Methodsmentioning

confidence: 99%

“…The microcosms used for metabolite identification were incubated at UC Berkeley and have previously been described. [13,20] In summary, fresh material from a pilot-scale wetland (Discovery Bay, CA, USA) receiving nitrified, non-disinfected secondary wastewater effluent was used to set up three different microcosm types, from two different kinds of wetlands. The wetlands were chosen as representative of two different designs which have very different dissolved oxygen (DO) conditions, expected to affect compound transformation rates and possible metabolic pathways.…”

Section: Microcosm Setupmentioning

confidence: 99%

“…Their occurrence and degradation in environmental matrices have been previously studied in stressed degradation studies for transformation product identification, during ozonation and in wastewater treatment plants . Through chiral separations and enantiomeric fraction measurements their enantioselective degradation has also been determined, to assess their chiral fate and potentially enantioselective degradation pathway . Jasper et al .…”

Section: Introductionmentioning

confidence: 99%

“…[18] Through chiral separations and enantiomeric fraction measurements their enantioselective degradation has also been determined, to assess their chiral fate and potentially enantioselective degradation pathway. [19,20] Jasper et al [13] have recently studied the biodegradation of these β-blocking agents in microcosm models and pilot-scale open water wetlands, focusing on removal ability and rates. A limited investigation of previously known degradation products was performed using low resolution mass spectrometry.…”

Section: Introductionmentioning

confidence: 99%

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Identification of transformation products from β‐blocking agents formed in wetland microcosms using LC‐Q‐ToF

et al. 2016

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Identification of degradation products from trace organic compounds, which may retain the biological activity of the parent compound, is an important step in understanding the long-term effects of these compounds on the environment. Constructed wetlands have been successfully utilized to remove contaminants from wastewater effluent, including pharmacologically active compounds. However, relatively little is known about the transformation products formed during wetland treatment. In this study, three different wetland microcosm treatments were used to determine the biotransformation products of the β-adrenoreceptor antagonists atenolol, metoprolol and propranolol. LC/ESI-Q-ToF run in the MS(E) and MS/MS modes was used to identify and characterize the degradation products through the accurate masses of precursor and product ions. The results were compared with those of a reference standard when available. Several compounds not previously described as biotransformation products produced in wetlands were identified, including propranolol-O-sulfate, 1-naphthol and the human metabolite N-deaminated metoprolol. Transformation pathways were significantly affected by microcosm conditions and differed between compounds, despite the compounds' structural similarities. Altogether, a diverse range of transformation products in wetland microcosms were identified and elucidated using high resolving MS. This work shows that transformation products are not always easily predicted, nor formed via the same pathways even for structurally similar compounds.

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Section: Methodsmentioning

confidence: 99%

Section: Microcosm Setupmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Identification of transformation products from β‐blocking agents formed in wetland microcosms using LC‐Q‐ToF

et al. 2016

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“…1 Some enantiomers of β-blockers used in this study were previously separated on two different polysaccharide-based CSPs (Chiralpak IB-3 and Chiralpak AD columns) by SFC. 37,38 Almost 20 years ago, Berger and…”

Section: Introductionmentioning

confidence: 98%

Enantioselective potential of polysaccharide‐based chiral stationary phases in supercritical fluid chromatography

2017

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The enantioselective potential of two polysaccharide-based chiral stationary phases for analysis of chiral structurally diverse biologically active compounds was evaluated in supercritical fluid chromatography using a set of 52 analytes. The chiral selectors immobilized on 2.5 μm silica particles were tris-(3,5-dimethylphenylcarmabate) derivatives of cellulose or amylose. The influence of the polysaccharide backbone, different organic modifiers, and different mobile phase additives on retention and enantioseparation was monitored. Conditions for fast baseline enantioseparation were found for the majority of the compounds. The success rate of baseline and partial enantioseparation with cellulose-based chiral stationary phase was 51.9% and 15.4%, respectively. Using amylose-based chiral stationary phase we obtained 76.9% of baseline enantioseparations and 9.6% of partial enantioseparations of the tested compounds. The best results on cellulose-based chiral stationary phase were achieved particularly with propane-2-ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO , respectively. Methanol and basic additive isopropylamine were preferred on amylose-based chiral stationary phase. The complementary enantioselectivity of the cellulose- and amylose-based chiral stationary phases allows separation of the majority of the tested structurally different compounds. Separation systems were found to be directly applicable for analyses of biologically active compounds of interest.

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Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

Batra

Bhushan

2017

Biomedical Chromatography

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Atenolol, a β-adrenergic receptor antagonist, is a chiral compound used for the treatment of cardiovascular diseases and to treat hypertension, coronary heart disease, arrhythmias, sinus tachycardia and myocardial infarction, where it acts preferentially upon the β-adrenergic receptors in the heart. It is marketed as a racemate, but only the (S)-enantiomer of (RS)-atenolol is responsible for the β-adrenoceptor blocking activity. Different chromatographic methods have been applied for the separation and determination of enantiomers. In this article a review is presented on liquid chromatographic methods for enantioseparation of (RS)-atenolol by both direct and indirect approaches involving practical applications of several chiral stationary phases, chiral derivatization reagents and ligand exchange and impregnation methods. These include methods using both HPLC and TLC for separation, determination and bioassay of enantiomers of atenolol. In addition, some aspects of enantioseparation under achiral phases of liquid chromatography have been briefly mentioned as applicable to (RS)-atenolol. This review provides current available enantioseparation choices not only for (RS)-atenolol but also for other applicable racemic drugs.

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Rapid chiral separation of atenolol, metoprolol, propranolol and the zwitterionic metoprolol acid using supercritical fluid chromatography–tandem mass spectrometry – Application to wetland microcosms

Cited by 31 publications

References 47 publications

Identification of transformation products from β‐blocking agents formed in wetland microcosms using LC‐Q‐ToF

Identification of transformation products from β‐blocking agents formed in wetland microcosms using LC‐Q‐ToF

Enantioselective potential of polysaccharide‐based chiral stationary phases in supercritical fluid chromatography

Bioassay, determination and separation of enantiomers of atenolol by direct and indirect approaches using liquid chromatography: A review

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