Chiral analysis of selected enantiomeric drugs relevant in doping controls

Rubio, Ana; Görgens, Christian; Guddat, Sven; Piper, Thomas; Garzinsky, Ann-Marie; Krug, Oliver; Thevis, Mario

doi:10.1016/j.jcoa.2021.100017

Cited by 6 publications

(4 citation statements)

References 12 publications

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“…Today, enantiopure versions of these drugs exist with levosalbutamol and arformoterol, and the question was raised whether analytical means are required to determine the concentration of the pharmacologically relevant enantiomer in order to avoid athletes exceeding the permissive dose of the bioactive isomer. Analytical strategies enabling such analyses were reported, 71 preferably employing chiral LC–HRMS/MS analysis as presented, for example, by Rubio et al 72 Urine samples were subjected to enzymatic hydrolysis and LLE, and extracts were injected onto a chiral column with teicoplanin‐based stationary phase. The effluent was directed via positive ESI to a Q/orbitrap MS system, operated in full MS and PRM mode, allowing for LODs of 0.1 ng/ml for salbutamol and formoterol.…”

Section: β2‐agonists Hormone and Metabolic Modulators And Diureticsmentioning

confidence: 99%

Annual banned‐substance review—Analytical approaches in human sports drug testing 2021/2022–

Thevis

Kuuranne

Geyer

2022

Drug Testing and Analysis

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Also in 2021/2022, considerable efforts were invested into advancing human sports drug testing programs, recognizing and taking into account existing as well as emerging challenges in anti-doping, especially with regard to substances and methods of doping specified in the World Anti-Doping Agency's 2022 Prohibited List. In this edition of the annual banned-substance review, literature on recent developments published between October 2021 and September 2022 is summarized and discussed.Focus is put particularly on enhanced analytical approaches and complementary testing options in human doping controls, appreciating the exigence and mission in anti-doping and, equally, the contemporary "new normal" considering, for example, the athlete's exposome versus analytical sensitivity and applicable anti-doping regulations for result interpretation and management.

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Section: β2‐agonists Hormone and Metabolic Modulators And Diureticsmentioning

confidence: 99%

Annual banned‐substance review—Analytical approaches in human sports drug testing 2021/2022–

Thevis

Kuuranne

Geyer

2022

Drug Testing and Analysis

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“…Several researchers have been working to develop strategies to identify and quantify Clb enantiomers in biological matrixes like lamb, beef, horse, and swine tissues and human urine. Currently, HPLC‐MS, GC‐MS, and capillary electrophoresis are the most common methods used to carry out enantiomeric analyses of this β‐agonist 13,18–22 …”

Section: Introductionmentioning

confidence: 99%

“…Currently, HPLC-MS, GC-MS, and capillary electrophoresis are the most common methods used to carry out enantiomeric analyses of this β-agonist. 13,[18][19][20][21][22] The aims of this study were to develop a rapid, sensitive, accurate method for identifying and quantifying Clb in several bovine tissues and to carry out an enantiomeric analysis to evaluate its distribution.…”

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confidence: 99%

Quantification and enantiomeric distribution of clenbuterol in several bovine tissues using UHPLC–tandem mass spectrometry: Evaluation of a risk factor associated with meat contamination

Velasco-Bejarano

Espinoza-Muñoz

Álvarez-Sánchez

et al. 2023

Drug Testing and Analysis

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Clenbuterol (Clb) (4-amino-α-[(tert-butylamine) methyl]-3,5-dichlorobenzyl alcohol) is a sympathomimetic agent that exhibits β2-agonist activity. It is applied as a bronchodilatory, tocolytic, and mucolytic agent and is authorized for clinical management in both human and veterinary therapeutics as a racemic mixture. However, its use is strictly prohibited in animals destined for food production in countries in the European Union and in the United States and Mexico, among many others. The R-(À) enantiomer in clenbuterol stimulates β2-receptors, whereas the S-(+) enantiomer blocks the effect of β1-receptors. The aims of this study were to develop a method for detecting and quantifying Clb and its enantiomeric distribution in several bovine tissues. The UHPLC-MS/MS method developed to quantify the target compound at trace levels in these tissues combines high sensitivity with good selectivity and short chromatographic run time. The tissue samples tested were found to contain racemic Clb in concentrations of 5-447 pg g À1 . The enantiomeric analysis of Clb showed that R-(À)-Clb is present at higher concentrations in some tissues, whereas S-(+)-Clb was detected in a ratio of 55/45 in the liver and heart tissues.

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“…The separation of chiral compounds has been performed with chromatographic techniques, such as GC, supercritical fluid chromatography, and HPLC utilizing the direct resolution method employing chiral stationary phases (CSPs). Proteins, macrocyclic antibiotics, cyclodextrins, and polysaccharides have been largely applied as chiral selectors [2,3]. Recently, miniaturized separation/sample preparation techniques, following sustainability trends and principles of green analytical chemistry, have been proposed [4], offering some advantages such as reduced analysis time and costs, as well as the limited consumption of organic solvents and sample volume.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric analysis of drugs in water samples by using liquid–liquid microextraction and nano‐liquid chromatography

et al. 2023

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The nano‐LC technique is increasingly used for both fast studies on enantiomeric analysis and test beds of novel stationary phases due to the small volumes involved and the short conditioning and analysis times. In this study, the enantioseparation of 10 drugs from different families was carried out by nano‐LC, utilizing silica with immobilized amylose tris(3‐chloro‐5‐methylphenylcarbamate) column. The effect on chiral separation caused by the addition of different salts to the mobile phase was evaluated. To simultaneously separate as many enantiomers as possible, the effect of buffer concentration in the mobile phase was studied, and, to increase the sensitivity, a liquid–liquid microextraction based on the use of isoamyl acetate as sustainable extraction solvent was applied to pre‐concentrate four chiral drugs from tap and environmental waters, achieving satisfactory recoveries (>70%).

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Chiral analysis of selected enantiomeric drugs relevant in doping controls

Cited by 6 publications

References 12 publications

Annual banned‐substance review—Analytical approaches in human sports drug testing 2021/2022–

Annual banned‐substance review—Analytical approaches in human sports drug testing 2021/2022–

Quantification and enantiomeric distribution of clenbuterol in several bovine tissues using UHPLC–tandem mass spectrometry: Evaluation of a risk factor associated with meat contamination

Enantiomeric analysis of drugs in water samples by using liquid–liquid microextraction and nano‐liquid chromatography

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