Gas-phase dissociation pathways of Beta-2 agonists

Carlo, Matthew J.; York, Peyton; Patrick, Amanda L.

doi:10.1016/j.ijms.2021.116548

Cited by 4 publications

(7 citation statements)

References 25 publications

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“…In both the IS-CID and collision-cell CID, m / z 222 maximizes at relatively low energy, and then begins to be replaced by m / z 166 and m / z 148 at higher energies, with the latter becoming dominant at the highest energies studied. The full rationale behind the trends have been explored in a previous publication from our group . Overall, the observations for protonated salbutamol from the IS-CID and the collision-cell CID are very similar after intentional activation begins.…”

Section: Resultssupporting

confidence: 68%

Energy-Resolved In-Source Collison-Induced Dissociation for Isomer Discrimination

Carlo,

Nanney,

Patrick

2024

J. Am. Soc. Mass Spectrom.

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Section: Resultssupporting

confidence: 68%

Energy-Resolved In-Source Collison-Induced Dissociation for Isomer Discrimination

Carlo,

Nanney,

Patrick

2024

J. Am. Soc. Mass Spectrom.

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“…Here, we revisit the CID of the beta blockers acebutolol, atenolol, bisoprolol, carteolol, and labetalol, with a goal of fully mapping the dissociation pathways, supported by MS n , energy‐resolved breakdown curves, and density functional theory (DFT) calculations. This builds upon previous similar work we have reported for another pharmaceutical class regulated under antidoping schemes, beta‐2 agonists 72 . Further, we compare the energy‐resolved breakdown curves obtained using a qToF instrument to those obtained using an ion trap instrument—both via resonant ion trap CID and via IS‐CID—to illustrate the potential analytical utility of IS‐CID breakdown curves for improving selectivity and gaining pathway insights.…”

Section: Introductionsupporting

confidence: 57%

“…This builds upon previous similar work we have reported for another pharmaceutical class regulated under antidoping schemes, beta-2 agonists. 72 Further, we compare the energy-resolved breakdown curves obtained using a qToF instrument to those obtained using an ion trap instrument-both via resonant ion trap CID and via IS-CID-to illustrate the potential analytical utility of IS-CID breakdown curves for improving selectivity and gaining pathway insights.…”

mentioning

confidence: 99%

Further exploration of the collision‐induced dissociation of select beta blockers: Acebutolol, atenolol, bisoprolol, carteolol, and labetalol

Carlo,

Patrick

2023

J Mass Spectrom

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Beta blockers are a class of drugs commonly used to treat heart‐related diseases; they are also regulated under the World Anti‐Doping Agency. Tandem mass spectrometry is often used in the pharmaceutical industry, clinical analysis laboratory, and antidoping laboratory for detection and characterization of drugs and their metabolites. A deeper chemical understanding of dissociation pathways may eventually lead to an improved ability to predict tandem mass spectra of compounds based strictly on their chemical structure (or vice versa), which is especially important for characterization of unknowns such as emerging designer drugs or novel metabolites. In addition to providing insights into dissociation pathways, the use of energy‐resolved breakdown curves can produce improved selectivity and lend insights into optimal fragmentation conditions for liquid chromatography‐tandem mass spectrometry LC–MS/MS workflows. Here, we perform energy‐resolved collision cell and multistage ion trap collision‐induced dissociation‐mass spectrometry (CID‐MS) experiments, along with complementary density functional theory calculations, on five beta blockers (acebutolol, atenolol, bisoprolol, carteolol, and labetalol), to better understand the details of the pathways giving rise to the observed MS/MS patterns. Results from this work are contextualized within previously reported literature on these compounds. New insights into the formation of the characteristic product ion m/z 116 and the pathway leading to characteristic loss of 77 u are highlighted. We also present comparisons of breakdown curves obtained via qToF, quadrupole ion trap, and in‐source CID, allowing for differences between the data to be noted and providing a step toward allowing for improved selectivity of breakdown curves to be realized on simple instruments such as single quadrupoles or ion traps.

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“…Energy-resolved CID experiments, where the fragmentation of precursor ions is studied across a wide range of applied collision energies, has been shown to strengthen structural interpretation in distinguishing both isomeric small molecules and metal oxide clusters on the basis of experimentally derived appearance energies (AE). − The use of estimated threshold energies ( E 5% ) has also been applied to explore competing modes of bond homolysis in alkoxyamines . Energy-resolved CID has also been used to study the dissociation pathways of the Beta-2 agonist class of performance-enhancing drugs and to aid the structural characterization of N -glycans from their fragmentation patterns . Recently, these approaches have been extended to reveal characteristic differences between sets of related steroid monosulfates on the basis of estimated threshold energies ( E 5% ) .…”

Section: Introductionmentioning

confidence: 99%

“…30−34 The use of estimated threshold energies (E 5% ) has also been applied to explore competing modes of bond homolysis in alkoxyamines. 35 Energy-resolved CID has also been used to study the dissociation pathways of the Beta-2 agonist class of performance-enhancing drugs 36 and to aid the structural characterization of N-glycans from their fragmentation patterns. 37 Recently, these approaches have been extended to reveal characteristic differences between sets of related steroid monosulfates on the basis of estimated threshold energies (E 5% ).…”

Section: ■ Introductionmentioning

confidence: 99%

Energy-Resolved Fragmentation Aiding the Structure Elucidation of Steroid Biomarkers

Fitzgerald

Bowen²,

Elbourne

et al. 2022

J. Am. Soc. Mass Spectrom.

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The identification and confirmation of steroid sulfate metabolites in biological samples are essential to various fields, including anti-doping analysis and clinical sciences. Ultra-high-performance liquid chromatography with tandem mass spectrometry (UHPLC-MS/MS) is the leading method for the detection of intact steroid conjugates in biofluids, but because of the inherent complexity of biological samples and the low concentration of many targets of interest, metabolite identification based solely on mass spectrometry remains a major challenge. The confirmation of new metabolites typically depends on a comparison with synthetically derived reference materials that encompass a range of possible conjugation sites and stereochemistries. Herein, energy-resolved collision-induced dissociation (CID) is used as part of UHPLC-HRMS/MS analysis to distinguish between regio- and stereo-isomeric steroid sulfate compounds. This wholly MS-based approach was employed to guide the synthesis of reference materials to unambiguously confirm the identity of an equine steroid sulfate biomarker of testosterone propionate administration.

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Gas-phase dissociation pathways of Beta-2 agonists

Cited by 4 publications

References 25 publications

Energy-Resolved In-Source Collison-Induced Dissociation for Isomer Discrimination

Energy-Resolved In-Source Collison-Induced Dissociation for Isomer Discrimination

Further exploration of the collision‐induced dissociation of select beta blockers: Acebutolol, atenolol, bisoprolol, carteolol, and labetalol

Energy-Resolved Fragmentation Aiding the Structure Elucidation of Steroid Biomarkers

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