Evaluation of table-top lasers for routine infrared ion spectroscopy in the analytical laboratory

Outersterp, Rianne E. van; Martens, Jonathan; Péremans, A.; Lamard, Laurent; Cuyckens, Filip; Berden, Giel

doi:10.1039/d1an01406d

Cited by 13 publications

(21 citation statements)

References 69 publications

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“…Comparing IR spectra of the drug itself and various metabolites gives direct information on the formation of new functional groups, whereas computed IR spectra aid in final identification of biotransformation sites. The work here was performed at an open-access free electron laser facility, but IRIS can also be implemented with table-top laser systems 56 for easier and efficient application in pharmaceutical laboratories, although currently still over a restricted IR spectral range.…”

Section: Further Discussion and Conclusionmentioning

confidence: 99%

Identification of drug metabolites with infrared ion spectroscopy – application to midazolam in vitro metabolism

Outersterp

Martens

Berden

et al. 2022

Preprint

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The identification of biotransformation products of drug compounds is a crucial step in drug development. Over the last decades, liquid chromatography-mass spectrometry (LC-MS) has become the method of choice for metabolite profiling because of its high sensitivity and selectivity. However, determining the full molecular structure of the detected metabolites, including the exact biotransformation site, remains challenging on the basis of MS alone. Here we explore infrared ion spectroscopy (IRIS) as a novel MS-based method for the elucidation of metabolic pathways in drug metabolism research. Using the drug midazolam as an example, we identify several biotransformation products directly from an in vitro drug incubation sample. We show that IR spectra of the aglycone MS/MS fragment ions of glucuronide metabolites establish a direct link between detected phase I and phase II metabolites. Moreover, using quantum-chemically computed IR spectra of candidate structures, we are able to assign the exact sites of biotransformation in absence of reference standards. Additionally, we demonstrate the utility of IRIS for structural elucidation by identifying several ring-opened midazolam derivatives formed in an acidic environment.

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Section: Further Discussion and Conclusionmentioning

confidence: 99%

Identification of drug metabolites with infrared ion spectroscopy – application to midazolam in vitro metabolism

Outersterp

Martens

Berden

et al. 2022

Preprint

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“…In the 3 μm region, the same experiment is carried out with an optical parametric oscillator (OPO) pumped by a 80 MHz picosecond fiber laser. 42 The OPO pulses have a duration of 35 ps and a bandwidth of 0.5 cm –1 . The IR frequency is tuned between 3500 and 3700 cm –1 , where the output power of the OPO is around 400 mW.…”

Section: Methodsmentioning

confidence: 99%

“…In the 3 μm region, the same experiment is carried out with an optical parametric oscillator (OPO) pumped by a 80 MHz picosecond fiber laser . The OPO pulses have a duration of 35 ps and a bandwidth of 0.5 cm –1 .…”

Section: Methodsmentioning

confidence: 99%

Laboratory IR Spectra of the Ionic Oxidized Fullerenes C₆₀O⁺ and C₆₀OH⁺

2022

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We present the first experimental vibrational spectra of gaseous oxidized derivatives of C 60 in protonated and radical cation forms, obtained through infrared multiple-photon dissociation spectroscopy using the FELIX free-electron laser. Neutral C 60 O has two nearly iso-energetic isomers: the epoxide isomer in which the O atom bridges a CC bond that connects two six-membered rings and the annulene isomer in which the O atom inserts into a CC bond connecting a five- and a six-membered ring. To determine the isomer formed for C 60 O + in our experiment—a question that cannot be confidently answered on the basis of the DFT-computed stabilities alone—we compare our experimental IR spectra to vibrational spectra predicted by DFT calculations. We conclude that the annulene-like isomer is formed in our experiment. For C 60 OH + , a strong OH stretch vibration observed in the 3 μm range of the spectrum immediately reveals its structure as C 60 with a hydroxyl group attached, which is further confirmed by the spectrum in the 400–1600 cm –1 range. We compare the experimental spectra of C 60 O + and C 60 OH + to the astronomical IR emission spectrum of a fullerene-rich planetary nebula and discuss their astrophysical relevance.

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“…Here, we record vibrational spectra and derive molecular structures for retention-time and molecular-weight selected ions from UV-exposed sinapoyl malate samples, employing infrared ion spectroscopy (IRIS) implemented on a quadrupole ion trap (QIT) MS platform. The free-electron laser FELIX supplies intense and widely tunable IR radiation for IRIS experiments. , This approach allows us to differentiate isomeric UV photoproducts, which is of crucial importance as the photomolecular heating ability of SM is driven by cis-trans isomerization.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Solar Radiation-Induced Degradation Products of the Plant Sunscreen Sinapoyl Malate

Vink

Schermer²,

Martens

et al. 2023

ACS Agric. Sci. Technol.

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Agricultural activities at lower temperatures lead to lower yields due to reduced plant growth. Applying photomolecular heater agrochemicals could boost yields under these conditions, but UV-induced degradation of these compounds needs to be assessed. In this study, we employ liquid chromatography−mass spectrometry (LC−MS) coupled with infrared ion spectroscopy (IRIS) to detect and identify the degradation products generated upon simulated solar irradiation of sinapoyl malate, a proposed photomolecular heater/UV filter compound. All major irradiation-induced degradation products are identified in terms of their full molecular structure by comparing the IRIS spectra obtained after LC fractionation and mass isolation with reference IR spectra obtained from quantum-chemical calculations. In cases where physical standards are available, a direct experimental-toexperimental comparison is possible for definitive structure identification. We find that the major degradation products originate from trans-to-cis isomerization, ester cleavage, and esterification reactions of sinapoyl malate. Preliminary in silico toxicity investigations using the VEGAHUB platform suggest no significant concerns for these degradation products' human and environmental safety. The identification workflow presented here can analogously be applied to break down products from other agrochemical compounds. As the method records IR spectra with the sensitivity of LC−MS, application to agricultural samples, e.g., from field trials, is foreseen.

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Evaluation of table-top lasers for routine infrared ion spectroscopy in the analytical laboratory

Abstract: Evaluation of four table-top IR lasers for ion spectroscopy in ion trap mass spectrometers shows high rep-rate lasers offer better photodissociation efficiency and are more cost-effective and practical compared to low rep-rate or cw alternatives.

Cited by 13 publications

References 69 publications

Identification of drug metabolites with infrared ion spectroscopy – application to midazolam in vitro metabolism

Identification of drug metabolites with infrared ion spectroscopy – application to midazolam in vitro metabolism

Laboratory IR Spectra of the Ionic Oxidized Fullerenes C₆₀O⁺ and C₆₀OH⁺

Characterization of Solar Radiation-Induced Degradation Products of the Plant Sunscreen Sinapoyl Malate

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Evaluation of table-top lasers for routine infrared ion spectroscopy in the analytical laboratory

Abstract: Evaluation of four table-top IR lasers for ion spectroscopy in ion trap mass spectrometers shows high rep-rate lasers offer better photodissociation efficiency and are more cost-effective and practical compared to low rep-rate or cw alternatives.

Cited by 13 publications

References 69 publications

Identification of drug metabolites with infrared ion spectroscopy – application to midazolam in vitro metabolism

Identification of drug metabolites with infrared ion spectroscopy – application to midazolam in vitro metabolism

Laboratory IR Spectra of the Ionic Oxidized Fullerenes C60O+ and C60OH+

Characterization of Solar Radiation-Induced Degradation Products of the Plant Sunscreen Sinapoyl Malate

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Laboratory IR Spectra of the Ionic Oxidized Fullerenes C₆₀O⁺ and C₆₀OH⁺