Mass spectrometric fragmentation and photocatalytic transformation of nicotine and cotinine

Medana, Claudio; Santoro, V.; Bello, Federica Dal; Sala, Cecilia; Pazzi, Marco; Sarro, Marco; Calza, Paola

doi:10.1002/rcm.7758

Cited by 20 publications

(9 citation statements)

References 14 publications

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“…Product ions at m/z 136.0, 132.0, 130.0, 120.0 and 106.0 all result from neutral losses of the caffeine moiety bound to the six‐carbon linker as shown in Figure B. Previously reported product ions of nicotine ( m/z 132.0, 130.0, 120.0, and 106.0) are in agreement with those observed results in this study . In contrast, the product ion at m/z 110.5 has not been previously reported and may serve as a unique identifier for C 8 ‐6‐N.…”

Section: Resultssupporting

confidence: 90%

“…CID‐MS/MS of the singly charged [M + H] + precursor ion of C 8 ‐6‐N ( m/z 425.3) gave rise to three product ions (Figure B) that are in agreement with cleavage of the nicotine portion of C 8 ‐6‐N. The product ion at m/z 346.4 is the result of a neutral loss of pyridine (C 5 H 5 N, 79 Da) in agreement with the previously reported MS/MS analysis of nicotine and m/z 332.4 is proposed to result from loss of beta‐picoline (C 6 H 7 N, 93 Da) (Figure B). In the case of the product ion at m/z 110.5, the caffeine moiety is lost but with a truncated three‐carbon linker (1,3,7‐trimethyl‐8‐propylpurine‐2,6‐dione (C 11 H 16 N 4 O 2 , 236 Da)) in addition to the loss of pyridine (C 5 H 5 N, 79 Da).…”

Section: Resultssupporting

confidence: 89%

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Tandem mass spectrometric analysis of novel caffeine scaffold‐based bifunctional compounds for Parkinson's disease

Nwabufo

El‐Aneed

Krol

2019

Rapid Comm Mass Spectrometry

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Rationale Novel bifunctional compounds composed of a caffeine scaffold attached to nicotine (C8‐6‐N), 1‐aminoindan (C8‐6‐I), or caffeine (C8‐6‐C8) were designed as therapeutics or diagnostics for Parkinson's disease (PD). In order to probe their pharmacological and toxicological profile, an appropriate analytical method is required. The goal of this study is to establish a tandem mass spectrometric fingerprint for the development of quantitative and qualitative methods that will aid future assessment of the in vitro and in vivo absorption, distribution, metabolism, excretion (ADME) and pharmacokinetic properties of these lead bifunctional compounds for PD. Methods Accurate mass measurement was performed using a hybrid quadrupole orthogonal time‐of‐flight mass spectrometer while multistage MS/MS and MS3 analyses were conducted using a triple quadrupole linear ion trap mass spectrometer. Both instruments are equipped with an electrospray ionization (ESI) source and were operated in the positive ion mode. The source and compound parameters were optimized for all three tested bifunctional compounds. Results The MS/MS analysis indicates that the fragmentation of C8‐6‐N and C8‐6‐I is driven by the dissociation of the nicotine and 1‐aminoindan moieties, respectively, but not caffeine. A significant observation in the MS/MS fragmentation of C8‐6‐C8 suggests that a previously reported loss of acetaldehyde during caffeine dissociation is instead a loss of CO2. Conclusions The collision‐induced tandem mass spectrometry (CID‐MS/MS) analysis of these novel bifunctional compounds revealed compound‐specific diagnostic product ions and neutral losses for all three tested bifunctional compounds. The established MS/MS fingerprint will be applied to the future development of qualitative and quantitative methods.

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Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 89%

Tandem mass spectrometric analysis of novel caffeine scaffold‐based bifunctional compounds for Parkinson's disease

Nwabufo

El‐Aneed

Krol

2019

Rapid Comm Mass Spectrometry

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“…The most abundant TPs of gabapentin were hydroxylated species. The formation of hydroxylated TPs is consistent with previous studies of other compounds treated with TiO 2 /UV 21–23 . We identified three monohydroxylated molecules with [M + H] + ions at m/z 188.1281, corresponding to the elemental composition C 9 H 18 NO 3 .…”

Section: Resultssupporting

confidence: 90%

Liquid chromatography/mass spectrometry analytical determination of gabapentin transformation products by heterogeneous photocatalysis and environmental evaluation

Bello

Medana

Zorzi

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Gabapentin is a drug used to treat epilepsy and peripheral neuropathic pain. It is an analog of gamma‐aminobutyric acid, and it is a selective blocker of voltage‐gated calcium channels. The drug is excreted unmetabolized; it is stable in the environment and is classified as a persistent mobile organic contaminant. Because wastewater treatment plants (WWTPs) are not completely efficient, some bioactive molecules may be released unaltered into the environment. The aim of this study was to provide information about degradation pathways of gabapentin in water by studying its photoinduced transformation products (TPs) through laboratory simulation experiments. Gabapentin and its TPs were monitored in influent and effluent water samples from WWTPs in Germany and Italy. Methods The laboratory simulation used heterogeneous photodegradation mediated by titanium dioxide (TiO2). Chromatographic separation was achieved using a C18 reverse‐phase column, and the structural identification of TPs was performed using high‐resolution electrospray ionization high‐resolution mass spectrometry (ESI‐HRMS) and multistage MSn experiments. Results Several TPs were observed during TiO2 photodegradation. Nine new compounds were detected, and potential structures were assigned by studying the fragmentation pathways of the [M + H]+ ions of these TPs and gabapentin. Gabapentin and some of the newly identified TPs were found in environmental samples from WWTPs. Conclusions The developed high‐performance liquid chromatography/high‐resolution mass spectrometry method was used to identify TPs from gabapentin. It was then successfully applied to real environmental samples to monitor the TPs as potential environmental pollutants.

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“…There is limited information regarding the abiotic and biotic transformations of nicotine in the environment. Relatively rapid photocatalytic oxidation has been demonstrated under laboratory conditions [30]. Half-life values estimated in a laboratory study of monoprotonated nicotine (pH 6.5-7.0) ranged from months to a year [31].…”

Section: Nicotinementioning

confidence: 99%

A Review of Environmental Pollution from the Use and Disposal of Cigarettes and Electronic Cigarettes: Contaminants, Sources, and Impacts

et al. 2021

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While the impacts of cigarette smoking on human health are widely known, a less recognized impact of tobacco product use and disposal is environmental pollution. This review discusses the current literature related to cigarette and e-cigarette contamination in the context of environmental sources and impacts, with a focus on the documented influences on biota, ranging from bacteria to mammals. Cigarette butts and electronic cigarette components can leach contaminants into soil, water, and air. Cellulose acetate cigarette filters comprising the butts are minimally degradable and are a source of bulk plastic and microplastic pollution, especially in aquatic ecosystems where they tend to accumulate. Cigarette combustion and aerosol production during e-cigarette use result in air contamination from sidestream, exhaled, and thirdhand pathways. The chemical byproducts of tobacco product use contaminate wastewater effluents, landfill leachates, and urban storm drains. The widespread detection of nicotine and cotinine in the environment illustrates the potential for large-scale environmental impacts of tobacco product waste. Studies show that cigarette butt leachate and nicotine are toxic to microbes, plants, benthic organisms, bivalves, zooplankton, fish, and mammals; however, there remain critical knowledge gaps related to the environmental impacts of tobacco product waste on environmental health and ecosystem functioning.

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Mass spectrometric fragmentation and photocatalytic transformation of nicotine and cotinine

Cited by 20 publications

References 14 publications

Tandem mass spectrometric analysis of novel caffeine scaffold‐based bifunctional compounds for Parkinson's disease

Tandem mass spectrometric analysis of novel caffeine scaffold‐based bifunctional compounds for Parkinson's disease

Liquid chromatography/mass spectrometry analytical determination of gabapentin transformation products by heterogeneous photocatalysis and environmental evaluation

A Review of Environmental Pollution from the Use and Disposal of Cigarettes and Electronic Cigarettes: Contaminants, Sources, and Impacts

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