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2. Innovative analytical methodologies for characterizing chemical exposure with a view to next-generation risk assessment

Author

Tkalec, Žiga, Antignac, Jean-Philippe, Bandow, Nicole, Béen, Frederic M., Belova, Lidia, Bessems, Jos, Le Bizec, Bruno, Brack, Werner, Cano-Sancho, German, Chaker, Jade, Covaci, Adrian, Creusot, Nicolas, David, Arthur, Debrauwer, Laurent, Dervilly, Gaud, Duca, Radu Corneliu, Fessard, Valérie, Grimalt, Joan O., Guerin, Thierry, Habchi, Baninia, Hecht, Helge, Hollender, Juliane, Jamin, Emilien L., Klánová, Jana, Kosjek, Tina, Krauss, Martin, Lamoree, Marja, Lavison-Bompard, Gwenaelle, Meijer, Jeroen, Moeller, Ruth, Mol, Hans, Mompelat, Sophie, Van Nieuwenhuyse, An, Oberacher, Herbert, Parinet, Julien, Van Poucke, Christof, Roškar, Robert, Togola, Anne, Trontelj, Jurij, and Price, Elliott J.

Published
2024
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3. Charge‐solvated versus protonated salt forms of cyclodepsipeptide toxins in electrospray: Dissociation of alkali‐cationized forms enables straightforward sequencing of cereulide.

Author

Liuu, Sophie, Trinh, Kam eng, Darii, Ekaterina, Cao, Chenqin, Damont, Annelaure, Gimbert, Yves, Fenaille, François, Makni, Yassine, Inthavong, Chanthadary, Lavison‐Bompard, Gwenaëlle, Hennekinne, Jacques‐Antoine, Firmesse, Olivier, and Tabet, Jean‐Claude

Subjects
DAUGHTER ions, ALKALI metal ions, FOOD contamination, SALT, BACILLUS cereus, TOXINS
Abstract

Bacillus cereus is responsible for foodborne outbreaks worldwide. Among the produced toxins, cereulide induces nausea and vomiting after 30 min to 6 h following the consumption of contaminated foods. Cereulide, a cyclodepsipeptide, is an ionophore selective to K+ in solution. In electrospray, the selectivity is reduced as [M + Li]+; [M + Na]+ and [M + NH4]+ can also be detected without adding corresponding salts. Two forms are possible for alkali‐cationized ions: charge‐solvated (CS) that exclusively dissociates by releasing a bare alkali ion and protonated salt (PS), yielding alkali product ions by covalent bond cleavages (CBC) promoted by mobile proton. Based on a modified peptide cleavage nomenclature, the PS product ion series (b, a, [b + H2O] and [b + CnH2nO] [n = 4, 5]) are produced by Na+/Li+/K+‐cationized cereulide species that specifically open at ester linkages followed by proton mobilization promoting competitive ester CBC as evidenced under resonant collision activation. What is more, unlike the sodiated or lithiated cereulide, which regenerates little or no alkali cation, the potassiated forms lead to an abundant K+ regeneration. This occurs by splitting of (i) the potassiated CS forms with an appearance threshold close to that of the PS first fragment ion generation and (ii) eight to four potassiated residue product ions from the PS forms. Since from Na+/Li+‐cationized cereulide, (i) the negligible Na+/Li+ regeneration results in a higher sensibility than that of potassiated forms that abundantly releasing K+, and (ii) a better sequence recovering, the use of Na+ (or Li+) should be more pertinent to sequence isocereulides and other cyclodepsipeptides. [ABSTRACT FROM AUTHOR]

Published
2024
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11. AVIS de l'Agence nationale de sécurité sanitaire de l'alimentation, de l'environnement et du travail sur les projets de décret relatif à la sécurité sanitaire des eaux et d'arrêtés relatifs à laproduction d'eau de mer propre et à son utilisation au contact des produits de la pêche

Author

Westerberg, Estelle (ed.), Carré, J., Cerf, Olivier, Chubilleau, Catherine, Garry, Pascal, Gonzalez, J.L., Jitaru, Petru, Lavison-Bompard, Gwenaëlle, Leclercq, A., Le Garrec, Raphaële, Sarter, Samira, and Welté, Bénédicte

Published
2019

18. Origin and characterization of cyclodepsipeptides: Comprehensive structural approaches with focus on mass spectrometry analysis of alkali‐cationized molecular species.

Author

Liuu, Sophie, Damont, Annelaure, Perret, Alain, Firmesse, Olivier, Becher, François, Lavison‐Bompard, Gwenaëlle, Hueber, Amandine, Woods, Amina S., Darii, Ekaterina, Fenaille, François, and Tabet, Jean‐Claude

Subjects
*TANDEM mass spectrometry, *NUCLEAR magnetic resonance, *STEREOCHEMISTRY, *DAUGHTER ions, *MOLECULAR interactions
Abstract

Cyclodepsipeptides (CDPs) represent a huge family of chemically and structurally diverse molecules with a wide ability for molecular interactions. CDPs are cyclic peptide‐related natural products made up of both proteinogenic and nonproteinogenic amino acids linked by amide and ester bonds. The combined use of different analytical methods is required to accurately determine their integral structures including stereochemistry, thus allowing deeper insights into their often‐intriguing bioactivities and their possible usefulness. Our goal is to present the various methods developed to accurately characterize CDPs. Presently, Marfey's method and NMR (nuclear magnetic resonance) are still considered the best for characterizing CDP configuration. Nevertheless, electrospray‐high resolution tandem mass spectrometry (ESI‐HRMS/MS) is of great value for efficiently resolving CDP's composition and sequences. For instance, recent data shows that the fragmentation of cationized CDPs (e.g., [M + Li]+ and [M + Na]+) leads to selective cleavage of ester bonds and specific cationized product ions (b series) useful to get unprecedented sequence information. Thus, after a brief presentation of their structure, biological functions, and biosynthesis, we also provide a historic overview of these various analytical approaches as well as their advantages and limitations with a special emphasis on the emergence of methods based on HRMS/MS through recent fundamental works and applications. [ABSTRACT FROM AUTHOR]

Published
2024
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19. Characterization of the contamination of aquatic systems by psychotropic compounds : development of a reference method including a multifactorial selection approach

Author

Brieudes, Vincent, Budzinski, Hélène, Allan, Ian, Lardy-Fontan, Sophie, Randon, Jérôme, Rosin, Christophe, Lavison-Bompard, Gwenaëlle, Laprévote, Olivier, Fenet, Hélène, Lévi, Yves, Environnements et Paléoenvironnements OCéaniques (EPOC), Observatoire aquitain des sciences de l'univers (OASU), Université Sciences et Technologies - Bordeaux 1-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université Sciences et Technologies - Bordeaux 1-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-École pratique des hautes études (EPHE), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS), Université de Bordeaux, and Hélène Budzinski

Subjects
Measurement uncertainties, Isotopic dilution, Compounds, Mass spectrometry (ID-MS), Water, Environment, Psychotropic, Métrologie, Environnement, Reference method, Psychotropes, [SDV.EE.ECO]Life Sciences [q-bio]/Ecology, environment/Ecosystems, Pharmaceutiques, Contamination, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Eau, Pharmaceuticals, Spectrométrie de masse (DI-MS), Méthode de référence, Dilution isotopique, Incertitudes
Abstract

Pharmaceuticals and their residues belong to the so-called “emerging” pollutants for which no current regulation is applied regarding their presence in the environment. Monitoring the contamination of aquatic resources by these kinds of micropollutants is a necessity in order to anticipate potential effects regarding human health and ecosystems. In this context, data quality (traceability and comparability) is compulsory so as to take better decisions regarding policies to be driven. Psychotropic compounds, which are widely consumed, display a great concern in that field.This thesis aimed at characterizing occurrence of psychotropic compounds in the environment and putting forward metrological tools insuring accuracy, traceability, comparability as well as representativity of the measurement results.To that purpose, a SPE-LC-MS² multi-residue method has been developed for a selection of psychotropic compounds and other commonly consumed drugs. Method limits of quantification were in the range of ng.L-1 which enabled to characterize their occurrence in several surface waters and treated wastewaters. Concurrently, usage of integrative samplers was evaluated and applied on the field in different locations. Occurrence levels of 68 selected compounds were established by implementation of this complementary strategy in aquatic systems. Furthermore, results from measurement campaigns were used to rank studied compounds into a short list of interest. Finally, a reference method using isotopic dilution and mass spectrometry (DI-MS) was developed for the characterization of 24 psychotropic compounds in surface waters. Expanded uncertainties (k=2) inferior to 10% were obtained. Last be not least, implementing this method to environmental analysis emphasized the importance of sampling related uncertainties regarding to global measurement uncertainties.; Les résidus de médicaments font partie des polluants dits « émergents » pour lesquels il n’existe actuellement pas de réglementation quant à leur présence dans l’environnement. Afin d’anticiper un risque éventuel pour l’Homme et les milieux aquatiques il est, entre autres, nécessaire de réaliser un état des lieux de la contamination des systèmes aquatiques par ce type de micropolluants. Dans ce contexte, disposer de données de mesures de qualité (traçables et comparables) constitue un prérequis indispensable pour décider au mieux des politiques à conduire dans ce domaine. L’étude des psychotropes présente un enjeu important d’autant plus qu’il s’agit de molécules abondamment consommées.Les travaux conduits lors de cette thèse avaient deux objectifs principaux. Le premier était de caractériser l’occurrence environnementale de composés psychotropes. Le second objectif était de proposer des outils métrologiques permettant d’assurer l’exactitude, la traçabilité, la comparabilité mais également la représentativité des résultats de mesure.Dans un premier temps, une méthode multi-résidus par SPE-LC-MS² a été développée pour une sélection de composés psychotropes et d’autres médicaments de consommation courante. Les limites de quantification de la méthode étaient de l’ordre du ng.L-1. Cela a permis de caractériser leur occurrence dans différents cours d’eau et rejets de station d’épuration en France. En parallèle, une approche par échantillonnage intégratif a été développée et déployée dans différents sites. Cette stratégie complémentaire a permis d’établir les niveaux d’occurrence des 68 psychotropes et traceurs sélectionnés et de conduire une démarche de hiérarchisation dans le but d’établir une liste restreinte de composés d’intérêt. Enfin, une méthode de référence associant la dilution isotopique à la spectrométrie de masse (DI-MS) a été développée pour l’analyse de 24 psychotropes dans les eaux de surface. Elle se caractérise par des incertitudes élargies (k=2) inférieures à 10%. La mise en oeuvre de cette méthode dans des études environnementales a permis de mettre en évidence l’importance de la contribution de l’incertitude liée à l’échantillonnage par rapport à l’incertitude totale de mesure.

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