Detection of Contaminants of High Environmental Impact by Means of Fluorogenic Probes

Abstract

This personal account describes our contribution to the design of selective fluorogenic probes for contaminants of high environmental impact. For this purpose, we have developed a new family of highly versatile fluorogenic reagents that were able to show large differences in their fluorescence in the presence of selected analytes. They were used in the preparation of fluorogenic probes for the detection of contaminants of high environmental impact which currently have no good solutions: phosphorylating agents, such as chemical weapons; methyl mercury(II); the cyanide anion; amino-acid metabolites, such as doping substances; and biogenic amine mimics, such as drugs of abuse and recreational drugs. The development of new materials for specific sensing was achieved by anchoring selected probes to silica nanomaterials, suitable for the selective detection of organic analytes in water for immediate application to toxicological or environmental purposes.

A smart material for the in situ detection of mercury in fish

“…7 The use of these probes permitted the speciation of MeHg + and Hg 2+ in samples containing mixtures of both cations. 8 Now, with the purpose of preparing new portable fluorescent sensors for practical applications, we have bonded the best fluorogenic probe to a polymeric hydrophilic matrix to develop a new fluorescent polymer capable of detecting the presence of mercury contamination in fish samples. In this communication, we report the direct measurements of the presence of mercury in fish samples with a polymeric probe.…”

Manipulation of Transmembrane Transport by Synthetic K+ Ionophore Depsipeptides and Its Implications in Glucose‐Stimulated Insulin Secretion in β‐Cells

“…In parallel, synthetic sCereulide JG100 was obtained by cyclization of JG99B . For live imaging experiments, we selected 9‐[2‐(piperazin‐1‐yl)pyrimidin‐5‐yl]perylene‐3,4‐dicarboximide JG117 as a fluorescent tag (Scheme ), obtained from the Suzuki reaction of 9‐bromoperylene‐3,4‐dicarboximide and [2‐( N ‐Boc‐piperazin‐1‐yl)pyrimidin‐5‐yl]boronic ester, used for extended conjugation and the activation of fluorogenic probes, followed by acid‐mediated deprotection of the amine group. The formation of an amide between the depsipeptide JG115B and the fluorescent tag JG117 gave the fluorescent depsipeptide JG121 (Scheme ).…”

“…Our approach consisted of the substitution of the first (S)-2hydroxy-3-methylbutanoica cid by (S)-5-(benzyloxy)-2-hydroxy-5-oxopentanoic acidt hrough ac lassical sequence, [3] followed by synthesis of the new depsipeptide JG113B,w hich was then cyclized [16,17] to give JG115,w hich in turn wasd ebenzylated under hydrogenation conditions to give JG115B,w hich bears af ree carboxylic acid in the lateral chain. In parallel, synthetic sCereulide JG100 was obtained by cyclization of JG99B.F or live imaging experiments, we selected 9-[2-(piperazin-1-yl)pyri-midin-5-yl]perylene-3,4-dicarboximide JG117 as af luorescent tag (Scheme 1), obtainedf rom the Suzukir eactiono f9 -bromoperylene-3,4-dicarboximide [18] and [2-(N-Boc-piperazin-1-yl)pyrimidin-5-yl]boronic ester,u sed for extended conjugation and the activation of fluorogenicp robes, [19] followed by acid-mediated deprotection of the amine group. The formation of an amide between the depsipeptide JG115B and the fluorescent tag JG117 gave the fluorescent depsipeptide JG121 (Scheme 1).…”

From food defence to food supply chain integrity

“…The SNIFFER project investigated the use of fluorogenic probes for the detection of cereulide, the emetic toxin from Bacillus cereus , in food matrices, which has of course considerable food safety relevance. Previous studies have shown how these probes can differentiate between different heavy metal contaminants (Díaz de Greñu et al , 2016), chemical warfare agents (Díaz de Greñu et al , 2014) and pyrrolizidine alkaloids (García-Calvo et al , 2016). The probes were successfully combined with commercially available technologies to form a sensor network capable of rapidly detecting and identifying chemical and biological contaminants in the milk production food chain (SNIFFER working paper).…”