Selective sample pretreatment by molecularly imprinted polymer for the determination of LSD in biological fluids

Chapuis-Hugon, Florence; Cruz-Vera, Marta; Savane, Ramatoulaye; Ali, Wassim Hadj; Valcárcel, Miguel; Deveaux, Marc; Pichon, Valérie

doi:10.1002/jssc.200900247

Cited by 21 publications

(8 citation statements)

References 25 publications

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“…Non-imprinted polymers (NIP 1 to NIP 5), were synthesized following the same procedure as their corresponding MIP except that the template was absent. The five polymers were generated using a ratio 1/4/20,the most common ratio used in the literature [25][26][27][28][29][30][31], between the template, the monomer, and the cross linker. For all the syntheses, the template (1 mmol) and monomer (4 mmol) were first mixed with 1.8 mL of the corresponding porogen in a glass vial the "template-monomer" complex was allowed to form in an ultra-sonication bath for 10 minutes.…”

Section: Synthesis Of Molecularly Imprinted Polymers and Preparation mentioning

confidence: 99%

Development and application of water-compatible molecularly imprinted polymers for the selective extraction of carbamazepine from environmental waters

et al. 2019

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A molecularly imprinted polymer (MIP) was designed in order to allow the selective solid-phase extraction of carbamazepine (CBZ), an anticonvulsant and mood-stabilizing drug, at ultra-trace level from aqueous environmental samples. A structural analog of CBZ was selected as a dummy template and different synthesis conditions were screened. The selectivity of the resulting imprinted polymers was evaluated by studying the retention of CBZ in a solvent similar to the one used for the synthesis. The presence of imprinted cavities in the polymers was then demonstrated by comparing the elution profiles (obtained by using MIP and a non-imprinted polymer, NIP, as a control) of the template, of CBZ, and of a structural analog of CBZ. Then the extraction procedure was further optimized for the treatment of aqueous samples on the two most promising MIPs, with a special attention being paid to the volume and composition of the percolation and washing solutions. The best MIP provided a highly selective retention in tap water with 81 % extraction recovery for CBZ in the elution fraction of the MIP and only 14% for NIP. The repeatability of the extraction procedure was demonstrated for both tap and river waters (RSD below 4% in river water) for the drugs CBZ, oxcarbamazepine, and one metabolite (carbamazepine 10,11-epoxide). A MIP capacity of 1.15 µmol g-1 was determined. Finally, an analytical procedure involving the MIP was developed allowing the detection of CBZ at a concentration level of only a few ng L-1 in river water. The selectivity provided by the MIP resulted in a 3000-fold increase of the signal-to-noise ratio in LC/MS analysis as compared to the use of conventional sorbent.

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Section: Synthesis Of Molecularly Imprinted Polymers and Preparation mentioning

confidence: 99%

Development and application of water-compatible molecularly imprinted polymers for the selective extraction of carbamazepine from environmental waters

et al. 2019

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“…A successful imprinted polymer towards lysergic acid diethylamine (LSD) was developed by Chapuis-Hugon et al 21 using ergometrine as template molecule. However, the selectivity towards the six ergot alkaloids and epimers was not tested.…”

Section: Introductionmentioning

confidence: 99%

Development of Suspension Polymerized Molecularly Imprinted Beads with Metergoline as Template and Application in a Solid-Phase Extraction Procedure toward Ergot Alkaloids

Lenain

Mavungu²,

Dubruel³

et al. 2012

Anal. Chem.

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The first successfully developed molecularly imprinted polymer toward six ergot alkaloids and their respective epimers is described. A new imprinting molecule, metergoline, was used as template analogue in the production of suspension polymerized beads. These spherical particles functioned as selective sorbent in a solid-phase extraction column. The application of this column in the cleanup of barley samples prior to liquid chromatography coupled with tandem mass spectrometry allowed simple and cost-efficient sample preparation. The performance of the imprinted polymer and a non-imprinted control polymer was evaluated. This includes determination of the recovery values and the matrix effect of each of the 12 tested ergot alkaloids as well as a crossreactivity study with 25 common mycotoxins. The binding isotherms were obtained for metergoline, thus allowing comparison with other (imprinted) sorbents. A comparison between bulk and suspension polymerization is provided to determine the appropriate production technique. E rgot alkaloids are mycotoxins produced by Claviceps species, specifically Claviceps purpurea. These fungi can be found on cereals and produce sclerotia, which vary in composition and concentration of ergot alkaloids. The sclerotia are harvested together with the grains and only up to 80% of the kernels can be removed with the mechanical separation techniques currently available. Especially in periods of drought these techniques become unreliable as smaller sclerotia, similar in size to the grains, are produced. Generally, sclerotia are also broken during transport, allowing them to enter the food chain more easily.These ergot alkaloids possess toxicity due to interactions with α-adrenergic, serotinergic, and dopaminergic receptors. 1−3 Excess intake by humans can cause nausea, convulsions, hallucinations, and vasoconstriction and can even lead to gangrenous symptoms and abortion. Animals are infected through consumption of contaminated feed. This is a widespread phenomenon in livestock leading to adverse effects ranging from weight loss to death of infected animals. [4][5][6]2,7 The European Food Safety Authority (EFSA) stated in 2005 that the degree of variability in ergot alkaloid pattern in relation to fungal species, host plant, and geographical distribution is not known. 5 Six ergot alkaloidsergometrine, ergosine, ergotamine, ergocristine, ergocryptine, and ergocornine which are considered the most important ones according to EFSA, are depicted in Figure 1. An isomerization from the biologically active R-form to the biologically inactive S-form occurs at the C 8 stereogenic center of the tetracyclic ergoline structure in a reversible epimerization reaction. 8,9,6 The suffix "-ine" is used in the nomenclature if the side chain is present in the R-form at the C 8 stereogenic center, for example, ergotamine. The side chain is present in the S-orientation in the corresponding epimer which is expressed by the suffix "-inine", for example, ergotaminine. This reaction is promoted in humid, aqueous,...

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“…An imprinted polymer toward lysergic acid diethylamide (LSD) that was synthesized using methacrylic acid (MAA) functional monomers and ergometrine as a template showed 82% extraction recovery of LSD analogs from hair and urine samples. Similarly, an MIP synthesized from an MAA monomer cross-linked with ethylene glycol dimethacrylate (EGDMA) in chloroform further imprinted with metergoline as a template exhibited high selectivity toward the same when compared to non-imprinted polymers (NIPs) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Evaluation, and Characterization of an Ergotamine Imprinted Styrene-Based Polymer for Potential Use as an Ergot Alkaloid Selective Adsorbent

et al. 2021

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Alkaloid toxicities negatively impact livestock health and production. To assess alkaloid occurrences, adsorbent technologies may offer effective means to their extraction and isolation from a complex feed matrix. In this study, molecularly imprinted polymers (MIPs) were synthesized and evaluated for their specificity of binding to various ergot alkaloids. Co-polymers of styrene and hydroxyethyl methacrylate were synthesized in the absence or presence of an ergotamine (ETA) template, yielding non-imprinted polymer (NIP) and molecularly imprinted polymer (MIP), respectively. The influence of parameters such as pH, temperature, and initial concentration on the adsorption of ergot alkaloids was evaluated along with their application as solid phase extraction materials. Chemical and morphological properties were characterized. Adsorption was generally greater for MIP compared to NIP. Cross-reactivity with related alkaloids existed due to similarities in structure and functional groups and was dependent on the type and concentration of alkaloid and polymer type (alkaloid type × concentration × product; P < 0.05). The pH of the medium had no influence on the binding properties of polymers toward ETA within a pH range of 2–10. Binding was independent of temperature between 36 and 42 °C. When kinetics of adsorption were evaluated, the Langmuir isotherm had a better fit (R 2 > 0.95) to adsorption equilibrium data than the Freundlich equation. The maximum amounts adsorbed (Q o) from the Langmuir model were 8.68 and 7.55 μM/g for MIP and NIP, respectively. Fourier transform infrared, scanning and tandem electron microscopy, and Brunauer–Emmett–Teller analysis confirmed a highly porous MIP structure with a greater surface area compared to NIP. Binding characteristics evaluated with computational strategy using molecular docking experiments and in vitro in a complex media (rumen fluid) indicated a stronger ETA adsorption by the tested composition selected among other polymeric materials and affinity of MIP compared with NIP. This study suggested the possible utility of MIP as a solid phase extraction sorbent for applications in analytical chemistry or sensing devices tailored to track ergot alkaloid incidence and the fate of those alkaloids in complex ruminal digestive samples.

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Selective sample pretreatment by molecularly imprinted polymer for the determination of LSD in biological fluids

Cited by 21 publications

References 25 publications

Development and application of water-compatible molecularly imprinted polymers for the selective extraction of carbamazepine from environmental waters

Development and application of water-compatible molecularly imprinted polymers for the selective extraction of carbamazepine from environmental waters

Development of Suspension Polymerized Molecularly Imprinted Beads with Metergoline as Template and Application in a Solid-Phase Extraction Procedure toward Ergot Alkaloids

Synthesis, Evaluation, and Characterization of an Ergotamine Imprinted Styrene-Based Polymer for Potential Use as an Ergot Alkaloid Selective Adsorbent

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