Computational and experimental investigation of molecular imprinted polymers for selective extraction of dimethoate and its metabolite omethoate from olive oil

Bakas, Idriss; Oujji, Najwa Ben; Moczko, Ewa; Istamboulié, Georges; Piletsky, Sergey A.; Piletska, Elena; Ait-Addi, Elhabib; Ait-Ichou, Ihya; Noguer, Thierry; Rouillon, Régis

doi:10.1016/j.chroma.2012.11.061

Cited by 55 publications

(44 citation statements)

References 25 publications

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“…Despite the use of different functional monomers and cross-linkers, the IF data obtained for MIP3 with deltamethrin as template is higher than the IF values of those imprinting systems. However, regarding imprinting systems for dimethoate recognition, the values obtained for MIP1 are relatively lower than the data described in other studies [36,37]. Moreover, the porous intrinsic nature of the MIPs, together with several other factors, like shape recognition, hydrogen bond formation and hydrophophic interactions contribute strongly to the retention of the analyte, which is reflected in the varieties of IF values listed in Table 1.…”

Section: Imprinting Capacitycontrasting

confidence: 42%

Tailor-made molecularly imprinted polymers for dimethoate and deltamethrin recognition: synthesis, characterization and chromatographic evaluation

et al. 2014

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This work concerns the development of molecularly imprinted polymers (MIPs) for the selective extraction of dimethoate (dmt) and deltamethrin (dm) from food matrices. To achieve this goal, the non-covalent methodology has been applied for the preparation of MIPs using metacrylic acid (MAA) as a functional monomer and ethylene glycol dimethacrylate (EGDMA) and triethylene glycol dimethacrylate (TEGDMA) as cross-linkers in order to evaluate the influence of the nature of the cross-linker on the efficiency and selectivity of those MIPs for the target pesticides. Non-imprinted polymers (NIPs), which do not contain template, have been also prepared in parallel with the MIP synthesis using the same synthetic protocol to assess the specificity of the interactions. Chemical and physical characterization was carried out using conventional techniques, such as Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy and thermogravimetric analysis (TGA). Morphological characterization of MIPs and NIPs has been also performed using scanning electron microscopy (SEM) in order to assess the polymer's surface topography. The performance of each polymer was evaluated by conducting binding property measurements, namely imprinting factor determinations and adsorption studies using high performance liquid chromatography (HPLC).The results obtained in this study seem to show that there is a correlation between the polymer structure (including its physical characteristics) and their binding properties.

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Section: Imprinting Capacitycontrasting

confidence: 42%

Tailor-made molecularly imprinted polymers for dimethoate and deltamethrin recognition: synthesis, characterization and chromatographic evaluation

et al. 2014

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“…Thus, optimization polymerization conditions suggested that 0.3 mmol of sulpiride, 1.2 mmol of ITA, 4.5 mmol of EGDMA, 60 mg of AIBN and 6 mL of methanol for a MIP formulation, corresponding to the molar ratio of 1:4:15 for template-sulpiride/monomer-ITA/crosslinker-EGDMA, achieving a best value of specific adsorption. Recent publications frequently used the molar ratio of 1:4 although monomer could be ranging from 1 to 10 times the template in mole [25,26,27,28,29,30,31,32,33,34,35]. …”

Section: Resultsmentioning

confidence: 99%

Preparation, Characterization and Application of a Molecularly Imprinted Polymer for Selective Recognition of Sulpiride

et al. 2017

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A novel molecular imprinting polymer (MIP) was prepared by bulk polymerization using sulpiride as the template molecule, itaconic acid (ITA) as the functional monomer and ethylene glycol dimethacrylate (EGDMA) as the crosslinker. The formation of the MIP was determined as the molar ratio of sulpiride-ITA-EGDMA of 1:4:15 by single-factor experiments. The MIP showed good adsorption property with imprinting factor α of 5.36 and maximum adsorption capacity of 61.13 μmol/g, and was characterized by scanning electron microscopy (SEM), Fourier-transform infrared spectroscopy (FT-IR) and surface area analysis. With the structural analogs (amisulpride, tiapride, lidocaine and cisapride) and small molecules containing a mono-functional group (p-toluenesulfonamide, formamide and 1-methylpyrrolidine) as substrates, static adsorption, kinetic adsorption, and rebinding experiments were also performed to investigate the selective adsorption ability, kinetic characteristic, and recognition mechanism of the MIP. A serial study suggested that the highly selective recognition ability of the MIP mainly depended on binding sites provided by N-functional groups of amide and amine. Moreover, the MIP as solid-phase extractant was successfully applied to extraction of sulpiride from the mixed solution (consisted of p-toluenesulfonamide, sulfamethoxazole, sulfanilamide, p-nitroaniline, acetanilide and trimethoprim) and serum sample, and extraction recoveries ranged from 81.57% to 86.63%. The tentative tests of drug release in stimulated intestinal fluid (pH 6.8) demonstrated that the tablet with the MIP–sulpiride could obviously inhibit sulpiride release rate. Thus, ITA-based MIP is an efficient and promising alternative to solid-phase adsorbent for extraction of sulpiride and removal of interferences in biosample analysis, and could be used as a potential carrier for controlled drug release.

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“…Moreover, our research group have been focused on the development of MIP-based SPE sorbents for the isolation of several pesticide residues with relevance to olive oil production [13e17]. Recently, the isolation/pre-concentration of dimethoate from spiked olive oil samples has been implemented successfully using a MISPE-based methodology [13,18]. More recently, a new formatted MIP combining the pre-defined selectivity for dimethoate with a magnetic feature has proved to be a very promising smart-material for the development of selective sample preparation methodologies for the pre-concentration of this target pesticide in a very highly complex food matrix, as olive oil [17].…”

Section: Introductionmentioning

confidence: 99%

A photoswitchable “host-guest” approach for the selective enrichment of dimethoate from olive oil

García

Carreiro

Ramalho

et al. 2018

Analytica Chimica Acta

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This work describes the development of a new selective photocontrollable molecularly imprinted-based sorbent for the selective enrichment/pre-concentration of dimethoate from spiked olive oil samples. To achieve this goal an improved molecularly imprinted strategy relying on the embedding of a functional monomer containing an azobenzene chromophore as light-responsive element, on the crosslinked tridimensional molecular imprinted network, has been assessed. To address the mechanisms underlying template recognition and uptake/release of the analyte from the functional imprinted material, computational studies using a quantum chemical approach, have been explored. This new functional sorbent provides a straightforward controllable uptake/release of the target template using light as the stimuli tool, which is highly advantageous due to light manipulation characteristics, such as superior clean, precision and remote controllable properties. In general, this work will contribute to the implementation of a photoswitchable analytical methodology that proves to be suitable for the selective isolation and further quantification of dimethoate from olive oil matrices at levels similar to the maximum residues limits imposed by the legislation. The limits of detection, calculated based on 3σ, was 1.6 mgL and the limit of quantification, based on 10σ, was 5.2 mgL. The implemented sample preparation shows high reproducibility and recoveries (93.3 ± 0.4%).

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Computational and experimental investigation of molecular imprinted polymers for selective extraction of dimethoate and its metabolite omethoate from olive oil

Cited by 55 publications

References 25 publications

Tailor-made molecularly imprinted polymers for dimethoate and deltamethrin recognition: synthesis, characterization and chromatographic evaluation

Tailor-made molecularly imprinted polymers for dimethoate and deltamethrin recognition: synthesis, characterization and chromatographic evaluation

Preparation, Characterization and Application of a Molecularly Imprinted Polymer for Selective Recognition of Sulpiride

A photoswitchable “host-guest” approach for the selective enrichment of dimethoate from olive oil

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