Unexpected AChE inhibitory activity of (2E)α,β-unsaturated fatty acids

Loesche, Anne; Wiemann, Jana; Halabi, Zayan Al; Karasch, Julia; Sippl, Wolfgang

doi:10.1016/j.bmcl.2018.09.013

Cited by 15 publications

(9 citation statements)

References 23 publications

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“…75% for 1.1 × 10 −7 mol/L (500 ppb)). previously outlined (1:20 v/v ratio in buffer) resulted in the inhibition of AChE, that, independently of the olive oil:organic solvent ratio used, ranged from 6% to 16%, which is in full agreement with the data published by Loesche et al where AChE inhibition was found to vary from 7% to 18% [48].…”

Section: Measurements In Spiked Olive Oil Samplessupporting

confidence: 91%

“…It is worth noting that, irrespective of the ratio employed, a yellow tint could be discerned in all filtrates, indicating that filtration does not completely remove all the fat content from acetonitrile. Subsequent incubation of the fabricated sensors with the filtrates obtained following the four different protocols previously outlined (1:20 v/v ratio in buffer) resulted in the inhibition of AChE, that, independently of the olive oil:organic solvent ratio used, ranged from 6% to 16%, which is in full agreement with the data published by Loesche et al where AChE inhibition was found to vary from 7% to 18% [48]. In order to account for this, all subsequent % inhibitions of the enzyme activity were calculated taking this into consideration; thus, we are reporting only the additional % inhibition of the enzyme caused by the extracted pesticide.…”

Section: Measurements In Spiked Olive Oil Samplessupporting

confidence: 89%

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Facile and Low-Cost SPE Modification Towards Ultra-Sensitive Organophosphorus and Carbamate Pesticide Detection in Olive Oil

et al. 2020

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Despite the fact that a considerable amount of effort has been invested in the development of biosensors for the detection of pesticides, there is still a lack of a simple and low-cost platform that can reliably and sensitively detect their presence in real samples. Herein, an enzyme-based biosensor for the determination of both carbamate and organophosphorus pesticides is presented that is based on acetylcholinesterase (AChE) immobilized on commercially available screen-printed carbon electrodes (SPEs) modified with carbon black (CB), as a means to enhance their conductivity. Most interestingly, two different methodologies to deposit the enzyme onto the sensor surfaces were followed; strikingly different results were obtained depending on the family of pesticides under investigation. Furthermore, and towards the uniform application of the functionalization layer onto the SPEs’ surfaces, the laser induced forward transfer (LIFT) technique was employed in conjunction with CB functionalization, which allowed a considerable improvement of the sensor’s performance. Under the optimized conditions, the fabricated sensors can effectively detect carbofuran in a linear range from 1.1 × 10−9 to 2.3 × 10−8 mol/L, with a limit of detection equal to 0.6 × 10−9 mol/L and chlorpyrifos in a linear range from 0.7 × 10−9 up to 1.4 × 10−8 mol/L and a limit of detection 0.4 × 10−9 mol/L in buffer. The developed biosensor was also interrogated with olive oil samples, and was able to detect both pesticides at concentrations below 10 ppb, which is the maximum residue limit permitted by the European Food Safety Authority.

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Section: Measurements In Spiked Olive Oil Samplessupporting

confidence: 91%

Section: Measurements In Spiked Olive Oil Samplessupporting

confidence: 89%

Facile and Low-Cost SPE Modification Towards Ultra-Sensitive Organophosphorus and Carbamate Pesticide Detection in Olive Oil

et al. 2020

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“…Hydrophobic compounds like the fatty acids present in the extracted matrices have been found to penetrate into the gorge; nevertheless, and unlike the fatty acids, these compounds are mostly polycyclic. A possible explanation of AChE’s inhibition by fatty acids has been provided by Loesche et al [ 45 ]. They have shown that α,β-unsaturated fatty could fit very well into the AChE hydrophobic binding pocket that acts as the active site, while the carboxyl groups of the compounds fit reasonably into the PAS.…”

Section: Resultsmentioning

confidence: 99%

AChE-based electrochemical biosensor for pesticide detection in vegetable oils: matrix effects and synergistic inhibition of the immobilized enzyme

et al. 2022

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Enzyme-based electrochemical biosensors have been widely deployed for the detection of a range of contaminants in different food products due to their significant advantages over other (bio)sensing techniques. Nevertheless, their performance is greatly affected by the sample matrix itself or by the matrix they are presented with in pretreated samples, both of which can impact the accuracy as well as the sensitivity of the measurements. Therefore, and in order to acquire reliable and accurate measurements, matrix effects and their influence on sensor performance should be taken into consideration. Herein, acetylcholinesterase (AChE)-modified electrochemical sensors were employed for the detection of pesticides in vegetable oils. Sensor interrogation with pretreated oil samples, spiked with carbofuran, revealed the inhibitory potential of the extracted matrix varies between different types of vegetable oil and their fatty acid content. In addition, synergies between the extracted matrix from different types of vegetable oils and the carbamate pesticide, carbofuran, were observed, which led to significant deviations of the sensor’s performance from its anticipated behavior in buffered solution. Taking the aforementioned into consideration, appropriate calibration curves for each type of vegetable oil were drafted, which allowed for the highly reproducible determination of different pesticide concentrations in pretreated real samples. Collectively, a better understanding of AChE inhibition by single or multiple contaminants present in vegetable oils was gained, which can find many applications in numerous fields, ranging from sensor development to the design of new pesticides and medicinal products.

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“…Instrumentation as previously 9 reported. The purity of the compounds was determined by HPLC (Merck-Hitachi LaChrom D-7000 HPLC-DAD/RI system, column, Aminex HPX-87P; 300x7.8 mm; 60°C; H2O; flow 0.5 mL/min) > 98%.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, it demonstrates that the potential of -unsaturated fatty acids as inhibitors of the enzymes acetyl-and butyrylcholinesterase 9 , and the antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides was described 10,11 These glycolipids are known to destabilize biological membranes resulting most often in antifungal or antibacterial properties 12 . It was shown that especially tetradecyl and hexadecyl -D-glucopyranosides hold good antimicrobial activity against some strains of Grampositive bacteria.…”

Section: Introductionmentioning

confidence: 99%