Pesticide Residues: Conazoles

Tasheva, Maria

doi:10.1016/b978-0-12-378612-8.00241-9

Cited by 2 publications

(3 citation statements)

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“…The term pesticide includes fungicides, herbicides, insecticides, molluscicides, nematicides, rodenticides, plant growth regulators, and other compounds which are classified according to the target pest [ 2 , 3 ]. For example, herbicides, fungicides, and insecticides are commonly used worldwide in agriculture to kill weeds or unwanted plants, fungi, and insects, respectively [ 3 , 4 , 5 ]. If, on the one hand, the use of pesticides has brought great benefits, both in increasing the availability and quality of food and for public health in general [ 6 ], on the other hand, exposure to them is a source of various diseases for animals and humans [ 2 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

Molecular Physicochemical Properties of Selected Pesticides as Predictive Factors for Oxidative Stress and Apoptosis-Dependent Cell Death in Caco-2 and HepG2 Cells

Silva

Martins-Gomes

Ferreira

et al. 2022

IJMS

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In this work, three pesticides of different physicochemical properties: glyphosate (GLY, herbicide), imidacloprid (IMD, insecticide), and imazalil (IMZ, fungicide), were selected to assess their cytotoxicity against Caco-2 and HepG2 cells. Cell viability was assessed by the Alamar Blue assay, after 24 and 48 h exposure to different concentrations, and IC50 values were calculated. The mechanisms underlying toxicity, namely cellular reactive oxygen species (ROS), glutathione (GSH) content, lipid peroxidation, loss of mitochondrial membrane potential (MMP), and apoptosis/necrosis induction were assessed by flow cytometry. Cytotoxic profiles were further correlated with the molecular physicochemical parameters of pesticides, namely: water solubility, partition coefficient in an n-octanol/water (Log Pow) system, topological polar surface area (TPSA), the number of hydrogen-bonds (donor/acceptor), and rotatable bonds. In vitro outputs resulted in the following toxicity level: IMZ (Caco-2: IC50 = 253.5 ± 3.37 mM, and HepG2: IC50 = 94 ± 12 mM) > IMD (Caco-2: IC50 > 1 mM and HepG2: IC50 = 624 ± 24 mM) > GLY (IC50 > >1 mM, both cell lines), after 24 h treatment, being toxicity time-dependent (lower IC50 values at 48 h). Toxicity is explained by oxidative stress, as IMZ induced a higher intracellular ROS increase and lipid peroxidation, followed by IMD, while GLY did not change these markers. However, the three pesticides induced loss of MMP in HepG2 cells while in Caco-2 cells only IMZ produced significant MMP loss. Increased ROS and loss of MMP promoted apoptosis in Caco-2 cells subjected to IMZ, and in HepG2 cells exposed to IMD and IMZ, as assessed by Annexin-V/PI. The toxicity profile of pesticides is directly correlated with their Log Pow, as affinity for the lipophilic environment favours interaction with cell membranes governs, and is inversely correlated with their TPSA; however, membrane permeation is favoured by lower TPSA. IMZ presents the best molecular properties for membrane interaction and cell permeation, i.e., higher Log Pow, lower TPSA and lower hydrogen-bond (H-bond) donor/acceptor correlating with its higher toxicity. In conclusion, molecular physicochemical factors such as Log Pow, TPSA, and H-bond are likely to be directly correlated with pesticide-induced toxicity, thus they are key factors to potentially predict the toxicity of other compounds.

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Section: Introductionmentioning

confidence: 99%

Molecular Physicochemical Properties of Selected Pesticides as Predictive Factors for Oxidative Stress and Apoptosis-Dependent Cell Death in Caco-2 and HepG2 Cells

Silva

Martins-Gomes

Ferreira

et al. 2022

IJMS

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show abstract

“…It is commonly accepted that they play an important role in the development of agriculture by reducing the loss of products while improving the yield and food quality [ 1 , 2 , 3 , 4 ]. The term “pesticides” comprises a vast number of compounds, such as fungicides, herbicides, insecticides, molluscicides, nematicides, rodenticides, plant growth regulators and others, according to the pest target [ 2 , 5 ]; for example, herbicides, insecticides and fungicides are used worldwide to kill weeds, or unwanted plants, insects and fungi, respectively [ 1 , 5 , 6 ]. Undoubtedly, the use of pesticides has brought great benefits both in increasing the availability and quality of food and in supporting public health in general [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

“…It is commonly accepted that they play an important role in the development of agriculture by reducing the loss of products while improving the yield and food quality [1][2][3][4]. The term Toxics 2022, 10, 378. https://doi.org/10.3390/toxics10070378 https://www.mdpi.com/journal/toxics "pesticides" comprises a vast number of compounds, such as fungicides, herbicides, insecticides, molluscicides, nematicides, rodenticides, plant growth regulators and others, according to the pest target [2,5]; for example, herbicides, insecticides and fungicides are used worldwide to kill weeds, or unwanted plants, insects and fungi, respectively [1,5,6].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Assessment of Pesticides Toxicity and Data Correlation with Pesticides Physicochemical Properties for Prediction of Toxicity in Gastrointestinal and Skin Contact Exposure

Silva

Martins-Gomes

Silva

et al. 2022

Toxics

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In this work, three pesticides of different physicochemical properties, namely, glyphosate (herbicide), imidacloprid (insecticide) and imazalil (fungicide), were selected to assess their cytotoxicity against distinct cell models (Caco-2, HepG2, A431, HaCaT, SK-MEL-5 and RAW 264.7 cells) to mimic gastrointestinal and skin exposure with potential systemic effect. Cells were subjected to different concentrations of selected pesticides for 24 h or 48 h. Cell viability was assessed by Alamar Blue assay, morphological changes by bright-field microscopy and the IC50 values were calculated. Cytotoxic profiles were analysed using the physico-chemical parameters of the pesticides, namely: molecular weight, water solubility, the partition coefficient in the n-octanol/water (Log Pow) system, the topological polar surface area (TPSA), and number of hydrogen-bonds (donor/acceptor) and rotatable bonds. Results showed that glyphosate did not reduce cell viability (up to 1 mM), imidacloprid induced moderate toxicity (IC50 > 1 mM for Caco-2 cells while IC50 = 305.9 ± 22.4 μM for RAW 264.7 cells) and imazalil was highly cytotoxic (IC50 > 253.5 ± 3.37 for Caco-2 cells while IC50 = 31.3 ± 2.7 μM for RAW 264.7 cells) after 24 h exposure. Toxicity was time-dependent as IC50 values at 48 h exposure were lower, and decrease in cell viability was accompanied by changes in cell morphology. Pesticides toxicity was found to be directly proportional with their Log Pow, indicating that the affinity to a lipophilic environment such as the cell membranes governs their toxicity. Toxicity is inverse to pesticides TPSA, but lower TPSA favours membrane permeation. The lower toxicity against Caco-2 cells was attributed to the physiology and metabolism of cell barriers equipped with various ABC transporters. In conclusion, physicochemical factors such as Log Pow, TPSA and H-bond are likely to be directly correlated with pesticide-induced toxicity, thus being key factors to potentially predict the toxicity of other compounds.

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Pesticide Residues: Conazoles

Cited by 2 publications

References 1 publication

Molecular Physicochemical Properties of Selected Pesticides as Predictive Factors for Oxidative Stress and Apoptosis-Dependent Cell Death in Caco-2 and HepG2 Cells

Molecular Physicochemical Properties of Selected Pesticides as Predictive Factors for Oxidative Stress and Apoptosis-Dependent Cell Death in Caco-2 and HepG2 Cells

In Vitro Assessment of Pesticides Toxicity and Data Correlation with Pesticides Physicochemical Properties for Prediction of Toxicity in Gastrointestinal and Skin Contact Exposure

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