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Biochimica Et Biophysica Acta Sep 1978Thiabendazole, 2-(4'-thiazolyl)benzimidazole, at 80 micrometer completely inhibits mitosis in hyphae of Aspergillus nidulans, growing in liquid culture. DNA and RNA...
Thiabendazole, 2-(4'-thiazolyl)benzimidazole, at 80 micrometer completely inhibits mitosis in hyphae of Aspergillus nidulans, growing in liquid culture. DNA and RNA synthesis and mycelial growth are only partially inhibited at this concentration. Binding studies with cell-free mycelial extracts from Penicillium expansum showed that thiabendazole competitively inhibits [14C]carbendazim binding to tubulin, which suggests that the antimitotic activity of thiabendazole is based on interference with microtubule assembly. Tubulin from a thiabendazole-resistant and carbendazim-highly sensitive mutant of P. expansum has a lower affinity to thiabendazole and a higher affinity to carbendazim than tubulin from a wide-type strain. This indicates that in this mutant the structure of the binding site is affected. The data presented suggest that several sites of both the tubulin and ligand molecule are involved in the binding of benzimidazole compounds to fungal tubulin.
Topics: Aspergillus nidulans; Benzimidazoles; Carbamates; DNA; Fungicides, Industrial; Glycoproteins; Kinetics; Mitosis; Penicillium; Protein Binding; RNA; Species Specificity; Thiabendazole; Tubulin
PubMed: 361093
DOI: 10.1016/0304-4165(78)90456-7 -
Environmental Toxicology and Chemistry Feb 2023Carbendazim is a systemic fungicide used in several countries, particularly in Brazil. However, studies suggest that it is related to the promotion of tumors, endocrine...
Carbendazim is a systemic fungicide used in several countries, particularly in Brazil. However, studies suggest that it is related to the promotion of tumors, endocrine disruption, and toxicity to organisms, among other effects. As a result, carbendazim is not allowed in the United States, Australia, and some European Union countries. Therefore, further studies are necessary to evaluate its effects, and zebrafish is a model routinely used to provide relevant information regarding the acute and long-term effects of xenobiotics. In this way, zebrafish water tank samples (water samples from aquari containing zebrafish) and liver samples from animals exposed to carbendazim at a concentration of 120 μg/L were analyzed by liquid chromatography coupled to high-resolution mass spectrometry, followed by multivariate and univariate statistical analyses, using the metabolomics approach. Our results suggest impairment of lipid metabolism with a consequent increase in intrahepatic lipids and endocrine disruption. Furthermore, the results suggest two endogenous metabolites as potential biomarkers to determine carbendazim exposure. Finally, the present study showed that it is possible to use zebrafish water tank samples to assess the dysregulation of endogenous metabolites to understand biological effects. Environ Toxicol Chem 2023;42:437-448. © 2022 SETAC.
Topics: Animals; Zebrafish; Water Pollutants, Chemical; Metabolomics; Liver; Lipids; Water
PubMed: 36484755
DOI: 10.1002/etc.5534 -
Environmental Science and Pollution... Nov 2023Dip-coating TiO (Degussa P25) onto the glass-fiber pre-filter using different binders (PEG1000, 2000, 4000, 6000, and Duramax B1000) for carbendazim degradation in...
Dip-coating TiO (Degussa P25) onto the glass-fiber pre-filter using different binders (PEG1000, 2000, 4000, 6000, and Duramax B1000) for carbendazim degradation in Chinese chives was studied. To investigate the effects of binder types, TiO concentration was fixed at 1 % w/v, and amounts of binders were varied in a range of 0.3 to 1 wt% based on the TiO content. Then, effects of TiO and binder concentrations were further studied on the most effective binder type (PEG6000). It was revealed that 2 wt% of PEG6000 yielded the highest carbendazim degradation efficiency. The efficiency increased with the increased concentration of TiO. At the best condition of coating, i.e., 1-1.5 % w/v of TiO and 2 wt% of PEG6000, more than 90% degradation efficiency was obtained although the initial carbendazim concentration in the chives was as high as 168.4 mg/kg.
Topics: Chive; Titanium
PubMed: 37831268
DOI: 10.1007/s11356-023-30274-5 -
Environmental Pollution (Barking, Essex... Jul 2023Plant-microbe interactions have been effectively used in phytoremediation to reduce agrochemical contamination of crops and soils, but little information is available...
Plant-microbe interactions have been effectively used in phytoremediation to reduce agrochemical contamination of crops and soils, but little information is available regarding the general effect of such association on rhizosphere soil homeostasis. In this study, we immobilized Stenotrophomonas pavanii DJL-M3, a carbendazim (CBZ)-degrading endophyte, in rice husk-derived biochar to control fungicide residue in the rice microenvironment. The influence of biochar inoculated with strain DJL-M3 on rhizobacterial communities was also investigated, including activity and fundamental function predictions. An adsorption kinetics test showed that strain DJL-M3 slowed the adsorption rate slightly without sacrificing the adsorption capacity of rice-husk biochar on CBZ. Immobilization in biochar helped S. pavanii DJL-M3 to establish an ecological niche in rhizosphere soils. This process significantly reduced CBZ levels in rice and rhizosphere soil while maintaining stable heterotrophic microbial respiration and carbon (C) metabolic activity. Soil amendment with the strain DJL-M3-biochar composite resulted in relatively little disturbance of fundamental soil functions, such as nitrogen (N) and sulfur (S) cycling, which explained the better plant growth and higher soil fertility observed with CBZ contamination. Overall, the combination of biochar and S. pavanii DJL-M3 demonstrated the potential to safeguard the microbiological environment of rice.
Topics: Oryza; Rhizosphere; Soil; Charcoal; Homeostasis; Soil Microbiology; Soil Pollutants
PubMed: 37105458
DOI: 10.1016/j.envpol.2023.121723 -
Food Chemistry Aug 2023Carbendazim (CBZ), a well-known benzimidazole pesticide, is utilized in agriculture to prevent and cure plant diseases caused by fungi. Residual CBZ in food poses...
Carbendazim (CBZ), a well-known benzimidazole pesticide, is utilized in agriculture to prevent and cure plant diseases caused by fungi. Residual CBZ in food poses serious threat to human health. Herein, a fluorescent two-dimensional terbium-based metal-organic framework (2D Tb-MOF) nanosheet sensor was developed for the rapid and ultrasensitive detection of CBZ. The 2D Tb-MOF nanosheets, prepared with Tb ions and 5-borono-1,3-benzenedicarboxylic acid (BBDC) as the precursors, exhibited excellent optical properties. Upon the addition of CBZ, the fluorescence of Tb-MOF nanosheets was quenched because of the inner filter effect (IFE) and dynamic quenching. The fluorescence sensor offered two linear ranges of 0.06-4 and 4-40 µg/mL with a low detection limit of 17.95 ng/mL. Furthermore, the proposed sensing platform was successfully applied to assay CBZ in apples and tea, and satisfactory results were obtained. This study provides an effective alternative strategy for the qualitative and quantitative determination of CBZ to ensure food safety.
Topics: Humans; Metal-Organic Frameworks; Terbium; Benzimidazoles; Coloring Agents; Food Safety
PubMed: 36893637
DOI: 10.1016/j.foodchem.2023.135853 -
Environmental Pollution (Barking, Essex... Sep 2023Novel nanomaterial-based pesticide formulations are increasingly perceived as promising aids in the transition to more efficient agricultural production systems. The...
Novel nanomaterial-based pesticide formulations are increasingly perceived as promising aids in the transition to more efficient agricultural production systems. The current understanding of potential unintended (eco)toxicological impacts of nano-formulated pesticides is scarce, in particular with regard to (non-target) aquatic organisms and ecosystems. The present study reports the results of a long-term freshwater mesocosm experiment which assessed responses of individual zooplankton taxa and communities to a novel TiO-coated nano-formulation of the fungicide carbendazim. Population- and community trends were assessed and compared in response to the nano-formulation and its constituents applied individually (i.e. nano-sized TiO, carbendazim) and in combination (i.e. nano-sized TiO & carbendazim). Minimal differences were observed between effects induced by the nano-formulation and its active ingredient (i.e. carbendazim) when applied at equivalent nominal test concentrations (4 μg L). Nano-sized TiO was found to affect zooplankton community trends when applied separately at environmentally realistic concentrations (20 μg L nominal test concentration). However, when nano-sized TiO was applied in combination with carbendazim, nano-sized TiO was found not to alter effects on community trends induced by carbendazim. The findings of the current study provide an extensive and timely addition to the current body of work available on non-target impacts of nano-formulated pesticides.
Topics: Animals; Zooplankton; Ecosystem; Pesticides; Water Pollutants, Chemical
PubMed: 37271364
DOI: 10.1016/j.envpol.2023.121894 -
Current Microbiology Jul 2023The impact of fungicide residues on non-target soil bacterial communities is relatively unexplained. We hypothesize that the persistence of fungicide residues in the...
The impact of fungicide residues on non-target soil bacterial communities is relatively unexplained. We hypothesize that the persistence of fungicide residues in the soil will affect the soil bacterial populations. Persistence depends on biotic and abiotic factors, primarily determined by agricultural activities. Activities such as fallow soil (F), farmyard manure (FYM) amendment, rice straw (RS) mulching, and cultivation of maize (Zea mays) and clover (Trifolium alexandrinum) were used as treatments. The soil CO efflux showed no effect of Carbendazim on dormant bacteria (unwatered condition). However, in irrigated condition, Carbendazim enhanced the CO efflux by 8, 164, 131, 249, and 182% in fallow, FYM, RS, maize, and Trifolium treatments, respectively. However, 16S rRNA metagenome study after 30 days of carbendazim treatment showed that maize rhizosphere microflora was most susceptible, decreasing the Shannon diversity index from 0.321 to 0.165. Diversity indices generally increased in maize and RS treatments, and Proteobacteria was the most prominent bacterial phyla in the maize rhizosphere. The microbial communities separated into distinct groups on the Principal Co-ordinate analysis (PCoA) plot. The separation on scale 1 (35%) and scale 2 (13%) was based, respectively, on microbial activity and carbendazim treatments. Functionally Maize+Carbendazim treatment showed the highest enzyme activities dehydrogenase (82.25%), acid phosphatase (78.10%), alkaline phosphatase (48.26%), β-glucosidase (59.99%), protease (126.65%), and urease (50.66%) compared to fallow soil. Overall, Carbendazim enhanced non-target bacterial activity in metabolically active niches, while it did not affect the dormant microflora. Thus, organic amendments and cultivation of fungicide-contaminated soil may help render the contaminant through bacterial activity.
Topics: Soil; Rhizosphere; Fungicides, Industrial; RNA, Ribosomal, 16S; Carbon Dioxide; Bacteria; Soil Microbiology; Zea mays
PubMed: 37439951
DOI: 10.1007/s00284-023-03391-0 -
Environmental Microbiology Oct 2022Strains Rhodococcus qingshengii djl-6 and Rhodococcus jialingiae djl-6-2 both harbour the typical carbendazim degradation pathway with the hydrolysis of carbendazim to...
Strains Rhodococcus qingshengii djl-6 and Rhodococcus jialingiae djl-6-2 both harbour the typical carbendazim degradation pathway with the hydrolysis of carbendazim to 2-aminobenzimidazole (2-AB) as the initial step. However, the enzymes involved in this process are still unknown. In this study, the previous reported carbendazim hydrolase MheI was found in strain djl-6, but not in strain djl-6-2, then another carbendazim hydrolase CbmA was obtained by a four-step purification strategy from strain djl-6-2. CbmA was classified as a member of the amidase signature superfamily with conserved catalytic site residues Ser157, Ser181, and Lys82, while MheI was classified as a member of the Abhydrolase superfamily with conserved catalytic site residues Ser77 and His224. The catalytic efficiency (k /K ) of MheI (24.0-27.9 μM min ) was 200 times more than that of CbmA (0.032-0.21 μM min ). The mheI gene (plasmid encoded) was highly conserved (>99% identity) in the strains from different bacterial genera and its plasmid encoded flanked by mobile genetic elements. The cmbA gene was highly conserved only in strains of the genus Rhodococcus and it was chromosomally encoded. Overall, the function, diversity, and distribution of carbendazim hydrolases MheI and CbmA will provide insights into the microbial degradation of carbendazim.
Topics: Amidohydrolases; Benzimidazoles; Carbamates; Hydrolases; Rhodococcus
PubMed: 35880585
DOI: 10.1111/1462-2920.16139 -
Food Chemistry Jul 2024We describe a simple and sensitive liquid-crystal (LC)-based method for quantifying carbendazim (CBZ) by exploiting aptamer-specific recognition at the aqueous-LC...
We describe a simple and sensitive liquid-crystal (LC)-based method for quantifying carbendazim (CBZ) by exploiting aptamer-specific recognition at the aqueous-LC interface. The method relies on the interfacial interaction between an aptamer and cetyltrimethylammonium bromide (CTAB); this interaction varies depending on the amount of CBZ. In the absence of CBZ, the aptamer disrupts the CTAB monolayer through electrostatic attraction, leading to a transition from homeotropic to tilted ordering of the LCs. As CBZ concentrations rise, the formation of aptamer-CBZ complexes increases, preserving the vertical alignment of the LCs by reducing collapse of the CTAB layer caused by electrostatic interactions. Using these methods, we achieved a CBZ detection limit of 3.12 pM (0.000597 μg/L) over a linear range of 0.05-5 nM. Moreover, we quantified CBZ levels in peach, soil, and tap water samples. Our LC-based detection method has significant research potential, offering sensitive, and straightforward detection of CBZ.
Topics: Liquid Crystals; Cetrimonium; Biosensing Techniques; Aptamers, Nucleotide; Water; Benzimidazoles; Carbamates
PubMed: 38394911
DOI: 10.1016/j.foodchem.2024.138789 -
Journal of Chemical Information and... Nov 2023Carbendazim derivatives, commonly used as antiparasitic drugs, have shown potential as anticancer agents due to their ability to induce cell cycle arrest and apoptosis...
Carbendazim derivatives, commonly used as antiparasitic drugs, have shown potential as anticancer agents due to their ability to induce cell cycle arrest and apoptosis in human cancer cells by inhibiting tubulin polymerization. Crystallographic structures of α/β-tubulin multimers complexed with nocodazole and mebendazole, two carbendazim derivatives with potent anticancer activity, highlighted the possibility of designing compounds that occupy both benzimidazole- and colchicine-binding sites. In addition, previous studies have demonstrated that the incorporation of a phenoxy group at position 5/6 of carbendazim increases the antiproliferative activity in cancer cell lines. Despite the significant progress made in identifying new tubulin-targeting anticancer compounds, further modifications are needed to enhance their potency and safety. In this study, we explored the impact of modifying the phenoxy substitution pattern on antiproliferative activity. Alchemical free energy calculations were used to predict the binding free energy difference upon ligand modification and define the most viable path for structure optimization. Based on these calculations, seven compounds were synthesized and evaluated against lung and colon cancer cell lines. Our results showed that compound , which incorporates an α-naphthyloxy substitution, exhibits the highest antiproliferative activity against both cancer lines (SK-LU-1 and SW620, IC < 100 nM) and induces morphological changes in the cells associated with mitotic arrest and mitotic catastrophe. Nevertheless, the tubulin polymerization assay showed that has a lower inhibitory potency than nocodazole. Molecular dynamics simulations suggested that this low antitubulin activity could be associated with the loss of the key H-bond interaction with V236. This study provides insights into the design of novel carbendazim derivatives with anticancer activity.
Topics: Humans; Tubulin Modulators; Molecular Structure; Structure-Activity Relationship; Nocodazole; Tubulin; Cell Proliferation; Molecular Docking Simulation; Antineoplastic Agents; Polymerization; Drug Screening Assays, Antitumor
PubMed: 37947759
DOI: 10.1021/acs.jcim.3c01379