Assessing the toxicity of the benzamide fungicide zoxamide in zebrafish (Danio rerio): Towards an adverse outcome pathway for beta-tubulin inhibitors

Zhang, Xujia; Zhang, Peng; Perez‐Rodriguez, Veronica; Souders, Christopher L.; Martyniuk, Christopher J.

doi:10.1016/j.etap.2020.103405

Cited by 24 publications

(8 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Besides alkaloid-related metabolites, we found a higher accumulation of the metabolite benzamide in the fat bodies of larvae reared on T. harzianum-inoculated plants. Benzamides are amide derivatives of benzoic acid widely used as pesticides [72]. Treatment with benzamide chemicals has been related to an enhanced tissue lipid peroxidation and oxidative damage in juvenile catfish [73] and deformities in zebra fish embryos [74].…”

Section: Discussionmentioning

confidence: 99%

Cascading Effects of Root Microbial Symbiosis on the Development and Metabolome of the Insect Herbivore Manduca sexta L.

et al. 2021

View full text Add to dashboard Cite

Root mutualistic microbes can modulate the production of plant secondary metabolites affecting plant–herbivore interactions. Still, the main mechanisms underlying the impact of root mutualists on herbivore performance remain ambiguous. In particular, little is known about how changes in the plant metabolome induced by root mutualists affect the insect metabolome and post-larval development. By using bioassays with tomato plants (Solanum lycopersicum), we analyzed the impact of the arbuscular mycorrhizal fungus Rhizophagus irregularis and the growth-promoting fungus Trichoderma harzianum on the plant interaction with the specialist insect herbivore Manduca sexta. We found that root colonization by the mutualistic microbes impaired insect development, including metamorphosis. By using untargeted metabolomics, we found that root colonization by the mutualistic microbes altered the secondary metabolism of tomato shoots, leading to enhanced levels of steroidal glycoalkaloids. Untargeted metabolomics further revealed that root colonization by the mutualists affected the metabolome of the herbivore, leading to an enhanced accumulation of steroidal glycoalkaloids and altered patterns of fatty acid amides and carnitine-derived metabolites. Our results indicate that the changes in the shoot metabolome triggered by root mutualistic microbes can cascade up altering the metabolome of the insects feeding on the colonized plants, thus affecting the insect development.

show abstract

Section: Discussionmentioning

confidence: 99%

Cascading Effects of Root Microbial Symbiosis on the Development and Metabolome of the Insect Herbivore Manduca sexta L.

et al. 2021

View full text Add to dashboard Cite

show abstract

“…oxysporum β-tubulin ( Fo βT), compound 3e exhibited the best binding free energy (−47.07 kcal/mol) and docking outcome. β-tubulin polymerization inhibitor fungicides help induce mitotic arrest by binding to this enzyme . The interactions observed between 3e and Fo βT showed hydrophobic-type interactions with residues Val236, Cys239, Leu240, Leu246, Leu250, Leu253, Ile316, Ala352, and Ile368 (Figures b and S1b).…”

Section: Resultsmentioning

confidence: 95%

“…β-tubulin polymerization inhibitor fungicides help induce mitotic arrest by binding to this enzyme. 58 The interactions observed between 3e and FoβT showed hydrophobic-type interactions with residues Val236, Cys239, Leu240, Leu246, Leu250, Leu253, Ile316, Ala352, and Ile368 (Figures 5b and S1b). They presented polar-type interactions with residues Thr237, Gln245, Asn247, Ser248, Ans156, Ser314, Gln350, and Thr351.…”

Section: ■ Results and Discussionmentioning

confidence: 96%

Synthesis (Z) vs (E) Selectivity, Antifungal Activity against Fusarium oxysporum, and Structure-Based Virtual Screening of Novel Schiff Bases Derived from l-Tryptophan

et al. 2022

View full text Add to dashboard Cite

Schiff bases are widely used molecules due to their potential biological activity. In this manuscript, we presented the synthesis and NMR study of new enamine Schiff bases derived from l -tryptophan, showing that the Z-form of the enamine is the main tautomeric form for aliphatic precursors. The DFT-B3LYP methodology at the 6-311+G**(d,p) level suggested that the tautomeric imine forms are less stable than the corresponding enamine forms. Their isomerism depends on the formation of intramolecular hydrogen bonds and steric factors associated with the starting carbonyl precursors. The in vitro biological activity tests against Fusarium oxysporum revealed that acetylacetone derivatives are the most active agents (IC 50 < 0.9 mM); however, the antifungal activity could be disfavored by bulky groups on ester and enamine moieties. Finally, the structure-based virtual screening through molecular docking and MM-GBSA rescoring revealed that Schiff bases 3e , 3g , and 3j behave putatively as binders for target proteins involved in the life processes of F. oxysporum . In this sense, molecular dynamics analysis showed that the ligand–protein complexes have good stability with root-mean-square deviation (RMSD) values within the allowed range. Therefore, the present study paves the way for designing new antifungal compounds based on l -tryptophan-derived Schiff bases.

show abstract

“…In the Ectimar ® specification, etisazole hydrochloride is a broad-spectrum fungicide used to control trichophytosis and microsporosis in cattle, swine, and horses. Since some fungicides could have induced the hazardous effects such as genotoxic or teratogenic effects [8,9], it is required to review the other toxico-logical aspects of etisazole hydrochloride, thoroughly.…”

Section: Introductionmentioning

confidence: 99%

Establishment of Acceptable Daily Intakes (ADIs) and Risk Assessment for Ephedrine, Menichlopholan, Anacolin, and Etisazole Hydrochloride

Kim¹,

Kim²,

Choi³

et al. 2022

Korean Journal of Environmental Agriculture

View full text Add to dashboard Cite

BACKGROUND: Prior to implementing a positive list system (PLS), there is a need to establish acceptable daily intake (ADI) and maximum residue limit (MRL) for veterinary drugs that have been approved a few decades ago in South Korea. On top of that, chronic dietary exposure assessment of veterinary drug residues should be performed to determine whether the use of these veterinary drugs would cause health concerns or not. METHODS AND RESULTS: To establish the ADI, the relevant toxicological data were collected from evaluation reports issued by international organizations. A slightly modified global estimate of chronic dietary exposure (GECDE) model was employed in the exposure assessment owing to the limited residual data. Therefore, only the ADI of ephedrine was established due to insufficient data for the other veterinary drugs. Thus, instead of ADI, the threshold of toxicological concern (TTC) value was used for the other drugs. Lastly, the haz-ard index (HI) was calculated, except for etizazole hydrochloride, due to the potential of mutagenicity. CONCLUSION(S):The HI values of ephedrine, menichlopholan, and anacolin were found to be as high as 6.4%, suggesting that chronic dietary exposure to the residues from these uses was unlikely to be a public health concern. Further research for exposure assessment of veterinary drug residues should be performed using up-todate Korean national health and nutrition examination survey (KNHANES) food consumption data. In addition, all relevant available data sources should be utilized for identifying the potentials of toxicity.

show abstract

Assessing the toxicity of the benzamide fungicide zoxamide in zebrafish (Danio rerio): Towards an adverse outcome pathway for beta-tubulin inhibitors

Cited by 24 publications

References 23 publications

Cascading Effects of Root Microbial Symbiosis on the Development and Metabolome of the Insect Herbivore Manduca sexta L.

Cascading Effects of Root Microbial Symbiosis on the Development and Metabolome of the Insect Herbivore Manduca sexta L.

Synthesis (Z) vs (E) Selectivity, Antifungal Activity against Fusarium oxysporum, and Structure-Based Virtual Screening of Novel Schiff Bases Derived from l-Tryptophan

Establishment of Acceptable Daily Intakes (ADIs) and Risk Assessment for Ephedrine, Menichlopholan, Anacolin, and Etisazole Hydrochloride

Contact Info

Product

Resources

About