Assessment of the electronic structure and properties of trichothecene toxins using density functional theory

Appell, Michael; Bosma, Wayne B.

doi:10.1016/j.jhazmat.2015.01.051

Cited by 13 publications

(12 citation statements)

References 51 publications

(100 reference statements)

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“…Because all seven of the Devosia strains tested possessed the 3-keto- DON to 3-epi -DON reducing activity, despite the fact that several originate from environments where DON is not expected to be present, it is likely that the natural substrate of the enzyme is not 3-keto- DON but an intermediary metabolite produced by Devosia spp. that possesses a ketone group on a rigid skeleton resembling the constrained cyclopentane ring of trichothecenes 23 – 25 . The identification of the enzyme responsible for the reduction of 3-keto- DON to 3-epi -DON and the localization of its gene, perhaps within a biosynthetic pathway, might help unravel the biological function of this activity.…”

Section: Discussionmentioning

confidence: 99%

“…Secondary toxic effects of trichothecenes have been studied for decades 2 , 27 but the molecular mechanism of protein synthesis inhibition has only recently been unraveled 16 , explaining the essential role of the epoxide group and hydroxyl group on C3 in binding to the inside the peptidyl transfer center of the ribosome. While the spiro-attachment of the epoxide group prevents conformation flexibility, the hydroxyl group on C3 was predicted by molecular modeling to exhibit significant rotation 23 and multiple energetically equivalent conformations 24 . The loss of a hydrogen bond between the C3-hydroxyl and uracil residue 2869 of the ribosome might account for the loss of toxicity of 3-epi- DON in comparison to DON 28 .…”

Section: Discussionmentioning

confidence: 99%

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The enzymatic epimerization of deoxynivalenol by Devosia mutans proceeds through the formation of 3-keto-DON intermediate

Hassan

Perilla

et al. 2017

Sci Rep

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The enzymatic detoxification of deoxynivalenol (DON) is a promising mitigation strategy for addressing this mycotoxin contamination of cereal grains. A recently described bacterium, Devosia mutans 17-2-E-8, capable of transforming DON into its non-toxic stereoisomer 3-epi-DON, holds promise for the development of such applications. Earlier observations suggested that DON epimerization proceeds via a two-step catalysis with 3-keto-DON as an intermediate. The results of this study indicate that NADPH is required for DON epimerization by cell-free protein extracts of D. mutans, while high concentrations of glucose and sucrose have a suppressive effect. Chemically synthesized 3-keto-DON incubated with D. mutans protein fractions enriched by ammonium sulfate precipitation at 35–55% saturation selectively reduced 3-keto-DON to 3-epi-DON, but fell short of supporting the complete epimerization of DON. In addition, seven Devosia species investigated for DON epimerization were all able to reduce 3-keto-DON to 3-epi-DON, but only a few were capable of epimerizing DON. The above observations collectively confirm that the enzymes responsible for the oxidation of DON to 3-keto-DON are physically separate from those involved in 3-keto-DON reduction to 3-epi-DON. The enzymatic nature of DON epimerization suggests that the process could be used to develop genetically engineered crops or microorganisms, ultimately reducing foodborne exposure of consumers and farm animals to DON.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

The enzymatic epimerization of deoxynivalenol by Devosia mutans proceeds through the formation of 3-keto-DON intermediate

Hassan

Perilla

et al. 2017

Sci Rep

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“…It is well known that natural bond orbital (NBO) theory can be used to analyze optimal conformation and bond order of complicated organic molecules. 37 -39 For MG and its complicated degradation intermediates, NBO analysis was calculated on conformations optimized at B3LYP/6-311 + G * level. The optimized conformations of MG and leucomalachite green (LMG) are shown in Fig.…”

Section: Possible Degradation Pathways Of Mg Optimization and Theoretmentioning

confidence: 99%

Ag₃PO₄/TiO₂‐assisted degradation of malachite green in aqueous solution treated by dielectric barrier discharge plasma

Sun

Feng

2015

J of Chemical Tech & Biotech

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BACKGROUND: A new method of malachite green (MG) degradation by dielectric barrier discharge (DBD) plasma with an Ag 3 PO 4 /TiO 2 composite photocatalyst was investigated. Ag 3 PO 4 /TiO 2 was synthetized by an in situ precipitation method under room conditions, and analyzed by XRD, SEM, TEM, XRF and BET. The catalytic activity, the reaction mechanisms, the intermediates of MG degradation and the proposed degradation pathways were also evaluated.

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“…This method has previously been applied to several classes of molecules to elucidate the contributions of chemical structure to diverse activities. The method could evaluate the cytotoxicity, phytotoxicity, and detection reliability of structurally related trichothecene mycotoxins [14]. The method was recently applied to evaluate the antifungal properties of phenolic compounds against six types of mycotoxin-producing fungi [12].…”

Section: Introductionmentioning

confidence: 99%

“…The predictive models developed demonstrate the method and serve as tools to develop new antimicrobial compounds based on the triazolothiadiazine structure. This approach has proven successful for chalcones, phenolic compounds, coumarin derivatives, and other heterocyclic compounds [12,14,22].…”

Section: Introductionmentioning

confidence: 99%

Predictive Quantitative Structure–Activity Relationship Modeling of the Antifungal and Antibiotic Properties of Triazolothiadiazine Compounds

Appell

Compton

Evans

2020

MPs

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Predictive models were developed using two-dimensional quantitative structure activity relationship (QSAR) methods coupled with B3LYP/6-311+G** density functional theory modeling that describe the antimicrobial properties of twenty-four triazolothiadiazine compounds against Aspergillus niger, Aspergillus flavus and Penicillium sp., as well as the bacteria Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. B3LYP/6-311+G** density functional theory calculations indicated the triazolothiadiazine derivatives possess only modest variation between the frontier orbital properties. Genetic function approximation (GFA) analysis identified the topological and density functional theory derived descriptors for antimicrobial models using a population of 200 models with one to three descriptors that were crossed for 10,000 generations. Two or three descriptor models provided validated predictive models for antifungal and antibiotic properties with R2 values between 0.725 and 0.768 and no outliers. The best models to describe antimicrobial activities include descriptors related to connectivity, electronegativity, polarizability, and van der Waals properties. The reported method provided robust two-dimensional QSAR models with topological and density functional theory descriptors that explain a variety of antifungal and antibiotic activities for structurally related heterocyclic compounds.

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Assessment of the electronic structure and properties of trichothecene toxins using density functional theory

Cited by 13 publications

References 51 publications

The enzymatic epimerization of deoxynivalenol by Devosia mutans proceeds through the formation of 3-keto-DON intermediate

The enzymatic epimerization of deoxynivalenol by Devosia mutans proceeds through the formation of 3-keto-DON intermediate

Ag₃PO₄/TiO₂‐assisted degradation of malachite green in aqueous solution treated by dielectric barrier discharge plasma

Predictive Quantitative Structure–Activity Relationship Modeling of the Antifungal and Antibiotic Properties of Triazolothiadiazine Compounds

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Assessment of the electronic structure and properties of trichothecene toxins using density functional theory

Cited by 13 publications

References 51 publications

The enzymatic epimerization of deoxynivalenol by Devosia mutans proceeds through the formation of 3-keto-DON intermediate

The enzymatic epimerization of deoxynivalenol by Devosia mutans proceeds through the formation of 3-keto-DON intermediate

Ag3PO4/TiO2‐assisted degradation of malachite green in aqueous solution treated by dielectric barrier discharge plasma

Predictive Quantitative Structure–Activity Relationship Modeling of the Antifungal and Antibiotic Properties of Triazolothiadiazine Compounds

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Ag₃PO₄/TiO₂‐assisted degradation of malachite green in aqueous solution treated by dielectric barrier discharge plasma