Selectivity of diacylhydrazine insecticides to the predatory bug <i>Orius laevigatus: in vivo</i> and modelling/docking experiments

Amor, F.; Christiaens, Olivier; Bengochea, Paloma; Medina, Pilar; Rougé, Pierre; Viñuela, Elisa; Smagghe, Guy

doi:10.1002/ps.3353

Cited by 9 publications

(12 citation statements)

References 52 publications

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“…We used the T. castaneum structure as a template by accounting for its phylogenetic relationship with that suggested in the phylogenetic tree; however, we also modelled the F. auricularia EcR‐LBD based on B. tabaci structure as a control. As previously reported (Soin et al ., 2009; Amor et al ., 2012), different solutions resulted from the docking of tebufenozide to the ecdysone‐binding site of TcEcR‐LBD. A solution that seems to be particularly relevant includes the binding of the ethyl‐phenyl ring (B ring of the DBH) of the agonist in a cavity, which extends the binding site of TcEcR‐LBD to a location that is opposite to the cavity that harbours the alkyl chain of the ecdysteroid (Fig.…”

Section: Resultsmentioning

confidence: 99%

Structural changes under low evolutionary constraint may decrease the affinity of dibenzoylhydrazine insecticides for the ecdysone receptor in non‐lepidopteran insects

Zotti

Christiaens

Rougé

et al. 2012

Insect Molecular Biology

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Understanding how variations in genetic sequences are conveyed into structural and biochemical properties is of increasing interest in the field of molecular evolution. In order to gain insight into this process, we studied the ecdysone receptor (EcR), a transcription factor that controls moulting and metamorphosis in arthropods. Using an in silico homology model, we identified a region in the lepidopteran EcR that has no direct interaction with the natural hormone but is under strong evolutionary constraint. This region causes a small indentation in the three-dimensional structure of the protein which facilitates the binding of tebufenozide. Non-Mecopterida are considered much older, evolutionarily, than Lepidoptera and they do not have this extended cavity. This location shows differences in evolutionary constraint between Lepidoptera and other insects, where a much lower constraint is observed compared with the Lepidoptera. It is possible that the higher flexibility seen in the EcR of Lepidoptera is an entirely new trait and the higher constraint could then be an indication that this region does have another important function. Finally, we suggest that Try123, which is evolutionarily constrained and is up to now exclusively present in Lepidoptera EcRs, could play a critical role in discriminating between steroidal and non-steroidal ligands.

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Section: Resultsmentioning

confidence: 99%

Structural changes under low evolutionary constraint may decrease the affinity of dibenzoylhydrazine insecticides for the ecdysone receptor in non‐lepidopteran insects

Zotti

Christiaens

Rougé

et al. 2012

Insect Molecular Biology

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Section: Level 3: Individual Amino Acid Residue Comparisonmentioning

confidence: 98%

“…Diacylhydrazines, including methoxyfenozide, were discovered in the 1980s, followed by the commercial analog, tebufenozide (Carlson et al, 2001 Diacylhydrazine (DAH) and bisacylhydrazine (BAH) chemicals (e.g., methoxyfenozide and tebufenozide, respectively), also known as molt-accelerating compounds, act as nonsteroidal agonists of the ecdysteroid receptor (EcR) (Amor et al, 2012). Molting is a necessary process for normal growth and development in insects and other invertebrates.…”

Section: Case Example 1: Susceptibility Of Beneficial Insects To Moltmentioning

confidence: 99%

“…For the Level 2 assessment of functional domain(s), the NCBI CDD displays two specific hits for the tobacco budworm EcR, the ligand binding domain (accession cd06938) and the for cross species evaluation as both methoxyfenozide and tebufenozide have been shown to interact via the LBD (Carmichael et al, 2005;Amor et al, 2012). From this evaluation, selecting the 2 nd local minimum for the same reason described above and therefore placing the susceptibility cut-off at 45.8, SeqAPASS data predict that species within the Insecta, Merostomata, Malacostraca, Arachnida, Branchiopoda, Chilopoda, Maxillopoda, and Priapulidae (marine worm) classes would likely be susceptible to chemicals that interact with the LBD of the tobacco budworm (Figure 2b).…”

Section: Level 2: Functional Domain Analysismentioning

confidence: 99%

“…Toxicity assays exposing Insidious flower bug to molt-accelerating compounds, including methoxyfenozide and tebufenozide, showed that this Hemiptera insect is insensitive to these types of chemicals (Amor et al, 2012). Exposure methoxyfenozide or tebufenozide did not cause decreased survival or sublethal effects on reproductive parameters (Amor et al, 2012). Followup homology modeling of the flower bug EcR LBD and docking studies with both chemicals revealed steric hindrance caused by isoleucine 55 (I55), essentially preventing interaction with tebufenozide (Amor et al, 2012).…”

Section: Level 3: Individual Amino Acid Residue Comparisonmentioning

confidence: 99%

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Editor’s Highlight: Sequence Alignment to Predict Across Species Susceptibility (SeqAPASS): A Web-Based Tool for Addressing the Challenges of Cross-Species Extrapolation of Chemical Toxicity

LaLone

Villeneuve

Lyons³

et al. 2016

Toxicol. Sci.

123

108

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Conservation of a molecular target across species can be used as a line-of-evidence to predict the likelihood of chemical susceptibility. The web-based Sequence Alignment to Predict Across Species Susceptibility (SeqAPASS; https://seqapass.epa.gov/seqapass/) application was developed to simplify, streamline, and quantitatively assess protein sequence/structural similarity across taxonomic groups as a means to predict relative intrinsic susceptibility. The intent of the tool is to allow for evaluation of any potential protein target while remaining amenable to variable degrees of protein characterization, in the context of available information about the chemical/protein interaction and the molecular target itself. To accommodate this flexibility in the analysis, 3 levels of evaluation were developed. The first level of the SeqAPASS analysis compares primary amino acid sequences to a query sequence, calculating a metric for sequence similarity (including detection of orthologs); the second level evaluates sequence similarity within selected functional domains (eg, ligand-binding domain); and the third level of analysis compares individual amino acid residue positions of importance for protein conformation and/or interaction with the chemical upon binding. Each level of the SeqAPASS analysis provides additional evidence to apply toward rapid, screening-level assessments of probable cross species susceptibility. Such analyses can support prioritization of chemicals for further evaluation, selection of appropriate species for testing, extrapolation of empirical toxicity data, and/or assessment of the cross-species relevance of adverse outcome pathways. Three case studies are described herein to demonstrate application of the SeqAPASS tool: the first 2 focused on predictions of pollinator susceptibility to molt-accelerating compounds and neonicotinoid insecticides, and the third on evaluation of cross-species susceptibility to strobilurin fungicides. These analyses illustrate challenges in species extrapolation and demonstrate the broad utility of SeqAPASS for risk-based decision making and research.

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Demographic parameters of the insecticide-exposed predator Podisus nigrispinus: implications for IPM

et al. 2014

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Selectivity of diacylhydrazine insecticides to the predatory bug Orius laevigatus: in vivo and modelling/docking experiments

Cited by 9 publications

References 52 publications

Structural changes under low evolutionary constraint may decrease the affinity of dibenzoylhydrazine insecticides for the ecdysone receptor in non‐lepidopteran insects

Structural changes under low evolutionary constraint may decrease the affinity of dibenzoylhydrazine insecticides for the ecdysone receptor in non‐lepidopteran insects

Editor’s Highlight: Sequence Alignment to Predict Across Species Susceptibility (SeqAPASS): A Web-Based Tool for Addressing the Challenges of Cross-Species Extrapolation of Chemical Toxicity

Demographic parameters of the insecticide-exposed predator Podisus nigrispinus: implications for IPM

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