Cyhalothrin biodegradation in Cunninghamella elegans

Palmer-Brown, William; Souza, Paula Letícia de Melo; Murphy, Cormac D.

doi:10.1007/s11356-018-3689-0

Cited by 38 publications

(13 citation statements)

References 27 publications

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“…The spectra are of supernatant (S/N) and biomass from cultures incubated with the pesticide at different time points. Figure 15 was reprinted from [ 106 ].…”

Section: Reviewmentioning

confidence: 99%

“…In our previous review [4], we highlighted 19 F NMR's usefulness in following the biodegradation of compounds such as fluorophenols and fluorobenzoates. The technique has since been applied to monitor the biotransformation/biodegradation of fluorinated drugs such as flurbiprofen [105], and the pesticide cyhalothrin [106] by the fungus Cunninghamella elegans. In the former, 19 F NMR demonstrated the appearance of phase 1 (oxidative) and phase 2 (conjugative) metabolites, and in the latter, it was possible to monitor the migration of the pesticide into the biomass in the first 24 h after its introduction before being biotransformed to new trifluoromethyl-containing metabolites (Figure 15).…”

Section: Metabolism Studies Biotransformation Of Fluorinated Xenobioticsmentioning

confidence: 99%

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¹⁹F NMR as a tool in chemical biology

Giménez¹,

Phelan²,

Murphy³

et al. 2021

Beilstein J. Org. Chem.

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We previously reviewed the use of 19F NMR in the broad field of chemical biology [Cobb, S. L.; Murphy, C. D. J. Fluorine Chem. 2009, 130, 132–140] and present here a summary of the literature from the last decade that has the technique as the central method of analysis. The topics covered include the synthesis of new fluorinated probes and their incorporation into macromolecules, the application of 19F NMR to monitor protein–protein interactions, protein–ligand interactions, physiologically relevant ions and in the structural analysis of proteins and nucleic acids. The continued relevance of the technique to investigate biosynthesis and biodegradation of fluorinated organic compounds is also described.

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“…The spectra are of supernatant (S/N) and biomass from cultures incubated with the pesticide at different time points. Figure 15 was reprinted from [ 106 ].…”

Section: Reviewmentioning

confidence: 99%

Section: Metabolism Studies Biotransformation Of Fluorinated Xenobioticsmentioning

confidence: 99%

¹⁹F NMR as a tool in chemical biology

Giménez¹,

Phelan²,

Murphy³

et al. 2021

Beilstein J. Org. Chem.

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“…However, we do not know much about the processes occurring in natural conditions with the participation of microorganisms. Cunninghamella elegans and Trametes versicolor are well known for their ability to eliminate different hazardous pollutants, including drugs, pesticides, dyes and personal care products [ 41 , 42 , 43 , 44 ]. Despite the fact that chloroxylenol is a micropollutant occurring in the natural environment, there is still little information available about its elimination and fate.…”

Section: Resultsmentioning

confidence: 99%

“…has the ability to biotransform pharmaceuticals and other xenobiotics by oxidation and conjugation reactions, forming compounds similar to those found in humans and other mammals. These fungi have been widely investigated as xenobiotic metabolism models in mammals [ 43 ]. In our work, we analysed the activity of CYP450 and cytochrome reductase (CRP) genes to evaluate the participation of these monooxygenase systems in the biodegradation of PCMX by C. elegans .…”

Section: Resultsmentioning

confidence: 99%

Biodegradation of Chloroxylenol by Cunninghamella elegans IM 1785/21GP and Trametes versicolor IM 373: Insight into Ecotoxicity and Metabolic Pathways

Nowak

Zawadzka

Szemraj

et al. 2021

IJMS

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Chloroxylenol (PCMX) is applied as a preservative and disinfectant in personal care products, currently recommended for use to inactivate the SARS-CoV-2 virus. Its intensive application leads to the release of PCMX into the environment, which can have a harmful impact on aquatic and soil biotas. The aim of this study was to assess the mechanism of chloroxylenol biodegradation by the fungal strains Cunninghamella elegans IM 1785/21GP and Trametes versicolor IM 373, and investigate the ecotoxicity of emerging by-products. The residues of PCMX and formed metabolites were analysed using GC-MS. The elimination of PCMX in the cultures of tested microorganisms was above 70%. Five fungal by-products were detected for the first time. Identified intermediates were performed by dechlorination, hydroxylation, and oxidation reactions catalysed by cytochrome P450 enzymes and laccase. A real-time quantitative PCR analysis confirmed an increase in CYP450 genes expression in C. elegans cells. In the case of T. versicolor, spectrophotometric measurement of the oxidation of 2,20-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) showed a significant rise in laccase activity during PCMX elimination. Furthermore, with the use of bioindicators from different ecosystems (Daphtoxkit F and Phytotoxkit), it was revealed that the biodegradation process of PCMX had a detoxifying nature.

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“…Previously we investigated the biotransformation of the fluorinated pyrethroid cyhalothrin in planktonic and biofilm cultures of C. elegans (Palmer-Brown et al 2019b ). In this paper we describe the biotransformation of the related pesticides transfluthrin and β-cyfluthrin by Cunninghamella fungi and compare the metabolites produced to those found in experiments with rat liver microsomes.…”

Section: Introductionmentioning

confidence: 99%

Cunninghamella spp. produce mammalian-equivalent metabolites from fluorinated pyrethroid pesticides

Khan

Murphy

2021

AMB Expr

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Cunninghamella spp. are fungi that are routinely used to model the metabolism of drugs. In this paper we demonstrate that they can be employed to generate mammalian-equivalent metabolites of the pyrethroid pesticides transfluthrin and β-cyfluthrin, both of which are fluorinated. The pesticides were incubated with grown cultures of Cunninghamella elegans, C. blakesleeana and C. echinulata and the biotransformation monitored using fluorine-19 nuclear magnetic resonance spectroscopy. Transfluthrin was initially absorbed in the biomass, but after 72 h a new fluorometabolite appeared in the supernatant; although all three species yielded this compound, it was most prominent in C. blakesleeana. In contrast β-cyfluthrin mostly remained in the fungal biomasss and only minor biotransformation was observed. Gas chromatography-mass spectrometry (GC–MS) analysis of culture supernatant extracts revealed the identity of the fluorinated metabolite of transfluthrin to be tetrafluorobenzyl alcohol, which arose from the cytochrome P450-catalysed cleavage of the ester bond in the pesticide. The other product of this hydrolysis, dichlorovinyl-2,2-dimethylcyclopropane carboxylic acid, was also detected by GC–MS and was a product of β-cyfluthrin metabolism too. Upon incubation with rat liver microsomes the same products were detected, demonstrating that the fungi can be used as models of mammalian metabolism of fluorinated pesticides.

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Cyhalothrin biodegradation in Cunninghamella elegans

Cited by 38 publications

References 27 publications

¹⁹F NMR as a tool in chemical biology

¹⁹F NMR as a tool in chemical biology

Biodegradation of Chloroxylenol by Cunninghamella elegans IM 1785/21GP and Trametes versicolor IM 373: Insight into Ecotoxicity and Metabolic Pathways

Cunninghamella spp. produce mammalian-equivalent metabolites from fluorinated pyrethroid pesticides

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Cyhalothrin biodegradation in Cunninghamella elegans

Cited by 38 publications

References 27 publications

19F NMR as a tool in chemical biology

19F NMR as a tool in chemical biology

Biodegradation of Chloroxylenol by Cunninghamella elegans IM 1785/21GP and Trametes versicolor IM 373: Insight into Ecotoxicity and Metabolic Pathways

Cunninghamella spp. produce mammalian-equivalent metabolites from fluorinated pyrethroid pesticides

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¹⁹F NMR as a tool in chemical biology

¹⁹F NMR as a tool in chemical biology