One step N -glycosylation by filamentous fungi biofilm in bioreactor of a new phosphodiesterase-3 inhibitor tetrazole

Souza, Paula Letícia de Melo; Arruda, Evilanna Lima; Pazini, Francine; Menegatti, Ricardo; Vaz, Boniek G.; Lião, Luciano M.; Oliveira, Valéria de

doi:10.1016/j.bmcl.2016.04.085

Cited by 7 publications

(1 citation statement)

References 24 publications

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“…These fungi are known to catabolise fluorinated xenobiotics (Amadio et al 2010 ) and non-fluorinated pesticides such as diazinon (Zhao et al 2020 ) and fenitrothion (Zhu et al 2017 ). In addition, the fungi can form biofilms that can be applied to the continuous production of drug metabolites (Bianchini et al 2021 ; Souza et al 2016 ) and dye decolorisation (Hussain et al 2017 ).…”

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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Section: Introductionmentioning

confidence: 99%

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

Khan

Murphy

2021

AMB Expr

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Biotransformation of fluorinated drugs and xenobiotics by the model fungus Cunninghamella elegans

Khan,

Hof,

Niemcova

et al. 2024

Methods in Enzymology

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Regulation of Cunninghamella spp. biofilm growth by tryptophol and tyrosol

Khan

Saleem

Murphy

2021

Biofilm

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Fungi belonging to the genus Cunninghamella are often used as microbial models of mammalian metabolism owing to their ability to transform a range of xenobiotic compounds. Furthermore, under specific growth conditions species such as Cunninghamella elegans and Cunninghamella echinulata grow as biofilms enabling a convenient semi-continuous production of valuable drug metabolites. However, the molecular mechanism of biofilm regulation is not understood, thus controlling biofilm thickness limits the productive applications of it. In this paper we describe the identification of two molecules, tyrosol and tryptophol, that were identified in C. blakesleeana cultures, but not in C. elegans and C. echinulata . The molecules are known quorum sensing molecules (QSMs) in yeast and their potential role in Cunninghamella biofilm regulation was explored. Both were present in higher concentrations in C. blakesleeana planktonic cultures compared with biofilms; they inhibited the growth of the fungus on agar plates and selectively inhibited biofilm growth in liquid cultures. The molecules had a comparatively minor impact on the biofilm growth of C. elegans and C. echinulata and on the growth of these fungi on agar plates. Finally, when exogenous tyrosol or tryptophol was added to previously grown C. blakesleeana biofilm, detachment was visible and new additional planktonic culture was measured, confirming that these molecules specifically regulate biofilm growth in this fungus.

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One step N -glycosylation by filamentous fungi biofilm in bioreactor of a new phosphodiesterase-3 inhibitor tetrazole

Cited by 7 publications

References 24 publications

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

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

Biotransformation of fluorinated drugs and xenobiotics by the model fungus Cunninghamella elegans

Regulation of Cunninghamella spp. biofilm growth by tryptophol and tyrosol

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