Biotransformation of fluorophenyl pyridine carboxylic acids by the model fungus Cunninghamella elegans

Abstract

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19F NMR as a tool in chemical biology

“…biotransformation of drug-like fluorophenylpyridine carboxylic acids in the same fungus [107]. However, aside from these few examples, the technique is not widely used by those investigating the biodegradation of fluorinated xenobiotics, with researchers more commonly relying on liquid or gas chromatography-mass spectrometry methods.…”

Enzymatic synthesis of fluorinated compounds

“…Therefore, the exploration has never stopped for the role of fluorine in drug design since the first fluorinated drug (9α-fluoro-substituted corticosteroid fludrocortisone) was approved in the 1950s (Fried and Sabo 1954 ). Nowadays, fluorine functional groups are contained in more than 25–30% of drugs, such as mefloquine, teriflunomide, citalopram, sorafenib, efavirenz, tedizolid phosphate, donepezil, and vorapaxar (Adler et al 2019 ; Izquierdo et al 2019 ; Khosravan et al 2017 ; Markakis et al 2020 ; Mei et al 2019 , 2020b ; Palmer-Brown et al 2017 ; Zhang et al 2020b ).…”

Aryl (β,β′,β″-Trifluoro)-tert-butyl: A Candidate Motif for the Discovery of Bioactives

“…There is a growing concern regarding persistent fluorochemicals, and it is becoming increasingly important that any new motifs that contain fluorine should be able to metabolize . To this end we have explored the metabolism of both tert -butylbenzene 38 as a control and then 18 in cultures of Cunninghamella elegans , a fungus that has been used to model human metabolism, as it is rich in P-450 activity . Aliquots of 38 and 18 were subject to incubations with C. elegans under previously established protocols (see the SI).…”

“… 22 To this end we have explored the metabolism of both tert -butylbenzene 38 as a control and then 18 in cultures of Cunninghamella elegans , a fungus that has been used to model human metabolism, as it is rich in P-450 activity. 23 Aliquots of 38 and 18 were subject to incubations with C. elegans under previously established protocols (see the SI ). After up to three days of incubation, the fungal culture supernatants were extracted into ethyl acetate.…”