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. 2021 Dec;105(24):9359-9369.
doi: 10.1007/s00253-021-11675-3. Epub 2021 Nov 10.

Bacterial degradation of the anti-depressant drug fluoxetine produces trifluoroacetic acid and fluoride ion

Mohd Faheem Khan  1 , Cormac D Murphy  2
Affiliations

Bacterial degradation of the anti-depressant drug fluoxetine produces trifluoroacetic acid and fluoride ion

Mohd Faheem Khan et al. Appl Microbiol Biotechnol. 2021 Dec.

Abstract

Fluoxetine (FLX) is a blockbuster drug with annual sales in the billions of dollars. Its widespread use has resulted in its detection in water courses, where it impacts aquatic life. Investigations on the biodegradation of FLX by microorganisms are important, since augmentation of secondary wastewater treatment by an effective degrader may be one method of improving the drug's removal. In this paper, we demonstrate that common environmental bacteria can use FLX as a sole carbon and energy source. Investigations into the metabolites formed using fluorine-19 nuclear magnetic resonance spectroscopy (19F NMR) and gas chromatography-mass spectrometry indicated that the drug was initially hydrolysed to yield 4-(trifluoromethyl)phenol (TFMP) and 3-(methylamino)-1-phenylpropan-1-ol. Since the fluorometabolite accumulated, the bacteria presumably used the latter compound for carbon and energy. Further growth studies revealed that TFMP could also be used as a sole carbon and energy source and was most likely catabolised via meta-cleavage, since semialdehyde products were detected in culture supernatants. The final products of the degradation pathway were trifluoroacetate and fluoride ion; the former is a dead-end product and was not further catabolised. Fluoride ion most likely arises owing to spontaneous defluorination of the meta-cleavage products that were shown to be photolabile.Key points• Bacteria can use FLX and TFMP as sole carbon and energy sources for their growth.• Biodegradation produces fluorometabolites that were detected by 19F NMR and GC-MS.• Trifluoroacetic acid and fluoride ion were identified as end products.

Keywords: 4-(Trifluoromethyl)phenol; Biodegradation; Fluoride ion; Fluoxetine; Photodegradation; Trifluoroacetate.

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