Trifluoromethyl Phenol Research Articles

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

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.

Prozac® removal promoted by HAP:Nb2O5 nanoparticles system: by‐products, mechanism, and cytotoxicity assessment

The elucidation of photocatalysis and adsorption mechanisms in the pollutant removal, as well as the efficiency for each process, provide key information for polluted water remediation. In this respect, the present study analyzed the application of nanomaterials based on niobium pentoxide (Nb2O5) and hydroxyapatite (HAP) during Prozac® and 4-(trifluoromethyl)phenol (TFMP) photodegradation. Removals for Prozac® and TFMP were respectively 93% after 2 min and 64% after 5 min. The photodegradation kinetic constants by Nb2O5 nanoparticles were 2.1 min‐1 (R2 = 0.943) and 0.185 min‐1 (R2 = 0.994), respectively, for Prozac® and TFMP, using a Hg-MDEL reactor operating at 70 W microwave power. A detailed study of the mechanisms for Prozac® and TFMP photodegradation was carried out, confirming that the adsorptive, oxidative, and photolytic processes work together to remove and/or convert the compounds into by-products. Therefore, Prozac® and the main by-products were quantified, and the cytotoxicity response was evaluated using the Lepidium sativum and Allium cepa plants. The results showed that 3-phenyl-propyl-methylamine (PPMA) by-product was more toxic than Prozac® to plant growth, exhibiting seed seability of 4% (PPMA), 33% (Prozac®), 77% (α-[2-(Methylamino) ethyl] benzyl-alcohol, MAEB), and 81% (TFMP). Furthermore, the presence of these contaminants may increase phytotoxicity at the cellular level, fostering mutation, and cell death.

An in vivo evaluation of the ontogeny of stereoselective fluoxetine metabolism and disposition in lambs from birth to one year of age

1. The objective was to determine the ontogeny of stereoselective fluoxetine (FX) disposition in postnatal sheep from newborn to adulthood.2. Catheters were implanted in a carotid artery and jugular vein. FX was administered intravenously, followed by serial arterial blood and cumulative urine collection. The concentrations of R,S-FX and R,S-norfluoxetine (R,S-NFX) in samples were measured using a validated enantioselective LC/MS/MS analytical method.3. The metabolism of FX at 4.2 ± 0.4 days was limited compared to adults, but had developed compared to the fetus. Total body clearance (ClTB) did not significantly increase up to 33.6 ± 0.9 days, but significantly increased at 98.5 ± 2.0 days, with no further changes up to 397.3 ± 8.5 days. Up to 13.4 ± 0.8 days, the disposition of FX included Phase I metabolism to NFX and trifluoromethylphenol (TFMP), and renal elimination. At 32.9 ± 0.9 days, metabolism included Phase II conjugates of FX and NFX. Renal elimination of these compounds was low.4. The elimination of FX increased in a non-linear manner during the first year in sheep. The metabolism and disposition of FX and NFX in plasma and urine were stereoselective and this appeared due to both stereoselective protein binding and metabolism.

The Rate of Excited-state Proton Transfer to Solvent from Trifluoromethylphenols in Water

Abstract The proton-transfer reactions to solvent from electronically excited o-, m-, and p-(trifluoromethyl)phenols (TFOHs) in water have been investigated by picosecond time-resolved fluorescence measurements. The rate constants for the proton dissociation of o-, m-, and p-TFOH are obtained to be 2.2×109, 8.6×108, and 2.5×108 s−1, respectively. On the basis of the rate constants, the effects of substituent and deuterium isotope effects on the proton-transfer reactions are revealed.