PUBLICATION
Transformation products of fluoxetine formed by photodegradation in water and biodegradation in zebrafish embryos (Danio rerio)
- Authors
- Tisler, S., Zindler, F., Freeling, F., Nödler, K., Toelgyesi, L., Braunbeck, T., Zwiener, C.
- ID
- ZDB-PUB-190529-5
- Date
- 2019
- Source
- Environmental science & technology 53(13): 7400-7409 (Journal)
- Registered Authors
- Braunbeck, Thomas
- Keywords
- none
- MeSH Terms
-
- Animals
- Fluoxetine
- Photolysis
- Water
- Water Pollutants, Chemical*
- Zebrafish*
- PubMed
- 31136157 Full text @ Env. Sci. Tech.
Citation
Tisler, S., Zindler, F., Freeling, F., Nödler, K., Toelgyesi, L., Braunbeck, T., Zwiener, C. (2019) Transformation products of fluoxetine formed by photodegradation in water and biodegradation in zebrafish embryos (Danio rerio). Environmental science & technology. 53(13):7400-7409.
Abstract
The present study investigates the transformation of the antidepressant fluoxetine (FLX) by photo and biodegradation and shows similarities and differences in transformation products (TPs). TPs were identified using LC-high resolution mass spectrometry (LC-HRMS) with positive and negative electrospray ionization. In a sunlight simulator, photodegradation was carried out using ultra-pure water (pH 6, 8, and 10) and surface water (pH 8) to study the effect of direct and indirect photolysis, respectively. The well-known metabolite norfluoxetine (NFLX) proved to be a minor TP in photolysis (≥2% of degraded FLX). In addition, 26 TPs were detected, which were formed by cleavage of the phenolether bond (O-dealkylation) which primarily formed 3-(methylamino)-1-phenyl-1-propanol (TP 166) and 4-(trifluoromethyl)phenol (TFMP)), by hydroxylation of the benzyl moiety, by CF3 substitution to benzoic aldehyde/acid and by adduct formation at the amine group (N-acylation with aldehydes and carboxylic acids). Higher pH favors the neutral species of FLX and the neutral/anionic species of primary TPs and therefore photodegradation. In zebrafish embryos the bioconcentration factor of FLX was found to be 110, and about 1% of FLX taken up by the embryos was transformed to NFLX. Seven metabolites known from photodegradation and formed by hydrolysis, hydroxylation and N-acylation as well as three new metabolites formed by N-hydroxylation, N-methylation and attachment of an amine group were identified in zebrafish embryos. The study highlights the importance to consider a broad range of TPs of FLX in fresh water systems and in ecotoxicity tests and to include TP formation in both environmental processes and metabolism in organisms.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping