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首页> 外文期刊>Environmental Science & Technology >Transformation Products of Fluoxetine Formed by Photodegradation in Water and Biodegradation in Zebrafish Embryos (Danio rend)
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Transformation Products of Fluoxetine Formed by Photodegradation in Water and Biodegradation in Zebrafish Embryos (Danio rend)

机译：水中光降解和斑马鱼胚胎生物降解形成氟西汀的转化产物（达尼奥·伦德）

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摘要

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 with positive and negative electrospray ionization. In a sunlight simulator, photodegradation was carried out using ultrapure 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, 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 of considering 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.
机译：本研究调查了通过光降解和生物降解法对抗抑郁药氟西汀（FLX）的转化，并显示了转化产物（TPs）的异同。使用具有正电喷雾和负电喷雾电离的LC高分辨率质谱法鉴定了TP。在阳光模拟器中，分别使用超纯水（pH 6、8和10）和地表水（pH 8）进行光降解，以研究直接和间接光解的效果。众所周知，代谢产物去氟西汀（NFLX）在光解中是次要的TP（<=降解FLX的2％）。此外，检测到26个TP，它们是通过裂解主要形成3-（甲基氨基）-1-苯基-1-丙醇（TP 166）和4-（三氟甲基）苯酚的酚醚键（O-脱烷基）形成的，通过苄基部分的羟基化，CF3取代为苯甲酸醛/酸，以及在胺基上形成加合物（与醛和羧酸进行N-酰化）。较高的pH值有利于FLX的中性物种和初级TP的中性/阴离子物种，因此有利于光降解。在斑马鱼的胚胎中，发现FLX的生物浓缩因子为110，并且胚胎吸收的FLX的约1％被转化为NFLX。在斑马鱼的胚胎中鉴定出了七种通过光降解已知的代谢物，它们是通过水解，羟基化和N-酰化形成的，还有三种新的代谢物是通过N-羟基化，N-甲基化和氨基的附着形成的。这项研究强调了在淡水系统和生态毒性测试中考虑广泛的FLX TP的重要性，并包括环境过程和生物体内新陈代谢中TP的形成。

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  • 来源
    《Environmental Science & Technology》 |2019年第13期|7400-7409|共10页
  • 作者

    Tisler Selina; Zindler Florian; Freeling Finnian; Noedler Karsten; Toelgyesi Laszlo; Braunbeck Thomas; Zwiener Christian;

  • 作者单位

    Univ Tubingen, ZAG, Environm Analyt Chem, Holderlinstr 12, D-72074 Tubingen, Germany;

    Heidelberg Univ, Ctr Organismal Studies, Aquat Ecol & Toxicol, Neuenheimer Feld 504, D-69120 Heidelberg, Germany;

    TZW DVGW Technol Zentrum Wasser, D-76139 Karlsruhe, Germany;

    TZW DVGW Technol Zentrum Wasser, D-76139 Karlsruhe, Germany;

    Agilent Technol, D-76337 Waldbronn, Germany;

    Heidelberg Univ, Ctr Organismal Studies, Aquat Ecol & Toxicol, Neuenheimer Feld 504, D-69120 Heidelberg, Germany;

    Univ Tubingen, ZAG, Environm Analyt Chem, Holderlinstr 12, D-72074 Tubingen, Germany;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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