Moreira Irina S, Ribeiro Ana R, Afonso Carlos M, Tiritan Maria E, Castro Paula M L
CBQF - Centro de Biotecnologia e Química Fina- Laboratório Associado, Escola Superior de Biotecnologia, Universidade Católica Portuguesa/Porto, Rua Dr. António Bernardino de Almeida, 4200-072 Porto, Portugal.
CBQF - Centro de Biotecnologia e Química Fina- Laboratório Associado, Escola Superior de Biotecnologia, Universidade Católica Portuguesa/Porto, Rua Dr. António Bernardino de Almeida, 4200-072 Porto, Portugal; Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP), Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal; CESPU, Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde, Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal.
Chemosphere. 2014 Sep;111:103-11. doi: 10.1016/j.chemosphere.2014.03.022. Epub 2014 Apr 19.
Fluoxetine (FLX) is a chiral fluorinated pharmaceutical indicated mainly for the treatment of depression and is one of the most dispensed drugs in the world. There is clear evidence of environmental contamination with this drug and its active metabolite norfluoxetine (NFLX). In this study the enantioselective biodegradation of racemic FLX and of its enantiomers by Labrys portucalensis strain F11 was assessed. When 2μM of racemic FLX was supplemented as sole carbon source, complete removal of both enantiomers, with stoichiometric liberation of fluoride, was achieved in 30d. For racemic FLX concentration of 4 and 9μM, partial degradation of the enantiomers was obtained. In the presence of acetate as an additional carbon source, at 4, 9 and 21μM of racemic FLX and at 25μM of racemic FLX, (S)-FLX or (R)-FLX, complete degradation of the two enantiomers occurred. At higher concentrations of 45 and 89μM of racemic FLX, partial degradation was achieved. Preferential degradation of the (R)-enantiomer was observed in all experiments. To our knowledge, this is the first time that enantioselective biodegradation of FLX by a single bacterium is reported.
氟西汀（FLX）是一种手性氟化药物，主要用于治疗抑郁症，是世界上处方量最大的药物之一。有明确证据表明该药物及其活性代谢产物去甲氟西汀（NFLX）对环境造成了污染。在本研究中，评估了葡萄牙拉布立酶菌F11菌株对消旋氟西汀及其对映体的对映选择性生物降解。当添加2μM消旋氟西汀作为唯一碳源时，在30天内实现了两种对映体的完全去除，并化学计量地释放出氟化物。对于4μM和9μM的消旋氟西汀浓度，对映体发生了部分降解。在存在乙酸作为额外碳源的情况下，对于4μM、9μM和21μM的消旋氟西汀以及25μM的消旋氟西汀、（S）-氟西汀或（R）-氟西汀，两种对映体都发生了完全降解。在45μM和89μM的更高消旋氟西汀浓度下，实现了部分降解。在所有实验中都观察到了（R）-对映体的优先降解。据我们所知，这是首次报道单一细菌对氟西汀的对映选择性生物降解。
