title: Enantioselective biodegradation of fluoxetine by the bacterial strain Labrys portucalensis F11.
abstract: 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.
authors.affiliation: 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.
authors.forename: Irina S
authors.initials: IS
authors.lastname: Moreira
authors.affiliation: 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.
authors.forename: Ana R
authors.initials: AR
authors.lastname: Ribeiro
authors.affiliation: Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP), Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal.
authors.forename: Carlos M
authors.initials: CM
authors.lastname: Afonso
authors.affiliation: 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.
authors.forename: Maria E
authors.initials: ME
authors.lastname: Tiritan
authors.affiliation: 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. Electronic address: plcastro@porto.ucp.pt.
authors.forename: Paula M L
authors.initials: PM
authors.lastname: Castro
mesh_terms: D020561:Alphaproteobacteria / Q000378:metabolism*; D001673:Biodegradation, Environmental; D018533:Biomass; D002244:Carbon / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005459:Fluorides / Q000032:analysis; D005473:Fluoxetine / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism
chemical_list: D005473:Fluoxetine; D002244:Carbon; C036139:norfluoxetine; D005459:Fluorides
keywords: Biodegradation; Enantioselectivity; Fluoxetine; Labrys portucalensis