title: Endophytic fungi as models for the stereoselective biotransformation of thioridazine.
abstract: The stereoselective kinetic biotransformation of thioridazine, a phenothiazine neuroleptic drug, by endophytic fungi was investigated. In general, the sulfur of lateral chain (position 2) or the sulfur of phenothiazinic ring (position 5) were oxidated yielding the major human metabolites thioridazine-2-sulfoxide and thioridazine-5-sulfoxide. The quantity of metabolites biosynthesized varied among the 12 endophytic fungi evaluated. However, mono-2-sulfoxidation occurred in higher ratio and frequency. Among the 12 fungi evaluated, 4 of them deserve prominence for presenting an evidenced stereoselective biotransformation: Phomopsis sp. (TD2), Glomerella cingulata (VA1), Diaporthe phaseolorum (VR4), and Aspergillus fumigatus (VR12). Both enantiomers of thioridazine were consumed by the fungi; however, the 2-sulfoxidation yielded preferentially the R configuration at the sulfur atom.
authors: Departament of Physics and Chemistry, Faculty of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Ribeirão Preto, Brazil.
authors: Keyller Bastos
authors: KB
authors: Borges
authors: Warley De Souza
authors: Wde S
authors: Borges
authors: Mônica Tallarico
authors: MT
authors: Pupo
authors: Pierina Sueli
authors: PS
authors: Bonato
mesh_terms: D001203:Ascomycota / Q000378:metabolism*; D001232:Aspergillus fumigatus / Q000378:metabolism*; D001711:Biotransformation; D020081:Phyllachorales / Q000378:metabolism; D013237:Stereoisomerism; D013881:Thioridazine / Q000737:chemistry / Q000378:metabolism*
chemical_list: D013881:Thioridazine