Biodegradation of the analgesic naproxen by Trametes versicolor and identification of intermediates using HPLC-DAD-MS and NMR.
The white-rot fungus Trametes vesicolor degraded naproxen (10 mg L(-1)) in a liquid medium to non-detectable levels after 6h. When naproxen was added in the range of concentrations typically found in the environment (55 microg L(-1)), it was almost completely degraded (95%) after 5h. In vitro degradation experiments with purified laccase and purified laccase plus mediator 1-hydroxybenzotriazol showed slight and almost complete naproxen degradation, respectively. A noticeable inhibition on naproxen degradation was also observed when the cytochrome P450 inhibitor 1-aminobenzotriazole was added to the fungal cultures. These data suggest that both enzymatic systems could play a role in naproxen degradation. 2-(6-hydroxynaphthalen-2-yl)propanoic acid and 1-(6-methoxynaphthalen-2-yl)ethanone were structurally elucidated by HPLC-DAD-MS and NMR as degradation intermediates of naproxen. After 6h of incubation, both parent compound and intermediates disappeared from the medium. The non-toxicity of the treated medium was confirmed by Microtox test.
Marco-Urrea
Ernest
E
Departament d'Enginyeria Química, Institut de Ciència i Tecnologia Ambiental, Universitat Autònoma de Barcelona (UAB), 08193 Bellaterra, Spain.
Pérez-Trujillo
Miriam
M
Blánquez
Paqui
P
Vicent
Teresa
T
Caminal
Gloria
G
D048908:Aliivibrio fischeri / Q000187:drug effects; D000700:Analgesics / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity; D001673:Biodegradation, Environmental / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D042845:Laccase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods*; D053858:Metabolic Networks and Pathways / Q000187:drug effects; D009288:Naproxen / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity; D013997:Time Factors; D018675:Toxicity Tests; D055454:Trametes / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism*; D014230:Triazoles / Q000494:pharmacology
D000700:Analgesics; D065607:Cytochrome P-450 Enzyme Inhibitors; D014230:Triazoles; C033020:1-aminobenzotriazole; D009288:Naproxen; D003577:Cytochrome P-450 Enzyme System; D042845:Laccase