Bacterial production of hydroxylated and amidated metabolites of flurbiprofen

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Title: Bacterial production of hydroxylated and amidated metabolites of flurbiprofen
Authors: Bright, Tara V.
Clark, Benjamin R.
O'Brien, Eimear
Murphy, Cormac D.
Permanent link: http://hdl.handle.net/10197/4233
Date: Nov-2011
Abstract: Several Streptomyces and Bacillus strains were examined for their ability to transform the anti-inflammatory drug flurbiprofen 1 to the hydroxylated metabolites that are found in humans after ingestion of this compound. Of the seven Streptomyces spp. examined, all but one transformed flurbiprofen to the main mammalian metabolite 4′-hydroxyflurbiprofen 2, and the majority also produced 3′,4′-dihydroxyflurbiprofen 3. Three strains, Streptomyces griseus DSM40236 and ATCC13273, and Streptomyces subrutilis DSM40445, also elaborated 3′-methoxy, 4′-hydroxy-flurbiprofen 4. None of the Bacillus spp. examined yielded these metabolites. Examination of the extracted supernatants of Streptomyces lavenduligriseus and Streptomyces rimosus by fluorine-19 nuclear magnetic resonance (19F NMR), indicated new resonances and these new fluorometabolites were purified by HPLC and revealed to be flurbiprofenamide 5 and 7-hydroxyflurbiprofenamide 6 after MS and NMR analyses. Subsequent re-examination of the culture supernatants from Bacillus subtilis IM7, Bacillus megaterium NCIMB8291 and B. megaterium ATTC14581 showed that these strains also produced 5 and 6. Resting cell investigations suggested that the amidation reaction employed nitrogen from an as yet unidentified amino acid.
Type of material: Journal Article
Publisher: Elsevier
Copyright (published version): 2011 Elsevier B.V.
Keywords: F-19 NMR;Biotransformation;Fluorometabolite
DOI: 10.1016/j.molcatb.2011.05.008
Language: en
Status of Item: Peer reviewed
Appears in Collections:Biomolecular and Biomedical Science Research Collection

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