Bacterial production of hydroxylated and amidated metabolites of flurbiprofen

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dc.contributor.authorBright, Tara V.-
dc.contributor.authorClark, Benjamin R.-
dc.contributor.authorO'Brien, Eimear-
dc.contributor.authorMurphy, Cormac D.- Elsevier B.V.en
dc.identifier.citationJournal of Molecular Catalysis B : Enzymaticen
dc.description.abstractSeveral 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.en
dc.rightsThis is the author’s version of a work that was accepted for publication in Journal of Molecular Catalysis B: Enzymatic. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Molecular Catalysis B: Enzymatic (Volume 72, Issues 3–4, November 2011) DOI:10.1016/j.molcatb.2011.05.008 Elsevier B.V.en
dc.subjectF-19 NMRen
dc.titleBacterial production of hydroxylated and amidated metabolites of flurbiprofenen
dc.typeJournal Articleen
dc.internal.availabilityFull text availableen
dc.statusPeer revieweden
dc.neeo.contributorBright|Tara V.|aut|-
dc.neeo.contributorClark|Benjamin R.|aut|-
dc.neeo.contributorMurphy|Cormac D.|aut|-
dc.description.adminAuthor has checked copyrighten
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