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.
Murphy, Cormac D.
|Permanent link:||http://hdl.handle.net/10197/4233||Date:||Nov-2011||Online since:||2013-04-08T15:13:01Z||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||Journal:||Journal of Molecular Catalysis B : Enzymatic||Volume:||72||Issue:||3-4||Start page:||116||End page:||121||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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