Production of anticancer polyenes through precursor-directed biosynthesis

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Title: Production of anticancer polyenes through precursor-directed biosynthesis
Authors: Clark, Benjamin R.
O'Connor, Stephen
Fox, Deirdre
Leroy, Jacques
Murphy, Cormac D.
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Date: Sep-2011
Abstract: The biosynthesis of the pyrrolyl moiety of the fungal metabolite rumbrin originates from pyrrole-2-carboxylic acid. In an effort to produce novel derivatives with enhanced biological activity a series of substituted pyrrole-2-carboxylates were synthesised and incubated with the producing organism, Auxarthron umbrinum. Several 4-halo-pyrrole-2-carboxylic acids were incorporated into the metabolite yielding three new derivatives: 3-fluoro-, 3-chloro- and 3-bromo-isorumbrin, which were generated in milligram quantities enabling cytotoxicity assays to be conducted. The 3-chloro- and 3-bromo-isorumbrins had improved activity against HeLa cells compared with rumbrin; 3-bromoisorumbrin also showed dramatically improved activity towards a lung cancer cell line (A549).
Type of material: Journal Article
Publisher: RSC Publishing
Copyright (published version): 2011, RSC Publishing
Keywords: BiosynthesisPolyenes
DOI: 10.1039/C1OB05667K
Language: en
Status of Item: Peer reviewed
Appears in Collections:Biomolecular and Biomedical Science Research Collection

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