N-Caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors

Michalet, Serge, Cartier, Gilbert, David, Bruno, Mariotte, Anne-Marie, Dijoux-Franca, Marie-Geneviève, Kaatz, Glenn W., Stavri, Michael and Gibbons, Simon (2007) N-Caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors. Bioorganic & Medicinal Chemistry Letters, 17 (6). pp. 1755-1758. ISSN 0960-894X

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As part of an ongoing project to identify plant natural products as efflux pump inhibitors (EPIs), bioassay-guided fractionation of the methanolic extract of Mirabilis jalapa Linn. (Nyctaginaceae) led to the isolation of an active polyphenolic amide: N-trans-feruloyl 4′-O-methyldopamine. This compound showed moderate activity as an EPI against multidrug-resistant (MDR) Staphylococcus aureus overexpressing the multidrug efflux transporter NorA, causing an 8-fold reduction of norfloxacin MIC at 292 μM (100 μg/mL). This prompted us to synthesize derivatives in order to provide structure–activity relationships and to access more potent inhibitors. Among the synthetic compounds, some were more active than the natural compound and N-trans-3,4-O-dimethylcaffeoyl tryptamine showed potentiation of norfloxacin in MDR S. aureus comparable to that of the standard reserpine.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 19 Jun 2020 00:07
Last Modified: 22 Oct 2022 06:20
URI: https://ueaeprints.uea.ac.uk/id/eprint/75701
DOI: 10.1016/j.bmcl.2006.12.059

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