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Molecules 2017, 22(7), 1124; doi:10.3390/molecules22071124

Substituted Caffeic and Ferulic Acid Phenethyl Esters: Synthesis, Leukotrienes Biosynthesis Inhibition, and Cytotoxic Activity

Department of Chemistry and Biochemistry, Université de Moncton, Moncton, NB E1A 3E9, Canada
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Received: 21 June 2017 / Revised: 4 July 2017 / Accepted: 4 July 2017 / Published: 6 July 2017
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Glioblastoma multiforme (GBM) is an aggressive brain tumor that correlates with short patient survival and for which therapeutic options are limited. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE, 1a), have been investigated for their anticancer properties in several types of cancer. To further explore these properties in brain cancer cells, a series of caffeic and ferulic acid esters bearing additional oxygens moieties (OH or OCH3) were designed and synthesized. (CAPE, 1a), but not ferulic acid phenethyl ester (FAPE, 1b), displayed substantial cytotoxicity against two glioma cell lines. Some but not all selected compounds derived from both (CAPE, 1a) and (FAPE, 1b) also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO), however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Molecular docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds. Overall, this work highlights the relevance of exploring polyphenolic compounds in cancer models and provides additional leads in the development of novel therapeutic strategies in gliomas. View Full-Text
Keywords: glioblastoma multiforme; 5-lipoxygenase; temozolomide; polyphenols glioblastoma multiforme; 5-lipoxygenase; temozolomide; polyphenols
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MDPI and ACS Style

Morin, P.; St-Coeur, P.-D.; Doiron, J.A.; Cormier, M.; Poitras, J.J.; Surette, M.E.; Touaibia, M. Substituted Caffeic and Ferulic Acid Phenethyl Esters: Synthesis, Leukotrienes Biosynthesis Inhibition, and Cytotoxic Activity. Molecules 2017, 22, 1124.

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