A comparative study of the antiangiogenic activity of hydroxytyrosyl alkyl ethers

•A series of hydroxytyrosyl alkyl ethers show antiangiogenic potential in vitro.•Studied compounds inhibit endothelial cell growth, migration and tube formation.•Hydroxytyrosyl hexyl ether is a potent antiangiogenic compound in vitro and in vivo.•Hydroxytyrosyl hexyl ether induces apoptosis in endot...

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Published in:Food chemistry 2020-12, Vol.333, p.127476-127476, Article 127476
Main Authors: Marrero, Ana Dácil, Castilla, Laura, Espartero, José L., Madrona, Andrés, R. Quesada, Ana, Medina, Miguel Ángel, Martínez-Poveda, Beatriz
Format: Article
Language:English
Subjects:
Angiogenesis
Angiogenesis Inhibitors - pharmacology
Animals
Aorta
Apoptosis
Bovine aorta endothelial cells (BAEC)
Chorioallantoic membrane (CAM) assay
Endothelial Cells - drug effects
Endothelial Cells - physiology
Ethers - chemistry
Ethers - pharmacology
Hydroxytyrosyl alkyl ethers
Olive Oil - chemistry
Phenols - chemistry
Phenols - pharmacology
Phenylethyl Alcohol - analogs & derivatives
Phenylethyl Alcohol - chemistry
Phenylethyl Alcohol - pharmacology
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Summary:•A series of hydroxytyrosyl alkyl ethers show antiangiogenic potential in vitro.•Studied compounds inhibit endothelial cell growth, migration and tube formation.•Hydroxytyrosyl hexyl ether is a potent antiangiogenic compound in vitro and in vivo.•Hydroxytyrosyl hexyl ether induces apoptosis in endothelial cells. The phenolic compound hydroxytyrosol and its derivatives are responsible for some of the health benefits of the intake of virgin olive oil, having shown antiangiogenic properties. In this study, we explored the antiangiogenic potential of six synthetic hydroxytyrosyl alkyl ethers (HT C1, C2, C4, C6, C8 and C12). Our results showed that all compounds affected endothelial cell viability in vitro at low micromolar doses. In addition, compounds HT C1, C2, C4 and C6 inhibited endothelial cell migration and formation of tubular-like structures. In these assays, hydroxytyrosyl hexyl ether (HT C6) exhibited the most potent inhibitory activity in vitro, activating as well apoptosis in endothelial cells. Furthermore, the antiangiogenic activity of HT C6 was confirmed in vivo in the chick chorioallantoic membrane assay. Hence, we present hydroxytyrosol synthetic derivative HT C6 as a new antiangiogenic compound and as a good candidate for an antiangiogenic drug in the treatment of angiogenesis-dependent diseases.
ISSN:0308-8146
1873-7072
DOI:10.1016/j.foodchem.2020.127476