1. Synthesis and antiangiogenic activity study of new hop chalcone Xanthohumol analogues.
- Author
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Nuti E, Bassani B, Camodeca C, Rosalia L, Cantelmo A, Gallo C, Baci D, Bruno A, Orlandini E, Nencetti S, Noonan DM, Albini A, and Rossello A
- Subjects
- Angiogenesis Inhibitors chemical synthesis, Angiogenesis Inhibitors chemistry, Apoptosis drug effects, Cell Adhesion drug effects, Cell Movement drug effects, Cell Proliferation drug effects, Cells, Cultured, Chalcone chemical synthesis, Chalcone chemistry, Dose-Response Relationship, Drug, Flavonoids chemical synthesis, Flavonoids chemistry, Humans, Molecular Structure, Propiophenones chemical synthesis, Propiophenones chemistry, Structure-Activity Relationship, Angiogenesis Inhibitors pharmacology, Chalcone pharmacology, Flavonoids pharmacology, Human Umbilical Vein Endothelial Cells drug effects, Neovascularization, Physiologic drug effects, Propiophenones pharmacology
- Abstract
Angiogenesis induction is a hallmark of cancer. Antiangiogenic properties of Xanthohumol (XN), a naturally occurring prenylated chalcone from hops, have been widely reported. Here we describe the synthesis and study the antiangiogenic activity in vitro of a series of XN derivatives, where different substituents on the B-ring of the chalcone scaffold were inserted. The new XN derivatives inhibited human umbilical-vein endothelial cell (HUVEC) proliferation, adhesion, migration, invasion and their ability to form capillary-like structures in vitro at 10 μM concentration. The preliminary results indicate that the phenolic OH group in R, present in natural XN, is not necessary for having antiangiogenic activity. In fact, the most effective compound from this series, 13, was characterized by a para-methoxy group in R and a fluorine atom in R
2 on B-ring. This study paves the way for future development of synthetic analogues of XN to be used as cancer angiopreventive and chemopreventive agents., (Copyright © 2017 Elsevier Masson SAS. All rights reserved.)- Published
- 2017
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