Synthesis and antiangiogenic activity study of new hop chalcone Xanthohumol analogues

Elisa Nuti, Barbara Bassani, Caterina Camodeca, Lea Rosalia, AnnaRita Cantelmo, Cristina Gallo, Denisa Baci, Antonino Bruno, Elisabetta Orlandini, Susanna Nencetti, Douglas M Noonan, Adriana Albini, Armando Rossello

Research output: Contribution to journalArticlepeer-review

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 R2on B-ring. This study paves the way for future development of synthetic analogues of XN to be used as cancer angiopreventive and chemopreventive agents.

Original languageEnglish
Pages (from-to)890-899
Number of pages10
JournalEuropean Journal of Medicinal Chemistry
Volume138
DOIs
Publication statusPublished - Sep 29 2017

Keywords

  • Angiogenesis Inhibitors
  • Apoptosis
  • Cell Adhesion
  • Cell Movement
  • Cell Proliferation
  • Cells, Cultured
  • Chalcone
  • Dose-Response Relationship, Drug
  • Flavonoids
  • Human Umbilical Vein Endothelial Cells
  • Humans
  • Molecular Structure
  • Neovascularization, Physiologic
  • Propiophenones
  • Structure-Activity Relationship
  • Journal Article

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