Synthesis and antiangiogenic activity study of new hop chalcone Xanthohumol analogues

Autor: Susanna Nencetti, Caterina Camodeca, Barbara Bassani, A.R. Cantelmo, Armando Rossello, Denisa Baci, Elisabetta Orlandini, Elisa Nuti, Douglas M. Noonan, Adriana Albini, Antonino Bruno, Cristina Gallo, Lea Rosalia
Přispěvatelé: Nuti, E, Bassani, B, Camodeca, C, Rosalia, L, Cantelmo, A, Gallo, C, Baci, D, Bruno, A, Orlandini, E, Nencetti, S, Noonan, D, Albini, A, Rossello, A
Rok vydání: 2017
Předmět:
0301 basic medicine
Chalcone
Xanthohumol analogues
Prenylated chalcones
Antiangiogenic activity
Chemopreventive agents
Stereochemistry
Angiogenesis
Prenylated chalcones
Neovascularization
Physiologic
Angiogenesis Inhibitors
Apoptosis
Antiangiogenic activity
Chemopreventive agents
Xanthohumol analogues
Pharmacology
Drug Discovery3003 Pharmaceutical Science
Organic Chemistry
Hop (networking)
Structure-Activity Relationship
03 medical and health sciences
chemistry.chemical_compound
0302 clinical medicine
Cell Movement
Drug Discovery
Cell Adhesion
Human Umbilical Vein Endothelial Cells
Humans
Structure–activity relationship
Cell adhesion
Cells
Cultured
Cell Proliferation
Flavonoids
Propiophenones
Dose-Response Relationship
Drug
Molecular Structure
Cell growth
General Medicine
030104 developmental biology
chemistry
030220 oncology & carcinogenesis
Xanthohumol
Zdroj: European Journal of Medicinal Chemistry. 138:890-899
ISSN: 0223-5234
DOI: 10.1016/j.ejmech.2017.07.024
Popis: 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.
Databáze: OpenAIRE
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