1. Home page
  2. Search

New hydroxystilbenoid derivatives endowed with neuroprotective activity and devoid of interference with estrogen and aryl hydrocarbon receptor-mediated transcription

This item is provided by the institution :
National Hellenic Research Foundation (NHRF)   

Repository :
Helios - Repository of the National Hellenic Research Foundation (NHRF)  | repositories EKT   

see the original item page
in the repository's web site and access all digital files if the item*



New hydroxystilbenoid derivatives endowed with neuroprotective activity and devoid of interference with estrogen and aryl hydrocarbon receptor-mediated transcription
Μίχα-Σκρέττα, Μαρία
Σκρέττας, Κωνσταντίνος Γ.
Βιλλιαλονγκα-Μπαρμπέρ, Καρολίνα
Meligova, Aggeliki K.
Kouzinos, Constantinos E.
Alexi, Xanthippi
Στηλ, Μπάρυ
Αλέξης, Μιχαήλ Ν.
Katsanou, Efrosini S.
Άρθρο σε επιστημονικό περιοδικό
2011-01-01
OXFORD
We have synthesized a series of new (E) stilbenoid derivatives containing hydroxy groups at ring positions identical or similar to those of trans-resveratrol and bearing one or two bulky electron donating groups ortho to 4'-OH and we have evaluated their neuroprotective activity using glutamate-challenged HT22 hippocampal neurons to model oxidative stress-induced neuronal cell death. The most active derivatives, 5-{(E)-2-[3,5-bis(1-ethylpropyl)-4-hydroxyphenyl]ethenyl}-1,3-benzenediol (2), 5-[(E)-2-(3,5-di-tert-butyl-4-hydroxyphenylethenyl)]-1,3-benzenediol (4) and 5-{(1E, 3E)-4-[3,5-bis(1-ethylpropyl)-4-hydroxyphenyl]-1,3-butadienyl}-1,3-benzenediol (6), had EC(50) values of 30, 45 and 12 nM, respectively, and were ca. 100 to 400-fold more potent than resveratrol. Derivatives 2, 4 and 6 lacked cytotoxic activity against HT22 cells and estrogen receptor agonist or antagonist activity in estrogen response element-dependent gene expression and in estrogen-dependent proliferation of MCF-7 human breast cancer cells. In addition, they were incapable of interfering with aryl hydrocarbon receptor-mediated xenobiotic response element-dependent gene expression. Derivatives 2, 4 and 6 might assist in the development of lead candidates against oxidative stress-driven neurodegenerative diseases that will not increase endocrine cancer risk nor affect drug activation and detoxification mechanisms.
Οργανική χημεία (EL)
Βιολογία (Γενικά) (EL)
Χημεία (Γενικά) (EL)
Φαρμακευτική (EL)
Biology (General) (EN)
Organic chemistry (EN)
Pharmacy and materia medica (EN)
Chemistry (General) (EN)
Oxidative stress
Estrogen receptor
Arylhydrocarbon receptor
Neuronal damage
Stilbenoid derivatives
Chemistry, Medicinal
English
Pergamon
Bioorganic & Medicinal Chemistry
https://rightsstatements.org/page/InC/1.0/?language=en
© 2010 Elsevier Ltd. All rights reserved.
© 2010 Elsevier Ltd. All rights reserved. (EN)
National Hellenic Research Foundation (NHRF)
Helios - Repository of the National Hellenic Research Foundation (NHRF)



*Institutions are responsible for keeping their URLs functional (digital file, item page in repository site)