Flavylium salts as in vitro precursors of potent ligands to brain GABA-A receptors.
The synthesis of a series of derivatized flavylium cations was undertaken and the affinity to the benzodiazepine binding site of the GABA-A receptor evaluated. The observed high affinity for some derivatives (sub-muM range) was explained by an in vitro transformation of the flavylium cations into the corresponding trans-retrochalcones, components which are proposed to be the active species in this series.
Kueny-Stotz
Marie
M
Laboratoire de Chimie des Polyphénols, UMR 7177 CNRS, Institut Le Bel, 4, rue Blaise Pascal, Université Louis Pasteur Strasbourg, F-67008 Strasbourg, France.
Chassaing
Stefan
S
Brouillard
Raymond
R
Nielsen
Mogens
M
Goeldner
Maurice
M
D000818:Animals; D001569:Benzodiazepines / Q000378:metabolism; D001665:Binding Sites / Q000502:physiology; D001921:Brain / Q000378:metabolism*; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D005459:Fluorides / Q000737:chemistry / Q000378:metabolism*; D008024:Ligands; D008297:Male; D010710:Phosphates / Q000737:chemistry / Q000378:metabolism*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D051381:Rats; D017208:Rats, Wistar; D011963:Receptors, GABA-A / Q000378:metabolism*; D012492:Salts
D005419:Flavonoids; D008024:Ligands; D010710:Phosphates; D011084:Polycyclic Aromatic Hydrocarbons; D011963:Receptors, GABA-A; D012492:Salts; D001569:Benzodiazepines; C012980:fluorophosphate; D005459:Fluorides