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6,2'-Dihydroxyflavone Sale

(Synonyms: 6,2-二羟基黄酮) 目录号 : GC30943


6,2'-Dihydroxyflavone Chemical Structure

Cas No.:92439-20-8

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10mM (in 1mL DMSO)

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Cell experiment:

Membranes from HEK 293T cell are used in this study. Briefly, aliquots of membranes are incubated with 1 nM [3H]-flunitrazepam or 8 nM [3H]-Ro15-4513 at 4°C for 90 min in the presence or absence of 6,2'-Dihydroxyflavone. After incubation, the mixtures are filtered onto Whatman GF/B filters with a Brandel 24-well harvester. Each filter is incubated for at least 1 h with 4 mL scintillation cocktail before measurement of radioactivity in a Beckman-Coulter LS 6500 scintillation counter. For saturation analysis, the membranes are incubated with increasing concentrations of [3H]-flunitrazepam or [3H]-Ro15-4513. Binding affinity is determined by nonlinear regression analysis[1].

Animal experiment:

Male ICR mice are randomized into six groups (n=12 to 16/group), and receive 0.4 mg/kg scopolamine (i.p.) 45 min prior to training, followed with vehicle (dd water, pH 9.0, p.o.), 2, 4, 8 or 16 mg/kg 6,2'-Dihydroxyflavone (p.o.), or 30 mg/kg FG-7142 (i.p.) 30 min prior to training. On the training trials, each mouse is placed into the lighted chamber of a two-compartment box, and the door leading to the dark chamber is opened 10 s later. Once the mouse enters the dark compartment, the door is closed and an inescapable electric foot-shock (0.4 mA, 1 s) is delivered from the grid floor. The mouse is removed from the apparatus 10 s later. The step-through latency is recorded, with the cut-off step-through latency set at 300 s[1].


[1]. Wang F, et al. 6,2'-Dihydroxyflavone, a subtype-selective partial inverse agonist of GABAA receptor benzodiazepine site. Neuropharmacology. 2007 Sep;53(4):574-82.


6,2'-Dihydroxyflavone is a novel antagonist of GABAA receptor.

6,2'-Dihydroxyflavone is a novel antagonist of GABAA receptor. 6,2'-Dihydroxyflavone inhibits [3H]-flunitrazepam binding to the rat cerebral cortex membranes with a Ki of 37.2±4.5 nM. The current elicited with the EC50 concentration of GABA is decreased to 73.6±1.9% of control by co-application of 5 μM 6,2'-Dihydroxyflavone (n=5), compare to a decrease to 65.9±3.0% by 1 μM FG-7142 (n=5). The EC50 for GABA dose response increases from 47.6 to 59.7 μM upon co-application of 5 μM 6,2'-Dihydroxyflavone, and the maximal GABA-current is decreased[1].

6,2'-Dihydroxyflavone-treated mice exhibit significant differences from control mice with respect to the percentage of open arms entries [F(4,73)=8.01, P<0.0001] and the percentage of time spent in open arms [F (4,73)=5.19, P<0.002], but not the number of entries to closed arms [F(4,73)= 0.79,P=0.54]. The post-hoc NewmaneKeuls' tests confirm that 6,2'-Dihydroxyflavone significantly decreases the percentage of open arm entries and time spent in open arms at the doses of 8 and 16 mg/kg. 6,2'-Dihydroxyflavone treatment similarly increases step-through latency [F(4,75)=4.71, P<0.002], suggesting enhanced cognitive performance[1].

[1]. Wang F, et al. 6,2'-Dihydroxyflavone, a subtype-selective partial inverse agonist of GABAA receptor benzodiazepine site. Neuropharmacology. 2007 Sep;53(4):574-82.

Chemical Properties

Cas No. 92439-20-8 SDF
别名 6,2-二羟基黄酮
Canonical SMILES O=C1C=C(C2=CC=CC=C2O)OC3=CC=C(O)C=C13
分子式 C15H10O4 分子量 254.24
溶解度 DMSO : 155 mg/mL (609.66 mM) 储存条件 Store at -20°C
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1 mM 3.9333 mL 19.6665 mL 39.3329 mL
5 mM 0.7867 mL 3.9333 mL 7.8666 mL
10 mM 0.3933 mL 1.9666 mL 3.9333 mL
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Research Update

6,2'-Dihydroxyflavone, a subtype-selective partial inverse agonist of GABAA receptor benzodiazepine site

Neuroactivity of a number of flavonoids is mediated by modulation of type A gamma-aminobutyric acid (GABA(A)) receptor function via benzodiazepine sites, mostly as partial agonists. In the present study, 6,2'-dihydroxyflavone (DHF) was characterized for potential inverse agonistic activity, and its mechanism of action was explored for receptor subtype selectivity. In whole-cell patch clamp studies on neuroblastoma IMR-32 cells expressing native GABA(A) receptors, DHF decreased GABA-induced currents, to an extent similar to that induced by the partial inverse agonist FG-7142, which could be blocked by flumazenil, a BZ site antagonist. In mouse behavioral models, DHF elicited significant anxiogenic-like effects in the elevated plus-maze test, and enhanced cognitive performance in the step-through passive avoidance test, as expected for an inverse agonist. However, DHF did not exhibit any proconvulsant effects, a typical action of inverse agonists. In electrophysiological studies on subtypes of recombinant GABA(A) receptors expressed in HEK 293T cells, DHF decreased GABA-induced currents in alpha(1)beta(3)gamma(2), alpha(2)beta(3)gamma(2), or alpha(5)beta(3)gamma(2), but not alpha(3)beta(3)gamma(2) receptors. The results demonstrated DHF as a partial inverse agonist-like modulator of GABA(A) receptors with selectivity in receptor subtypes as well as behavioral effects. The DHF subtype-selectivity suggested that alpha(3)-containing subtypes could be a mediator of the convulsion activities of GABA(A) receptor inverse agonists. Moreover, the pharmacological profile displayed in mouse behavioral models supported DHF as a useful lead compound for the development of cognition-enhancing agents devoid of convulsion side effects.

Effects of flavone 6-substitutions on GABAA receptors efficacy

Flavones have been studied for their activities via benzodiazepine site on the type-A 污-aminobutyric acid (GABA(A)) receptors, for which knowledge on structure-efficacy relationships has been rather limited in comparison to that on structure-affinity relationships. The present study focused on flavone 6-substitution, implied in previous studies being relevant to efficacy. Structure analogs, each varying only at position 6, were compared, including 6-fluoroflavone, 6-chloroflavone, 6-bromoflavone, and 2'-hydroxyflavone analyzed in the present study, as well as 6,2'-dihydroxyflavone reported earlier. Radio-ligand binding assays, whole-cell patch-clamp, and mouse behavioral experiments were performed. In consistent with a previous report, the present whole-cell patch-clamp and animal behavior experiments demonstrated 6-bromoflavone to be a positive modulator at GABA(A) receptors acting through flumazenil-sensitive high-affinity benzodiazepine site. In contrast, the other two 6-haloflavones were both neutralizing modulators. In vitro electrophysiological and in vivo animal experiments showed that 2'-hydroxyflavone was a neutralizing modulator, different in efficacy from its structural analog, 6,2'-dihydroxyflavone, a negative modulator of GABA(A) receptors. The fact that flavone analogs differing only at position 6 showed drastically different pharmacological properties clearly points to 6-substitution being an important determinant of efficacy. The results suggest that a large width of the first atom on the 6-substituent favors a high binding affinity of the 6-substituted flavone, whereas a large overall volume of the 6-substituent favors positive modulator activity, which could be modified by, e.g., 2'-hydroxyl substitution. These findings have contributed to the understanding of quantitative structure-efficacy relationships for flavones acting at GABA(A) receptors, and hence facilitation of flavone-based drug development.