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Benzoquinonium dibromide

inhibitor of AChR and ganglion CAS# 311-09-1

Benzoquinonium dibromide

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Chemical structure

Benzoquinonium dibromide

3D structure

Chemical Properties of Benzoquinonium dibromide

Cas No. 311-09-1 SDF Download SDF
PubChem ID 9393 Appearance Powder
Formula C34H50Br2N4O2 M.Wt 706.6
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 5 mM in water with gentle warming
Chemical Name benzyl-[3-[[4-[3-[benzyl(diethyl)azaniumyl]propylamino]-3,6-dioxocyclohexa-1,4-dien-1-yl]amino]propyl]-diethylazanium;dichloride
SMILES CC[N+](CC)(CCCNC1=CC(=O)C(=CC1=O)NCCC[N+](CC)(CC)CC2=CC=CC=C2)CC3=CC=CC=C3.[Cl-].[Cl-]
Standard InChIKey WQRJZLXQCYZJEU-UHFFFAOYSA-N
Standard InChI InChI=1S/C34H48N4O2.2ClH/c1-5-37(6-2,27-29-17-11-9-12-18-29)23-15-21-35-31-25-34(40)32(26-33(31)39)36-22-16-24-38(7-3,8-4)28-30-19-13-10-14-20-30;;/h9-14,17-20,25-26H,5-8,15-16,21-24,27-28H2,1-4H3;2*1H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Benzoquinonium dibromide

DescriptionNicotinic antagonist, ganglion blocker. Activates single channels but blocks open channels at nicotinic receptors.

Benzoquinonium dibromide Dilution Calculator

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Benzoquinonium dibromide Molarity Calculator

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Preparing Stock Solutions of Benzoquinonium dibromide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.4152 mL 7.0761 mL 14.1523 mL 28.3046 mL 35.3807 mL
5 mM 0.283 mL 1.4152 mL 2.8305 mL 5.6609 mL 7.0761 mL
10 mM 0.1415 mL 0.7076 mL 1.4152 mL 2.8305 mL 3.5381 mL
50 mM 0.0283 mL 0.1415 mL 0.283 mL 0.5661 mL 0.7076 mL
100 mM 0.0142 mL 0.0708 mL 0.1415 mL 0.283 mL 0.3538 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Benzoquinonium dibromide

Benzoquinonium Dibromide (BZQ) is an inhibitor of acetylcholine receptor (AChR) and ganglion. BZQ activates nicotinic single channels but blocks open channels at the neuronal AChRs.
AChR is an integral membrane protein that responds to the binding of acetylcholine, a neurotransmitter. Nicotinic acetylcholine receptor (nAChR) are particularly responsive to nicotine and is a Na+ and K+ channel.
The effects of BZQ on α-BGT sensitive neuronal nAChRs were evaluated on outside-out patches excised from fetal rat hippocampal neurons cultured for 11 to 35 days and found that BZQ (0.1-10 μM) could activate single-channel currents. BZQ was also able to activate various channel conductance states. The two most frequently encountered conductance states activated by BZQ were 43 ± 3.3 pS and 30 ± 4.2 p5. In frog muscle fibers, BZQ is an open-channel blocker of the nAChR and also activates single-channel currents that are not blocked by a-BGT.
References:
[1]. Pereira EF, Reinhardt-Maelicke S, Schrattenholz A, et al. Identification and functional characterization of a new agonist site on nicotinic acetylcholine receptors of cultured hippocampal neurons. J Pharmacol Exp Ther, 1993, 265(3): 1474-1491.

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References on Benzoquinonium dibromide

Identification and functional characterization of a new agonist site on nicotinic acetylcholine receptors of cultured hippocampal neurons.[Pubmed:8510023]

J Pharmacol Exp Ther. 1993 Jun;265(3):1474-91.

Electrophysiological and biochemical techniques were used to demonstrate that alpha-bungarotoxin-, methyllycaconitine-sensitive neuronal nicotinic acetylcholine receptors (nAChRs) can be activated via a novel agonist site(s). The residue proposed to be essential to this site is the amino acid Lys-125 of the receptor alpha subunit. In outside-out patches excised from cultured hippocampal neurons, physostigmine (PHY) and 1-methyl-PHY activated single channels whose main conductances were 46 and 23 pS. This action was insensitive to DL-2-amino-5-phosphonovaleric acid, atropine, tetrodotoxin and competitive nicotinic antagonists, but blocked by benzoquinonium or FK1, a nAChR-specific antibody raised against rat muscle nAChR alpha subunits that binds to the novel site. Indirect immunofluorescence staining demonstrated that FK1 binds to the hippocampal neurons, as would be expected based on the high degree of homology among nAChR alpha subunits from diverse sources in the region surrounding Lys-125. PHY prevented the binding of FK1, thus supporting that FK1 is a specific probe for the PHY site. High-affinity sites (KD approximately 35 nM) for 1-methyl-PHY were identified in hippocampal neurons. Similar to PHY, benzoquinonium (0.1-10 microM) and galanthamine (1-10 microM) activated nicotinic single channels. The agonists benzoquinonium and PHY were also open-channel blockers at the neuronal nAChRs, whereas galanthamine was predominantly a desensitizing agent. In mouse fibroblasts transfected with cDNAs of alpha 4 and beta 2 neuronal nAChR subunits, PHY also activated single channels that were blocked by FK1. In these cells, dihydro-beta-erythroidine blocked single channels activated by (+)-anatoxin-a and did not affect those opened by PHY. Thus, the present results suggest that the novel agonist site located on the receptor alpha subunit is a common feature of neuronal nAChRs.

Description

Nicotinic antagonist

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