Protein Information

Name acetylcholine receptor (protein family or complex)
Synonyms Acetylcholine receptor; Acetylcholine receptors

Compound Information

Name azobenzene
CAS diphenyldiazene

Reference List

PubMed Abstract RScore(About this table)
2423118 Delcour AH, Hess GP: Chemical kinetic measurements of the effect of trans- and cis-3,3'-Bis [(trimethylammonio) methyl] azobenzene bromide on acetylcholine receptor mediated ion translocation in Electrophorus electricus and Torpedo californica. Biochemistry. 1986 Apr 8;25(7):1793-8.

A quench-flow technique was used to study the effect of trans- and cis-3,3'-bis [(trimethylammonio) methyl] azobenzene bromide (trans- and cis-Bis-Q), photoisomerizable ligands, on the acetylcholine receptor in vesicles prepared from the electric organ of Electrophorus electricus and of Torpedo californica.
112(1,2,2,2) Details
6181515 Wassermann NH, Penn AS, Freimuth PI, Treptow N, Wentzel S, Cleveland WL, Erlanger BF: Anti-idiotypic route to anti-acetylcholine receptor antibodies and experimental myasthenia gravis. Proc Natl Acad Sci U S A. 1982 Aug;79(15):4810-4.

trans-3,3'-Bis [alpha-(trimethylammonio) methyl] azobenzene bromide (BisQ) is a potent agonist of the acetylcholine receptor (AcChoR) of Electrophorus electricus.
82(1,1,1,2) Details
4525321 Chang HW: Purification and characterization of acetylcholine receptor-I from Electrophorus electricus. Proc Natl Acad Sci U S A. 1974 May;71(5):2113-7.

Specific elution of the acetylcholine receptor-I (AcChR-I) with low concentration of a bis-quaternary agonist, 3,3'-bis [alpha-(trimethylammonium) methyl]-azobenzene bromide (Bis-Q), gave a 35% yield of toxin-binding components in the crude extract.
32(0,1,1,2) Details
284340 Wassermann NH, Bartels E, Erlanger BF: Conformational properties of the acetylcholine receptor as revealed by studies with constrained depolarizing ligands. Proc Natl Acad Sci U S A. 1979 Jan;76(1):256-9.

Among the compounds synthesized was 3,3'-bis [alpha-(trimethylammonium)-methyl] azobenzene dibromide (3,3'-bisQ).
2(0,0,0,2) Details
7285232 Wassermann NH, Erlanger BF: Agents related to a potent activator of the acetylcholine receptor of Electrophorus electricus. Chem Biol Interact. 1981 Sep;36(3):251-8.

The synthesis of a number of compounds related to trans-3,3'-bis [alpha-(trimethylammonium) methyl] azobenzene dibromide (trans-3,3'-BisQ) (1) is described.
2(0,0,0,2) Details
1460456 Chabala LD: Voltage dependence of acetylcholine receptor channel gating in rat myoballs. J Gen Physiol. 1992 Oct;100(4):729-48.

Myoballs were bathed in a solution containing a low concentration of the inactive isomer of the photoisomerizable azobenzene derivative, cis-Bis-Q.
2(0,0,0,2) Details
6604226 Cleveland WL, Wassermann NH, Sarangarajan R, Penn AS, Erlanger BF: Monoclonal antibodies to the acetylcholine receptor by a normally functioning auto-anti-idiotypic mechanism. Nature. 1983 Sep 1-7;305(5929):56-7.

Antibodies were prepared in rabbits to a structurally constrained agonist of AChR, trans-3,3'-bis [alpha-(trimethylammonio) methyl] azobenzene bromide (BisQ).
2(0,0,0,2) Details
2413914 Chabala LD, Gurney AM, Lester HA: Photoactivation and dissociation of agonist molecules at the nicotinic acetylcholine receptor in voltage-clamped rat myoballs. Biophys J. 1985 Aug;48(2):241-6.

The photochemical properties of the azobenzene derivative, Bis-Q, were exploited to carry out an agonist concentration jump followed by a molecular rearrangement of bound agonist molecules at acetylcholine (ACh) receptor channels of voltage-clamped rat myoballs.
1(0,0,0,1) Details
6835200 Nerbonne JM, Sheridan RE, Chabala LD, Lester HA: cis-3,3'-Bis-[alpha-(trimethylammonium) methyl] azobenzene (cis-Bis-Q). Mol Pharmacol. 1983 Mar;23(2):344-9.

Purification and properties at acetylcholine receptors of Electrophorus electroplaques..
1(0,0,0,1) Details
5288770 Bartels E, Wassermann NH, Erlanger BF: Photochromic activators of the acetylcholine receptor. . Proc Natl Acad Sci U S A. 1971 Aug;68(8):1820-3.

Trans-3,3'-bis [alpha-(trimethylammonium) methyl] azobenzene dibromide (Bis-Q), one of the most potent ever reported, is active at concentrations of less than 10 (-7) M.
1(0,0,0,1) Details
4045419 Krouse ME, Lester HA, Wassermann NH, Erlanger BF: Rates and equilibria for a photoisomerizable antagonist at the acetylcholine receptor of Electrophorus electroplaques. J Gen Physiol. 1985 Aug;86(2):235-56.

Voltage-jump and light-flash experiments have been performed on isolated Electrophorus electroplaques exposed simultaneously to nicotinic agonists and to the photoisomerizable compound 2,2'-bis-[alpha-(trimethylammonium) methyl]-azobenzene (2BQ).
1(0,0,0,1) Details
2422352 Chabala LD, Gurney AM, Lester HA: Dose-response of acetylcholine receptor channels opened by a flash-activated agonist in voltage-clamped rat myoballs. J Physiol. 1986 Feb;371:407-33.

To minimize problems associated with bath applied agonists, myoballs were bathed in a solution containing the inactive (cis) isomer of the photo-isomerizable azobenzene derivative, Bis-Q.
1(0,0,0,1) Details
6308248 Weinstock MM: Activation and desensitization of acetylcholine receptors in fish muscle with a photoisomerizable agonist. J Physiol. 1983 May;338:423-33.

Voltage-clamped muscle fibres of the fish Xenomystus nigris were bathed in a solution containing 3,3-bis [alpha-(trimethylammonium) methyl] azobenzene (cis-Bis-Q; 100 nM).
1(0,0,0,1) Details