cis-3,3'-Bis-[alpha-(trimethylammonium)methyl]azobenzene (cis-Bis-Q). Purification and properties at acetylcholine receptors of Electrophorus electroplaques.

The cis and trans isomers of the photoisomerizable compound, 3,3'-bis-[alpha-(trimethylammonium)methyl]azobenzene (Bis-Q), were purified by high-performance liquid chromatography using the ion-pair partitioning technique on a reverse-phase column. Solutions of cis-Bis-Q are stable at -20 degrees; at 25 degrees, thermal isomerization proceeds at a rate of 0.65%/day. cis-Bis-Q is less than 1% as potent a nicotinic agonist as the trans configuration. At concentrations of 1.5 microM or less, cis-Bis-Q exerts little or no blockade of the conductances induced by agonists. In voltage-clamped Electrophorus electroplaques exposed to cis-Bis-Q, laser flashes induce cis leads to trans photoisomerizations and increase the agonist-induced current by a factor of 20 within a few milliseconds.