QAQ dichloride

• CAT Number: I011212
• Molecular Formula: C28H44Cl2N6O2
• Molecular Weight: 567.59
• Purity: ≥95%
• Synonyms: triethyl-[2-oxo-2-[4-[[4-[[2-(triethylazaniumyl)acetyl]amino]phenyl]diazenyl]anilino]ethyl]azanium;dichloride
• InChI: InChI=1S/C28H42N6O2.2ClH/c1-7-33(8-2,9-3)21-27(35)29-23-13-17-25(18-14-23)31-32-26-19-15-24(16-20-26)30-28(36)22-34(10-4,11-5)12-6;;/h13-20H,7-12,21-22H2,1-6H3;2*1H
• InChIKey: VHURBRSYOFCHNY-UHFFFAOYSA-N
• SMILES: CC[N+](CC)(CC)CC(=O)NC1=CC=C(C=C1)N=NC2=CC=C(C=C2)NC(=O)C[N+](CC)(CC)CC.[Cl-].[Cl-]

QAQ dichloride, a photoswitchable voltage-gated Nav and Kv channels blocker, blocks channels in its trans form (of the azobenzene photoswitch), but not in its cis form. QAQ dichloride is membrane-impermeant and only infiltrates pain-sensing neurons that express endogenous import channels. QAQ dichloride acts as a light-sensitive analgesic and can be used for studying of signaling mechanisms in acute and chronic pain[1][2].
QAQ dichloride (100 μM) does not cross the membrane and can be injected into cells through a micropipette to photosensitize a single cell and afford subcellular control of action potential propagation. It blocks Shaker-IR current in the trans configuration and unblocks it in the cis configuration[1].
QAQ dichloride can be used to develop red-shifted derivatives of QAQ, powerful doubly charged photochromic blockers.These derivatives allow for remote control of Kv and Nav channel conductance with light and offer the opportunity to silence neuronal activity reversibly[2].

Reference

[1]. Timm Fehrentz, et al. Exploring the Pharmacology and Action Spectra of Photochromic Open-Channel Blockers. Chembiochem. 2012 Aug 13;13(12):1746-9.
 [Content Brief]

[2]. Alexandre Mourot, et al.Photochromic Potassium Channel Blockers: Design and Electrophysiological Characterization. Methods Mol Biol. 2013;995:89-105.
 [Content Brief]