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525331 Sigma-Aldrich

Photochromic Ion Channel Blocker, QAQ - Calbiochem

Synonym: 2,2′-((diazene-1,2-diylbis(4,1-phenylene))bis(azanediyl))bis(N,N,N-triethyl-2-oxoethanaminium) formate, Quaternary Ammonium–Azobenzene–Quaternary Ammonium, 2,2′-((diazene-1,2-diylbis(4,1-phenylene))bis(azanediyl))bis(N,N,N-triethyl-2-oxoethanaminium) formate, Quaternary Ammonium–Azobenzene–Quaternary Ammonium

  • Empirical Formula (Hill Notation) C30H46N6O6

  • Molecular Weight 586.72

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Properties

Related Categories Bioactive Small Molecules, Cell Biology More...
brand family   Calbiochem
feature productdata solubility   DMSO (25 mg/ml)
form   Brown solid
purity   ≥95% by HPLC
shipped in   wet ice
storage conditions   +2C to +8C
  Ok to freeze
  Protect from light

Description

Biochem/physiol Actions

Cell permeable: no

Primary Target
Ion Channels

Reversible: yes

General description

A membrane-impermeant Na+, K+, and Ca2+ channel blocker that is structurally composed of two azo-linked QX-314 (Cat. No. 552234) type quaternary amines. Both QX-314 and QAQ are shown to selectively target excitability of nociceptor neurons via TRPV1-dependent cellular uptake. Unlike QX-314, the channel blocking activity of QAQ can be quickly switched on and off via optical cis-to-trans (500 nm) and trans-to-cis (320 nm) isomerization. Its efficacy as a pain-selective, photochromic anesthetic has been demonstrated in rats in vivo. QAQ cellular uptake can also be achieved by ATP-activated P2X7 receptor.

A membrane-impermeant Na+, K+, and Ca2+ channel blocker that is structurally composed of two azo-linked QX-314 (Cat. No. 552233) type quaternary amines. Both QX-314 and QAQ are shown to selectively target excitability of nociceptor neurons via TRPV1-dependent cellular uptake upon TRPV1 activation by Capsaicin (Cat. No. 211275). Unlike QX-314, the channel blocking potency of QAQ can be quickly switched off by an optical trans to cis isomerization upon 320 nm illumination, which in turn can be reversed back to the active trans configuration via 500 nm illumination. Its in vivo efficacy as a pain-selective, photochromic anesthetic has been demonstrated in modulating rat cornea tolerance to mechanical pressure (200 nmol QAQ/100 pmol Capsaicin/10 µl/eye). QAQ cellular uptake can also be achieved by ATP-activated P2X7 receptor, but not activated TRPA1 or TRPM8. In addition, QAQ is reported not to affect Kir (inward-rectifier) or HCN (hyperpolarization-activated cyclic nucleotide-gated) channels.

Other Notes

Mourot, A., et al. 2012. Nat Methods.9, 396.
Banghart, M., et al. 2009. Angew Chem Int Ed Engl.48, 9097.

Packaging

Packaged under inert gas

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Warning

Standard Handling (A)

Safety & Documentation

Safety Information

Safety Information for this product is unavailable at this time.

Documents

Certificate of Analysis

Protocols & Articles
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