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525331 Photochromic Ion Channel Blocker, QAQ - Calbiochem

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

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

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      Overview

      Replacement Information
      Description
      Overview

      This product has been discontinued.



      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.
      Catalogue Number525331
      Brand Family Calbiochem®
      Synonyms2,2'-((diazene-1,2-diylbis(4,1-phenylene))bis(azanediyl))bis(N,N,N-triethyl-2-oxoethanaminium) formate, Quaternary Ammonium–Azobenzene–Quaternary Ammonium
      References
      ReferencesMourot, A., et al. 2012. Nat Methods. 9, 396.
      Banghart, M., et al. 2009. Angew Chem Int Ed Engl. 48, 9097.
      Product Information
      FormBrown solid
      Hill FormulaC₃₀H₄₆N₆O₆
      Chemical formulaC₃₀H₄₆N₆O₆
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetIon Channels
      Purity≥95% by HPLC
      Physicochemical Information
      Cell permeableN
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Shipped at Ambient Temperature or with Blue Ice or with Dry Ice
      Toxicity Standard Handling
      Storage +2°C to +8°C
      Protect from Light Protect from light
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications
      Global Trade Item Number
      Catalogue Number GTIN
      525331 0

      Documentation

      Photochromic Ion Channel Blocker, QAQ - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      Photochromic Ion Channel Blocker, QAQ - Calbiochem Certificates of Analysis

      TitleLot Number
      525331

      References

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

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision28-March-2013 JSW
      Synonyms2,2'-((diazene-1,2-diylbis(4,1-phenylene))bis(azanediyl))bis(N,N,N-triethyl-2-oxoethanaminium) formate, Quaternary Ammonium–Azobenzene–Quaternary Ammonium
      DescriptionA 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.
      FormBrown solid
      Intert gas (Yes/No) Packaged under inert gas
      Chemical formulaC₃₀H₄₆N₆O₆
      Structure formulaStructure formula
      Purity≥95% by HPLC
      SolubilityDMSO (25 mg/ml)
      Storage Protect from light
      +2°C to +8°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Toxicity Standard Handling
      ReferencesMourot, A., et al. 2012. Nat Methods. 9, 396.
      Banghart, M., et al. 2009. Angew Chem Int Ed Engl. 48, 9097.