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ANNINE-6plus

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ANNINE-6plus
Names
Preferred IUPAC name 3-isoquinolin-2-ium-2-yl]-N,N,N-trimethylpropan-1-aminium dibromide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C39H47N3.2BrH/c1-6-8-23-41(24-9-7-2)31-13-16-32-29(27-31)11-14-36-34(32)17-19-39-37-15-12-30-28-40(22-10-26-42(3,4)5)25-21-33(30)35(37)18-20-38(36)39;;/h11-21,25,27-28H,6-10,22-24,26H2,1-5H3;2*1H/q+2;;/p-2Key: LGXPDFMRHWKUGJ-UHFFFAOYSA-L
  • InChI=1/C39H47N3.2BrH/c1-6-8-23-41(24-9-7-2)31-13-16-32-29(27-31)11-14-36-34(32)17-19-39-37-15-12-30-28-40(22-10-26-42(3,4)5)25-21-33(30)35(37)18-20-38(36)39;;/h11-21,25,27-28H,6-10,22-24,26H2,1-5H3;2*1H/q+2;;/p-2Key: LGXPDFMRHWKUGJ-NUQVWONBAZ
SMILES
  • C(C)(C)CCC1=CC(C=C2)=C(C=C1)C3=C2C(C=C4)=C(C=C3)C5=C4C6=CC=C(N(CCCC)CCCC)C=C6C=C5..
Properties
Chemical formula C39H47Br2N3
Molar mass 717.634 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

ANNINE-6plus is a water soluble voltage sensitive dye (also called potentiometric dyes). This compound was developed at the Max Planck Institute for Biochemistry in Germany. It is used to optically measure the changes in transmembrane voltage of excitable cells, including neurons, skeletal and cardiac myocytes.

Voltage sensitivity

ANNINE-6plus has a fractional fluorescent intensity change (ΔF/F per 100 mV change) of about 30% with single-photon excitation (~488 nm) and >50% with two-photon excitation (~1060 nm).

Applications

ANNINE-6plus has been applied in the microscopic imaging of action potentials of cardiomyocyte in perfused mice heart. Using confocal microscopy in conjunction with ANNINE-6plus, single sweep action potentials with high peak signal-to-noise ratio (SNR) have been recorded from single transverse tubule (t-tubule) of a few micrometers in the ventricular cardiomyocyte.

References

  1. Peter Fromherz; et al. (2008). "ANNINE-6plus, a voltage-sensitive dye with good solubility, strong membrane binding and high sensitivity". European Biophysics Journal. 37 (4): 509–514. doi:10.1007/s00249-007-0210-y. PMC 2755735. PMID 17687549.
  2. Guixue Bu; et al. (2009). "Uniform action potential repolarization within the sarcolemma of in situ ventricular cardiomyocytes". Biophysical Journal. 96 (6): 2532–2546. Bibcode:2009BpJ....96.2532B. doi:10.1016/j.bpj.2008.12.3896. PMC 2907679. PMID 19289075.
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