ANNINE-6plus

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.[1] It is used to optically measure the changes in transmembrane voltage of excitable cells, including neurons, skeletal and cardiac myocytes.

ANNINE-6plus
Names
Preferred IUPAC name
3-[10-(Dibutylamino)chryseno[2,1-f]isoquinolin-2-ium-2-yl]-N,N,N-trimethylpropan-1-aminium dibromide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
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-2
    Key: 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-2
    Key: LGXPDFMRHWKUGJ-NUQVWONBAZ
SMILES
  • C[N+](C)(C)CCC[N+]1=CC(C=C2)=C(C=C1)C3=C2C(C=C4)=C(C=C3)C5=C4C6=CC=C(N(CCCC)CCCC)C=C6C=C5.[Br-].[Br-]
Properties
Chemical formula
 C39H47Br2N3
Molar mass 717.634 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[2] 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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