Synonym
ANNINE-6plus; ANNINE 6plus; ANNINE6plus;
IUPAC/Chemical Name
10-(dibutylamino)-2-(3-(trimethylammonio)propyl)chryseno[2,1-f]isoquinolin-2-ium bromide
InChi Key
LGXPDFMRHWKUGJ-UHFFFAOYSA-L
InChi Code
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
SMILES Code
CCCCN(CCCC)C1=CC=C2C(C=CC3=C2C=CC4=C3C=CC5=C4C=CC6=C5C=C[N+](CCC[N+](C)(C)C)=C6)=C1.[Br-].[Br-]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
ANNINE-6plus is a salt with a double positively charged chromophore and two bromide counterions. It is derived from the zwitterionic dye ANNINE-6. While ANNINE-6 is insoluble in water, ANNINE-6plus exhibits a high solubility of around 1 mM. Nonetheless, it displays a strong binding to lipid membranes. In contrast to ANNINE-6, the novel dye can be used to stain cells from aqueous solution without surfactants or organic solvents. In neuronal membranes, ANNINE-6plus exhibits the same molecular Stark effect as ANNINE-6. As a consequence, a high voltage-sensitivity is achieved with illumination and detection in the red end of the excitation and emission spectra, respectively. ANNINE-6plus will be particularly useful for sensitive optical recording of neuronal excitation when organic solvents and surfactants must be avoided as with intracellular or extracellular staining of brain tissue.
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.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
717.63
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Ramamoorthy S, Wilson TM, Wu T, Nuttall AL. Non-uniform distribution of outer hair cell transmembrane potential induced by extracellular electric field. Biophys J. 2013 Dec 17;105(12):2666-75. doi: 10.1016/j.bpj.2013.11.021. PubMed PMID: 24359738; PubMed Central PMCID: PMC3882456.
2: Wegner LH, Frey W, Schönwälder S. A critical evaluation of whole cell patch clamp studies on electroporation using the voltage sensitive dye ANNINE-6. Bioelectrochemistry. 2013 Aug;92:42-6. doi: 10.1016/j.bioelechem.2013.03.002. Epub 2013 Apr 3. PubMed PMID: 23603150.
3: Pagès S, Côté D, De Koninck P. Optophysiological approach to resolve neuronal action potentials with high spatial and temporal resolution in cultured neurons. Front Cell Neurosci. 2011 Oct 10;5:20. doi: 10.3389/fncel.2011.00020. eCollection 2011. PubMed PMID: 22016723; PubMed Central PMCID: PMC3191737.
4: Vignali S, Peter N, Ceyhan G, Demir IE, Zeller F, Senseman D, Michel K, Schemann M. Recordings from human myenteric neurons using voltage-sensitive dyes. J Neurosci Methods. 2010 Oct 15;192(2):240-8. doi: 10.1016/j.jneumeth.2010.07.038. Epub 2010 Aug 5. PubMed PMID: 20691728.
5: Flickinger B, Berghöfer T, Hohenberger P, Eing C, Frey W. Transmembrane potential measurements on plant cells using the voltage-sensitive dye ANNINE-6. Protoplasma. 2010 Nov;247(1-2):3-12. doi: 10.1007/s00709-010-0131-y. Epub 2010 Mar 23. PubMed PMID: 20309592.
6: Mennerick S, Chisari M, Shu HJ, Taylor A, Vasek M, Eisenman LN, Zorumski CF. Diverse voltage-sensitive dyes modulate GABAA receptor function. J Neurosci. 2010 Feb 24;30(8):2871-9. doi: 10.1523/JNEUROSCI.5607-09.2010. PubMed PMID: 20181584; PubMed Central PMCID: PMC2840391.
7: Bu G, Adams H, Berbari EJ, Rubart M. Uniform action potential repolarization within the sarcolemma of in situ ventricular cardiomyocytes. Biophys J. 2009 Mar 18;96(6):2532-46. doi: 10.1016/j.bpj.2008.12.3896. PubMed PMID: 19289075; PubMed Central PMCID: PMC2907679.
8: Fromherz P, Hübener G, Kuhn B, Hinner MJ. ANNINE-6plus, a voltage-sensitive dye with good solubility, strong membrane binding and high sensitivity. Eur Biophys J. 2008 Apr;37(4):509-14. Epub 2007 Aug 9. PubMed PMID: 17687549; PubMed Central PMCID: PMC2755735.
