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D8064

Sigma-Aldrich

4-(2-(6-(Dibutylamino)-2-naphthalenyl)ethenyl)-1-(3-sulfopropyl)pyridinium hydroxide inner salt

≥95% purity (HPLC), solid

Synonym(s):

Di-4-ANEPPS

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About This Item

Empirical Formula (Hill Notation):
C28H36N2O3S
CAS Number:
90134-00-2
Molecular Weight:
480.66
MDL number:
MFCD03453609
UNSPSC Code:
12171500
PubChem Substance ID:
329798855
NACRES:
NA.47

product name

4-(2-(6-(Dibutylamino)-2-naphthalenyl)ethenyl)-1-(3-sulfopropyl)pyridinium hydroxide inner salt, ≥95% (HPLC), solid

Quality Level

100

assay

≥95% (HPLC)

form

solid

mol wt

480.66

color

orange to dark red

solubility

DMF: soluble
DMSO: soluble
ethanol: soluble

ε (extinction coefficient)

≥38000 at 493-499 nm in methanol

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

2-8°C

SMILES string

CCCCN(CCCC)c1ccc2cc(\C=C\c3cc[n+](CCCS([O-])(=O)=O)cc3)ccc2c1

InChI

1S/C28H36N2O3S/c1-3-5-17-30(18-6-4-2)28-13-12-26-22-25(10-11-27(26)23-28)9-8-24-14-19-29(20-15-24)16-7-21-34(31,32)33/h8-15,19-20,22-23H,3-7,16-18,21H2,1-2H3

InChI key

HAPJROQJVSPKCJ-UHFFFAOYSA-N

Related Categories

Application

4-(2-(6-(Dibutylamino)-2-naphthalenyl)ethenyl)-1-(3-sulfopropyl)pyridinium hydroxide inner salt has been used as a voltage sensitive dye in cardiac cells.

Biochem/physiol Actions

Membrane potential dye that responds to changes in membrane potential monitored by fluorescence excitation changes at 440 and 505 nm; correlated to changes in membrane potential of the cell.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Andrew D Bachtel et al.
IEEE transactions on bio-medical engineering, 58(7), 2120-2126 (2011-05-04)
We developed a new method for ratiometric optical mapping of transmembrane potential (V(m)) in cardiac preparations stained with di-4-ANEPPS. V(m)-dependent shifts of excitation and emission spectra establish two excitation bands (<481 and >481 nm) that produce fluorescence changes of opposite
P Fromherz et al.
Biochimica et biophysica acta, 1068(2), 149-156 (1991-09-30)
The voltage sensitivity of fluorescence of an aminobenzstyryl-pyridinium dye (di4-ANEPPS) is characterized in Retzius cells dissociated from the leech. The modulation of the complete spectra of excitation and emission is determined. The spectral changes induced by depolarization are described by
Engineering a freestanding biomimetic cardiac patch using biodegradable poly(lactic-co-glycolic acid) (PLGA) and human embryonic stem cell-derived ventricular cardiomyocytes (hESC-VCMs).
Chen Y, et al.
Macromolecular Bioscience, 15, 426-436 (2015)
J M Davidenko et al.
Nature, 355(6358), 349-351 (1992-01-23)
Excitable media can support spiral waves rotating around an organizing centre. Spiral waves have been discovered in different types of autocatalytic chemical reactions and in biological systems. The so-called 're-entrant excitation' of myocardial cells, causing the most dangerous cardiac arrhythmias
Zachary Laksman et al.
Scientific reports, 7(1), 5268-5268 (2017-07-15)
Since current experimental models of Atrial Fibrillation (AF) have significant limitations, we used human embryonic stem cells (hESCs) to generate an atrial-specific tissue model of AF for pharmacologic testing. We generated atrial-like cardiomyocytes (CMs) from hESCs which preferentially expressed atrial-specific
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