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D1065

Sigma-Aldrich

4-(2-[6-(Dioctylamino)-2-naphthalenyl]ethenyl)-1-(3-sulfopropyl)pyridinium inner salt

≥95% purity (HPLC), solid

Synonym(s):

Di-8-ANEPPS

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About This Item

Empirical Formula (Hill Notation):
C36H52N2O3S
CAS Number:
157134-53-7
Molecular Weight:
592.87
MDL number:
MFCD03453608
UNSPSC Code:
12171500
PubChem Substance ID:
329798667
NACRES:
NA.47

product name

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

Quality Level

100

assay

≥95% (HPLC)

form

solid

mol wt

592.88

color

orange to red

solubility

DMSO: soluble
ethanol: soluble

ε (extinction coefficient)

≥37 at 495-501  nm in methanol

fluorescence

λex 710-716 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

2-8°C

SMILES string

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

InChI

1S/C36H52N2O3S/c1-3-5-7-9-11-13-25-38(26-14-12-10-8-6-4-2)36-21-20-34-30-33(18-19-35(34)31-36)17-16-32-22-27-37(28-23-32)24-15-29-42(39,40)41/h16-23,27-28,30-31H,3-15,24-26,29H2,1-2H3

Inchi Key

IXFSUSNUALIXLU-UHFFFAOYSA-N

Biochem/physiol Actions

Fast-responding membrane potential dye.

Linkage

More suitable for long-term membrane potential studies than di-4-ANEPPS (Cat. No. D8064) because of better retention in the outer leaflet of plasma membranes.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT4343
MKCQ9449
MKCQ7451
MKCM4886
MKCJ2322

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Antonio Celestino-Montes et al.
Life sciences, 264, 118700-118700 (2020-11-02)
Ventricular myocytes (VM) depolarization activates L-type Ca2+ channels (LCC) allowing Ca2+ influx (ICa) to synchronize sarcoplasmic reticulum (SR) Ca2+ release, via Ca2+-release channels (RyR2). The resulting whole-cell Ca2+ transient triggers contraction, while cytosolic Ca2+ removal by SR Ca2+ pump (SERCA2)
Carlos A Valverde et al.
Cardiovascular research, 115(3), 556-569 (2018-09-01)
Abnormal Ca2+ release from the sarcoplasmic reticulum (SR), associated with Ca2+-calmodulin kinase II (CaMKII)-dependent phosphorylation of RyR2 at Ser2814, has consistently been linked to arrhythmogenesis and ischaemia/reperfusion (I/R)-induced cell death. In contrast, the role played by SR Ca2+ uptake under
Kirby R Campbell et al.
The journal of physical chemistry. B, 121(8), 1749-1757 (2017-02-09)
Extensive remodeling of the extracellular matrix (ECM) occurs in many epithelial cancers. For example, in ovarian cancer, upregulation of collagen isoform type III has been linked to invasive forms of the disease, and this change may be a potential biomarker.
Sanaya N Shroff et al.
iScience, 23(4), 100974-100974 (2020-04-17)
Precise measurement of action potentials (APs) is needed to observe electrical activity and cellular communication within cardiac tissue. Voltage-sensitive dyes (VSDs) are traditionally used to measure cardiac APs; however, they require acute chemical addition that prevents chronic imaging. Genetically encoded
S Antić et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 15(2), 1392-1405 (1995-02-01)
We carried out experiments to monitor optically the generation and spread of action potentials and subthreshold potentials in the processes of individual neurons in ganglia of the snail, Helix aspersa. The neurons were selectively stained by intracellular pressure injection of
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