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280135

Sigma-Aldrich

2-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide

Dye content 95 %

Synonym(s):

2-Di-1-ASP

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About This Item

Empirical Formula (Hill Notation):
C16H19IN2
CAS Number:
2156-29-8
Molecular Weight:
366.24
Beilstein:
3776369
EC Number:
218-460-8
MDL number:
MFCD00011980
UNSPSC Code:
12352103
PubChem Substance ID:
57648287
NACRES:
NA.23

form

solid

composition

Dye content, 95%

mp

280 °C (dec.) (lit.)

λmax

466 nm

fluorescence

λex 466 nm; λem 504 nm in methanol
λex 475 nm; λem 589 nm in methanol

SMILES string

[I-].CN(C)c1ccc(cc1)\C=C\c2cccc[n+]2C

InChI

1S/C16H19N2.HI/c1-17(2)15-10-7-14(8-11-15)9-12-16-6-4-5-13-18(16)3;/h4-13H,1-3H3;1H/q+1;/p-1

InChI key

XPOIQAIBZGSIDD-UHFFFAOYSA-M

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General description

2-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide (DASPMI) is a mitochondria staining styryl dye that is used to generate a quick responsive mechanism by applying changes in transmembrane potential. DASPMI can be used as a low toxic stain that shows a fluorescent behavior for mitochondria.
2-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide (DASPMI) is a styrylcyanine dye.

Application

DASPMI is a polar sensitive dye that measures the membrane potential of mitochondria in living cells. It may be used as a light absorber in the development of a photoinitiator based system.
DASPMI is popularly used in selective staining of mitochondria in living cells.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL8555
MKBR0101V
04305MX
11620DD

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S C Chang et al.
The Journal of biological chemistry, 273(24), 14933-14941 (1998-06-17)
In eukaryotic cells, cardiolipin (CL) synthase catalyzes the final step in the synthesis of CL from phosphatidylglycerol and CDP-diacylglycerol. CL and its synthesis are localized predominantly to the mitochondrial inner membrane, and CL is generally thought to be an essential
Use of fluorescent probes to investigate the metabolic state of Pneumocystis carinii mitochondria.
F Chen et al.
The Journal of eukaryotic microbiology, 41(5), 79S-79S (1994-09-01)
J W Li et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 29(4), 316-319 (1994-01-01)
A reversed phase high performance liquid chromatography (RP-HPLC) method for determination of 2-(p-dimethylaminostyryl) pyridine methiodide (DSPM) concentration in rabbit plasma is reported. The stationary phase was YWG-C18H37. The mobile phase consisted of 80% CH3OH, 20% CH3COOH-CH3COONa buffer (pH 4.0, 0.20
Dibakar Sahoo et al.
The journal of physical chemistry. B, 114(5), 2044-2050 (2010-01-22)
The mode of binding of 2-(4-(dimethylamino)styryl)-1-methylpyridinium iodide (DASPMI) with calf thymus DNA as revealed from different steady state and time-resolved emission spectroscopic measurements has been reported in this paper. Fluorescence enhancement of DASPMI and its quenching by potassium iodide (KI)
Distribution pattern of viable mitochondria in bovine lens epithelial cells.
O Leip et al.
Developments in ophthalmology, 26, 90-96 (1994-01-01)
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