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Sigma-Aldrich

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

Dye content 95 %

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Synonym(s):
2-Di-1-ASP
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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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
Microtubules mediate mitochondrial distribution in fission yeast
Yaffe MP, et al.
Proceedings of the National Academy of Sciences of the USA, 93, 11664-11668 (1996)
Distribution pattern of viable mitochondria in bovine lens epithelial cells.
O Leip et al.
Developments in ophthalmology, 26, 90-96 (1994-01-01)
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)
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