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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Dimethylaminostyrylmethylpyridiniumiodine (DASPMI) as a fluorescent probe for mitochondria in situ
Bereiter-Hahn J, et al.
Biochimica et Biophysica Acta, 423(1), 1-14 (1976)
G P Gorbenko et al.
Biofizika, 38(4), 699-702 (1993-07-01)
Using fluorescent probe 4-(n-dimethyl-aminostyryl)-1-methyl-pyridine (DSM) the effect of electrons with the energy 5 MeV on the structure of erythrocyte membrane has been investigated. It was found that in the irradiated erythrocyte ghosts the number of DSM binding sites increases. Irradiation
Styrylpyridinium borate salts as dye photoinitiators of free-radical polymerization
Jedrzejewska B, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 40(10), 1433-1440 (2002)
Aged mother cells of Saccharomyces cerevisiae show markers of oxidative stress and apoptosis
Laun P, et al.
Molecular Biology, 39(5), 1166-1173 (2001)
Photophysical Properties of DASPMI as Revealed by Spectrally Resolved Fluorescence Decays
Ramadass R and Bereiter-Han J
The Journal of Physical Chemistry B, 111 (26), 7681?7690-7681?7690 (2007)
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