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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:
Molecular Weight:
366.24
Beilstein:
3776369
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
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

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

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Anamika Manna et al.
The journal of physical chemistry. B, 116(8), 2464-2471 (2012-02-07)
We report an interesting pH-tunable energy transfer between an acceptor ionic styryl dye 2-(4-(dimethylamino)styryl)-1-methylpyridinium iodide and a donor charge-transfer dye 1,8-naphthalimide in a vesicular medium. The polyethylene-b-polyethylene glycol block copolymer intercalates with the sodium dodecyl sulfate anionic surfactant to form
Spectral signature of 2-[4-(dimethylamino) styryl]-1-methylquinolinium iodide: A case of negative solvatochromism in water
Sahoo D, et al.
The Journal of Physical Chemistry B, 115(37), 10983-10989 (2011)
Mitochondrial Function Is Involved in LDL Oxidation Mediated by Human Cultured Endothelial Cells
Mabile L, et al.
Arteriosclerosis, Thrombosis, and Vascular Biology, 17, 1575-1582 (1997)
Anamika Manna et al.
The journal of physical chemistry. B, 116(17), 5226-5233 (2012-04-18)
This paper reports an interesting transformation of binding mode of 2-(4-(dimethylamino)styryl)-1-methylpyridinium iodide (DASPMI) with calf thymus DNA from minor groove binding in buffer solution to intercalative binding when the dye is encapsulated inside a vesicle formed by the interaction of
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

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