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Merck

309800

Dihydroethidium

A cell-permeable, chemically-reduced ethidium derivative.

Synonym(s):

Dihydroethidium, 2,7-Diamino-10-ethyl-9-phenyl-9,10-dihydrophenanthridine, DHE

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About This Item

Empirical Formula (Hill Notation):
C21H21N3
CAS Number:
104821-25-2
Molecular Weight:
315.41
MDL number:
MFCD00077335
UNSPSC Code:
12161505
NACRES:
NA.25

Product Name

Dihydroethidium, A cell-permeable, chemically-reduced ethidium derivative.

SMILES string

Nc1c2c(cnc1)c3c(cc(cc3)N)C(C2CC)c4ccccc4

InChI

1S/C21H21N3/c1-2-15-20(13-6-4-3-5-7-13)17-10-14(22)8-9-16(17)18-11-24-12-19(23)21(15)18/h3-12,15,20H,2,22-23H2,1H3

InChI key

ZDWPSSBKIMIPMY-UHFFFAOYSA-N

description

RTECS - SF7935000

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

pink

solubility

DMSO: 20 mg/mL
DMF: soluble

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Useful fluorogenic probe for the detection of reactive oxygen species (ROS)
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Irritant (B)

General description

A cell-permeable, chemically reduced ethidium derivative that can be used as a fluorogenic probe for the detection of reactive oxygen species (ROS). It undergoes significant oxidation in resting leukocytes, possibly through the uncoupling of mitochondrial oxidative phosphorylation. Cytosolic dihydroethidium displays blue fluorescence, however, following oxidation to ethidium and subsequent intercalation to DNA, a bright red fluorescence is achieved. Often used to determine the level of superoxide anion in cells by flow cytometry.
A cell-permeable, chemically-reduced ethidium derivative. Commonly used to analyze respiratory burst in phagocytes. Useful fluorogenic probe for the detection of reactive oxygen species (ROS). It undergoes significant oxidation in resting leukocytes, possibly through the uncoupling of mitochondrial oxidative phosphorylation. Cytosolic dihydroethidium displays blue fluorescence, whereas after oxidation of this probe to ethidium, it intercalates cell’s DNA, staining the nucleus with a bright red fluorescence.

Other Notes

Haugen, T.S., et al. 1999. Eur. Respir. J.14, 1100.
Mancini, M., et al. 1997. J. Cell Biol.138, 449.
Carter, W.O., et al. 1994. J. Leukoc. Biol.55, 253.
Cinco, M., et al. 1994. FEMS Microbiol. Lett. 122, 187.
Perticarari, S., et al. 1994. J. Immunol. Methods 170, 117.
Perticarari, S., et al. 1991. Cytometry 12, 687.
Bucana, C.D., et al. 1990. Exp. Cell Res.190, 69.
Rothe, G., and Valet, G. 1990. J. Leukoc. Biol.47, 440.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot, flush with an inert gas, and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 3

Certificates of Analysis (COA)

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