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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
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Quality Level

100

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

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

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.

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

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.

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.

Legal Information

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

Disclaimer

Toxicity: Irritant (B)

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This Item
37291D7008309825
Dihydroethidium A cell-permeable, chemically-reduced ethidium derivative.

Sigma-Aldrich

309800

Dihydroethidium

Dihydroethidium BioReagent, suitable for fluorescence, ≥95% (HPCE)

Sigma-Aldrich

37291

Dihydroethidium

Dihydroethidium ≥95%

Sigma-Aldrich

D7008

Dihydroethidium

Dihydrorhodamine 123 Cell-permeable fluorogenic probe that is useful for the detection of reactive oxygen species (ROS) such as peroxide and peroxynitrite.

Sigma-Aldrich

309825

Dihydrorhodamine 123

color

pink

color

-

color

pink to very dark red

color

pink-white

solubility

DMSO: 20 mg/mL, DMF: soluble

solubility

acetonitrile: soluble, methanol: soluble

solubility

chloroform: 20 mg/mL

solubility

DMSO: 5 mg/mL

form

solid

form

solid

form

powder

form

solid

assay

≥95% (HPLC)

assay

≥95% (HPCE)

assay

≥95%

assay

≥95% (HPLC)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Global Trade Item Number

SKUGTIN
309800-25MG04055977216806

Questions

  1. I noticed that a compound from your catalogue is described as chemically reduced. I was wondering what the reducing agent used for this is?

    1 answer

    1. The reduction reagent used for this compound was sodium borohydride. The exact protocol used is proprietary to the lab and has not been disclosed, but the following publication may be of interest as a reference: Thomas G, Roques B., FEBS Lett. 1972; 26:169–175. The publication describes the process as follows: ...under nitrogen, in the dark and at 0°C, 500 mg of EB in 10 ml absolute methanol were added to 220 mg NaBH4. After 24 hr stirring, methanol was removed by evaporation in vacuum and 15 ml of 3% sodium hydroxide solution were added. After several extractions with ether, the phases were washed with water and dried over anhydrous sodium sulfate. Solvent was evaporated. The precipitate was recrystallized in ether to yield a light brown powder.

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