309800

Dihydroethidium

A cell-permeable, chemically-reduced ethidium derivative.

• Synonym(s): Dihydroethidium, 2,7-Diamino-10-ethyl-9-phenyl-9,10-dihydrophenanthridine, DHE
• Empirical Formula (Hill Notation): C₂₁H₂₁N₃
• CAS Number: 38483-26-0
• Molecular Weight: 315.41
• MDL number: MFCD00077335
• UNSPSC Code: 12161505
• NACRES: NA.25

Properties

• 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

Description

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

Warning

Toxicity: Irritant (B)

Reconstitution

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3