46065

Ethidium bromide

for fluorescence, ≥95.0% (HPLC)

• Sinónimos: 3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide, EtBr, Homidium bromide
• Fórmula empírica (notación de Hill): C₂₁H₂₀BrN₃
• Número de CAS: 1239-45-8
• Peso molecular: 394.31
• Beilstein/REAXYS Number: 3642536
• EC Number: 214-984-6
• MDL number: MFCD00011724
• UNSPSC Code: 12352200
• PubChem Substance ID: 57650683

Propiedades

• grade: for fluorescence
• assay: ≥95.0% (HPLC)
• mp: 260-262 °C (dec.) (lit.)
• solubility: H₂O: 10 mg/mL, opaque, very dark red
• fluorescence: λ_ex 480 nm; λ_em 620 nm in H₂O; λ_ex 530 nm; λ_em 600 nm in 50 mM phosphate buffer pH 7.0 (upon binding to DNA)
• SMILES string: [Br-].CC[n+]1c(-c2ccccc2)c3cc(N)ccc3c4ccc(N)cc14
• InChI: 1S/C21H19N3.BrH/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14;/h3-13,23H,2,22H2,1H3;1H
• InChI key: ZMMJGEGLRURXTF-UHFFFAOYSA-N

Descripción

General description

Ethidium bromide (EtBr) undergoes complexation with nucleic acids (DNA and RNA) specifically to the saturated sites. These complexes decomposes by employing a cation-exchange resin. It has been reported to inhibit the production of mitochondrial RNA in HeLa cells. On interaction with helical polynucleotides under high salt medium, it forms fluorescent complex (having high fluorescence quantum yield).

Application

Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids. It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA. Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.

Frameshift mutagen which intercalates double-stranded DNA and RNA.

Ethidium bromide has been used to prepare fluorescent stock solution for the evaluation of cell viability during the live/dead assay of adipose-derived stem cells (ADSCs) seeded on irradiated hydrogels.

Biochem/physiol Actions

Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.

Reconstitution

Para la coloración de un gel después de electroforesis diluya una muestra de la solución madre hasta 0,5 μg/ml con agua e incube el gel durante 15 a 30 min. La decoloración no suele ser necesaria, pero puede llevarse a cabo durante 15 minutos si es preciso disminuir el fondo. Las bandas de ADN pueden detectarse en una caja de luz UV (254 nm de longitud de onda). También puede incorporarse bromuro de etidio en el gel para que actúe como tampón (0,5 μg/ml) y visualizarse inmediatamente por electroforesis.

Other Notes

Intercalating agent and fluorescent label for DNA. Review; Destruction and decontamination of solutions

Información de seguridad

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H302,H330,H341
• pcodes: P202 - P260 - P264 - P270 - P301 + P312 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 1 Inhalation - Acute Tox. 4 Oral - Muta. 2
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges