46065

Ethidium bromide

for fluorescence, ≥95.0% (HPLC)

• Sinônimo(s): 3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide, EtBr, Homidium bromide
• Fórmula empírica (Notação de Hill): C₂₁H₂₀BrN₃
• Número CAS: 1239-45-8
• Peso molecular: 394.31
• Beilstein: 3642536
• Número CE: 214-984-6
• Número MDL: MFCD00011724
• Código UNSPSC: 12352200
• ID de substância PubChem: 57650683

Propriedades

• grau: for fluorescence
• Ensaio: ≥95.0% (HPLC)
• pf: 260-262 °C (dec.) (lit.)
• solubilidade: H₂O: 10 mg/mL, opaque, very dark red
• fluorescência: 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)
• cadeia de caracteres SMILES: [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
• chave InChI: ZMMJGEGLRURXTF-UHFFFAOYSA-N

Descrição

Descrição geral

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).

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Reconstituição

For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.

Outras notas

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

Informações de segurança

• Pictogramas: GHS06,GHS08
• Palavra indicadora: Danger
• Frases de perigo: H302,H330,H341
• Declarações de precaução: P202 - P260 - P264 - P270 - P301 + P312 - P304 + P340 + P310
• Classificações de perigo: Acute Tox. 1 Inhalation - Acute Tox. 4 Oral - Muta. 2
• Código de classe de armazenamento: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de risco de água (WGK): WGK 1
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges