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69898

Sigma-Aldrich

Bromobimane

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

Sinónimos:

Monobromobimane

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About This Item

Fórmula empírica (notación de Hill):
C10H11BrN2O2
Número de CAS:
71418-44-5
Peso molecular:
271.11
Beilstein:
4430959
Número MDL:
MFCD00036951
Código UNSPSC:
12171500
ID de la sustancia en PubChem:
57652223
NACRES:
NA.32

Línea del producto

BioReagent

Ensayo

≥95% (HPCE)

Formulario

solid

mp

152-154 °C (lit.)

solubilidad

DMF: soluble
DMSO: soluble
acetonitrile: soluble
methanol: soluble

fluorescencia

λex 390 nm; λem 478 nm in 0.1 M phosphate pH 7.5 (after derivatization with glutathione)
λex 398 nm

idoneidad

suitable for fluorescence

temp. de almacenamiento

2-8°C

cadena SMILES

CC1=C(C)C(=O)N2N1C(CBr)=C(C)C2=O

InChI

1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3

Clave InChI

AHEWZZJEDQVLOP-UHFFFAOYSA-N

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Descripción general

Bromobimane, also called probe for thiols, is a fluorescent reagent activated upon a photolysis reaction. Bromobimane in solution reacts with small thiol groups (e.g., GSH) and with reactive protein thiol groups (e.g., hemoglobin). The reaction of Bromobimane with thiols is of second-order and dependent on pH. And, upon reacting with thiolate, it activates the water-soluble fluorescent product for detection.

Aplicación

Bromobimane is used for the determination of thiols by the HPLC method. It is suitable as a pre-column derivatization agent for fluorometric determination of 2,3-dimercaptopropane-1-sulfonic acid and other dithiols. Bromobimane has been used as a fluorescent label in studying oligomycin-sensitive ATPase from beef heart mitochondria.

Características y beneficios

The benefits of using Bromobimane for the analysis of low molecular weight thiols are: Highly selective.
  • Rapid reactivity.
  • Ease of separation of derivatives by reverse HPLC.
  • Ability to penetrate cells.

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Otras notas

Fluorescent thiol-specific reagent

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
BCCM0976
BCCB2263
BCCB4375
BCCB4376
BCBF5306V

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Visite la Librería de documentos

P C Chinn et al.
Analytical biochemistry, 159(1), 143-149 (1986-11-15)
A highly sensitive and specific assay for Escherichia coli thioredoxin was developed using the thiol-specific reagent monobromobimane. Treatment of dithiothreitol-reduced thioredoxin with an excess of monobromobimane in Tris buffer (pH 8.0, 23 degrees C) for 30 min resulted in the
R M Maiorino et al.
Journal of chromatography, 374(2), 297-310 (1986-01-24)
The increasing therapeutic use of dithiol metal binding agents, such as 2,3-dimercaptopropane-1-sulfonic acid (DMPS), has stimulated the need for a sensitive and selective method for their determination in biological fluids. A method has now been developed in which DMPS was
Determination of low-molecular-weight thiols using monobromobimane fluorescent labeling and high-performance liquid chromatography.
R C Fahey et al.
Methods in enzymology, 143, 85-96 (1987-01-01)
Brigitte Bauer et al.
Chemical research in toxicology, 24(5), 737-743 (2011-04-14)
Allergic contact dermatitis is the most prevalent form of human immunotoxicity. It is caused by reactive low molecular weight chemicals, that is, haptens, coming in contact with the skin where hapten-peptide complexes are formed, activating the immune system. By using
Michael Hall et al.
Proteomics, 10(5), 987-1001 (2010-01-06)
The light-dependent regulation of stromal enzymes by thioredoxin (Trx)-catalysed disulphide/dithiol exchange is known as a classical mechanism for control of chloroplast metabolism. Recent proteome studies show that Trx targets are present not only in the stroma but in all chloroplast
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