69898
Bromobimane
suitable for fluorescence, BioReagent, ≥95% (HPCE)
Sinónimos:
Monobromobimane
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Fórmula empírica (notación de Hill):
C10H11BrN2O2
Número CAS:
Peso molecular:
271.11
UNSPSC Code:
12171500
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4430959
Servicio técnico
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BioReagent
Quality Level
assay
≥95% (HPCE)
form
solid
mp
152-154 °C (lit.)
solubility
DMF: soluble, DMSO: soluble, acetonitrile: soluble, methanol: soluble
fluorescence
λex 390 nm; λem 478 nm in 0.1 M phosphate pH 7.5 (after derivatization with glutathione), λex 398 nm
suitability
suitable for fluorescence
storage temp.
2-8°C
SMILES string
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
InChI key
AHEWZZJEDQVLOP-UHFFFAOYSA-N
General description
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.
Application
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.
Features and Benefits
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.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Other Notes
Fluorescent thiol-specific reagent
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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