69898
Bromobimane
suitable for fluorescence, BioReagent, ≥95% (HPCE)
Synonym(s):
Monobromobimane
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About This Item
Empirical Formula (Hill Notation):
C10H11BrN2O2
CAS Number:
Molecular Weight:
271.11
Beilstein:
4430959
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.32
Recommended Products
product line
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
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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
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
Florencia Sardi et al.
Analytical biochemistry, 435(1), 74-82 (2013-01-09)
A method based on the differential reactivity of thiol and thiolate with monobromobimane (mBBr) has been developed to measure nucleophilicity and acidity of protein and low-molecular-weight thiols. Nucleophilicity of the thiolate is measured as the pH-independent second-order rate constant of
Joachim Volk et al.
Dental materials : official publication of the Academy of Dental Materials, 25(12), 1556-1563 (2009-09-01)
Camphorquinone (CQ) is cytotoxic in cell cultures. The mechanism of this toxic action, however, is not yet clearly understood. Aim of this investigation was to analyze the effects of non-irradiated CQ on intracellular formation of reactive oxygen species (ROS), intracellular
G Zimmer et al.
FEBS letters, 150(1), 207-210 (1982-12-13)
Using a bromobimane fluorescent label the Mr 31 000 protein band oligomycin-sensitive (OS)-ATPase from beef heart mitochondria is shown to become much intensified by 2-mercaptopropionylglycine. In the presence of 3.5 nmol/mg protein of the thiol reagent ATP-Pi exchange activity is
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