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69898

Sigma-Aldrich

Bromobimane

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

Synonym(s):

Monobromobimane

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About This Item

Empirical Formula (Hill Notation):
C10H11BrN2O2
CAS Number:
71418-44-5
Molecular Weight:
271.11
Beilstein/REAXYS Number:
4430959
MDL number:
MFCD00036951
UNSPSC Code:
12171500
PubChem Substance ID:
57652223
NACRES:
NA.32

product line

BioReagent

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Carl Simonsson et al.
The Journal of investigative dermatology, 131(7), 1486-1493 (2011-01-14)
Allergic contact dermatitis (ACD) is the most prevalent form of human immunotoxicity. It is caused by skin exposure to haptens, i.e., protein-reactive, low-molecular-weight chemical compounds, which form hapten-protein complexes (HPCs) in the skin, triggering the immune system. These immunogenic HPCs
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