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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:
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 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

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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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
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
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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