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Merck
CN

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:
71418-44-5
Molecular Weight:
271.11
UNSPSC Code:
12171500
NACRES:
NA.32
PubChem Substance ID:
57652223
MDL number:
MFCD00036951
Beilstein/REAXYS Number:
4430959

Key Documents

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Product Name

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

InChI

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

SMILES string

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

InChI key

AHEWZZJEDQVLOP-UHFFFAOYSA-N

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

Quality Level

100

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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.

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.

Other Notes

Fluorescent thiol-specific reagent

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0976
BCCB2263
BCCB4375
BCCB4376
BCBF5306V

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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
Edward A Wintner et al.
British journal of pharmacology, 160(4), 941-957 (2010-07-02)
Hydrogen sulphide (H(2)S) is a labile, endogenous metabolite of cysteine, with multiple biological roles. The development of sulphide-based therapies for human diseases will benefit from a reliable method of quantifying H(2)S in blood and tissues. Concentrations of reactive sulphide in
Xiao Jie Yao et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(23), 9501-9506 (2009-05-28)
G protein-coupled receptors (GPCRs) mediate the majority of physiologic responses to hormones and neurotransmitters. However, many GPCRs exhibit varying degrees of agonist-independent G protein activation. This phenomenon is referred to as basal or constitutive activity. For many of these GPCRs
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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