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Merck

69898

Bromobimane

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

Synonyme(s) :

Monobromobimane

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A propos de cet article

Formule empirique (notation de Hill) :
C10H11BrN2O2
Numéro CAS:
71418-44-5
Poids moléculaire :
271.11
UNSPSC Code:
12171500
NACRES:
NA.32
PubChem Substance ID:
57652223
MDL number:
MFCD00036951
Beilstein/REAXYS Number:
4430959

Principaux documents

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Nom du produit

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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Catégories apparentées

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.

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
BCCM0976
BCCB2263
BCCB4375
BCCB4376
BCBF5306V

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Consulter la Bibliothèque de documents

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)
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
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
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