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Sigma-Aldrich

Bromobimane

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

Synonyme(s) :

Monobromobimane

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About This Item

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

Gamme de produits

BioReagent

Pureté

≥95% (HPCE)

Forme

solid

Pf

152-154 °C (lit.)

Solubilité

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

Adéquation

suitable for fluorescence

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

AHEWZZJEDQVLOP-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.

Caractéristiques et avantages

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

Fluorescent thiol-specific reagent

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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)
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
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
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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