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69898

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
Beilstein:
4430959
Numéro MDL:
MFCD00036951
Code UNSPSC :
12171500
ID de substance PubChem :
57652223
Nomenclature NACRES :
NA.32

Gamme de produits

BioReagent

Niveau de qualité

100

Essai

≥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

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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)

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Certificats d'analyse (COA)

Lot/Batch Number
BCCB2263
BCCB4375
BCCB4376
BCBF5306V
1371745V

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Consulter la Bibliothèque de documents

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
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
Justin W Taraska et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(38), 16227-16232 (2009-10-07)
The structure and dynamics of proteins underlies the workings of virtually every biological process. Existing biophysical methods are inadequate to measure protein structure at atomic resolution, on a rapid time scale, with limited amounts of protein, and in the context
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
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