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Key Documents

B4380

Sigma-Aldrich

Bromobimane

≥97% purity, powder

Synonyme(s) :

Monobromobimane

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About This Item

Formule empirique (notation de Hill):
C10H11BrN2O2
Numéro CAS:
Poids moléculaire :
271.11
Numéro Beilstein :
4430959
Numéro MDL:
Code UNSPSC :
12171500
ID de substance PubChem :
Nomenclature NACRES :
NA.47

product name

Bromobimane, ≥97% (HPLC)

Niveau de qualité

Pureté

≥97% (HPLC)

Forme

powder

Couleur

yellow

Pf

161 °C

Solubilité

acetonitrile: 20 mg/mL

ε (coefficient d'extinction)

4.6-5.1 at 396-398 nm in H2O

Application(s)

diagnostic assay manufacturing
hematology
histology

Température de stockage

−20°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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Description générale

Bromobimane is also known as monobromobimane. It is also a known probe for thiols and is a fluorescent reagent activated upon a photolysis reaction.

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.
Bromobimane has been used for the quantitative measurement of free hydrogen sulfide in vivo and in vitro. It has been used for the labeling of proteins containing thiol groups.

Actions biochimiques/physiologiques

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.

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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Les clients ont également consulté

Bromobimane probes for thiols.
E M Kosower et al.
Methods in enzymology, 251, 133-148 (1995-01-01)
N S Kosower et al.
Proceedings of the National Academy of Sciences of the United States of America, 76(7), 3382-3386 (1979-07-01)
The bimane fluorescent labels, monobromobimane, dibromobimane, and monobromotrimethylammoniobimane, are derivatives of syn-9,10-dioxabimane:1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione. They efficiently label hemoglobin (reactive thiol groups), membrane proteins, and glutathione of normal human red cells under physiological conditions. Monobromobimane and dibromobimane are effective on intact cells while
Differing effects of mechanical dough development and sheeting development methods on aggregated glutenin proteins.
Sutton KH, et al.
Cereal Chem., 80.6, 707-711 (2003)
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
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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