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69899

Sigma-Aldrich

Monochlorobimane

suitable for fluorescence, ≥70.0% (HPCE)

Synonyme(s) :

mBCl, Chlorobimane

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About This Item

Formule empirique (notation de Hill):
C10H11ClN2O2
Numéro CAS:
76421-73-3
Poids moléculaire :
226.66
Numéro Beilstein :
4440901
Numéro MDL:
MFCD00077379
Code UNSPSC :
12352108
ID de substance PubChem :
329762099
Nomenclature NACRES :
NA.32

Niveau de qualité

100

Pureté

≥70.0% (HPCE)

Forme

powder

Pf

135-136 °C (lit.)

Solubilité

DMF: soluble
DMSO: soluble
acetonitrile: soluble
methanol: soluble

Fluorescence

λex 380 nm; λem 461 nm in methanol
λex 390 nm; λem 478 nm in 0.1 M phosphate pH 7.5 (after derivatization with glutathione)

Adéquation

suitable for fluorescence

Chaîne SMILES 

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

InChI

1S/C10H11ClN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3

Clé InChI

SUIPVTCEECPFIB-UHFFFAOYSA-N

Description générale

Monochlorobimane is a glutathione (GSH) fluorescent cell-permeable probe. When incubated with the test cell culture, it readily enters the cells and forms a fluorescent complex. The Monochlorobimane-GSH reaction is catalyzed by glutathione-S-transferase, which is detected fluorometrically.

Monochlorobimane, also known as mBCl, is a non-fluorescent compound that forms a fluorescent complex upon reaction. The fluorescence is detected at 394/490nm.

Application

Monochlorobimane is used as a fluorescent agent in fluorometric glutathione assays. It is used to detect the principal intracellular low-molecular-weight thiols, which play a pivotal role in the defense mechanism.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

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

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCCK0958
BCCB4880
BCBM2356V
BCBB2166V
BCBB2166

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Birgitta I Eklund et al.
Analytical biochemistry, 309(1), 102-108 (2002-10-17)
A rapid and facile colony assay has been developed for catalytically active enzymes in combinatorial cDNA libraries of mutated glutathione transferases (GST), expressed in Escherichia coli. The basis of the method is the conjugation of glutathione (GSH) with the fluorogenic
Peter Schröder et al.
Environmental science and pollution research international, 14(2), 114-122 (2007-04-26)
Numerous herbicides and xenobiotic organic pollutants are detoxified in plants to glutathione conjugates. Following this enzyme catalyzed reaction, xenobiotic GS-conjugates are thought to be compartmentalized in the vacuole of plant cells. In the present study, evidence is presented from experiments
Jana Wünschmann et al.
Phytochemistry, 71(1), 54-61 (2009-11-10)
Xenobiotics are widely used as pesticides. The detoxification of xenobiotics frequently involves conjugation to glutathione prior to compartmentalization and catabolism. In plants, degradation of glutathione-S-conjugates is initiated either by aminoterminal or carboxyterminal amino acid cleavage catalyzed by a gamma-glutamyl transpeptidase
A Jos et al.
Toxicology in vitro : an international journal published in association with BIBRA, 23(3), 546-553 (2009-05-16)
Reduced glutathione (GSH) protects cells against injury by oxidative stress and maintains a range of vital functions. In vitro cell cultures have been used as experimental models to study the role of GSH in chemical toxicity in mammals; however, this
Anke Grzam et al.
FEBS letters, 580(27), 6384-6390 (2006-11-14)
Monochlorobimane was used as a model xenobiotic for Arabidopsis to directly monitor the compartmentation of glutathione-bimane conjugates in situ and to quantify degradation intermediates in vitro. Vacuolar sequestration of the conjugate was very fast and outcompeted carboxypeptidation to the gamma-glutamylcysteine-bimane
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