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69899

Sigma-Aldrich

Monochlorobimane

suitable for fluorescence, ≥70.0% (HPCE)

Synonym(s):

mBCl, Chlorobimane

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About This Item

Empirical Formula (Hill Notation):
C10H11ClN2O2
CAS Number:
76421-73-3
Molecular Weight:
226.66
Beilstein:
4440901
MDL number:
MFCD00077379
UNSPSC Code:
12352108
PubChem Substance ID:
329762099
NACRES:
NA.32

Quality Level

100

Assay

≥70.0% (HPCE)

form

powder

mp

135-136 °C (lit.)

solubility

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)

suitability

suitable for fluorescence

SMILES string

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

InChI key

SUIPVTCEECPFIB-UHFFFAOYSA-N

General description

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB4880
BCBM2356V
BCBB2166V
BCBB2166
1393526

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Jordi Sebastià et al.
Cytometry. Part A : the journal of the International Society for Analytical Cytology, 51(1), 16-25 (2002-12-25)
Reduced glutathione (GSH) protects cells against oxidative injury and maintains a range of vital functions. To study GSH content in human neuronal cell cultures, thiol-sensitive fluorescent techniques requiring a small number of cells may be of great value, but their
Natascha Rauch et al.
Insect biochemistry and molecular biology, 34(4), 321-329 (2004-03-26)
Glutathione S-transferases (GST) catalyzing the conjugation of reduced glutathione to a vast range of xenobiotics including insecticides were characterized in the whitefly Bemisia tabaci. GST activities were determined in susceptible and resistant strains of B. tabaci towards artificial substrates, i.e.
S Nair et al.
Cytometry, 12(4), 336-342 (1991-01-01)
We have used an enzymatic (spectro-photometric) and a flow cytometric (GSH-MBCL) method to compare the glutathione (GSH) content of doxorubicin sensitive (P388) and resistant (P388/R-84) murine leukemic and human lung cancer cells. The flow cytometric analysis revealed that GSH-MBCL conjugate
Jens Waak et al.
Neurochemical research, 31(12), 1409-1416 (2006-11-08)
Monochlorobimane (MCB) is often used to visualize glutathione (GSH) levels in cultured cells, since it is quickly converted to a fluorescent GSH conjugate (GS-MCB). To test for consequences of MCB application on the GSH metabolism of astrocytes, we have studied
Madushi Raththagala et al.
Analytical chemistry, 78(24), 8556-8560 (2006-12-15)
A method for the quantitative determination of the antioxidant form of glutathione (GSH) in red blood cells (RBCs) is described that does not require separation of the analyte of interest from the complex cellular matrix. The measurement portion of the
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