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Merck
CN

69899

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
UNSPSC Code:
12352108
NACRES:
NA.32
PubChem Substance ID:
329762099
MDL number:
MFCD00077379
Beilstein/REAXYS Number:
4440901

Key Documents

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Product Name

Monochlorobimane, suitable for fluorescence, ≥70.0% (HPCE)

InChI

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

SMILES string

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

InChI key

SUIPVTCEECPFIB-UHFFFAOYSA-N

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

Quality Level

100

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.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK0958
BCCB4880

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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
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.
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
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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