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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
BCCK0958
BCCB4880
BCBM2356V
BCBB2166V
BCBB2166

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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
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
Andreas J Meyer et al.
Plant physiology, 130(4), 1927-1937 (2002-12-14)
We have investigated what limits demand-driven de novo glutathione (GSH) biosynthesis in green Arabidopsis suspension culture cells. GSH is the most abundant low-molecular weight thiol in most plants and can be quantified using monochlorobimane to fluorescently label GSH in live
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
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