69899

Sigma-Aldrich

Monochlorobimane

suitable for fluorescence, ≥70.0% (HPCE)

Synonym(s):
Chlorobimane
Empirical Formula (Hill Notation):
C10H11ClN2O2
CAS Number:
Molecular Weight:
226.66
Beilstein/REAXYS Number:
4440901
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

≥70.0% (HPCE)

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

Contains up to 15% of an isomer (NMR)

Application

Cell-permeant probe for quantifying glutathione levels in cells. Suitable for the detection of thiol-groups.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
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...
Sabino Vesce et al.
The Journal of biological chemistry, 280(46), 38720-38728 (2005-09-21)
Decreases in GSH pools detected during ischemia sensitize neurons to excitotoxic damage. Thermodynamic analysis predicts that partial GSH depletion will cause an oxidative shift in the thiol redox potential. To investigate the acute bioenergetic consequences, neurons were exposed to monochlorobimane...
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...

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