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69899

Sigma-Aldrich

Monochlorobimane

suitable for fluorescence, ≥70.0% (HPCE)

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Synonym(s):
mBCl, Chlorobimane
Empirical Formula (Hill Notation):
C10H11ClN2O2
CAS Number:
Molecular Weight:
226.66
Beilstein:
4440901
MDL number:
PubChem Substance ID:

Quality Level

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

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Monochlorobimane suitable for fluorescence, ≥70.0% (HPCE)

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Monochlorobimane

Rhodamine 110 chloride suitable for fluorescence, BioReagent, ≥99.0% (UV)

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Bromobimane BioReagent, suitable for fluorescence, ≥95% (HPCE)

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69898

Bromobimane

form

powder

form

-

form

crystals

form

solid

solubility

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

solubility

-

solubility

ethanol: soluble, methanol: soluble

solubility

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

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

mp

135-136 °C (lit.)

mp

-

mp

>300 °C (lit.)

mp

152-154 °C (lit.)

fluorescence

λex 380 nm; λem 461 nm in methanol

fluorescence

λex 380 nm; λem 515 nm

fluorescence

λex 498 nm; λem 520 nm in methanol

fluorescence

λex 390 nm; λem 478 nm in 0.1 M phosphate pH 7.5 (after derivatization with glutathione), λex 398 nm

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

Signal Word

Warning

Hazard Statements

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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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
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
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
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
Yoshihiro Nakano et al.
Bioscience, biotechnology, and biochemistry, 70(7), 1790-1793 (2006-07-25)
Previously we reported the purification of soluble gamma-glutamyltransferases (GGTs) from radish cotyledon. Subcellular fractionation of radish cells revealed that soluble GGT is a vacuolar enzyme. Acivicin, a GGT inhibitor, mediated the in vivo catabolism inhibition of the glutathione S-conjugate generated

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Fluorescence lifetime measurement is advantageous over intensity-based measurements. Applications include fluorescence lifetime assays, sensing and FLI.

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