MONOBROMOBIMANE

MONOBROMOBIMANE Property

Melting point:

152-154 °C(lit.)

Boiling point:

327.8±44.0 °C(Predicted)

Density 

1.66±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMF: soluble

form 

powder

pka

-3.36±0.70(Predicted)

color 

Yellow

λmax

398 nm

ε(extinction coefficient)

4.6-5.1 at 396-398nm in H2O

BRN 

4430959

Stability:

Light Sensitive

Biological Applications

Glutathione S-transferase substrates; detecting glutathione S-transferase,thiols,sulfite,homocysteine,mycothiol,sulfur compounds; thiol-reactive probes

InChI

InChI=1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3

InChIKey

AHEWZZJEDQVLOP-UHFFFAOYSA-N

SMILES

N12C(C)=C(C)C(=O)N1C(=O)C(C)=C2CBr

CAS DataBase Reference

71418-44-5

Safety

Safety Statements 

22-24/25

WGK Germany 

3

F 

8

HS Code 

2933.99.8290

Hazard and Precautionary Statements (GHS)

MONOBROMOBIMANE Chemical Properties,Usage,Production

Description

Monobromobimane is a thiol-reactive fluorogenic probe. It is cell-permeable, reacts rapidly at physiological pH with available thiol groups, and generates a stable fluorescent signal. Monobromobimane can be used to evaluate or quantify a variety of compounds containing reactive sulfur or thiol groups, including H₂S, glutathione, proteins, and nucleotides. The absorption and emission maxima for monobromobimane are 398 and 490 nm, respectively.

Chemical Properties

Yellow Powder

Uses

Monobromobimane readily reacts with low molecular weight thiols. Bimanes are useful for detecting the distribution of protein thiols in cells before and after chemical reduction of disulfides. Fluorescence: max. Abs. 398nm; e x 10-3: 5.0

Uses

Monobromobimane is essentially nonfluorescent until conjugated to target molecule. It readily reacts with several low molecular weight thiols, including glutathione, mercaptopurine, peptides and plasma thiols, as well as with carboxylic acids.

Uses

double labeled product that can be fixed with aldehydes for cell-lineage tracing1, neuronal tracing2 and transplantation3.

Uses

Monobromobimane is a thiol-reactive fluorogenic probe. It is cell-permeable, reacts rapidly at physiological pH with available thiol groups, and generates a stable fluorescent signal. Monobromobimane can be used to evaluate or quantify a variety of compounds containing reactive sulfur or thiol groups, including H2S, glutathione, proteins, and nucleotides. The absorption and emission maxima for monobromobimane are 398 and 490 nm, respectively.

Definition

ChEBI: A pyrazolopyrazole that consists of 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione bearing three methyl substituents at positions 2, 5 and 6 as well as a bromomethyl substituent at the 3-position.

References

[1] N S KOSOWER. Bimane fluorescent labels: labeling of normal human red cells under physiological conditions.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1979, 76 7: 3382-3386. DOI: 10.1073/pnas.76.7.3382
[2] CANDICE M KLINGERMAN. H2S concentrations in the arterial blood during H2S administration in relation to its toxicity and effects on breathing.[J]. American journal of physiology. Regulatory, integrative and comparative physiology, 2013, 305 6: R630-8. DOI: 10.1152/ajpregu.00218.2013
[3] G C RICE. Quantitative analysis of cellular glutathione by flow cytometry utilizing monochlorobimane: some applications to radiation and drug resistance in vitro and in vivo.[J]. Cancer research, 1986, 46 12 Pt 1: 6105-6110.
[4] YU-TSUNG CHEN. Probing conformational changes in human DNA topoisomerase IIα by pulsed alkylation mass spectrometry.[J]. The Journal of Biological Chemistry, 2012: 25660-25668. DOI: 10.1074/jbc.m112.377606
[5] R COSSTICK  F E  L W McLaughlin. Fluorescent labelling of tRNA and oligodeoxynucleotides using T4 RNA ligase.[J]. Nucleic Acids Research, 1984, 12 4: 1791-1810. DOI: 10.1093/nar/12.4.1791