| Identification | Back Directory | [Name]
MONOBROMOBIMANE | [CAS]
71418-44-5 | [Synonyms]
MMB
MBBR
Nsc 608544
BROMOBIMANE
THIOLYTE(R) MB
MONOBROMOBIMANE
THIOLYTE(R) MB REAGENT
MBBr [MonobroMobiMane]
THIOLYTE MONOBROMOBIMANE REAGENT
MONOBROMOBIMANE, FOR FLUORESCENCE
THIOLYTE(R) MONOBROMOBIMANE REAGENT
3-(broMoMethyl)-2,5,6-triMethylpyrazolo[1,2-a]pyrazole-1,7-dione
THIOLYTE(R) MONOBROMOBIMANE REAGENT, FLUORESCENT LABELING COMPOUND | [Molecular Formula]
C10H11BrN2O2 | [MDL Number]
MFCD00036951 | [MOL File]
71418-44-5.mol | [Molecular Weight]
271.11 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Powder | [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 | [ε(extinction coefficient)]
4.6-5.1 at 396-398nm in H2O | [λmax]
398 nm | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Powder | [Uses]
double labeled product that can be fixed with aldehydes for cell-lineage tracing1, neuronal tracing2 and transplantation3. | [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]
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 | [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. | [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. | [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. | [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 |
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