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71418-44-5 | Bromobimane
CAS No: 71418-44-5 Catalog No: AG005IRC MDL No:MFCD00036951
Product Description
Catalog Number:
AG005IRC
Chemical Name:
Bromobimane
CAS Number:
71418-44-5
Molecular Formula:
C10H11BrN2O2
Molecular Weight:
271.1105
MDL Number:
MFCD00036951
IUPAC Name:
7-(bromomethyl)-1,2,6-trimethylpyrazolo[1,2-a]pyrazole-3,5-dione
InChI:
InChI=1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3
InChI Key:
AHEWZZJEDQVLOP-UHFFFAOYSA-N
SMILES:
BrCc1c(C)c(=O)n2n1c(C)c(c2=O)C
UNII:
V23UK0CYXL
NSC Number:
608544
Properties
Complexity:
437
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
270g/mol
Formal Charge:
0
Heavy Atom Count:
15
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
271.114g/mol
Monoisotopic Mass:
270g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
40.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.4
Literature
| Title | Journal |
|---|---|
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| Differential regulation of serine acetyltransferase is involved in nickel hyperaccumulation in Thlaspi goesingense. | The Journal of biological chemistry 20111125 |
| Characterization of flagellar cysteine-rich sperm proteins involved in motility, by the combination of cellular fractionation, fluorescence detection, and mass spectrometry analysis. | Cytoskeleton (Hoboken, N.J.) 20110901 |
| Caged fluorescent haptens reveal the generation of cryptic epitopes in allergic contact dermatitis. | The Journal of investigative dermatology 20110701 |
| Development of the fluorescent biosensor hCalmodulin (hCaM)L39C-monobromobimane(mBBr)/V91C-mBBr, a novel tool for discovering new calmodulin inhibitors and detecting calcium. | Journal of medicinal chemistry 20110609 |
| Modification and expulsion of keratins by human epidermal keratinocytes upon hapten exposure in vitro. | Chemical research in toxicology 20110516 |
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| Strategy for fluorescent labeling of human acidic fibroblast growth factor without impairment of mitogenic activity: a bona fide tracer. | Analytical biochemistry 20110401 |
| Automated tagging of pharmaceutically active thiols under flow conditions using monobromobimane. | Journal of pharmaceutical and biomedical analysis 20110325 |
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| Essential role of glutathione in acclimation to environmental and redox perturbations in the cyanobacterium Synechocystis sp. PCC 6803. | Plant physiology 20101201 |
| A monobromobimane-based assay to measure the pharmacokinetic profile of reactive sulphide species in blood. | British journal of pharmacology 20100601 |
| Determination of intracellular glutathione and cysteine using HPLC with a monolithic column after derivatization with monobromobimane. | Biomedical chromatography : BMC 20100501 |
| Cytosolic action of phytochelatin synthase. | Plant physiology 20100501 |
| Non-irradiated campherquinone induces DNA damage in human gingival fibroblasts. | Dental materials : official publication of the Academy of Dental Materials 20091201 |
| Assay of free captopril in human plasma as monobromobimane derivative, using RPLC/(+)ESI/MS/MS: validation aspects and bioequivalence evaluation. | Biomedical chromatography : BMC 20091001 |
| Bacillithiol is an antioxidant thiol produced in Bacilli. | Nature chemical biology 20090901 |
| The magnitude of the light-induced conformational change in different rhodopsins correlates with their ability to activate G proteins. | The Journal of biological chemistry 20090731 |
| Development and validation of a reversed-phase fluorescence HPLC method for determination of bucillamine in human plasma using pre-column derivatization with monobromobimane. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090715 |
| An alternative assay to discover potential calmodulin inhibitors using a human fluorophore-labeled CaM protein. | Analytical biochemistry 20090401 |
| Evidence for the amphipathic nature and tilted topology of helices 4 and 5 in the closed state of the colicin E1 channel. | Biochemistry 20090217 |
| Is ascorbate able to reduce disulfide bridges? A cautionary note. | Nitric oxide : biology and chemistry 20081101 |
| Structure and orientation of T4 lysozyme bound to the small heat shock protein alpha-crystallin. | Journal of molecular biology 20080125 |
| Acrosome stability in the spermatozoa of dasyurid marsupials. | Reproduction, fertility, and development 20080101 |
| Dynamics of arrestin-rhodopsin interactions: loop movement is involved in arrestin activation and receptor binding. | The Journal of biological chemistry 20070831 |
| Precision-cut tissue chips as an in vitro toxicology system. | Toxicology in vitro : an international journal published in association with BIBRA 20070801 |
| Thioredoxin-linked proteins are reduced during germination of Medicago truncatula seeds. | Plant physiology 20070701 |
| Assay of glutathione in must and wines using capillary electrophoresis and laser-induced fluorescence detection. Changes in concentration in dry white wines during alcoholic fermentation and aging. | Journal of chromatography. A 20070112 |
| Combining fluorescence detection and mass spectrometric analysis for comprehensive and quantitative analysis of redox-sensitive cysteines in native membrane proteins. | Analytical chemistry 20061201 |
| Coupling ligand structure to specific conformational switches in the beta2-adrenoceptor. | Nature chemical biology 20060801 |
| Effects of three resin monomers on the cellular glutathione concentration of cultured human gingival fibroblasts. | Dental materials : official publication of the Academy of Dental Materials 20060601 |
| Contribution of the mu loop to the structure and function of rat glutathione transferase M1-1. | Protein science : a publication of the Protein Society 20060601 |
| Metallothionein quantification in clams by reversed-phase high-performance liquid chromatography coupled to fluorescence detection after monobromobimane derivatization. | Journal of chromatography. A 20060224 |
| Thioredoxin target proteins in chloroplast thylakoid membranes. | Antioxidants & redox signaling 20060101 |
| Reactivity of zinc finger cysteines: chemical modifications within labile zinc fingers in estrogen receptor. | Journal of the American Society for Mass Spectrometry 20051201 |
| Site-directed fluorescence labeling reveals differences on the R-conformer of glucosamine 6-phosphate deaminase of Escherichia coli induced by active or allosteric site ligands at steady state. | Biochemistry 20051122 |
| Detection of neuronal growth inhibitory factor (metallothionein-3) in polyacrylamide gels and by Western blot analysis. | Journal of biochemical and biophysical methods 20050729 |
| Capillary zone electrophoresis for analysis of phytochelatins and other thiol peptides in complex biological samples derivatized with monobromobimane. | Electrophoresis 20050201 |
| Comparative study of sperm chromatin condensation in the excurrent ducts of the laboratory mouse Mus musculus and spinifex hopping mouse Notomys alexis. | Reproduction, fertility, and development 20050101 |
| Identification and characterization of a Pi isoform of glutathione S-transferase (GSTP1) as a zeaxanthin-binding protein in the macula of the human eye. | The Journal of biological chemistry 20041119 |
| Caspase-mediated apoptosis and caspase-independent cell death induced by irofulven in prostate cancer cells. | Molecular cancer therapeutics 20041101 |
| Preferential substrate binding orientation by the molecular chaperone HscA. | The Journal of biological chemistry 20040702 |
| Thioredoxin targets of developing wheat seeds identified by complementary proteomic approaches. | Phytochemistry 20040601 |
| Cy5 maleimide labelling for sensitive detection of free thiols in native protein extracts: identification of seed proteins targeted by barley thioredoxin h isoforms. | The Biochemical journal 20040301 |
| An electrophoretic profiling method for thiol-rich phytochelatins and metallothioneins. | Phytochemical analysis : PCA 20040101 |
| Monobromobimane occupies a distinct xenobiotic substrate site in glutathione S-transferase pi. | Protein science : a publication of the Protein Society 20031101 |
| Fluorescent labeling of disulfide proteins on 2D gel for screening allergens: a preliminary study. | Analytical chemistry 20030901 |
| Redox potential of human thioredoxin 1 and identification of a second dithiol/disulfide motif. | The Journal of biological chemistry 20030829 |
| Reductive dehalogenation of monobromobimane by tris(2-carboxyethyl)phosphine. | Analytical biochemistry 20030715 |
| Low-molecular-mass thiol compounds from a free-living highly pathogenic amoeba, Naegleria fowleri. | Biotechnology and applied biochemistry 20030401 |
| 20 S proteasome from Saccharomyces cerevisiae is responsive to redox modifications and is S-glutathionylated. | The Journal of biological chemistry 20030103 |
| Evaluation of fluorescent dyes for measuring intracellular glutathione content in primary cultures of human neurons and neuroblastoma SH-SY5Y. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20030101 |
| Vacuolar accumulation and extracellular extrusion of electrophilic compounds by wild-type and glutathione-deficient mutants of the methylotrophic yeast Hansenula polymorpha. | Cell biology international 20030101 |
| Nonselective currents and channels in plasma membranes of protoplasts from coats of developing seeds of bean. | Plant physiology 20020201 |
| Amount and redox state of cytoplasmic, membrane and periplasmic proteins in Escherichia coli redox mutants. | Research in microbiology 20010901 |
| Determination of monobromobimane derivatives of phenylmercapturic and benzylmercapturic acids in urine by high-performance liquid chromatography and fluorimetry. | Journal of chromatography. B, Biomedical sciences and applications 20010225 |
| Interaction of S100A8/S100A9-arachidonic acid complexes with the scavenger receptor CD36 may facilitate fatty acid uptake by endothelial cells. | Biochemistry 20010109 |
| Comparison of three different fluorescent visualization strategies for detecting Escherichia coli ATP synthase subunits after sodium dodecyl sulfate-polyacrylamide gel electrophoresis. | Proteomics 20010101 |
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