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8-Aminonaphthalene-1,3,6-trisulfonic acid disodium salt

SIGMA/08658 - BioReagent, suitable for fluorescence, ≥90% (CE)

Synonym: ANTS; Disodium 8-amino-1,3,6-naphthalenetrisulfonate

CAS Number: 5398-34-5
Empirical Formula (Hill Notation): C10H7NNa2O9S3
Molecular Weight: 427.34
EC Number: 226-431-6
MDL Number: MFCD00070572
Linear Formula: C10H7NNa2O9S3
Product Type: Chemical

Catalog Number PKG Qty. Price Quantity
45-08658-500MG 500 mg
$896.00
1/EA
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assay ≥90% (CE)
fluorescence λex 356 nm; λem 512 nm in 0.1 M phosphate pH 7.0
impurities ~8% water
InChI 1S/C10H9NO9S3.2Na/c11-8-3-6(21(12,13)14)1-5-2-7(22(15,16)17)4-9(10(5)8)23(18,19)20;;/h1-4H,11H2,(H,12,13,14)(H,15,16,17)(H,18,19,20);;/q;2*+1/p-2
InChI key KHJANRFXWPPWEL-UHFFFAOYSA-L
product line BioReagent
Quality Level 200 
SMILES string [Na+].[Na+].Nc1cc(cc2cc(cc(c12)S([O-])(=O)=O)S([O-])(=O)=O)S(O)(=O)=O
solubility 15% acetic acid: soluble
  H2O: soluble
suitability suitable for fluorescence
Application: Fluorescent label for saccharides and glycoproteins used for oligosaccharide sequencing.
Application: This molecular reagent is a polyanionic dye, which is often coupled with the cationic quencher DPX (X1525) for membrane fusion or permeability assays , including complement-mediated immune lysis. The fluorescence of ANTS has been shown to be effectively quenched by Thallium and Cesium ions. Utilized as a neuronal tracer. ANTS has a relatively high Stokes shift in water , which sufficiently separates its emission from the majority of the autofluorescence of biological samples. D2O increased the fluorescence quantum yield of ANTS four-fold, which has been demonstrated to be useful in the determination of water permeability in red blood cell ghosts and kidney collecting tubes . The reducing end of carbohydrates reacts with the primary amino group of the ANTS molecule, forming a Schiff base, which can then be reduced by sodium cyanoborohydride to a secondary amine. This reductive amination reaction is acid catalyzed, so the pH of the reaction solution can alter the kinetics and the degree of derivatization of the carbohydrate by ANTS. It is important to note this reaction is capable of proceeding at a neutral pH, which is favorable for the integrity of the sialic acid bonds in the oligosaccharide because they are sensitive to acid hydrolysis. Such labeling of carbohydrates with ANTS allows for complex mixtures to be separated via capillary electrophoresis .
RIDADR NONH for all modes of transport
WGK Germany WGK 1
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥90% (CE)
UNSPSC 12352106

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