08658

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

BioReagent, suitable for fluorescence, ≥90% (CE)

• Synonym(s): ANTS, Disodium 8-amino-1,3,6-naphthalenetrisulfonate
• Empirical Formula (Hill Notation): C₁₀H₇NNa₂O₉S₃
• CAS Number: 5398-34-5
• Molecular Weight: 427.34
• Beilstein/REAXYS Number: 3854839
• EC Number: 226-431-6
• MDL number: MFCD00070572
• UNSPSC Code: 12352106
• PubChem Substance ID: 329748624
• NACRES: NA.32

Properties

• product line: BioReagent
• Quality Level: 200
• assay: ≥90% (CE)
• impurities: ~8% water
• solubility: 15% acetic acid: soluble; H₂O: soluble
• fluorescence: λ_ex 356 nm; λ_em 512 nm in 0.1 M phosphate pH 7.0
• suitability: suitable for fluorescence
• SMILES string: [Na+].[Na+].Nc1cc(cc2cc(cc(c12)S([O-])(=O)=O)S([O-])(=O)=O)S(O)(=O)=O; [Na+].[Na+].Nc1cc(cc2cc(cc(c12)S([O-])(=O)=O)S([O-])(=O)=O)S(O)(=O)=O
• 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

Description

Application

Fluorescent label for saccharides and glycoproteins used for oligosaccharide sequencing.[1][2]

Fluorescent label for saccharides and glycoproteins, which is used for oligosaccharide sequencing and the study of membrane permeability and liposome lysis.

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 .

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)