10417

8-Anilino-1-naphthalenesulfonic acid ammonium salt

for fluorescence, ≥97.0% (HPLC)

• Synonym(s): 1,8-ANS NH₄, ANSA, Ammonium 8-anilino-1-naphthalenesulfonate, N-Phenyl peri acid
• Linear Formula: C₁₆H₁₃NO₃S · NH₃
• CAS Number: 28836-03-5
• Molecular Weight: 316.37
• Beilstein/REAXYS Number: 3581235
• EC Number: 249-265-6
• MDL number: MFCD00012560
• UNSPSC Code: 12352106
• PubChem Substance ID: 57646782
• NACRES: NA.32

Properties

• grade: for fluorescence
• Quality Level: 200
• assay: ≥97.0% (HPLC)
• form: solid
• loss: ≤2.5% loss on drying
• mp: 245-253 °C
• solubility: H₂O: 0.1 g/5mL, clear to very slightly hazy (hot); NaOH: 1 N; H₂O: soluble; acetone: soluble; methanol: soluble
• fluorescence: λ_ex 388 nm; λ_em 470 nm in 0.1 M Tris, 0.2 M KCl, pH 9.0, BSA
• SMILES string: N.OS(=O)(=O)c1cccc2cccc(Nc3ccccc3)c12
• InChI: 1S/C16H13NO3S.H3N/c18-21(19,20)15-11-5-7-12-6-4-10-14(16(12)15)17-13-8-2-1-3-9-13;/h1-11,17H,(H,18,19,20);1H3
• InChI key: IPBNQYLKHUNLQE-UHFFFAOYSA-N

Description

Application

ANS forms an inclusion complex with cyclodextrin. Such model systems are useful to mimic biological recognition and can be studied by measuring the change in fluorescence of free-ANS to complexed-ANS. When ANS enters the hydrophobic core of cyclodestrin, it′s fluorescence increases . Utilized in the reagent phase of a sodium-selective fiber-optic sensor. The reagent phase also contains a copper(II) polyelectrolyte, which binds to ANSA in the absence of sodium and quenches the fluorescence. In the presence of sodium, ANSA forms a cationic complex creating ion-pairs, causing it to fluoresce . ANS is often incorporated into di-block polymers and can be released by changes in the local environment (i.e., temperature, pH, etc.) . ANS is commonly used as a fluorescence probe to investigate molecular assemblies of surfactants and amphiphilic polymers because a blue shift of the emission maximum indicates the fluorophore is located in less polar media . Fluorescent probe for protein studies using methodologies such as steady-state and dynamic fluorescence measurements .

This product is an amphiphilic fluorescent probe for protein studies . Excitation of the unbound dye at 380 nm results in a low fluorescent emission with a maximum at 545 nm. The fluorescence intensity of ANS increases when the dye binds to the hydrophobic regions of a protein . The protein-ANS complex has an emission spectrum which is shifted to a broad maximum at 470 nm. At pH 8, protein causes a 40-fold increase in the relative quantum yield compared to free ANS in solution . ANS has been used to monitor protein conformational changes by binding to the hydrophobic regions of a protein , to gain new insight into protein binding interactions, often by acting as reporter or competitor ligands, to investigate the visual excitation process and structural aspects of photoreceptor cell membranes , and to probe (and disrupt) the structure of both high- and low-density lipoproteins. It has also been used as a substrate in a chemiluminescent enzyme immunoassay system and as a dye for yeast viability determination. The conformational states for apo- and holo- yeast alcohol dehydrogenase were reported under conditions of low pH using ANS fluorescence . ANS is also commonly used as a fluorescence probe to investigate molecular assemblies of surfactants and amphiphilic polymers because a blue shift of its emission maximum indicates the probe is located in less polar environment

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves