8-Anilino-1-naphthalenesulfonic acid ammonium salt

SIGMA/10417 - for fluorescence, ≥97.0% (HPLC)

Synonym: 1,8-ANS NH₄; ANSA; Ammonium 8-anilino-1-naphthalenesulfonate; N-Phenyl peri acid

CAS Number: 28836-03-5
Empirical Formula (Hill Notation): C₁₆H₁₆N₂O₃S
Molecular Weight: 316.37
EC Number: 249-265-6
MDL Number: MFCD00012560
Linear Formula: C₁₆H₁₃NO₃S · NH₃
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-10417-5G-F	5 g	$63.70 1/EAAdd To Favorites	Add To Favorites
45-10417-25G-F	25 g	$498.00 1/EAAdd To Favorites	Add To Favorites
45-10417-100G-F	100 g	$751.00 1/EAAdd To Favorites	Add To Favorites

assay	≥97.0% (HPLC)
fluorescence	λ_ex 388 nm; λ_em 470 nm in 0.1 M Tris, 0.2 M KCl, pH 9.0, BSA
form	solid
grade	for fluorescence
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
loss	≤2.5% loss on drying
mp	245-253 °C
Quality Level	200
SMILES string	N.OS(=O)(=O)c1cccc2cccc(Nc3ccccc3)c12
solubility	acetone: soluble
	H₂O: 0.1 g/5mL, clear to very slightly hazy (hot)
	H₂O: soluble
	methanol: soluble
	NaOH: 1 N

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 .

Application:

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

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable