8-Anilinonaphthalene-1-sulfonic acid

8-Anilinonaphthalene-1-sulfonic acid

Names
IUPAC name 8-(Phenylamino)-1-naphthalenesulfonic acid
Other names Phenylperi acid
Identifiers
CAS Number	82-76-8
ChEBI	CHEBI:39708
ChEMBL	ChEMBL285527
ChemSpider	1328
DrugBank	DB04474
Jmol interactive 3D	Image Image
KEGG	C11326
PubChem	1369
InChI InChI=1S/C16H13NO3S/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) Key: FWEOQOXTVHGIFQ-UHFFFAOYSA-N InChI=1/C16H13NO3S/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) Key: FWEOQOXTVHGIFQ-UHFFFAOYAB
SMILES O=S(=O)(O)c2c1c(cccc1ccc2)Nc3ccccc3 c1ccc(cc1)Nc2cccc3c2c(ccc3)S(=O)(=O)O
Properties
Chemical formula	C16H13NO3S
Molar mass	299.34 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

8-Anilinonaphthalene-1-sulfonic acid (ANS), also called 1-anilino-8-naphthalenesulfonate, is an organic compound containing both a sulfonic acid and an amine group. This compound is used as a fluorescent molecular probe.^[1] For example, ANS can be used to study conformational changes induced by ligand binding in proteins, as ANS's fluorescent properties will change as it binds to hydrophobic regions on the protein surface. Comparison of the fluorescence in the presence and absence of a particular ligand can thus give information about how the binding of the ligand changes the surface of the protein. Its permeability to mitochondrial membranes makes it particularly useful.^[2]

References

1. Andras Malnasi-Csizmadia; György Hegyi; Ferenc Tölgyesi; Andrew G. Szent-Györgyi & László Nyitray (1999). "Fluorescence measurements detect changes in scallop myosin regulatory domain". European Journal of Biochemistry 261 (2): 452–8. doi:10.1046/j.1432-1327.1999.00290.x. PMID 10215856.
2. Gains N; Dawson AP (April 1975). "8-Anilinonaphthalene-1-sulphonate interaction with whole and disrupted mitochondria: a re-evaluation of the use of double-reciprocal plots in the derivation of binding parameters for fluorescent probes binding to mitochondrial membranes". Biochem. J. 148 (1): 157–60. PMC 1165518. PMID 1156395.