dipotassium 8-(phenylamino)-5-[4-(phenylamino)-5-sulfonatonaphthalen-1-yl]naphthalene-1-sulfonate

• ChemBase ID: 102958
• Molecular Formular: C32H22K2N2O6S2
• Molecular Mass: 672.85348
• Monoisotopic Mass: 672.01934179
• SMILES: [K+].[K+].[O-]S(=O)(=O)c1cccc2c(ccc(Nc3ccccc3)c12)c1c2cccc(c2c(Nc2ccccc2)cc1)S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)c1cccc2c1c(ccc2c1ccc(c2c1cccc2S(=O)(=O)[O-])Nc1ccccc1)Nc1ccccc1.[K+].[K+]
• InChI: InChI=1S/C32H24N2O6S2.2K/c35-41(36,37)29-15-7-13-25-23(17-19-27(31(25)29)33-21-9-3-1-4-10-21)24-18-20-28(34-22-11-5-2-6-12-22)32-26(24)14-8-16-30(32)42(38,39)40;;/h1-20,33-34H,(H,35,36,37)(H,38,39,40);;/q;2*+1/p-2
• InChIKey: VWLWTJHKQHRTNC-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: dipotassium 8-(phenylamino)-5-[4-(phenylamino)-5-sulfonatonaphthalen-1-yl]naphthalene-1-sulfonate
• IUPAC Traditional name: dipotassium 8-(phenylamino)-5-[4-(phenylamino)-5-sulfonatonaphthalen-1-yl]naphthalene-1-sulfonate; dipotassium ion 8-(phenylamino)-5-[4-(phenylamino)-5-sulfonatonaphthalen-1-yl]naphthalene-1-sulfonate
• Synonyms: 4,4′-Dianilino-1,1′-binaphthyl-5,5′-disulfonic acid dipotassium salt; BIS-ANS; bis-(5,5')-8-ANILINO-1-NAPHTHALENE SULFONIC ACID DIPOTASSIUM SALT; 4,4'-Bis(phenylamino)-[1,1'-binaphthalene]-5,5'-disulfonic Acid Potassium Salt; 4,4'-Bis(1-anilinonaphthalene-8-sulfonic Acid) Dipotassium Salt; 8-Anilino-1-naphthalenesulfonic Acid Dimer Dipotassium Salt; 4,4'-Dianilino-1,1'-binaphthyl-5,5'-disulfonic Acid Dipotassium Salt; 4,4′-二苯胺基-1,1′-联萘-5,5′-二磺酸 二钾盐

Database IDs

• CAS Number: 63741-13-9; 65664-81-5
• MDL Number: MFCD00011592
• Beilstein Number: 5714637
• PubChem SID: 162090301; 24893823; 24872579
• PubChem CID: 16213473
• Council of Europe Number: 0000

CALCULATED PROPERTIES

• Acid pKa: -2.4337122
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 2.0883236
• LogD (pH = 7.4): 2.0882926
• Log P: 3.9024866
• Molar Refractivity: 160.0686 cm^3
• Polarizability: 66.73545 Å^3
• Polar Surface Area: 138.46 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: light yellow
• Fluorescence: λex 395 nm; λem 500 nm in methanol

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: for fluorescence; purum
• Linear Formula: [C6H5NHC10H5(SO3K)]2
• Empirical Formula (Hill Notation): C32H22K2N2O6S2

DETAILS

MP Biomedicals - 02150097

Potassium Salt
Far superior fluorescent probe used in protein studies. This is a dimer of ANS, with a dissociation constant two orders of magnitude smaller than ANS, making it extremely sensitive.

Sigma Aldrich - D4162

Application
Bifunctional fluorescent probe for proteins.

Sigma Aldrich - 49058

Other Notes
Potent inhibitor of in vitro microtubule assembly used to investigate structural changes in tubulin monomers & dimers1,2; particularly high affinity for nucleotide binding sites of some proteins3

Toronto Research Chemicals - D416480

4,4'-Dianilino-1,1'-binaphthyl-5,5'-disulfonic Acid is a bifunctional fluorescent probe for proteins.

REFERENCES

• Bohnert, J.L., et al., Biochemistry , 21 : 5570-5576, (1982).
• Hawe, A., et al.: Anal. Biochem., 378, 115 (2008)
• Hawe, A., et al.: Eur. J. Pharm. Sci., 38, 79 (2008)
• Hawe, A., et al.: Pharm. Res., 27, 314 (2008)