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Fluorescamine

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Fluorescamine
Names
IUPAC name 4'-phenylspiro-1,3'-dione
Other names Fluram
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.048.904 Edit this at Wikidata
MeSH D005450
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C17H10O4/c18-15-13(11-6-2-1-3-7-11)10-20-17(15)14-9-5-4-8-12(14)16(19)21-17/h1-10HKey: ZFKJVJIDPQDDFY-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C=C1)C2=COC3(C2=O)C4=CC=CC=C4C(=O)O3
Properties
Chemical formula C17H10O4
Molar mass 278.26 g/mol
Melting point 153 to 157 °C (307 to 315 °F; 426 to 430 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Fluorescamine is a spiro compound that is not fluorescent itself, but reacts with primary amines to form highly fluorescent products, i.e. it is fluorogenic. It hence has been used as a reagent for the detection of amines and peptides. 1-100 μg of protein and down to 10 pg of protein can be detected. Once bound to protein the excitation wavelength is 381 nm (near ultraviolet) and the emission wavelength is 470 nm (blue). This method is found to suffer from high blanks resulting from a high rate of hydrolysis due to requiring a large excess concentration. Alternative methods are based on ortho-phthalaldehyde (OPA), Ellman's reagent (DTNB), or epicocconone.

Reaction

Reaction of fluorescamine with an amine

See also

References

  1. Fluram at Sigma-Aldrich
  2. Doetsch, Paul W.; Cassady, John M.; McLaughlin, Jerry L. (1980). "Cactus alkaloids : XL. Identification of mescaline and other β-phenethylamines in Pereskia, Pereskiopsis and Islaya by use of fluorescamine conjugates". Journal of Chromatography A. 189: 79–85. doi:10.1016/S0021-9673(00)82285-2.
  3. Böhlen, Peter; Stein, Stanley; Dairman, Wallace; Udenfriend, Sidney (1973). "Fluorometric assay of proteins in the nanogram range". Archives of Biochemistry and Biophysics. 155 (1): 213–220. doi:10.1016/S0003-9861(73)80023-2. PMID 4736505.
  4. protocol by Fluoprobes
  5. Biotium. "Fluorescamine PRODUCT AND SAFETY DATA SHEET" (PDF). Biotium. Retrieved 21 February 2023.


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