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Fluorescamine

Summary

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.[2] 1-100 μg of protein and down to 10 pg of protein can be detected.[3][4] Once bound to protein the excitation wavelength is 381 nm (near ultraviolet) and the emission wavelength is 470 nm (blue).[5] This method is found to suffer from high blanks resulting from a high rate of hydrolysis due to requiring a large excess concentration.[6] Alternative methods are based on ortho-phthalaldehyde (OPA), Ellman's reagent (DTNB), or epicocconone.

Fluorescamine[1]
Names
IUPAC name
4'-phenylspiro[2-benzofuran-3,2'-furan]-1,3'-dione
Other names
Fluram
Identifiers
  • 38183-12-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 34768
ECHA InfoCard 100.048.904 Edit this at Wikidata
MeSH D005450
  • 37927
UNII
  • Y6859V58YW checkY
  • DTXSID50872017 Edit this at Wikidata
  • 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/h1-10H
    Key: ZFKJVJIDPQDDFY-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C2=COC3(C2=O)C4=CC=CC=C4C(=O)O3
Properties
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Reaction

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Reaction of fluorescamine with an amine

See also

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References

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  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[dead link‍] by Fluoprobes
  5. ^ Biotium. "Fluorescamine PRODUCT AND SAFETY DATA SHEET" (PDF). Biotium. Retrieved 21 February 2023.
  6. ^ [1]