Chemistry:Fluorescamine

From HandWiki
Fluorescamine[1]
Fluorescamine.png
Names
IUPAC name
4'-phenylspiro[2-benzofuran-3,2'-furan]-1,3'-dione
Other names
Fluram
Identifiers
3D model (JSmol)
ChemSpider
MeSH D005450
UNII
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).
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Infobox references

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.

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[|permanent dead link|dead link}}] by Fluoprobes
  5. Biotium. "Fluorescamine PRODUCT AND SAFETY DATA SHEET". Biotium. https://biotium.com/wp-content/uploads/2017/10/PI-90092.pdf. 
  6. [1]