Fluorescamine

Fluorescamine^[1]
Names
	IUPAC name 4'-phenylspiro[2-benzofuran-3,2'-furan]-1,3'-dione
	Other names Fluram
Identifiers
CAS Number	38183-12-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	34768;
ECHA InfoCard	100.048.904
MeSH	D005450
PubChem CID	37927;
UNII	Y6859V58YW ;
CompTox Dashboard (EPA)	DTXSID50872017 ;
	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/h1-10H Key: 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 [77 °F], 100 kPa). verify (what is ?) 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

References

^ Fluram at Sigma-Aldrich
^ 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.
^ 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.
^ protocol^{[dead link‍]} by Fluoprobes
^ Biotium. "Fluorescamine PRODUCT AND SAFETY DATA SHEET" (PDF). Biotium. Retrieved 21 February 2023.
^ [1]

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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] rotocol^{[dead link‍]} by Fluoprobes

[5] Biotium. "Fluorescamine PRODUCT AND SAFETY DATA SHEET" (PDF). Biotium. Retrieved 21 February 2023.

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See also

References