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(3-(2-Furoyl)-quinoline-2 carboxaldehyde)

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(Redirected from Draft:(3-(2-furoyl)-quinoline-2 carboxaldehyde)) Fluorogenic amine labelling dye
FQ
Names
IUPAC name 3-(furan-2-carbonyl)quinoline-2-carbaldehyde
Other names FQ, (3-(2-furoyl)-quinoline-2 carboxaldehyde), ATTO-TAG FQ, FQCA
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 635-028-8
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H9NO3/c17-9-13-11(15(18)14-6-3-7-19-14)8-10-4-1-2-5-12(10)16-13/h1-9HKey: PNCHURHVMDRFTR-UHFFFAOYSA-N
SMILES
  • C1=CC=C2C(=C1)C=C(C(=N2)C=O)C(=O)C3=CC=CO3
Properties
Chemical formula C15H9NO3
Molar mass 251.241 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

3-(2-Furoyl)-quinoline-2-carboxaldehyde (FQ) is a fluorogenic amine labeling dye that is not fluorescent itself, but reacts with primary amines to form fluorescent products. It was first reported in 1990. Cyanide, typically provided via KCN or NaCN salts, is a required co-substrate in the fluorogenic reaction. It has been used for the detection of amines and peptides, largely in CE-SDS, where it is recognized to reach a silver stain-like high sensitivity via laser-induced fluorescence. Once bound to protein the excitation wavelength is 480 nm (blue) and the emission wavelength is ~600 nm (orange).

Reaction

See also

References

  1. Stoyanov, Alexander V.; Ahmadzadeh, Hossein; Krylov, Sergey N. (2002-11-25). "Heterogeneity of protein labeling with a fluorogenic reagent, 3-(2-furoyl)quinoline-2-carboxaldehyde". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 780 (2): 283–287. doi:10.1016/s1570-0232(02)00535-4. ISSN 1570-0232. PMID 12401353.
  2. Beale, Stephen C.; Hsieh, You-Zung; Wiesler, Donald; Novotny, Milos (1990). "Application of 3-(2-furoyl)quinoline-2-carbaldehyde as a fluorogenic reagent for the analysis of primary amines by liquid chromatography with laser-induced fluorescence detection". Journal of Chromatography A. 499. Elsevier BV: 579–587. doi:10.1016/s0021-9673(00)97002-x. ISSN 0021-9673. PMID 2324216.
  3. Fisher Scientific, Thermo. "ATTO-TAG CBQCA and ATTO-TAG FQ - Product Information" (PDF). Thermo Fisher Scientific. Retrieved 8 April 2023.
  4. Arrell, Miriam S.; Kálmán, Franka (2016-10-19). "Estimation of protein concentration at high sensitivity using SDS-capillary gel electrophoresis-laser induced fluorescence detection with 3-(2-furoyl)quinoline-2-carboxaldehyde protein labeling". Electrophoresis. 37 (22). Wiley: 2913–2921. doi:10.1002/elps.201600246. ISSN 0173-0835. PMID 27570211. S2CID 11359248.
  5. "3-(2-Furoyl)quinoline-2-carboxaldehyde". sigmaaldrich.com. Retrieved 2023-03-09.


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