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

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.[1] It was first reported in 1990.[2] Cyanide, typically provided via KCN or NaCN salts, is a required co-substrate in the fluorogenic reaction.[3] 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.[4] Once bound to protein the excitation wavelength is 480 nm (blue) and the emission wavelength is ~600 nm (orange).[5]

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
3D model (JSmol)
ChemSpider
EC Number
  • 635-028-8
  • 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/h1-9H
    Key: PNCHURHVMDRFTR-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=C(C(=N2)C=O)C(=O)C3=CC=CO3
Properties
C15H9NO3
Molar mass 251.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. Elsevier BV. 499: 579–587. doi:10.1016/s0021-9673(00)97002-x. ISSN 0021-9673.
  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. Wiley. 37 (22): 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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