Pyrylium-1

Pyrylium-1 (Py-1) is a fluorogenic pyrylium & tetrafluoroborate salt and amine-labeling dye that is not fluorescent itself, but reacts with primary amines to form fluorescent products.[2] It is within the "chameleon labels" class,[1] so named due to their clear color-changing properties upon conjugation. Py-1 was first reported in 2004.[3] It has been used for the detection of amines and peptides, largely in CE-SDS, where it is recognized to reach a high sensitivity via laser-induced fluorescence.[2] Once bound to protein the excitation wavelength is 503 nm (green) and the emission wavelength is 603 nm (orange).[2] Similar to FQ, these fluorescence wavelengths makes Py-1 suitable for excitation with a 488 nm argon-ion laser.

Py-1
Names
IUPAC name
(E)-2,6-dimethyl-4-(2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)vinyl)pyrylium
Other names
P503,[1] Chromeo 503[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1InChI=1S/C21H24NO.BF4/c1-15-11-17(12-16(2)23-15)7-8-18-13-19-5-3-9-22-10-4-6-20(14-18)21(19)22;2-1(3,4)5/h7-8,11-14H,3-6,9-10H2,1-2H3;/q+1;-1/b8-7+;
    Key: JWQTUDQPRBQNPM-MIIBGCIDSA-M
  • CC1=CC(/C=C/C2=CC3=C4N(CCC3)CCCC4=C2)=CC(C)=[O+]1.F[B-](F)(F)F
Properties
C21H24NOBF4
Molar mass 393.23 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

Post conjugation, the Py-1 adduct (an addition of C21H21N) adds about 287.1674 Da to the target molecule.

See also

References
  1. Wolfbeis, Otto S (2021-08-12). "Fluorescent chameleon labels for bioconjugation and imaging of proteins, nucleic acids, biogenic amines and surface amino groups. a review". Methods and Applications in Fluorescence. IOP Publishing. 9 (4): 042001. Bibcode:2021MApFl...9d2001W. doi:10.1088/2050-6120/ac1a0a. ISSN 2050-6120. PMID 34340216. S2CID 236885329.
  2. Craig, Douglas B.; Wetzl, Bianca K.; Duerkop, Axel; Wolfbeis, Otto S. (2005). "Determination of picomolar concentrations of proteins using novel amino reactive chameleon labels and capillary electrophoresis laser-induced fluorescence detection". Electrophoresis. Wiley. 26 (11): 2208–2213. doi:10.1002/elps.200410332. ISSN 0173-0835. PMID 15880625. S2CID 19864669.
  3. Wetzl, Bianca K.; Yarmoluk, Sergiy M.; Craig, Douglas B.; Wolfbeis, Otto S. (2004-10-11). "Chameleon Labels for Staining and Quantifying Proteins". Angewandte Chemie International Edition. Wiley. 43 (40): 5400–5402. doi:10.1002/anie.200460508. ISSN 1433-7851. PMID 15468079.
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