Pyrylium-1

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, Chromeo 503
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	26666460;
	InChI 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;
	SMILES CC1=CC(/C=C/C2=CC3=C4N(CCC3)CCCC4=C2)=CC(C)=[O+]1.F[B-](F)(F)F;
Properties
Chemical formula	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

Pyrylium-1 (Py-1) is a fluorogenic salt of a pyrylium derivative and tetrafluoroborate. It is an 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.

Reaction[edit]

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

References[edit]

^ ^a ^b ^c 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. 9 (4). IOP Publishing: 042001. Bibcode:2021MApFl...9d2001W. doi:10.1088/2050-6120/ac1a0a. ISSN 2050-6120. PMID 34340216. S2CID 236885329.
^ ^a ^b ^c 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. 26 (11). Wiley: 2208–2213. doi:10.1002/elps.200410332. ISSN 0173-0835. PMID 15880625. S2CID 19864669.
^ 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. 43 (40). Wiley: 5400–5402. doi:10.1002/anie.200460508. ISSN 1433-7851. PMID 15468079.

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[Wolfbeis2021-1] 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. 9 (4). IOP Publishing: 042001. Bibcode:2021MApFl...9d2001W. doi:10.1088/2050-6120/ac1a0a. ISSN 2050-6120. PMID 34340216. S2CID 236885329.

[Craig2005-2] 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. 26 (11). Wiley: 2208–2213. doi:10.1002/elps.200410332. ISSN 0173-0835. PMID 15880625. S2CID 19864669.

[Wetzl_Yarmoluk_Craig_Wolfbeis_2004_pp._5400–5402-3] 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. 43 (40). Wiley: 5400–5402. doi:10.1002/anie.200460508. ISSN 1433-7851. PMID 15468079.

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Reaction[edit]

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References[edit]