Pyrylium-1

{{Short description|Fluorogenic amine labelling dye}}

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| Name = Py-1

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| ImageFile = Py-1_chemical_structure.svg

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| IUPACName = (E)-2,6-dimethyl-4-(2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)vinyl)pyrylium

| OtherNames = P503,{{cite journal | last=Wolfbeis | first=Otto S | title=Fluorescent chameleon labels for bioconjugation and imaging of proteins, nucleic acids, biogenic amines and surface amino groups. a review | journal=Methods and Applications in Fluorescence | publisher=IOP Publishing | volume=9 | issue=4 | date=2021-08-12 | issn=2050-6120 | doi=10.1088/2050-6120/ac1a0a | page=042001| pmid=34340216 | bibcode=2021MApFl...9d2001W | s2cid=236885329 }} Chromeo 503

|Section1={{Chembox Identifiers

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| ChemSpiderID = 26666460

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| SMILES = CC1=CC(/C=C/C2=CC3=C4N(CCC3)CCCC4=C2)=CC(C)=[O+]1.F[B-](F)(F)F

| 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+;

| InChIKey = JWQTUDQPRBQNPM-MIIBGCIDSA-M

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|Section2={{Chembox Properties

| C=21 | H=24 | N=1 | O=1 | B=1 | F=4

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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.{{cite journal | last1=Craig | first1=Douglas B. | last2=Wetzl | first2=Bianca K. | last3=Duerkop | first3=Axel | last4=Wolfbeis | first4=Otto S. | title=Determination of picomolar concentrations of proteins using novel amino reactive chameleon labels and capillary electrophoresis laser-induced fluorescence detection | journal=Electrophoresis | publisher=Wiley | volume=26 | issue=11 | year=2005 | issn=0173-0835 | doi=10.1002/elps.200410332 | pages=2208–2213| pmid=15880625 | s2cid=19864669 }} It is within the "chameleon labels" class, so named due to their clear color-changing properties upon conjugation. Py-1 was first reported in 2004.{{cite journal | last1=Wetzl | first1=Bianca K. | last2=Yarmoluk | first2=Sergiy M. | last3=Craig | first3=Douglas B. | last4=Wolfbeis | first4=Otto S. | title=Chameleon Labels for Staining and Quantifying Proteins | journal=Angewandte Chemie International Edition | publisher=Wiley | volume=43 | issue=40 | date=2004-10-11 | issn=1433-7851 | doi=10.1002/anie.200460508 | pages=5400–5402| pmid=15468079 }} 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. Once bound to protein the excitation wavelength is 503 nm (green) and the emission wavelength is 603 nm (orange). Similar to FQ, these fluorescence wavelengths makes Py-1 suitable for excitation with a 488 nm argon-ion laser.

Reaction

File:Py-1_reaction_scheme.svg

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

See also

References