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Reference type: Journal
Authors: Wan W, Descalzo AB, Shinde S, Wei▀hoff H, Orellana G, Sellergren B, Rurack K
Article Title: Ratiometric Fluorescence Detection of Phosphorylated Amino Acids Through Excited-State Proton Transfer by Using Molecularly Imprinted Polymer (MIP) Recognition Nanolayers.
Publication date: 2017
Journal: Chemistry - A European Journal
Volume: 23
Issue: (63)
Page numbers: 15974-15983.
DOI: 10.1002/chem.201703041
Alternative URL: https://www.researchgate.net/publication/326440804_Dual_channel_fluorescence_detection_of_phosphorylated_peptides_using_molecular_imprinted_polymers_with_built-in_excited_state_proton_transfer_emission

Abstract: A 2,3-diaminophenazine bis-urea fluorescent probe monomer (1) was developed. It responds to phenylphosphate and phosphorylated amino acids in a ratiometric fashion with enhanced fluorescence accompanied by the development of a redshifted emission band arising from an excited-state proton transfer (ESPT) process in the hydrogen-bonded probe/analyte complex. The two urea groups of 1 form a cleft-like binding pocket (Kb>1010 L2 mol-2 for 1:2 complex). Imprinting of 1 in presence of ethyl ester- and fluorenylmethyloxycarbonyl (Fmoc)-protected phosphorylated tyrosine (Fmoc-pTyr-OEt) as the template, methacrylamide as co-monomer, and ethyleneglycol dimethacrylate as cross-linker gave few-nanometer-thick molecularly imprinted polymer (MIP) shells on silica core microparticles with excellent selectivity for the template in a buffered biphasic assay. The supramolecular recognition features were established by spectroscopic and NMR studies. Rational screening of co-monomers and cross-linkers allowed to single out the best performing MIP components, giving significant imprinting factors (IF>3.5) while retaining ESPT emission and the ratiometric response in the thin polymer shell. Combination of the bead-based detection scheme with the phase-transfer assay dramatically improved the IF to 15.9, allowing sensitive determination of the analyte directly in aqueous media
Template and target information: ethyl ester- and fluorenylmethyloxycarbonyl (Fmoc)-protected phosphorylated tyrosine, Fmoc-pTyr-OEt
Author keywords: core-shell particles, excited-state proton transfer, fluorescence detection, molecular imprinting, phophorylated amino acids


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