Ratiometric fluorescence detection of phosphorylated amino acids through excited‐state proton transfer using molecularly imprinted polymer (MIP) recognition nanolayers

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Ratiometric fluorescence detection of phosphorylated amino acids through excited‐state proton transfer using molecularly imprinted polymer (MIP) recognition nanolayers

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Publication Article, peer reviewed scientific
Title Ratiometric fluorescence detection of phosphorylated amino acids through excited‐state proton transfer using molecularly imprinted polymer (MIP) recognition nanolayers
Author Wan, Wei ; Descalzo, Ana ; Shinde, Sudhirkumar ; Weishoff, Hardy ; Orellana, Guillermo ; Sellergren, Börje ; Rurack, Knut
Research Centre Biofilms - Research Center for Biointerfaces
Date 2017
English abstract
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 hydrogenbonded probe/analyte complex. The two urea groups of 1 form a cleft-like binding pocket (Kb>1010 L2mol@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 crosslinker 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 comonomers 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.
DOI https://doi.org/10.1002/chem.201703041 (link to publisher's fulltext.)
Link http://rdcu.be/C5vj/... (external link to publication)
Publisher Wiley
Host/Issue Chemistry : A European Journal;63
Volume 23
ISSN 1521-3765
Pages 15974–15983
Language eng (iso)
Subject Sciences
Research Subject Categories::NATURAL SCIENCES
Handle http://hdl.handle.net/2043/24192 Permalink to this page
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