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Ratiometric fluorescence detection of phosphorylated amino acids through excited‐state proton transfer using molecularly imprinted polymer (MIP) recognition nanolayers
Chemical and Optical Sensing Division, Bundesanstalt für Materialforschung und -prüfung (BAM), Richard-Willstätter-Strasse 11, 12489, Berlin, Germany.
Department of Organic Chemistry, Complutense University of Madrid (UCM), 28040, Madrid, Spain.
Malmö högskola, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö högskola, Biofilms Research Center for Biointerfaces.ORCID iD: 0000-0001-9460-0936
Department of Chemistry, Humboldt University Berlin, Brook-Taylor-Strasse 2, 12489, Berlin, Germany.
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2017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 63, p. 15974-15983Article in journal (Refereed)
Abstract [en]

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.

Place, publisher, year, edition, pages
John Wiley & Sons, 2017. Vol. 23, no 63, p. 15974-15983
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Natural Sciences
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URN: urn:nbn:se:mau:diva-3961DOI: 10.1002/chem.201703041ISI: 000414990400021PubMedID: 28869685Scopus ID: 2-s2.0-85033502492Local ID: 24192OAI: oai:DiVA.org:mau-3961DiVA, id: diva2:1400785
Available from: 2020-02-28 Created: 2020-02-28 Last updated: 2024-06-17Bibliographically approved

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Shinde, SudhirkumarSellergren, Börje

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