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

  • 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>10^10 L^2 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 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-linkersA 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>10^10 L^2 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 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.zeige mehrzeige weniger

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Metadaten
Autoren/innen:Wei Wan, A. B Descalzo, S. Shinde, Hardy Weißhoff, G. Orellana, B. Sellergren, Knut Rurack
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):Chemistry - A European Journal
Jahr der Erstveröffentlichung:2017
Organisationseinheit der BAM:1 Analytische Chemie; Referenzmaterialien
1 Analytische Chemie; Referenzmaterialien / 1.9 Chemische und optische Sensorik
Verlag:Wiley-VCH
Verlagsort:Weinheim
Jahrgang/Band:23
Ausgabe/Heft:63
Erste Seite:15974
Letzte Seite:15983
DDC-Klassifikation:Naturwissenschaften und Mathematik / Chemie / Analytische Chemie
Freie Schlagwörter:Core-shell particles; Excited-state proton transfer; Fluorescence; Molecular imprinting; Phosphorylated amino acids
Themenfelder/Aktivitätsfelder der BAM:Analytical Sciences
Analytical Sciences / Sensorik
DOI:https://doi.org/10.1002/chem.201703041
URL:http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=Alerting&SrcApp=Alerting&DestApp=WOS&DestLinkType=FullRecord;UT=WOS:000414990400021
ISSN:1521-3765
ISSN:0947-6539
Verfügbarkeit des Dokuments:Datei im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:24.11.2017
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:24.11.2017