Ratiometric fluorescence detection of phosphorylated amino acids through excited‐state proton transfer using molecularly imprinted polymer (MIP) recognition nanolayersShow others and affiliations
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
National Category
Natural Sciences
Identifiers
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
2020-02-282020-02-282024-06-17Bibliographically approved