Abstract:A fluorescence sensor of BINOL–xylose derivative was synthesized, which could only detect Fe3+ by 1 + 1 complex with high selectivity and sensitivity. The complex of the derivative with Fe3+ was found to perform secondary recognition of cysteine.
“…The plausible sensing mechanism of R -β- d - 1 . The article published by our group in 2022 was a monosubstituted xylose structure introduced by click reaction in BINOL, 35 and the fluorescence redshift of its sensor was not obvious after the addition of Fe 3+ and blueshifted to the initial fluorescence of the sensor after the addition of l -Cys, whereas in this paper, we introduced a double-substituted glucose on H 8 -BINOL, and the introduced glycan structures with different spatial resistances were not the same, and a significant redshift occurred after the addition of Fe 3+ and no blueshift to the initial fluorescence of the sensor after the addition of l -Cys in the case of R -β- d - 1 , a significant redshift occurred after the addition of Fe 3+ , and there was no blue shift to the initial fluorescence after the addition of l -Cys, so the fluorescence phenomenon and mechanism of the two are not the same.…”
A novel fluorescent “off” sensor, R-β-d-1, was obtained in high yield (91.2%) by using octahydronaphthol as a backbone, introducing an alkyne group at the 2-position, and linking azido-glucose via a click reaction.
“…The plausible sensing mechanism of R -β- d - 1 . The article published by our group in 2022 was a monosubstituted xylose structure introduced by click reaction in BINOL, 35 and the fluorescence redshift of its sensor was not obvious after the addition of Fe 3+ and blueshifted to the initial fluorescence of the sensor after the addition of l -Cys, whereas in this paper, we introduced a double-substituted glucose on H 8 -BINOL, and the introduced glycan structures with different spatial resistances were not the same, and a significant redshift occurred after the addition of Fe 3+ and no blueshift to the initial fluorescence of the sensor after the addition of l -Cys in the case of R -β- d - 1 , a significant redshift occurred after the addition of Fe 3+ , and there was no blue shift to the initial fluorescence after the addition of l -Cys, so the fluorescence phenomenon and mechanism of the two are not the same.…”
A novel fluorescent “off” sensor, R-β-d-1, was obtained in high yield (91.2%) by using octahydronaphthol as a backbone, introducing an alkyne group at the 2-position, and linking azido-glucose via a click reaction.
“…The association constant Ka for 3 with Cys was calculated from the plot of intensity of absorbance/fluorescence spectra of compound 3 against the concentration of Cys (ln [Cys]) for 1 : 1 stoichiometry of host-guest interaction, following the reported method. [32] The higher value K a (1.88 × 10 6 M À 1 ) for 3-Cys (Figure S20(a)), indicated the compound's higher affinity towards Cys which is comparably higher than the reported values [33][34][35] for the detection of Cys with other optical probes. The Stern-Volmer quenching constant of 3 with Hcy was determined by the Stern-Volmer equation, [36] which was observed to be 3469.08 � 0.8 M À 1 (Figure S21(b)).…”
A new fluorophore, α-acrylaldehyde 3-pyrrolyl BODIPY was synthesized by treating 3-pyrrolyl BODIPY with a mixture of 3-(dimethylamino) acrolein and POCl 3 under Vilsmeier-Haack reaction conditions. The X-ray structure revealed that the fluorophore was almost planar, and the appended pyrrole was in the same plane with a small deviation from the mean plane. We investigated the potential use of α-acrylaldehyde 3-pyrrolyl BODIPY for sensing thiol containing amino acids such as cysteine/homocysteine (Cys/Hcy). Our studies showed that the α-acrylaldehyde-3-pyrrolyl BODIPY was found to be useful for exclusive sensing of Cys/Hcy and to exhibit different optical signaling responses to Cys and Hcy at physiological pH in aq. CH 3 CN (1 : 1 v/v, PBS) medium. The enhancement in optical properties for Cys and quenching in same properties for Hcy was attributed to different binding modes of Cys/Hcy with αacrylaldehyde 3-pyrrolyl BODIPY.
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