Fused oxazolidine-based dual optical probe for galactosidase with a dramatic chromogenic and fluorescence turn-on effect

Chromo-fluorogenic probes for β-galactosidase detection

“…The sensing protocol of probes 1 to 15 shown in Chart 1 is based on the β-Gal-induced hydrolysis of a glycosidic bond. [25,26,27,28,29,30,31,32,33,34] The removal of the saccharide induced the release of the free fluorophore or chromophore accompanied with a revival of its fluorescence, shifts in the emission wavelength or marked colour changes (see Scheme 1a). Moreover, other reported probes for measuring β-Gal activity in solution (irradiated probe 1 in presence of TMB, and 16 to 25) presented more complex sensing mechanisms.…”

A Pyrone‐based Ratiometric Probe for Galactosidase with Dramatic Color and Fluorescence Changes

“…Preparation of AcGP. To a solution of acetylgalactose tethered benzaldehyde (1, 450 mg, 1.00 mmol) and piperidine (0.02 mL, 0.2 mmol) in 5 mL CH 3 CN, was added malonitrile condensed 2,6-dimethyl- [1,4]-pyrone (172 mg, 1.00 mmol). The resulting solution was heated under reflux for 12 h and then evaporated under reduced pressure.…”

“…2 Recently, various activatable fluorophores for the enzyme were developed from modified X-Gal, 3 that produced intense fluorescence signals by chemical reaction-based activation. [4][5][6][7][8][9][10][11] However, a few ratiometric fluorescent probes have been developed due to the environmental artifact-free signaling properties. [12][13][14] For example, Zhu group recently published an excellent ratiometric fluorophore for β-Gal from a precursor, benzopyrone.…”

“…Commonly, it is employed as a reporter marker to monitor gene expression of lac Z and known to be closely related with cellular scenescence . Recently, various activatable fluorophores for the enzyme were developed from modified X‐Gal, that produced intense fluorescence signals by chemical reaction‐based activation . However, a few ratiometric fluorescent probes have been developed due to the environmental artifact‐free signaling properties .…”

The coordination of a multidentate NxOy-donor (x and y ≤ 2) oxazolidine-based ligand with Cd(II) and Hg(II); Structural, spectral, and theoretical studies

“…Several substituted oxazolidines have been investigated extensively because of their importance as pharmacological active compounds (such as antidiabetic [1], anticonvulsant [2], antitubercular [3], and aldose reductase inhibitors [4]), chiral auxiliaries in the synthesis of a variety of chiral compounds, chain-protecting groups for amino alcohols [5,6], crosslinking agents [7] to stabilization of collagen [8,9], linkers in solid-phase synthesis of peptide aldehydes process [10], optical probe applications [11] and fungicidal activities [12].…”