A coumarin‐based fluorescent turn‐on probe for detection of biothiols in vitro

Abstract

A novel fluorescent probe (CA-N) was designed and synthesized for detection of biothiols. CA-N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β-unsaturated ketones. CA-N showed low detection limit for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), which were calculated as 3.16, 0.19 and 5.15 μM, respectively. At the same time, CA-N exhibited high selectivity toward biothiols compared with other biological amino acids. In vitro cell experiments proved that CA-N had no cytotoxicity, high cell permeability and could be employed in living cell imaging for biothiols.

Novel 7‐maleimido‐2(1H)‐quinolones as potential fluorescent sensors for the detection of sulphydryl groups

“…In recent years, Michael-type probes have been widely developed. The most popular are those which contain maleimide, squarine, acrylamide, a,b-unsaturated aldehyde, ketone, diester, and nitro-and malononitrile acceptors in their structures [12][13][14][15][16][17][18][19].…”

Coumarin-Based Small-Molecule Fluorescent Chemosensors

“…The addition of the homologous p-NO 2 -phenyl analogue 296 leads to the reduction of the reaction time by activation of the Michael-acceptor. 391 However, due to the absence of the electrostatic charge, the kinetics of probe 296 were similar for Cys and Hcy, whereas GSH reacted 5-fold slower. In the case of this compound, the analogous cyclization as for 294-o-Py and 294-p-Py was not observed and the fluorescence remained stable over the course of 1 h.…”

“…Aliaga et al described a series of chalcone compounds 295 , which can detect biothiols via a Michael addition as similar to 294 . The addition of the homologous p -NO 2 -phenyl analogue 296 leads to the reduction of the reaction time by activation of the Michael-acceptor . However, due to the absence of the electrostatic charge, the kinetics of probe 296 were similar for Cys and Hcy, whereas GSH reacted 5-fold slower.…”

Detecting and imaging of SO2 derivatives in living cells with zero cross-talk colorimetric mitochondria-targeted fluorescent probe

“…In this work, we aim to modify the nitrogen position of the indolenine group to obtain probes with large emission shifts. Inspired by the good photostability, high fluorescence quantum yield, and cell penetration capability of the coumarin group, 32,33 we first synthesize mitochondria-targeted CA-ID-MC ( Fig. 1A), where the indolenine is quaternary aminated with coumarin.…”