Highly Sensitive Coumarin–Pyrazolone Probe for the Detection of Cr³⁺ and the Application in Living Cells

Abstract

3-(7-(Diethylamino)-2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazol-5­(4H)-one (COPYR) was competently synthesized from methyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate and 2-hydrazino-4-phenyl thiazole. The interactions of receptor COPYR with various ions were investigated through absorption and steady-state fluorescence spectral studies, respectively. The results reveal that the complexation of Cr3+ ions with COPYR results in 1:1 stoichiometry, which resulted in a quick color response from fluorescent green to colorless with significant quenching of fluorescence at 506 nm in dimethyl sulfoxide medium. Theoretical calculations (density functional theory) confirm the photophysical changes such as absorbance and emission spectral changes. Furthermore, the confocal imaging of A-549 cells clearly points out that the synthesized probe COPYR could be applied for detecting Cr3+ in living cells.

Synthesis of 2H-pyrano[3,2-g]quinolin-2-ones containing a pyrimidinone moiety and characterization of their anticoagulant activity via inhibition of blood coagulation factors Xa and XIa

“…It has been demonstrated 42 that during the condensation of a salicylic aldehyde derivative with dimethyl 3-oxopentanedioate (dimethyl 1,3-acetonedicarboxylate), the reaction of two ester and methylene groups led to the formation of dicoumarinyl ketone. Subsequent studies [43][44][45][46][47][48][49][50] have shown that this reaction is applicable to the preparation of 3-oxo-3-( 2…”

Preparation and Application of a Fast, Naked-Eye, Highly Selective, and Highly Sensitive Fluorescent Probe of Schiff Base for Detection of Cu2+

“…Coumarin derivatives have been found in various plants, which are widely used in aqueous environmental monitoring, antibacterial and antitumor medications, and others [18]. Currently, coumarin-based fluorescent probes consist essentially of Schiff bases [19][20][21][22] and biological thiols [23,24]. In particular, a few studies on the coumarinbased pyrazolone fluorescent probes have been reported [23][24][25].…”

“…Currently, coumarin-based fluorescent probes consist essentially of Schiff bases [19][20][21][22] and biological thiols [23,24]. In particular, a few studies on the coumarinbased pyrazolone fluorescent probes have been reported [23][24][25].…”

One-Pot Cascade Access to Ru(II)-Catalyzed Regioselective C(sp2)-H Activation/Alkenylation of Chromeno[4,3-c]pyrazol-4-ones and Their Emission Solvatochromic Studies

“…In addition, coumarin- and pyrazole-based heterocyclic scaffolds could also be used as fluorescent materials, optical brighteners, and laser dyes . Owing to their significant importance, incisive and effective synthesis of these heterocyclic moieties and their functionalization have claimed continual attention from organic chemists . In 2013, Wu and his co-workers carried out C4 alkenylation of 1,3,5-trisubstituted pyrazoles (Scheme a) .…”