Abstract
Biothiols play important roles in various physiological and biological processes, which closely related to many diseases. Hydrazine is widely used in the chemical industry, but it is harmful to humans and animals. Therefore, it is very important to develop a fluorescent probe that can simultaneously detect biological thiols and hydrazine. In this work, a new fluorescent probe (2E,4Z)-2-(benzo[d]thiazol-2-yl)-5-chloro-5-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)penta-2,4-dienenitrile (BCD) was synthesized by integrating coumarin and benzothiazole acetonitrile. Featured with four binding sites and different bonding mechanism between probe with biothiols and hydrazine, this probe exhibited fluorescent turn-on for distinguishing Cys, Hcy, GSH and hydrazine with 760-, 8-, 6- and 637-fold fluorescent intensity increase at 502, 479, 476 and 458 nm, respectively, through different excitation wavelengths. Research on the effect of pH on the fluorescent performance of BCD shows that the probe exhibits superior stability in a weakly alkaline to weakly acidic environment, which will facilitate the detection of biological thiols or hydrazine hydrate by BCD. Selectivity studies have shown that the probe has high specificity to biological thiols and hydrazine, which is of great significance to the application of BCD.
Highlights
Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) are three very important biological thiols, which play important roles in various physiological and biological processes
Spectral response of probe BCD to N2H4 In order to evaluate the spectral response of BCD to N2H4, an optical response experiment was performed on N2H4 in DMF/Hepes (v/v = 7:3, pH = 7.4)
The strong absorption peak indicates that the addition of hydrazine hydrate reacts with the probe BCD to destroy the original conjugation structure of the probe molecule
Summary
Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) are three very important biological thiols, which play important roles in various physiological and biological processes. It is important to design and synthesize a new type of multi-site fluorescent probe with high sensitivity, strong specificity, and capable of simultaneously detecting and distinguishing Cys, Hcy and GSH.
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