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Fluorescent probe simultaneously detecting ONOO<-> and H2S, and synthesis method and application thereof

A technology of fluorescent probe and synthesis method, which is applied in the field of fluorescent probes for simultaneous detection of ONOO- and H2S and their synthesis, can solve the problems of low concentration and short life, and achieve high sensitivity, fast response speed and low background signal. Effect

Active Publication Date: 2018-10-23
SHANDONG NORMAL UNIV
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Problems solved by technology

[0004] H in biological systems 2 S and ONOO - The concentration in the cell is very low and the life span is very short, so it is difficult to measure it by general methods

Method used

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  • Fluorescent probe simultaneously detecting ONOO&lt;-&gt; and H2S, and synthesis method and application thereof
  • Fluorescent probe simultaneously detecting ONOO&lt;-&gt; and H2S, and synthesis method and application thereof
  • Fluorescent probe simultaneously detecting ONOO&lt;-&gt; and H2S, and synthesis method and application thereof

Examples

Experimental program
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Embodiment

[0042] Example: Synthesis of Fluorescent Probes

[0043]4-Diethylaminoketoacid (313.1 mg, 1.0 mmol) and 3-acetyl-6-bromocoumarin (266.0 mg, 1.0 mmol) were dissolved in 5.0 mL of concentrated sulfuric acid, and then heated at 90° C. for 12 h. After cooling to room temperature, the solution was slowly poured into 50 mL of ice water (purple solid precipitated out), stirred for 20 min, filtered, washed with cold water, and dried in vacuo to obtain a crude product. Further, silica gel column chromatography (CH 2 Cl 2 / MeOH=10:1, v / v) was purified to obtain purple solid compound RC-Br (450.2 mg, 83%). Mass Spectrometry and NMR Characterization:

[0044] HRMS-ESI(m / z): calcd for C 29 h 22 BrNO 5 [M+H] + 544.0754 / 546.0735; found 544.0700 / 546.0678.

[0045] 1 H NMR (400MHz, DMSO): δ8.84(s, 1H), 8.24(s, 1H), 7.95(d, J=7.6Hz, 1H), 7.85(q, J=6.4Hz, 1H), 7.80( t,J=6.5Hz,1H),7.70(t,J=7.4Hz,1H),7.46(d,J=8.2Hz,1H),7.37(d,J=6.0Hz,1H),6.60(s, 1H), 6.51 (d, J=5.9Hz, 3H), 3.38 (q, J=6....

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Abstract

The invention relates to the technical field of fluorescent sensing material preparation and biodetection, and particularly relates to a fluorescent probe simultaneously detecting ONOO<-> and H2S, anda synthesis method and an application thereof. The probe molecule has two reaction sites, one can be subjected to nucleophilic addition reaction with H2S, excitation wavelength being 480 nm and emitting wavelength being 580 nm, thus significantly enhancing a fluorescent signal; the other can be subjected to nucleophilic reaction with ONOO<->, excitation wavelength being 400 nm and emitting wavelength being 520 nm, then a rearrangement reaction is carried out to obtain two coumarin derivative products, the fluorescent signal, after the reactions, being significantly enhanced too. Therefore, RC-Br can detect the ONOO<-> and H2S in a double-excitation / double-emission manner. The fluorescent probe has high sensitivity and responding speed, can be applied to cell imaging well, and may be an effective analytic tool for researching interaction relationship of the ONOO<-> and H2S in a biology system.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensing material preparation and biological detection, in particular to a fluorescent probe for simultaneous detection of ONOO- and H2S, its synthesis method and application. Background technique [0002] h 2 As an important gas signal molecule in the body, S participates in a series of physiological and pathological processes. h 2 Too high or too low S concentration can cause disease, and an appropriate amount of H 2 S has various biological effects such as lowering blood pressure, relaxing blood vessels and inhibiting the proliferation of vascular smooth muscle cells. h 2 S plays an important role in the process of pathological activities such as hypertension, coronary heart disease, and ischemic myocardial injury, as well as in the later treatment process. [0003] ONOO - It is an important active oxygen molecule in the living body, which is produced by superoxide anion (O 2 ·- ) an...

Claims

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Application Information

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IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1088G01N21/6428
Inventor 唐波王栩肖永胜焦晓云赵志文解希雷李娜
Owner SHANDONG NORMAL UNIV
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