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Fluorescent probe for detecting hydrogen sulfide based on drug molecules and preparation method thereof

A technology of fluorescent probes and drug molecules, applied in the field of chemical analysis and detection, can solve the problems of 3-hydroxythalidomide and other problems, and achieve high selectivity and anti-interference ability, strong selectivity and high sensitivity

Active Publication Date: 2019-04-19
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no research on the use of 3-hydroxythalidomide as the fluorescent nucleus and the detection of H 2 Related reports on S Molecular Probe Mother Nucleus

Method used

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  • Fluorescent probe for detecting hydrogen sulfide based on drug molecules and preparation method thereof
  • Fluorescent probe for detecting hydrogen sulfide based on drug molecules and preparation method thereof
  • Fluorescent probe for detecting hydrogen sulfide based on drug molecules and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1 Preparation of (2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl)2,4-dinitrobenzenesulfonate

[0015] 3-Hydroxythalidomide (137 mg, 0.5 mmol) and N,N-diisopropylethylamine (130 mg, 1.0 mmol) were dissolved in dichloromethane (10 mL), cooled to 0°C, and divided 2,4-Dinitrobenzenesulfonyl chloride (160 mg, 0.6 mmol) was added in batches, stirred at room temperature under argon atmosphere for 16 h, then concentrated, and the pure probe product was obtained by column chromatography (yield: 148 mg, Yield: 58.8%).

[0016] 1 H NMR (400 MHz, DMSO- d6 ), δ : 11.13(s, 1H), 8.95(d, J = 2.8 Hz, 1H), 8.44 (dd, J = 9.2, 2.8 Hz, 1H), 8.07-7.97 (m, 1H), 7.91 (d, J = 7.3 Hz, 1H),7.76 (d, J = 8.1 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 5.09 (dd, J = 12.9, 5.3Hz, 1H), 2.94-2.75 (m, 1H), 2.63-2.52 (m, 1H), 2.47-2.31 (m, 1H), 2.05-1.92(m, 2H).

[0017] 13 C NMR (100 MHz, DMSO- d6 ) δ : 173.10, 170.02, 166.63, 164.71, 154.27, 149.80, 142.72, 139.86, 138.32, 134.3...

Embodiment 2

[0019] The change of fluorescence spectrum of the synthesized hydrogen sulfide fluorescent probe with the increase of NaHS addition equivalent

[0020] The hydrogen sulfide fluorescent probe prepared in Example 1 was dissolved in acetonitrile, diluted with PBS buffer solution, and NaHS standard solutions of different equivalents (0-30eq) were added to measure its fluorescence properties. Fluorescence spectrum such as figure 2 . It can be seen from the figure that the fluorescence intensity increases with the increase of NaHS addition equivalent.

Embodiment 3

[0022] Selectivity of Synthetic Fluorescent Probes for Hydrogen Sulfide to Different Ions

[0023] In order to verify whether the probe has specific selectivity and strong anti-interference ability, we selected various anions (Cl - , AcO - , H 2 PO 4 - , HCO 3 - , CO 3 2- , H 2 PO 4 - , SO 4 2- , Br - , I - , NO 2- , NO 3- , HS - , F - ) and perform a fluorescence test. It was found that there was little change in the fluorescence intensity, but the fluorescence of the probe was significantly enhanced after adding NaHS. Therefore, the probe of the present invention can be used as a method for detecting H 2 S is a highly selective fluorescent probe.

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Abstract

The invention discloses a synthesis method of a fluorescent probe for detecting hydrogen sulfide based on drug molecules, and particularly relates to a preparation method of [2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]2,4-dinitrobenzene sulphonate. According to the probe, with the drug molecules being a mother nucleus, a fluorescent nucleus is 3-hydroxy thalidomide. The synthesis process is simple, reaction conditions are mild, purification is easy, selectivity is high, anti-interference capacity is high, and hydrogen sulfide in a sample can be sensitively and rapidly detected. The method is easy to operate, has important actual application value in environment detection, and has potential application value in the fields of biomedicine and others.

Description

technical field [0001] The invention relates to a novel method for preparing a fluorescent probe for detecting hydrogen sulfide based on drug molecules, and belongs to the technical field of chemical analysis and detection. Background technique [0002] Hydrogen sulfide (H 2 S) is a colorless, flammable, water-soluble acidic gas with a pungent odor as a signal molecule. h 2 S not only pollutes the atmosphere, but also contains H 2 The water of S will stink, and it also has erosive and destructive effects on concrete and metal. In addition, the study found that H 2 S plays an important role in many physiological processes. At present, a variety of detection H 2 S fluorescent probe. Fluorescence-enhanced H that reduces the azido group to an amino group 2 S fluorescent probes are widely accepted and applied. Such probes are designed by varying fluorophores with different azide-containing groups. And this kind of probe is in cell, tissue or water body to H 2 Real-time...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 牟心茹孙国新刘晓磊梁帅
Owner UNIV OF JINAN
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