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Synthesis, preparation and application of fluorescent probe for identifying Cys, GSH and HOCl on basis of molecular logic gate

A fluorescent probe and logic gate technology, applied in fluorescence/phosphorescence, luminescent materials, material excitation analysis, etc., can solve the problems of lack of high sensitivity and unclear exact changes, and achieve good selectivity, wide application value, and detection low limit effect

Active Publication Date: 2019-06-21
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the exact changes of HOCl and Cys / GSH under oxidative stress are not well understood due to the lack of highly sensitive, specific and rapid detection methods

Method used

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  • Synthesis, preparation and application of fluorescent probe for identifying Cys, GSH and HOCl on basis of molecular logic gate
  • Synthesis, preparation and application of fluorescent probe for identifying Cys, GSH and HOCl on basis of molecular logic gate
  • Synthesis, preparation and application of fluorescent probe for identifying Cys, GSH and HOCl on basis of molecular logic gate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of fluorescent probe compound NPCC.

[0068] (1) Synthesis of Compound 1

[0069] The known compound 10-acetyl-9-hydroxy-2,3,6,7-tetrahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-11 (5H)-ketone (897 mg, 3 mmol) and benzaldehyde (334 mg, 3.15 mmol) were dissolved in 25 mL of ethanol, 6–9 drops of piperidine were added during stirring, and refluxed for 14 hours. After the reaction was complete, cool to room temperature, filter with suction, wash the filter cake with ice-cold ethanol, and dry in vacuo to obtain compound 1 as a red solid (896.4 mg, yield 77.2%).

[0070] H NMR spectrum determination: 1 H NMR (400 MHz, CDCl 3 , ppm):1.92-1.99 (m, 4H), 2.76-2.85 (m, 4H), 3.29-3.32 (m, 4H),7.42 (m, 4H), 7.70 (m, 2H), 7.94 (d, 1 H, J =15.8 Hz), 8.46 (d, 1 H, J = 15.8 Hz).

[0071] Carbon NMR Spectrum Determination: 13 C NMR (100 MHz, CDCl 3 , ppm): δ = 20.14, 20.25,21.22, 27.48, 49.82, 50.25, 98.06, 103.11, 105.36, 118.70, 122.75, 124.07,128.88, 128.96, 13...

Embodiment 2

[0084] When the probe of the present invention interacts with Cys, GSH and HOCl, the ultraviolet-visible spectrum and the fluorescence emission spectrum change.

[0085] The probe prepared in Example 1 was dissolved in DMSO to prepare a probe master solution with a probe concentration of 1 mM. The test solution was Tris-HCl (10 mM, 1 mM CTAB) buffer solution, and the pH value of the buffer solution was 7.4. Take 30 μL of the probe mother solution and add it to 3 mL of the test solution to obtain the probe mixed solution. The final concentration of the probe in the mixed solution is 10 μmol / L. The UV-visible spectrum and fluorescence spectrum changes of the probes when they interacted with Cys, GSH and HOCl were tested with a UV-visible spectrophotometer and a fluorescence spectrophotometer. from figure 1 It can be seen that after adding Cys (10 μM) or GSH (10 μM), the maximum ultraviolet absorption peak of the probe blue-shifted from 471 nm to 441 nm, and the fluorescence in...

Embodiment 3

[0087] Fluorescence titration experiment of the probe of the present invention recognizing Cys.

[0088] Example 2 Preparation of the probe mother solution 30 μL was added to 3 mL of the test solution, the final concentration of the probe was 10 μmol / L, and different equivalents (0–4 equivalents) of the Cys mother solution were added, such as figure 2 As shown, with the increase of Cys concentration, the fluorescence intensity of the maximum fluorescence emission peak at 514 nm gradually increased, and the detection limit of the probe to recognize Cys was 8.95 nM.

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Abstract

The invention relates to synthesis, preparation and application of a fluorescent probe for identifying Cys, GSH and HOCl on the basis of a molecular logic gate, belongs to the field of small-moleculefluorescent probes and relates to the technical field of molecular computers. The multi-identification fluorescent has a structural formula as shown in a formula (I): ( as shown in the description). The novel fluorescent probe for identifying the Cys, GSH and HOCl based on the molecular logic gate is reported for the first time, has the advantages of low detection limit, high sensitivity and highselectivity and can realize visible detection; the probe adopts cheap and easily available raw materials, high yield and low preparation cost, and is suitable for industrialized production; a to-be-detected liquid is a buffer solution of 100 percent and is consistent with the buffer ability of the physiological environment in an organism; the molecular logic gate is built by taking the Cys, GSH and HOCl as input signals as well as taking the maximal fluorescence emitting peak fluorescent intensity in the positions of 514 nm and 412 nm as output signals; the fluorescent probe for identifying the Cys, GSH and HOCl based on the molecular logic gate is reported for the first time and can solve the limitation caused by the single-identification fluorescent probe.

Description

technical field [0001] The invention belongs to the field of small-molecule fluorescent probes, relates to the technical field of molecular computers, and in particular relates to a method for synthesizing a multi-recognition fluorescent probe, a method for constructing a molecular logic gate and its application in detecting Cys, GSH and HOCl. Background technique [0002] The traditional semiconductor silicon material realizes the logic operation through the change of the voltage; the supramolecular chemistry is through the interaction process between the object and the host and the change of the corresponding spectral signal, and the input and output in the logic calculation process one by one. correspond. The logic operation of the fluorescent probe is to identify two or more target molecules through the probe molecules, and the fluorescence changes generated during the identification process. These target molecules are used as input signals, and fluorescence emission is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/16C09K11/06G01N21/64
Inventor 叶勇牛华伟彭淑新张永茹赵玉芬
Owner ZHENGZHOU UNIV
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