Preparation and application of endoplasmic reticulum targeted redox reversible fluorescent probe

A fluorescent probe, endoplasmic reticulum technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of not realizing endoplasmic reticulum redox reversible monitoring and other problems, achieve few steps, high sensitivity, easy The effect of preparation

Inactive Publication Date: 2020-11-24
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are many articles reporting the monitoring of active redox species in the endopla

Method used

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  • Preparation and application of endoplasmic reticulum targeted redox reversible fluorescent probe
  • Preparation and application of endoplasmic reticulum targeted redox reversible fluorescent probe
  • Preparation and application of endoplasmic reticulum targeted redox reversible fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0032] Example 1

[0033] Synthesis of fluorescent probe

[0034] The diphenyl diselenide (624.3mg, 2mmol) was dissolved into 15mL of anhydrous ethanol was added sodium borohydride (37.83mg, 1mmol), - 5 ~ 0 ℃, low temperature and stirred until a clear solution under nitrogen. 4-bromo -N- (2- aminoethyl) -4-methyl-benzenesulfonamide 1,8-naphthalimide (473mg, 1mmol) was dissolved in 5mL of absolute ethanol was added to the reaction solution to , reaction was continued for 12 hours, warmed to room temperature, solvent was distilled off under reduced pressure, purified on silica gel was removed, to give the target probe (86.5%). Characterization results are as follows: HRMS (ESI): m / z [M] + Theoretical value 550.0465, test result m / z [M + H] + 551.0454. 1 HNMR (400MHz, DMSO-D 6 ): Δ = 8.53-8.62 (m, 1H), 8.44-8.53 (m, 1H), 8.19-8.32 (m, 1H), 7.87-7.96 (q, 1H), 7.70-7.82 (s, 1H), 7.53 -7.67 (m, 5H), 7.41-7.50 (m, 3H), 7.16-7.25 (d, 2H), 3.23-3.50 (t, 2H), 3.03-3.13 (t, 2H), 2.17-2.3...

Example Embodiment

[0035] Example 2

[0036] Probe fluorescence titration experiments hypochlorous

[0037] The probe was added to 10μM of acetonitrile and phosphate buffer (v / v = 1: 99, pH = 7.4) in the mixed system, hypochlorous acid was added so that the concentration of hypochlorous acid are 0,1,2, 8, 9, 15,20,25,30,40, and 50 M, the reaction time after measuring the fluorescence intensity at each concentration, such as fluorescence curves figure 2 (A) shown. like figure 2 (B), with increasing concentrations of hypochlorous acid, the fluorescence intensity of the probe decreases at 506nm, detection limit was calculated to 0.85μM.

Example Embodiment

[0038] Example 3

[0039] Selective fluorescent probe experiments hypochlorous

[0040] The probe system of 10μM were added in 50 M hypochlorite and other active interferents analysis (concentration 50 M), the detection system of acetonitrile and phosphate buffer (v / v = 1: 99, pH = 7.4) mixed systems, different fluorescence intensity of the reaction system, the fluorescence intensity is calculated, and the results image 3 Indicated. The figure shows, the probe responsive only to hypochlorous acid, in the presence of other analytes and interferents of hypochlorous acid has a good response, experimental results show that the probe has a good selectivity and immunity of hypochlorous acid ability.

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Abstract

The invention discloses preparation and application of an endoplasmic reticulum targeted redox reversible fluorescent probe. The structural formula is shown in the specification. The fluorescent probeprovided by the invention can be used for reversible detection of redox in an endoplasmic reticulum, recognition of the probe on hypochlorous acid is based on a photoinduced electron transfer mechanism, a good linear relationship is shown when the concentration of hypochlorous acid is 0-50 microns, the detection limit is 0.85 microns, and the sensitivity is high; the probe is high in selectivityand is not interfered by determination of other active oxygen species, active nitrogen species, common amino acids and common anions and cations; the probe can realize reversible circulation of hypochlorous acid and glutathione for more than three times; the probe is low in cytotoxicity and has excellent biocompatibility; and the probe has excellent endoplasmic reticulum targeting ability, realizes fluorescence imaging of endogenous and exogenous hypochlorous acid in the endoplasmic reticulum and monitors the endoplasmic reticulum redox regulation process under the condition that the endoplasmic reticulum is induced by chlamydomycin to stress.

Description

technical field [0001] The invention relates to the field of fluorescent probe imaging, and more specifically, to the preparation and application of an endoplasmic reticulum targeting redox reversible fluorescent probe. Background technique [0002] Cells themselves have a complex antioxidant system to regulate the internal redox balance, and reactive oxygen species, as an inevitable product of cellular respiration and metabolism, play an important role in many physiological processes and disease mechanisms. Hypochlorous acid is a common reactive oxygen species in cells. Abnormally metabolized hypochlorous acid is related to many diseases, such as cardiovascular disease, neurodegeneration, liver ischemia-reperfusion injury, and even cancer. At the same time, there is a large amount of glutathione in the cell, which regulates the redox balance in the cell. Therefore, exploring powerful chemical tools to reveal redox processes in living cells is particularly important for und...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/643G01N21/6486G01N2021/6432
Inventor 敬静臧顺平张小玲
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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