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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 endoplasmic reticulum, but none of them have achieved reversible monitoring of redox in the endoplasmic reticulum

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

Embodiment 1

[0033] Synthesis of fluorescent probes

[0034] Dissolve diphenyldiselenide (624.3mg, 2mmol) in 15mL of absolute ethanol, add sodium borohydride (37.83mg, 1mmol), and stir at -5~0°C under nitrogen protection until the solution becomes clear. Dissolve 4-bromo-N-(2-aminoethyl)-4-methylbenzenesulfonamide-1,8-naphthalimide (473 mg, 1 mmol) in 5 mL of absolute ethanol and add to the above reaction solution , continue to react for 12 hours, warm up to room temperature, distill off the solvent under reduced pressure, and purify on silica gel to obtain the target probe (86.5%). The characterization results are as follows: HRMS(ESI):m / z[M] + The theoretical value is 550.0465, and the test results in 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),2.17-2.30(s, 3H). 13 C NMR (100MHz, DMSO-d 6 ): δ=163.63,142.87,141.02,...

Embodiment 2

[0036] Fluorescence titration experiment of probe to hypochlorous acid

[0037] Add 10 μM probe into the mixed system of acetonitrile and phosphate buffer (v / v=1:99, pH=7.4), and then add hypochlorous acid so that the concentrations of hypochlorous acid are 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 40 and 50 μM, measure the fluorescence intensity at each concentration after the reaction time ends, the fluorescence curve is as follows figure 2 (A) shown. Such as figure 2 As shown in (B), as the concentration of hypochlorous acid increases, the fluorescence intensity of the probe at 506 nm gradually decreases, and the detection limit is calculated to be 0.85 μM.

Embodiment 3

[0039] Selectivity Experiment of Fluorescent Probes for Hypochlorous Acid

[0040] Add 50 μM hypochlorous acid and other activity analysis interferers (50 μM concentration) to the 10 μM probe system, and the detection system is a mixed system of acetonitrile and phosphate buffer (v / v=1:99, pH=7.4), Measure the fluorescence intensity of different reaction systems, calculate the fluorescence intensity, the results are as follows image 3 shown. It can be seen from the figure that the probe only responds to hypochlorous acid, and has a good response to hypochlorous acid in the presence of other analytical interferences. The experimental results show that the probe has good selectivity and anti-interference to 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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