Mitochondrion-lysosome migration type membrane potential fluorescent probe CSP

A fluorescent probe, membrane potential technology, applied in fluorescence/phosphorescence, luminescent materials, material analysis by optical means, etc., can solve the problems of limited detection sensitivity, automatic acquisition, practical operation and inconvenience of detection, etc., to achieve real-time Tracking, good reversibility effects

Active Publication Date: 2020-10-16
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the detection sensitivity of the quenching type probe is limited due to the high background signal; the mitochondrial-nucleus migration type probe evaluates the membrane potential by calculating the ratio of the fluorescence i

Method used

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  • Mitochondrion-lysosome migration type membrane potential fluorescent probe CSP
  • Mitochondrion-lysosome migration type membrane potential fluorescent probe CSP
  • Mitochondrion-lysosome migration type membrane potential fluorescent probe CSP

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0031] Example 1

[0032] Preparation and characterization of a mitochondrial-lysosomal migration membrane potential fluorescent probe (CSP) with aggregation-induced emission characteristics:

[0033]

[0034] (1) In a round-bottom flask, add 4-bromophenylacetonitrile (0.588g, 3mmol) and t-BuOK (0.336g, 3mmol) to (30mL) absolute ethanol, and stir for 10 minutes at room temperature; 4-Diethylamino-2-methoxy-benzaldehyde (0.621g, 3mmol) was slowly added to the above mixture and refluxed for 6 hours; the system was cooled to room temperature, the solvent was concentrated in vacuo, and purified by silica gel column chromatography (petroleum Ether / ethyl acetate, 5:1, v / v) to obtain compound 2 (0.806 g, 70%) as a yellow solid. 1 H NMR(400MHz, CDCl 3 ): δ(ppm): 8.26(d,J=8.8Hz,1H),7.91(s,1H),7.53-7.48(m,4H),6.36(dd,J=9.2,2.0Hz,1H),6.11 (s, 1H), 3.87 (s, 3H), 3.43 (q, J = 6.8 Hz, 4H), 1.23 (t, J = 7.2 Hz, 6H).

[0035] (2) The compound 2 (0.346g, 0.9mmol), K 2 CO 3 (0.138g, 1mmol) and 4-pyr...

Example Embodiment

[0037] Example 2

[0038] The near-infrared aggregation induced fluorescence emission characteristics of the probe CSP in the acetonitrile / water mixed solvent of this example:

[0039] Dilute the probe with a mixed solvent of acetonitrile / water to a final concentration of 5μmol / L, a fixed excitation wavelength of 475nm, and record the fluorescence emission spectrum of the probe as a function of water content ( Figure 4 ), and plot the relative fluorescence intensity of the probe (I / I 0 ) Curve of variation with water content in an acetonitrile / water mixed system ( Figure 5 ). As the water volume ratio increased from 0% to 95%, the fluorescence intensity at 678nm increased in turn, and reached a maximum when the volume of water was 85%, indicating that the probe has typical aggregation-induced luminescence characteristics. The dynamic light scattering analysis showed that the probe formed an aggregate state with a hydration diameter of 135.1nm in the acetonitrile / water mixed solve...

Example Embodiment

[0040] Example 3

[0041] The solid-state fluorescence emission performance of the probe CSP of this example

[0042] The excitation wavelength is fixed at 475nm, and the solid-state fluorescence emission spectrum of the probe is recorded. Such as Figure 7 As shown, the maximum fluorescence emission intensity of the solid-state probe is 672nm, which is in the near-infrared emission range (fluorescence emission> 650nm), indicating that the probe has near-infrared emission aggregation inducing properties. At the same time, the Stoke displacement is as high as 197nm, which can effectively reduce the interference of excitation light. In addition, the solid-state probe exhibits bright red fluorescence under ultraviolet light (inset); the solid-state fluorescence quantum yield of the probe is calculated to be 9.8%.

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Abstract

The invention discloses a mitochondrion-lysosome migration type membrane potential fluorescent probe CSP, and belongs to the technical field of mitochondrion membrane potential fluorescent probes. Themitochondrion-lysosome migration type membrane potential fluorescent probe CSP has the near-infrared aggregation-induced fluorescence emission characteristic, and the positive charge structure of themitochondrion-lysosome migration type membrane potential fluorescent probe CSP is combined with the electrostatic interaction of mitochondrion negative membrane potential, so that the probe is aggregated in mitochondria in a targeted manner; the membrane potential is reduced; the probe is released from mitochondria and migrates to lysosome; the probe and the commercially available lysosome specific dye are subjected to co-localization fluorescence imaging, and the characteristic that the co-localization coefficient of the probe and the commercially available lysosome specific dye is increasedalong with reduction of membrane potential is utilized, so that real-time tracking of mitochondrial membrane potential in normal living cells is realized, and visual distinguishing application of dead living cells is realized.

Description

technical field [0001] The invention belongs to the technical field of mitochondrial membrane potential fluorescent probes, in particular to a mitochondrial-lysosome migration type membrane potential fluorescent probe CSP. Background technique [0002] During the mitochondrial tricarboxylic acid cycle, the protons inside the mitochondria will be actively transported to the outside of the mitochondria, thereby forming a mitochondrial membrane potential (-160mV ~ -180mV) that is negative inside and positive outside, which is an important indicator that reflects mitochondrial metabolic function and cell activity. parameter. Abnormal mitochondrial membrane potential can lead to mitochondrial dysfunction, which is often closely related to some cancers, obesity and Parkinson's disease. In addition, numerous studies have shown that the reduction of mitochondrial membrane potential is considered to be one of the earliest events in the process of apoptosis cascade, even before the e...

Claims

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Application Information

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IPC IPC(8): C07D213/57C09K11/06G01N21/64
CPCC07D213/57C09K11/06C09K2211/1029G01N21/6428
Inventor 樊丽王晓东张跃伟李峰董川
Owner SHANXI UNIV
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