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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AI-Extracted 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...

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Method used

[0042] The fixed excitation wavelength is 475nm, and the solid-state fluorescence emission spectrum of the record probe is recorded. As shown in Figure 7, 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 aggr...

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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.

Application Domain

Organic chemistryFluorescence/phosphorescence +1

Technology Topic

FluorescenceFluoProbes +6

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Examples

Experimental program(7)

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-pyridylboronic acid (0.123g, 1mmol) mixed and dissolved in THF/H 2 O(9mL/1mL) system, then add Pd(PPh 3 ) 4 (0.015g, 0.013mmol); reflux the system for 12 hours under nitrogen protection, cool to room temperature, concentrate the solvent in vacuo, and purify by silica gel column chromatography (petroleum ether/ethyl acetate, 1:1, v/v) to obtain orange The solid was compound 3 (0.166 g, 48%). 1 H NMR(400MHz, CDCl 3 ): δ(ppm): 8.67(d,J=5.2Hz,2H),7.82-7.48(m,7H),6.93(d,J=8.8Hz,1H),6.15-5.93(m,2H),5.39 –5.31(m,1H), 3.86(s,3H), 3.50–3.30(m,4H), 1.25–1.13(m,6H).

[0036] (3) Mix compound 3 (0.077g, 0.2mmol) and methyl iodide (0.036g, 0.25mmol) in acetonitrile (2mL) and reflux for 4 hours; cool the system to room temperature, add acetic anhydride (10mL), filter Precipitation, vacuum drying, to obtain crude product without purification. Dissolve the above crude product in acetone (2mL) and add KPF 6 (0.184mg, 1mmol); the reaction mixture was stirred at room temperature for 24 hours, the solvent was concentrated in vacuo, and purified by silica gel column chromatography (dichloromethane/anhydrous methanol, 10:1, v/v) to obtain a purple-red solid as the target product CSP (0.042mg, 39%). Such as figure 1 with figure 2 Said, 1 H NMR(400MHz, DMSO-d 6 ): δ(ppm): 8.98(d,J=6.8Hz,2H), 8.51(d,J=6.8Hz,2H), 8.21-8.10(m,3H), 8.08(s,1H), 7.82(d ,J=8.4Hz,2H),6.47(d,J=9.2Hz,1H),6.24(s,1H),4.32(s,3H),3.90(s,3H),3.52–3.45(m,4H) , 1.16(t,J=7.2Hz,6H). 13 C NMR(150MHz, DMSO-d 6 ):δ(ppm): 13.03,44.51,47.47,56.14,93.83,99.82,104.87,109.69,119.85,124.09,126.11,129.31,138.56,146.04,152.29,160.92.HR-MS m/z: [M+H ] + calclated for C 26 H 29 F 6 N 3 OP + ,546.4042; measured,546.4005.

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 solvent (water volume ratio is 85%) ( Image 6 ) The water volume ratio is 85%, further confirming the aggregation-induced fluorescence emission characteristics of the probe.

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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Mitochondrion-lysosome migration type membrane potential fluorescent probe CSP

AI-Extracted Technical Summary

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Abstract

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Example Embodiment

Example Embodiment

Example Embodiment

PUM

Description & Claims & Application Information

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