Two-channel two-photon fluorescent polar probe, preparation method and uses thereof

A two-photon fluorescence, two-channel technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis through optical means, etc., can solve the problems of long cycle, high cost, poor sensitivity, etc., and achieve the effect of good permeability

Active Publication Date: 2019-09-03
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these methods are costly, long cycle time and poor sensitivity, and

Method used

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  • Two-channel two-photon fluorescent polar probe, preparation method and uses thereof
  • Two-channel two-photon fluorescent polar probe, preparation method and uses thereof
  • Two-channel two-photon fluorescent polar probe, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of Fluorescent Probe Molecule Mito-PF

[0028] Compound 3-benzyl-2-methylbenzothiazole bromide salt (0.28g, 0.9mmol) and compound 1 (0.3g, 0.9mmol) were mixed in 50mL of absolute ethanol, and the mixed solution was refluxed under nitrogen Until TLC showed that the starting material reaction was complete (about 12 hours), after the mixture was cooled to room temperature, the solvent was removed by a rotary evaporator; the obtained crude product was washed with 30 mL saturated brine, and then extracted with DCM (3×50 mL) and vacuum The solvent was evaporated under low pressure, and the crude product was purified by column chromatography (dichloromethane / methanol=50:1 as eluent) to obtain the target product Mito-PF, 0.35 g, with a yield of 62%.

[0029] 1 H NMR(400MHz,DMSO)δ8.95(d,J=7.1Hz,1H), 8.51(d,J=15.4Hz,1H), 8.44(s,1H), 8.40–8.36(m,1H), 8.18 (m,J=14.4,10.1Hz,2H),8.12–8.09(m,1H),7.84–7.71(m,5H),7.66–7.60(m,2H),7.38(t,J=13.9,7.1Hz ,5H),7.29(t,J=8.9Hz,...

Embodiment 2

[0030] Example 2: Spectral measurement of fluorescent probe molecules

[0031] Dissolve the fluorescent probe Mito-PF of the present invention in DMSO to prepare a 2mM mother liquor. Take 15μL of the mother liquor in 3mL solvents of different polarity to obtain UV spectra of the probe Mito-PF in different solvents ( figure 1 a). With the increase in solvent polarity, the value of its fluorescence intensity at 436nm gradually decreases, and there is almost no change in fluorescence intensity at 589nm, thus providing a ratio response ( figure 1 b). And the fluorescence intensity (I 436nm / I 589nm ) And Δf have a linear relationship ( figure 1 c), which shows that Mito-PF can be used for dual-channel detection of the polarity of common solutions. In order to further prove the polar response characteristics of the probe Mito-PF, the absorption and fluorescence spectra of Mito-PF were measured in the polar range with different proportions of water and tetrahydrofuran at 25°C ( fi...

Embodiment 3

[0032] Example 3: Two-photon performance test of fluorescent probe molecules

[0033] Mito-PF in different water and tetrahydrofuran mixed solvents (the content of tetrahydrofuran is 90%, 50% and 20% respectively), the effective two-photon absorption cross section appears at the maximum at 720nm and gradually decreases from 87GM to 41GM as the content of tetrahydrofuran decreases. ( Figure 5 a). It is observed that the two-photon excitation fluorescence intensity of Mito-PF in different solvents is squared with the input power (300-800mw) ( Figure 5 b). Prove that Mito-PF is capable of two-photon confocal fluorescence imaging of intracellular polarity.

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Abstract

The invention discloses a two-channel two-photon fluorescent polar probe, a preparation method and uses thereof, wherein the structure of the two-channel two-photon fluorescent polar probe is definedin the specification. According to the present invention, the two-channel two-photon fluorescent polar probe has specific response to polarity in a system containing the probe and other interference factors; and the cytotoxicity test results show that the probe has almost no toxic side effects on cells, and the two-photon confocal fluorescence microscopy imaging experiment results show that the probe has good permeability to HeLa cells and can effectively locate the mitochondria in the cells (positioning coefficient of 0.95), such that the probe is suitable for the two-channel two-photon fluorescence imaging and quantitative detection of the polarity in cell mitochondrial.

Description

Technical field [0001] The invention relates to a dual-channel two-photon fluorescent polarity probe and a preparation method and application thereof, so as to realize the dual-channel two-photon fluorescence imaging to quantitatively detect the polarity in cell mitochondria, and has the advantages of specificity, high sensitivity and low biological toxicity The advantages. Background technique [0002] Mitochondria are very important organelles in eukaryotic cells. For example, adenosine triphosphate (ATP) is produced to provide energy for physiological processes, so it is called the cell's energy source. In addition, mitochondria are involved in many physiological processes such as providing energy for the biosynthesis of macromolecules and maintaining intracellular Ca 2+ Horizontal steady state etc. Mitochondria are closely related to microenvironmental parameters such as polarity, viscosity, and pH. And mitochondrial polarity is particularly important, it can affect mitocho...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06C09K2211/1037G01N21/6428
Inventor 冯燕孙川黄银亮王新茹陈晓华陈俊
Owner ANHUI UNIVERSITY
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