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Ratiometric pH fluorescent probe as well as preparation method and application thereof

A fluorescent probe and ratiometric technology, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of narrow pH value detection range and small application range, and achieve easy operation, improved sensitivity, and broadened The effect of detection range

Active Publication Date: 2016-06-22
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the technical scheme disclosed in the above-mentioned patent, the prepared fluorescent probe and its special detection kit have good responsiveness to the pH value of the solution, and can realize the labeling of lysosomes and the determination of the pH value of cell lysosomes, but Its pH value detection range is narrow, and it is limited to the detection of cell lysosome pH value, the scope of application is small, and it has great limitations

Method used

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  • Ratiometric pH fluorescent probe as well as preparation method and application thereof
  • Ratiometric pH fluorescent probe as well as preparation method and application thereof
  • Ratiometric pH fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of fluorescent probe Cy2:

[0058] (1) Preparation of 2,3,3-trimethyl-3H-indole (A):

[0059]

[0060] (2) Preparation of 1-(4-benzylbenzoic acid)-2,3,3-dimethylindole bromide (B):

[0061]

[0062] (3) Preparation of 1-(4-benzylbenzoic acid)-2-[2-(4 hydroxyphenyl)-vinyl]-3,3-dimethylindole bromide (Cy2):

[0063]

[0064] In step (3), compound A and compound B were dissolved in dehydrated dimethylformamide (DMF), heated and stirred at a temperature of 80 degrees for 24 hours, TLC followed the reaction, and after compound B was completely reacted, evaporated to dryness with a rotary evaporator to obtain The crude product was purified by column chromatography on silica gel, using dichloromethane:methanol=15:1 as the developing solvent, to obtain the product Cy2 as a dark red solid.

[0065] The basic data of probe Cy2 are as follows:

[0066] dark red solid powder

[0067] 1 HNMR (400MHz, DMSO-d 6 )δ8.52(d, J=15.8Hz, 1H), 8.11(t, J=8.7Hz, 2H), 7....

Embodiment 2

[0070] Color change of probe Cy2 in aqueous solution with different pH values:

[0071] Probe Cy2 was dissolved in dimethyl sulfoxide (DMSO) to prepare the probe mother solution. Take a certain volume of this mother solution and add it to 40mM 4-hydroxyethylpiperazineethanesulfonic acid (HEPES) buffer solution, so that the final concentration of probe Cy2 is 20μM, and adjust the pH value with 1N sodium hydroxide solution and 1N hydrochloric acid to obtain 10 different pH values. Take out the same volume of the probe solution under the condition of pH value and put it into a vial. It can be seen that the probe changes from acidic to alkaline, and its aqueous solution changes from light yellow to pink, which provides the possibility to obtain the pH value by visual observation. .

Embodiment 3

[0073] Spectral performance test of probe Cy2pH titration:

[0074] Probe Cy2 was dissolved in dimethyl sulfoxide (DMSO) to form 10 -3 M probe master solution. Take 200 μL of mother liquor and add it into ultrapure water to obtain 20ml of Cy2 aqueous solution with a concentration of 10 μM, adjust the pH with 0.1N hydrochloric acid and 0.1N sodium hydroxide solution, and measure the ultraviolet-visible absorption spectra of different pH (3-11) as figure 1 shown and the fluorescence emission spectrum spectrum as image 3 Shown (excitation wavelength is 471nm).

[0075] From figure 1 It can be concluded that the probe Cy2 has two absorption peaks, which are 431nm and 535nm respectively. As the pH value decreases, the absorption intensity at 431nm decreases, and the absorption intensity at 535nm increases, and the isosbestic point is 471nm.

[0076] figure 2 It represents the absorption intensity-pH value change curve at the maximum absorption 535nm, and the pKa value of the...

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Abstract

The invention relates to a ratiometric pH fluorescent probe as well as a preparation method and an application thereof. The chemical structural formula of the fluorescent probe is shown as formula I in the specification, wherein R is -OH or a subcellular organelle positioning receptor, and the subcellular organelle positioning receptor comprises either of two components shown in the specification. Compared with the prior art, the ratiometric pH fluorescent probe has good light stability, high selectivity, wide pH value detection range and high sensitivity, the preparation method is simple, and the ratiometric pH fluorescent probe can be used for detecting the pH value of a chemical system or the pH value in living cells of creatures.

Description

technical field [0001] The invention belongs to the field of small-molecule fluorescent probes, and relates to a ratio-type pH fluorescent probe and its preparation method and application, in particular to a ratio-type pH fluorescent probe based on an indole semicyanine structure and its preparation method and application. application. Background technique [0002] The progress or completion of chemical reactions is closely related to the pH value, and many physiological processes of tissues, cells or enzymes, such as cell proliferation or apoptosis, ion transport, endocytosis, multidrug resistance or muscle contraction, are also related to the human body. Changes in pH value will also affect nervous system activities such as synaptic transmission, neuron excitability and intercellular coupling through changes in gap junctions and signaling pathways. Abnormal pH can cause some diseases, such as cancer or Ahrler syndrome, and it has been reported that cell acidification is a...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07F9/572C09K11/06G01N21/64
CPCC07D209/12C07F9/572C09K11/06C09K2211/1029G01N21/64G01N21/6486
Inventor 黄楚森吴庐陵贾能勤贾倜
Owner SHANGHAI NORMAL UNIVERSITY
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