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Near infrared fluorescent probe capable of being used for responding to pH change in living cells in chronic wound development process and preparation method of probe

A fluorescent probe, chronic wound technology, applied in chemical instruments and methods, preparations for in vivo experiments, luminescent materials, etc. Fluorescence interference, avoidance of self-absorption, excellent selectivity

Active Publication Date: 2019-05-21
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Many near-infrared pH fluorescent probes currently reported are mainly focused on the research of acidic tissues and organelles, such as tumors and lysosomes, and there are no research reports on near-infrared pH fluorescent probes that can be applied to alkaline tissues.

Method used

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  • Near infrared fluorescent probe capable of being used for responding to pH change in living cells in chronic wound development process and preparation method of probe
  • Near infrared fluorescent probe capable of being used for responding to pH change in living cells in chronic wound development process and preparation method of probe
  • Near infrared fluorescent probe capable of being used for responding to pH change in living cells in chronic wound development process and preparation method of probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis routes of fluorescent probes 1, 2, and 3 that can be used for fluorescence imaging of exogenous pH changes in living cells are shown in the following reaction formula:

[0041]

[0042] Note: The structure of IR-780 is

[0043] (1) Synthesis of compound 1a

[0044] 2 g (13.1 mmol) of methyl 3-hydroxybenzoate were placed in a round bottom flask and dissolved in 8 mL of carbon tetrachloride. Then 0.7 mL (27.3 mmol) of bromine was slowly added dropwise at 0°C, and stirring was continued overnight at 50°C. After the reaction was completed, the reaction liquid was cooled at 0° C. for 2 h and then suction filtered. The crude product of the filter cake was recrystallized with carbon tetrachloride to obtain 2.1 g of white crystalline solid (1a) with a yield of 69%.

[0045] 1 H NMR (400MHz, DMSO-d 6 )δ10.12(s,1H),7.50(d,J=8.7Hz,1H),7.15(d,J=3.0Hz,1H),6.89(dd,J=8.7,3.0Hz,1H),3.83( s,3H). 13 C NMR (101MHz, DMSO-d 6 )δ166.49, 157.21, 135.21, 133.34, 120.7...

Embodiment 2

[0067] Example 2 Fluorescent Probes 1, 2, 3 Changes in UV Absorption Intensity and Fluorescence Intensity in Different pH Buffers

[0068] The prepared probes 1, 2, and 3 (10 μM) were placed in different buffers with a pH of 4.5-10.5 (phosphate-citric acid buffer for pH 4.5-pH 8.5, bicarbonate buffer for pH 9.0-pH 10.5) Salt buffer solution, all containing 10% DMSO), and test the ultraviolet absorption spectrum and fluorescence spectrum of the three, the results are as follows figure 1 and figure 2 As shown, the maximum absorption wavelength and maximum emission wavelength of probes 1-3 are 770nm and 798nm, respectively. Under acidic conditions, the nitrogen atom on the hydrazide group of the probe is protonated, and the photoinduced electron transfer (PET) is inhibited, so the three probes all reach the maximum fluorescence intensity at this time. As the pH increases, since the protonation of the nitrogen atom disappears, the PET effect of the probe itself recovers, result...

Embodiment 3

[0069] The pKa value contrast situation of embodiment 3 fluorescent probe 1,2,3

[0070] Fluorescence intensity changes at different pH values ​​were measured by fluorescence titration experiments (the working concentration of the probe was 10 μM, and the excitation wavelength of the test was 715 nm), and the nonlinear curves of the three probes were fitted using Origin to obtain the pKa of the three probes Condition. As shown in Figure 3, the three probes all have a relatively obvious pH response mutation range, which is very important for finely measuring small fluctuations in pH. In addition, probe 2 without any substituents on the benzene ring has a pKa value of 8.48; when a bromine atom with a certain electron-withdrawing ability is added to the benzene ring (such as probe 1), its pKa value decreases to 8.01; and After adding a methoxy group with a certain electron-donating ability to the benzene ring (such as probe 3), its pKa value increases to 8.89. The above shows th...

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Abstract

The invention discloses a near infrared fluorescent probe capable of being used for responding to the pH change in living cells in the chronic wound development process and a preparation method of theprobe, and belongs to the technical field of biological fluorescence analysis. The near infrared fluorescent probe is a near infrared cyanine probe based on a benzoyl hydrazine structure, and the general structural formula is shown in the description. A hydrazide group R3 or R4 serving as the group acting with the environment pH is utilized for construction through connection of benzoyl hydrazineand near infrared fluorophore (polymethine cyanines IR780) through an ether bond, and the near infrared fluorescence probe is obtained. The near infrared fluorescent probe can be used for bioimagingof changes of the endogenous PH and exogenous pH in living cells and the endogenous PH in the development process of chronic wounds on diabetic patients, the synthesis method is simple and easy to implement, and industrial popularization and production are facilitated.

Description

technical field [0001] The invention relates to a fluorescent dye used in the technical field of biological fluorescence analysis, in particular to a near-infrared fluorescent probe which can be used to respond to pH changes in living cells and during the development of chronic wounds and a preparation method thereof. Background technique [0002] The human body is a very complex microenvironment system, and pH is a very important indicator for studying some physiological and pathological processes. For example, the pH range of tumors is about 6.4-7.2, and the pH range of lysosomes is about 4.0-6.0. Maintaining the physiological pH value of cell tissue or interfering with the pH value of pathological tissue has very important scientific significance for clinical treatment. [0003] Fluorescence imaging technology has the advantages of high temporal and spatial resolution, high sensitivity, and good selectivity. Among them, near-infrared fluorescent dyes with emission wavele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/10C07D209/12C07D209/14C09K11/06G01N21/64A61K49/00
CPCY02P20/55
Inventor 吴松麦桁棠
Owner WUHAN UNIV
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