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High stability near-infrared second region small molecule fluorescent probe and its preparation method and application

A high-stability, fluorescent probe technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of poor stability and weak integration of diagnosis and treatment, and achieve significant effects and good active targeting. Effect

Active Publication Date: 2021-04-13
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Materials in the second near-infrared region refer to materials with emission wavelengths in the range of 1000-1700 nm. Compared with traditional materials in the first region of near-infrared, materials in the second region of near-infrared have longer emission wavelengths; however, materials in the second region of near-infrared are stable Poor performance, and weak ability to integrate diagnosis and treatment

Method used

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  • High stability near-infrared second region small molecule fluorescent probe and its preparation method and application
  • High stability near-infrared second region small molecule fluorescent probe and its preparation method and application
  • High stability near-infrared second region small molecule fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: Synthesis of a novel high-stability near-infrared second-region small-molecule fluorescent probe QT-RGD and a control probe MT

[0066] (1) Under nitrogen protection, add naphthalimide (2.53 g, 15.0 mmol), methyl 3-bromopropionate (8.15 g, 45.0 mmol) and 50 mL of anhydrous N, N -Dimethylformamide was used as a solvent, and the mixture was magnetically stirred and refluxed for 6 h. The reaction was completed, cooled to room temperature, the mixture was poured into 500 mL of ice-water mixture, and the pH was adjusted to neutral with 1 mol / L hydrochloric acid aqueous solution, filtered under reduced pressure, and the crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate Esters = 9:1, v / v), the product was yellow solid compound 1 (3.14 g, yield: 78 %). Maldi-Tof: m / z , cal : 256.10, found : 256.08 [M + ].

[0067] (2) Under nitrogen-protected ice-bath conditions, add compound 1 (1.35 g, 5.0 mmol) and 40 mL of anhy...

Embodiment 2

[0077] Example 2: Photophysical properties of a novel high-stability near-infrared second-region small-molecule fluorescent probe

[0078] Dilute the probe QT-RGD of the experimental group and the probe MT of the control group prepared in Example 1 to a concentration of 5 μM with ultrapure water, and measure their UV-visible-near-infrared spectrophotometer and fluorescence spectrophotometer. Infrared spectroscopy and fluorescence spectroscopy. Such as figure 2 As shown in (a), the results show that the best absorption of the probe QT-RGD is at 855 nm, while the best absorption of the probe MT of the control group is slightly blue-shifted to 840 nm; the fluorescence spectra in the second near-infrared region have obvious differences , the probe QT-RGD of the experimental group showed a strong emission fluorescence signal in the second near-infrared region in aqueous solution, while the probe MT of the control group had no significant fluorescence emission.

[0079] Dilute th...

Embodiment 3

[0082] Example 3: In vivo near-infrared second-region fluorescence imaging of a novel high-stability near-infrared second-region small molecule fluorescent probe

[0083] The probe QT-RGD of the experimental group and the probe MT of the control group prepared in Example 1 were dissolved in PBS solution (concentration: 100 μM, volume: 200 μL), and the probes were injected into the tail vein respectively. BALB / c / Nu female nude mice bearing tumors (4T1 mouse breast cancer) were placed in the small animal Serious II 900-1700 nm near-infrared second region in vivo imaging system (excitation wavelength: 808 nm) for real-time observation and imaging Finally, the in vivo imaging analysis software was used to calculate the fluorescence intensity of the tumor site in nude mice at different time points. In vivo fluorescence imaging of the probe QT-RGD in the experimental group and the probe MT in the control group at different time points: image 3 As shown in (a), the results show tha...

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Abstract

The invention discloses a high-stability small molecule fluorescent probe in the second near-infrared region, a preparation method and application thereof. The present invention designs and synthesizes a novel high-stability near-infrared second-region small-molecule fluorescent probe, which has deep tissue penetration ability and is hardly interfered by autofluorescence, and can realize living near-infrared second-region fluorescence and optical Acoustic imaging. Target probes can be radioactive using the chloramine T method 125 I radionuclide labeling to realize live SPECT / CT imaging of small animals. At the same time, the target probe has good active targeting to tumor tissue, and the photothermal therapy effect of tumor is remarkable, realizing the integration of diagnosis and treatment of tumor.

Description

technical field [0001] The invention belongs to the technical field of biological imaging of small-molecule probes in the second near-infrared region, and specifically relates to a novel high-stability small-molecule fluorescent probe in the second near-infrared region and a preparation method thereof, and the use of the probe in multimodal imaging and photothermal therapy Applications. Background technique [0002] As we all know, cancer is one of the most important diseases that threaten human life and health, and it has caused great obstacles to the healthy development of economy and society. According to the data released by the National Cancer Center, the incidence of cancer in my country is increasing year by year, and it is showing a younger trend. It is imminent to develop materials and new technologies for tumor diagnosis and treatment. In recent years, the integration of diagnosis and treatment, as a new strategy for tumor treatment, has attracted more and more at...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C09K11/06G01N21/64
CPCC07D403/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1074G01N21/6428G01N21/6456G01N2021/6439
Inventor 史海斌赵梦
Owner SUZHOU UNIV
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