High-stability second near-infrared small-molecule fluorescence probe and production method and application thereof

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

Active Publication Date: 2020-01-14
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 second near-infrared small-molecule fluorescence probe and production method and application thereof
  • High-stability second near-infrared small-molecule fluorescence probe and production method and application thereof
  • High-stability second near-infrared small-molecule fluorescence probe and production method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0066] (1) Under the protection of nitrogen, add naphthalimide (2.53 g, 15.0 mmol), methyl 3-bromopropionate (8.15 g, 45.0 mmol) and 50 mL of anhydrous N, N into a 150 mL round bottom flask. -Dimethylformamide is used as the solvent, and the mixture is magnetically stirred and refluxed for 6 h. After the reaction is complete, cool to room temperature, pour the mixture into 500 mL ice-water mixture, adjust the pH to neutral with 1 mol / L hydrochloric acid aqueous solution, filter under reduced pressure, and purify the crude product by silica gel column chromatography (petroleum ether: ethyl acetate Ester = 9:1, v / v), and the product is a yellow solid compound 1 (3.14 g, yield: 78%). Maldi-Tof: m / z , cal : 256.10, found :256.08[M + ].

[0067] (2) Under nitrogen protection and ice bath conditions, add compound 1 (1.35 g, 5.0 mmol) and 40...

Embodiment 2

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

[0078] The experimental group probe QT-RGD and the control probe MT prepared in Example 1 were diluted with ultrapure water to a concentration of 5 μM, and the UV-Vis spectrophotometer and fluorescence spectrophotometer were used to measure the UV-Vis. Near infrared spectrum and fluorescence spectrum. 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 control probe MT is slightly blue-shifted to 840 nm; the near-infrared two-zone fluorescence spectra have obvious differences , The experimental group probe QT-RGD showed a strong near-infrared two-zone fluorescence signal in aqueous solution, while the control probe MT had no significant fluorescence emission.

[0079] The experimental group probe QT-RGD, the control probe MT, and the near-infrared two-zone dye ICG p...

Embodiment 3

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

[0083] The experimental group probe QT-RGD and the control probe MT prepared in Example 1 were dissolved in PBS solution (concentration: 100 μM, volume: 200 μL), and the probes were injected into the charge by way of tail vein injection. Tumor (4T1 mouse breast cancer) BALB / c / Nu female nude mice, then placed in a small animal Serious II 900-1700 nm near-infrared two-zone live imaging system (excitation wavelength: 808 nm), and observe the imaging effect in real time Finally, the in vivo imaging analysis software calculates the fluorescence intensity of the tumor site of nude mice at different time points. The near-infrared two-zone in vivo fluorescence imaging of the experimental group probe QT-RGD and the control probe MT at different time points is as follows image 3 As shown in (a), the results show that the control probe MT...

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Abstract

The invention discloses a high-stability second near-infrared small-molecule fluorescence probe and a production method and application thereof. The novel high-stability second near-infrared small-molecule fluorescence probe is designed and synthesized, has strong tissue penetration capability, is almost free from interference of autofluorescence, and can achieve living second near-infrared fluorescent and photoacoustic imaging with high temporal-spatial resolution. The target probe can conduct radioactive 125I isotope labeling by means of a chloramine T method to achieve SPECT / CT imaging of small living animals. Meanwhile, the target probe has good active targeting to tumor tissues, a photothermal therapy effect on tumors is significant, and diagnosis and treatment integration of the tumors is achieved.

Description

Technical field [0001] The invention belongs to the technical field of near-infrared two-area small molecule probe bioimaging technology, and specifically relates to a novel high-stability near-infrared two-area small molecule fluorescent probe and a preparation method thereof, and the application 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 threatening human life and health, and it has caused great obstacles to the healthy development of the economy and society. According to the data released by the National Cancer Center, the incidence of tumors in my country is increasing year by year, and it is showing a trend of younger generation. It is urgent 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 attention fr...

Claims

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Application Information

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Patent Type & Authority Applications(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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