Near-infrared two-region fluorescent probe molecule and nanoparticle for multi-mode diagnosis and treatment integration

A fluorescent probe and nanoparticle technology, applied in the field of biomedical materials, can solve problems such as difficult synthesis and complex structure, achieve good cell compatibility, broad development prospects, and inhibit tumor growth.

Pending Publication Date: 2022-05-27
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The Chinese patent document with the publication number CN108864106A discloses a kind of organic small molecule fluorescent probe in the second near-infrared region, the main component of which is a diketopyrrolopyrrole (DPP) derivative. Nanoparticles with fluorescence imaging and photoacoustic imaging capabilities in the second infrared region, photodynamic and photothermal conversion properties, but the structure of the organic small molecule fluorescent probe in the second near infrared region is relatively complex and difficult to synthesize

Method used

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  • Near-infrared two-region fluorescent probe molecule and nanoparticle for multi-mode diagnosis and treatment integration
  • Near-infrared two-region fluorescent probe molecule and nanoparticle for multi-mode diagnosis and treatment integration
  • Near-infrared two-region fluorescent probe molecule and nanoparticle for multi-mode diagnosis and treatment integration

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The structural formula of the near-infrared second-region fluorescent probe molecule prepared in this example is shown in the following formula:

[0050]

[0051] The synthetic route of the near-infrared second-region fluorescent probe molecule (TP-TPA) includes the following 4 steps:

[0052] Step (1): Reduction Reaction

[0053]

[0054] In a protective gas atmosphere, compound 1-1 was mixed with zinc powder and ammonium chloride, and 10:1 methanol: water was added as a solvent, reacted at room temperature for 4 hours, and reduced to compound 1-2. Compound 1-2 can be It was directly put into the next step without purification, wherein, the compound 1-1 was disclosed in the literature (Synthesis and photovoltaic performance of a series of small band gap polymers, Journal of Materials Chemistry, 19(30), 5336-5342; 2009). Synthetic method Synthesis.

[0055] Step (2): Cyclization Reaction

[0056]

[0057] Compound 1-2 obtained in step (1) was mixed with benz...

Embodiment 2

[0065] The near-infrared second-region fluorescent probe molecule solution of Example 1 was mixed with the DSPE-PEG solution (the mass ratio of the near-infrared second-region fluorescent probe molecule and DSPE-PEG was 1:2), and added to water under ultrasonication, Nanoparticles (TP-TPANPs) were prepared by co-precipitation method.

[0066] Sample analysis

[0067] The hydrogen nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum of the near-infrared second-region fluorescent probe molecule prepared in Example 1 are as follows: figure 1 and figure 2 As shown, the successful synthesis of the near-infrared second region fluorescent probe molecule is proved.

[0068] The ultraviolet absorption spectrum and fluorescence emission spectrum of the near-infrared second-region fluorescent probe molecule prepared in Example 1 are as follows: image 3 As shown, the fluorescence emission wavelength is 958 nm; it belongs to the emission in the second...

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Abstract

The invention discloses a near-infrared two-region fluorescent probe molecule which is characterized in that a pyrazine derivative is used as an acceptor and connected with a donor unit, the near-infrared two-region fluorescent probe molecule has a donor-acceptor-donor molecular structure, the structural formula of the near-infrared two-region fluorescent probe molecule is as shown in formula (I), the near-infrared two-region fluorescent probe molecule has near-infrared two-region fluorescence emission, and the fluorescence emission wavelength is 958 nm; in addition, the material has the generation capability of singlet active oxygen up to 120 times and the photo-thermal temperature up to 70 DEG C, and integrates near-infrared two-region fluorescence emission, excellent active oxygen generation capability and photo-thermal effect. The nano particles for multi-mode diagnosis and treatment integration can be further prepared, the nano particles are high in tumor cell killing capacity, high in tissue penetrating power, excellent in imaging quality and good in biocompatibility, and growth of tumors in organisms can be inhibited while the health of the organisms is guaranteed.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and particularly relates to a near-infrared second-region fluorescent probe molecule and a nanoparticle used for the integration of multi-mode diagnosis and treatment. Background technique [0002] Optical imaging plays an increasingly important role in contemporary medicine, and fluorescence imaging has the advantages of high sensitivity, high stability, high temporal and spatial resolution, and real-time collection. Due to the high absorption, scattering and autofluorescence of biological tissues, the main bottlenecks of fluorescence imaging in vivo applications are the shallow tissue penetration depth, low signal-to-noise ratio (SBR), autofluorescence, quenching, and photobleaching. In order to solve the above problems, fluorescent materials in the near-infrared region have been developed, but most of them only have a single diagnostic imaging or therapeutic effect, and the penetration dept...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06A61K49/00A61K41/00A61K9/14A61K47/24A61P35/00G01N21/64
CPCC09K11/06A61K49/0021A61K49/0093A61K41/0052A61K9/146A61P35/00A61K41/0057G01N21/6428G01N21/6456Y02E10/549
Inventor 唐本忠杜楷洪秦安军胡蓉
Owner SOUTH CHINA UNIV OF TECH
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