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A near-infrared fluorescent probe and multimodal nano-contrast agent based on the probe and its preparation and application

A nano-contrast agent and fluorescent probe technology, which is applied in the field of biological and medical nanomaterials, can solve the problem of incomplete disease detection information, and achieve the effects of low detection cost, strong fluorescence intensity, and high detection sensitivity

Active Publication Date: 2020-04-21
JIANGSU PROVINCE HOSPITAL THE FIRST AFFILIATED HOSPITAL WITH NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Another object of the present invention is to provide a tumor-targeting multimodal nano-contrast agent and Its preparation method, as a tracer, can simultaneously realize more than two multimodal imaging functions in MRI, fluorescence, and photoacoustic imaging, and realize comprehensive and accurate diagnosis of tumors

Method used

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  • A near-infrared fluorescent probe and multimodal nano-contrast agent based on the probe and its preparation and application
  • A near-infrared fluorescent probe and multimodal nano-contrast agent based on the probe and its preparation and application
  • A near-infrared fluorescent probe and multimodal nano-contrast agent based on the probe and its preparation and application

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Embodiment 1

[0056] Embodiment 1 near-infrared fluorescent probe Met-IR-782 and its preparation method

[0057] 1) NH 2 - Preparation of IR-782

[0058] IR-782 (104.3 mg, self-made, its preparation can be found in S.A. Hilderbrand, et al. Bioconjugate Chem. 2005, 16: 1275-1281.) and mercaptoethylamine (27.3 mg) were dissolved in 5 mL of DMSO, nitrogen or argon protection, Reaction at 25°C for 16h. After the reaction was over, add excess toluene 30mL to the reaction solution and centrifuge (3000rpm / min, 10min) to obtain a precipitate, then add an excess of ether 30mL to the reaction solution and then centrifuge (3000rpm / min, 10min) to obtain a precipitate, and add the precipitate to 300 mesh silica gel chromatography column, with ethyl acetate / methanol (volume ratio 5:1) mixed solution as eluting solvent, obtain 88.1mg product intermediate product NH 2 -IR-782, about 67% yield.

[0059] 2) Preparation of Met-IR-782

[0060] Methionine (14.9mg), DCC (103mg) and NHS (57.5mg) were dissolv...

Embodiment 2

[0062] Example 2 The ultraviolet-visible absorption spectrum and fluorescence spectrum of the near-infrared fluorescent probe Met-IR-782

[0063] Dissolve 10 μg of Met-IR-782 probe in 1 mL of PBS (0.1 M, pH 7.2) buffer solution, mix well, add to a quartz cuvette and let stand for 5 min. Subsequently, the cuvette was put into a UV-Vis ultraviolet full-wavelength spectrophotometer (UV-3600, Shimadzu, Japan) to detect the absorption spectrum of the Met-IR-782 probe, and the results are shown in the attached Figure 4 As shown in A. Another portion of Met-IR-782 probe 10μg was added to 1mL PBS (0.1M, pH 7.2) buffer solution, mixed evenly and added to a quartz cuvette to stand for 5min. Subsequently, using a fluorescence full-wavelength detector (Hitachi F-4600, Japan) to detect the emission spectrum of the probe at an excitation wavelength of 782nm, the results are shown in the attached Figure 4 b. The absorption and emission peaks of IR-782, Met-IR-782 and ICG appear at aroun...

Embodiment 3

[0064] Photostability and thermal stability of embodiment 3 near-infrared fluorescent probe Met-IR-782

[0065] Dissolve 10 μg of the Met-IR-782 probe in 1 mL of PBS (0.1 M, pH 7.2) buffer solution, mix well, place under a 60W light bulb at 30 cm for 6 hours, and irradiate at 0, 1, 2, 3, 4, The average absorption intensity of the probe was detected at the time point of 5 and 6 hours, and the results are shown in the attached Figure 4 c. Another 10 μg of Met-IR-782 probe was dissolved in 1 mL of PBS (0.1 M, pH 7.2) buffer solution, mixed evenly, and placed in a constant temperature mixer (Eppendorf Thermo Mixer C, Germany). The average absorption intensity of the probes was detected at 25, 30, 35, 40, 45, 50, 55, and 60°C. The results are attached Figure 4 As shown in D, it can be seen that the average absorption intensity of Met-IR-782 is above 90% after it is irradiated under a 60W bulb for 1 hour. Meanwhile, ICG and NH 2 - The average absorption intensity of IR-782 wa...

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Abstract

The invention discloses a tumor-targeted near-infrared fluorescent probe Met-IR-782 and a preparation method thereof. The fluorescent probe has strong fluorescence intensity, good stability and high photothermal conversion efficiency. Based on the above-mentioned fluorescent probes, the present invention prepares a multi-modal nano-contrast agent, the multi-modal nano-contrast agent has a core-shell structure, and Fe 3 o 4 Nanoparticles as core, Prussian blue wrapped in Fe 3 o 4 The surface of the nanoparticle is a shell, and Met‑IR‑782 is bonded to Fe by amide bonds 3 o 4 on the nanoparticles. The multimodal nano-contrast agent of the present invention can realize multimodal imaging of MRI, fluorescence, and photoacoustic imaging, and realize comprehensive and accurate diagnosis of tumors; 3 o 4 The magneto-thermal properties of nanoparticles, the multi-modal nano-contrast agent can realize magneto-thermotherapy and photothermotherapy of tumors.

Description

technical field [0001] The invention belongs to the technical field of biological and medical nanomaterials, and relates to a near-infrared fluorescent probe, a nano-contrast agent for tumor multimodal imaging based on the probe, and their preparation method and application. Background technique [0002] With the development of molecular imaging technology, molecular imaging has been widely used in the disciplines of cells, tissues and clinical medical examinations. Among them, clinically used 11 C-labeled methionine ( 11 C-Met) etc. are used as PET / CT contrast agents to diagnose breast cancer, lung cancer, glioma, etc. Although these PET / CT contrast agents have their own advantages, there are also many disadvantages, such as damage to patients, easy to be affected by bones in the body, expensive equipment, and complicated operations. [0003] In addition to PET / CT imaging, common imaging techniques include magnetic resonance imaging (MRI), optical imaging, and ultrasound...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/10C09K11/06A61K49/22A61K49/18A61K49/00A61K41/00A61P35/00
CPCA61K41/0052A61K49/0002A61K49/0021A61K49/1821A61K49/225C07D209/10C09K11/06C09K2211/1007C09K2211/1029
Inventor 唐金海吴旸张薇李浩徐迪何蕴藉李建邓飞
Owner JIANGSU PROVINCE HOSPITAL THE FIRST AFFILIATED HOSPITAL WITH NANJING MEDICAL UNIV
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