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Application of heptamethine indocyanine small molecules with N-alkyl side chains with different chain lengths in preparation of photosensitizer for treating tumors

An indocyanine and small molecule technology, applied in the field of biomedical engineering, can solve the problems of remote metastatic tumor immunotherapy research, unsatisfactory phototherapy effect, and practical application limitations without phototherapy to activate the body's systemic anti-tumor immune response. , to amplify the immunogenic death of tumor cells, inhibit tumor growth, and enhance the effect of phototherapy

Pending Publication Date: 2022-06-28
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, due to its strong hydrophobicity, it is easy to aggregate and precipitate in the water environment, and the phototherapy effect of most heptacyanine small molecule photosensitizers is not ideal, and its practical application is also greatly limited.
More importantly, previous studies on small molecules of Heptacyanine and photosensitizers of this type of chemical structure were limited to the study of phototherapy for primary superficial tumors, and no phototherapy was performed to activate the body's systemic anti-tumor immune response and treat distant metastatic tumors. immunotherapy research

Method used

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  • Application of heptamethine indocyanine small molecules with N-alkyl side chains with different chain lengths in preparation of photosensitizer for treating tumors
  • Application of heptamethine indocyanine small molecules with N-alkyl side chains with different chain lengths in preparation of photosensitizer for treating tumors
  • Application of heptamethine indocyanine small molecules with N-alkyl side chains with different chain lengths in preparation of photosensitizer for treating tumors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Spectroscopic determination of small molecules C3-C11 of heptacyanine with different chain lengths

[0035] Accurately weigh the small molecules C3-C11 of heptamethine indocyanine with different chain lengths with a 1 / 10,000 analytical balance, and prepare a 10 mM dimethyl sulfoxide (DMSO) solution for later use. During the test, the dye solution was diluted to 4 μM with DMSO, and the UV absorption spectrum, fluorescence emission spectrum and fluorescence quantum yield (Φ) of compounds C3-C11 were measured by ShimadzuUV-3600 UV-Fluorescence Spectrophotometer and Lumina Fluorescence Spectrometer respectively. F). As shown in Table 1, the test results show that the maximum ultraviolet absorption wavelength and maximum fluorescence emission wavelength of all compounds are located in the near-infrared region (700-900nm), and the molar absorption coefficient (ε) is in the range of 100 000-350 000, showing excellent Light Harvesting Capability and Fluorescence Emis...

Embodiment 2

[0041] Example 2 Photothermal effects of small molecules C3-C11 of heptacyanine with different chain lengths

[0042] Compounds C3 to C11 were prepared as 10 mM stock solutions with DMSO and stored at -20°C. A certain amount of stock solution was drawn from the stock solutions of C3-C11 compounds prepared above and added to phosphate buffered saline (PBS, 10mM, PH=7.4) containing 1% HSA to prepare a 10 μM sample working solution, and 1.5 mL of each was added. in a centrifuge tube. Place the centrifuge tube containing the detection solution at 808nm, 1.0W / cm 2 The near-infrared laser (Laser) was irradiated for 5 minutes, and the temperature change was recorded every 30 seconds. The results are shown in figure 2 and image 3 . The experimental results show that compounds C3-C11 have the effect of inducing temperature rise, among which the temperature rise effect of C8 is the most excellent, which can reach above 55℃.

Embodiment 3

[0043] Example 3 Singlet Oxygen Generation of Heptamethanine Small Molecules C3~C11 with Different Chain Lengths

[0044] SOSG probes (prepared in 100% methanol solution) were added to 2 mL of 10 μM aqueous solution of heptamethanine small molecules with different chain lengths, so that the SOSG concentration was 1.5 μM and the methanol content was 2%. and then at 1W / cm 2 The 808 nm laser was irradiated for 5 minutes, followed by excitation at 495 nm, and the fluorescence emission spectrum at 500-600 nm was immediately measured, and the generation of singlet oxygen was quantified by the fluorescence intensity of the maximum emission peak at 525 nm. like Figure 4 As shown, C3-C11 can generate a large amount of singlet oxygen after being irradiated by near-infrared 808 nm laser, among which compound C8 has the strongest singlet oxygen generation ability, which provides feasibility for realizing tumor photodynamic therapy.

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Abstract

The invention relates to application of heptamethine indocyanine small molecules with N-alkyl side chains with different chain lengths in preparation of a photosensitizer for treating tumors. According to the application, self anti-tumor immune response is activated through tumor phototherapy. The photosensitizer has a good tumor preferential accumulation characteristic, accurate phototherapy guided by near-infrared imaging and tumor in-situ induced anti-tumor immune response, does not need to additionally take immunotherapy drugs, and has a bright application prospect in tumor targeted immunotherapy.

Description

technical field [0001] The invention belongs to the technical field of biomedical engineering, in particular to the application of heptamethine indocyanine small molecules with N-alkyl side chains of different chain lengths in the preparation of photosensitizers for treating tumors. Background technique [0002] Cancer is still a major disease that threatens human life and health. The limitations of the major tumor treatment modalities currently available in the clinic, such as surgery, radiotherapy, and chemotherapy, force more exploration into better tumor treatments [1,2] . Immunotherapy is a means of improving the body's natural defense against cancer, and has achieved very gratifying and important progress in recent years [3] . However, non-specific immune activation, low patient response rates, and immune-induced adverse outcomes are major obstacles to current clinical immunotherapy [4] . Systemic administration of immunotherapeutic agents, such as immune checkpoi...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61P35/00A61K49/00
CPCA61K41/0057A61K41/0052A61P35/00A61K49/0032
Inventor 罗圣霖
Owner ARMY MEDICAL UNIV
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