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Application of an activable photosensitizer in preparation of tumor photothermal therapeutic reagent

A technology of photothermal therapy and photosensitizer, which is applied in the direction of antineoplastic drugs, luminescent materials, medical preparations containing active ingredients, etc., and can solve problems such as heating and tissue burns

Inactive Publication Date: 2019-07-02
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, current PTT photosensitizers (e.g., ICG) are usually in a non-switchable form that, upon exposure, produce photothermal effects that lead to indifferent heating of normal and tumor tissues during treatment, which may lead to normal tissue burn

Method used

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  • Application of an activable photosensitizer in preparation of tumor photothermal therapeutic reagent
  • Application of an activable photosensitizer in preparation of tumor photothermal therapeutic reagent
  • Application of an activable photosensitizer in preparation of tumor photothermal therapeutic reagent

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preparation example Construction

[0099] And the preparation method of the activatable photosensitizer of the present invention as above can refer to as follows: NO 2 -R1-R 2 -Y 1 (i) with R 3 -Y 2 (ii) Mixing reaction, the target photosensitizer compound can be obtained, the preparation method is relatively convenient, and the operation is relatively simple, suitable for large-scale expanded production;

[0100] Among them, in compound (i), R 1 C5~C30 arylene, heteroarylene, substituted arylene, or substituted heteroarylene; preferably, R 1 Arylene, heteroarylene, substituted arylene, or substituted heteroarylene of C5-C15; more preferably, R 1 C5-C15 heteroarylene or substituted heteroarylene, wherein the heteroatoms in the heteroarylene or substituted heteroarylene are one or more of nitrogen, oxygen, and sulfur, and each The number of heteroatoms contained in heteroaryl or substituted heteroarylene is one or more; for example, R 1 Can be, but not limited to: furan, thiophene, pyrrole, imidazole, thi...

Embodiment 1

[0134] (1) Preparation of MZ-BOC molecules:

[0135] 2-Nitroimidazole (0.5g, 4.42mmol) was dissolved in 2mL of DMF, and then added to K in batches under stirring 2 CO 3 (0.915g, 6.63mmol) and N-Boc-bromoethylamine (0.99g, 4.42mmol), reacted overnight under nitrogen protection;

[0136] Then, the solvent was removed by rotary evaporation, dried in vacuo, the obtained solid was dissolved in water, extracted with ethyl acetate, the organic phase was collected, the solvent was removed by rotary evaporation, and the crude product was recrystallized with ethyl acetate to obtain a dark yellow solid product MZ-BOC (0.10 g, 89%).

[0137] The product MZ-BOC NMR and mass spectrometry test patterns are respectively referred to figure 1 with figure 2 , the graph analysis is as follows:

[0138] MZ-BOC: 1 HNMR (400MHz, DMSO-d 6 )δ7.46(s, 1H), 7.14(s, 1H), 4.43(t, J=5.6Hz, 2H), 3.36(q, J=5.9Hz, 2H), 1.31(s, 9H);

[0139] HRMS (ESI + ):m / zcalcdforC 10 h 16 N 4 o 4 :279.1064[M+N...

Embodiment 2

[0154] (1) Preparation of MZ-BOC molecules:

[0155] 2-Nitroimidazole (1.0g, 8.84mmol) was dissolved in 4mL of DMF, and then K was added in batches under stirring 2 CO 3 (1.83g, 13.26mmol), and N-Boc-bromoethylamine (1.98g, 8.84mmol), reacted overnight under nitrogen protection.

[0156] The solvent was removed by rotary evaporation, and the obtained solid was dissolved in water, then extracted with ethyl acetate, the organic phase was collected, and the solvent was removed by rotary evaporation. The obtained crude product was recrystallized from ethyl acetate to obtain dark yellow solid product MZ-BOC (0.19g, 83%).

[0157] The product MZ-BOC NMR and mass spectrometry detection spectrum and analysis results are the same as those in Example 1.

[0158] (2) Preparation of MZ molecules

[0159] Dissolve MZ-BOC (1.7g, 6.6mmol) in methanol (4mL), add 1.25M HCl in methanol (4mL) with stirring, and react at room temperature for 8h;

[0160] The solvent was removed by rotary eva...

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Abstract

The invention provides an application of an activable photosensitizer in the preparation of a tumor photothermal therapeutic reagent. The provided activable photosensitizer itself has no photothermaleffects, and can produce obvious photothermal effects when the activable photosensitizer is reduced by the nitroreductase in the tumor hypoxic environment, and thereby the targeted photothermal treatment of the tumor is realized without affecting normal cells.

Description

technical field [0001] The invention relates to the field of tumor treatment reagents, in particular to the application of an activatable photosensitizer in the preparation of tumor photothermal treatment reagents. Background technique [0002] As we all know, malignant tumors seriously endanger human life and health. Among them, solid tumors account for more than 85% of clinical malignant tumors, and hypoxia is one of the important characteristics of solid tumors. Tumor hypoxic cells undergo changes in metabolism, molecular genetics, and pathophysiology, which play a very important role in the evolution and progression of tumors, and resist chemotherapy and radiotherapy, leading to local tumor recurrence, distant metastasis, and poor prognosis. Phototherapy, including photodynamic therapy (PDT) and photothermal therapy (PTT), has been introduced into clinical trials for cancer treatment due to its advantages of improving antitumor effects, reducing side effects, and overcom...

Claims

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Application Information

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IPC IPC(8): C07D403/14C09K11/06A61K41/00A61P35/00
CPCA61K41/0052C07D403/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044
Inventor 蔡林涛孟晓青龚萍张佳丽周理华
Owner SHENZHEN INST OF ADVANCED TECH
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