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Photosensitizer based on thiadiazolo [3, 4-g] quinoxaline structure as well as synthesis method and application of photosensitizer

A synthesis method and technology of photosensitizers, which are applied in the directions of medical preparations, pharmaceutical formulations, and drug combinations containing active ingredients, can solve the problems such as no relevant reports on tumor treatment, influence on treatment effect, metabolic burden, etc., and achieve good application prospects. , highly modifiable, adjustable performance effects

Pending Publication Date: 2022-08-09
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the Na in tumor cells + / H + Channel proteins are highly expressed, producing H + Will be rapidly transported into the extracellular environment, thereby affecting the therapeutic effect
Moreover, the irreversible breakage of chemical bonds in some acid generators will produce small molecular by-products, which will also cause metabolic burden and potential biological toxicity to the body.
At present, photoacid therapy only shows a certain photosensitization effect at the cellular level, but there is no relevant report on the treatment of tumors at the living level.

Method used

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  • Photosensitizer based on thiadiazolo [3, 4-g] quinoxaline structure as well as synthesis method and application of photosensitizer
  • Photosensitizer based on thiadiazolo [3, 4-g] quinoxaline structure as well as synthesis method and application of photosensitizer
  • Photosensitizer based on thiadiazolo [3, 4-g] quinoxaline structure as well as synthesis method and application of photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Preparation of compound T1-a

[0062] The structural formula of compound T1-a is:

[0063]

[0064] (1) Compound 1 (1.92 g, 5 mmol), Pd (PPh 3 ) 2 Cl 2 (0.20g, 0.15mmol), 2-tri(n-butyl)thiophene tin reagent (4.48g, 12mmol) were placed in a 250mL three-necked round bottom flask, and after 30min of high-purity nitrogen protection, 50mL of ultra-dry tetrahydrofuran was added, and refluxed at 60°C The reaction was stopped after 12 h, the excess reaction solution was removed by rotary evaporation, and the residue was subjected to column chromatography to obtain compound 2 as an orange solid with a yield of about 85%. The characterization data is as follows:

[0065] 1 H NMR (CDCl 3 , 400MHz): δ (ppm) 7.75 (d, J=5.16, 2H), 7.53 (d, J=5.02, 2H), 7.24 (t, J=4.83, 2H)

[0066]

[0067] (2) 40 mL of glacial acetic acid was added to a 150 mL three-necked round-bottomed flask. After 30 min of high-purity nitrogen protection, compound 2 (0.3 g, 0.77 mmol) and activated ...

Embodiment 2

[0082] Synthesis of Compound T1-b

[0083]

[0084] The synthesis process of compound T1-b is basically the same as that of T1-a, except that the groups represented by R1 and R2 are different. The structural characterization of compound T1-b is as follows:

[0085] 1 H NMR (CDCl 3 , 400MHz): δ (ppm) 8.03 (d, J=5.32, 4H), 7.65 (t, J=5.09, 8H), 7.53 (t, J=5.07, 2H), 6.60 (d, J=4.39, 4H) ), 3.64 (m, 37H), 3.53 (t, J=2.35, 9H), 3.43 (q, J=2.29, 4H), 3.36 (s, 6H), 1.16 (J=0.77, 6H).

[0086] 13 C NMR (CDCl 3 , 100MHz): δ153.1, 149.1, 136.7, 135.4, 133.0, 131.8, 130.6, 128.9, 128.1, 127.7, 110.9, 72.1, 70.9, 70.8, 68.8, 59.2, 50.1, 45.7, 12.5.

[0087] HR-MS(ESI): m / z[M+H]+calculated for C 58 H 74 N 6 O 10 S, 1046.52; found, 1046.52731.

Embodiment 3

[0089] Preparation of water-insoluble photosensitizer nanoparticles:

[0090] 1 mg of compound T1-a and 1 mg of DSPE-PEG2000 in Example 1 were dissolved in 1 mL of tetrahydrofuran, and after sonicating for 30 min, they were added dropwise to 5 mL of stirred ultrapure water, and the solvent was removed by rotary evaporation after continuous stirring for 24 h. Tetrahydrofuran was filtered through an aqueous filter membrane with a pore size of 0.22 μm to remove oversized particles, and the preparation of nanoparticle T1-aNPs was completed. The 2100F TEM image of nanoparticle T1-a NPs is shown in figure 1 As shown, the size line in the picture is 50nm; the dynamic light scattering particle size distribution of its aqueous dispersion is as follows figure 2 As shown, the particle size of T1-a NPs is about 50 nm.

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Abstract

The invention discloses a photosensitizer based on a thiadiazolo [3, 4-g] quinoxaline structure, the photosensitizer has a strong absorption peak in a wavelength range of 450-750 nm and has efficient H < + > production performance under illumination, acid radicals have efficient H < + > abstraction performance in a dark state, a photoreaction and a dark reaction cooperate to kill tumors, and meanwhile, regeneration of a compound can be completed; and the tumor cell killing effect is not limited by the oxygen content. In addition, compounds included in the photosensitizer are simple in structure, small in molecular weight, high in modifiability, adjustable in performance and easy to prepare, purify and synthesize in batches. Therefore, the photosensitizer has a good application prospect in the aspect of preparing reversible acid tumor treatment drugs.

Description

technical field [0001] The present invention relates to the technical field of photosensitization treatment of tumors. More specifically, it relates to a photosensitizer based on thiadiazolo[3,4-g]quinoxaline structure and its synthesis method and application. Background technique [0002] Cancer has become the first major disease threatening human life. At present, the main clinical treatment methods include surgery, radiotherapy, chemotherapy and immunotherapy. As an emerging treatment modality with minimal invasiveness, high selectivity, and low toxicity, photosensitization therapy for tumors has received extensive attention in recent years. Photosensitization therapy is mainly divided into photodynamic therapy, photothermal therapy and photoacid therapy. Among them, photodynamic therapy has been successfully used to treat various surface, oral, and intracavitary tumors. However, due to the low content of oxygen, one of the three elements of photodynamics (light, oxyge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A61K41/00A61P35/00
CPCC07D513/04A61K41/0057A61P35/00Y02E10/542
Inventor 赵榆霞康琳张立鹏
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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