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Photodynamic/photothermal difunctional compound NS-STPA and application thereof

A photodynamic and compound technology, applied in the field of tumor treatment, can solve the problem of short absorption wavelength

Active Publication Date: 2021-09-10
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently used PS, such as porphyrins, chloroprene derivatives, and phthalocyanine derivatives, can only be excited by UV-visible light due to their short absorption wavelength, and the strong absorption of UV-visible light by biological tissues severely limits PDT. Effects on Deep Tumors
In addition to this, most photosensitizers do not possess both PDT and PTT therapeutic potential due to inherent structural properties

Method used

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  • Photodynamic/photothermal difunctional compound NS-STPA and application thereof
  • Photodynamic/photothermal difunctional compound NS-STPA and application thereof
  • Photodynamic/photothermal difunctional compound NS-STPA and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of compound NS-STPA

[0032] Synthesis of Intermediate 1: 2-Methyl-β-naphthothiazole (1.993 g, 0.010 mol) and 1,3-propane sultone (12.214 g, 0.100 mol) were dissolved in o-dichlorobenzene (4 mL) , protected by nitrogen, heated to 135°C, reacted for 6 hours, a beige solid precipitated, filtered while hot; then the filter cake was washed 3 times with acetone, and dried in vacuum to obtain intermediate NS.

[0033] Synthesis of intermediate 2: 5-formyl-2-thiophene boronic acid (1.55g 0.01mol), 4-bromotriphenylamine (3.88g, 0.012mol), anhydrous potassium carbonate (3.45g, 0.025mol) and tetra( Triphenylphosphine)palladium (0.347g, 0.3mmol) was dissolved in 30mLTHF / H 2 O (volume ratio 9:1), under nitrogen protection, the temperature was raised to 80° C., and the reaction was carried out for 18 hours. After completion of the reaction, add dichloromethane (20mL) and extract three times with 10mL water, add anhydrous MgSO 4 The organic phase was dried and spin-dried...

Embodiment 2

[0040] Synthesis conditions of compound NS-STPA Explore the synthesis conditions of intermediate 1. The reaction solvent is ethanol or other conventional statistics. Other reaction conditions are the same as in Example 1. Through the reaction process tracking, it is confirmed that the reaction is difficult to carry out, and it is confirmed that the reaction requires the solvent type to be non- Protic solvent, and the reaction temperature should be higher than 100 degrees Celsius.

[0041] No catalyst is added in the synthetic condition of intermediate 2, other conditions are identical with embodiment 1, confirm that reaction efficiency is low, intermediate 2 productive rate is low, therefore catalyst tetrakis (triphenylphosphine) palladium is necessary in this reaction, at zero Palladium catalyzed and suzuki coupling reaction under alkaline conditions for C-C coupling to generate the intermediate aldehyde STPA.

[0042] In the synthetic reaction of product NS-STPA, do not add ...

Embodiment 3

[0044] Optical Behavior of Compound NS-STPA

[0045] The NS-STPA test solution with a concentration of 10.0 μM and a volume of 2 mL was prepared with solvents of different polarities. Test its ultraviolet absorption spectrum and fluorescence emission spectrum respectively, the result is as follows Figure 4 , Figure 5 shown. The test results show that NS-STPA has a wide range of light absorption, reaching 400-700nm, and the absorption wavelength and intensity are different in different solvents; when excited by 560nm light, NS-STPA emits fluorescence in the spectral range of 600-900nm. The luminescence is obvious in medium grade solvents such as oxygen hexane (DIOX), but in water (H 2 O) and other polar solvents have weak luminescence, which belongs to solvation quenching. From the analysis of its spectral behavior, it can absorb light in the visible-infrared region. After reaching the excited state, the emitted light is very weak, that is, the energy dissipation is not m...

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Abstract

The invention provides a photodynamic / photo-thermal bifunctional compound NS-STPA. The compound is of a conjugated structure formed by connecting naphthothiazole inner salt with triphenylamine through a thiophene group, and the structure has photodynamic and photo-thermal activity, has photodynamic / photo-thermal synergistic treatment potential, and can be applied to tumor treatment. The synthesis method of the compound comprises the following steps of: synthesizing an intermediate 1 from 2-methyl-beta-naphthothiazole and 1, 3-propane sultone as raw materials under the condition of o-dichlorobenzene; and synthesizing an intermediate 2 from 5-formyl-2-thiopheneboronic acid and 4-bromotriphenylamine as raw materials under the condition of THF / H2O (reflux), and refluxing in ethanol to obtain the product NS-STPA. The invention further discloses application of the photodynamic / photothermal bifunctional compound NS-STPA as a catalyst in degradation of 9, 10-anthryl-bis (methylene) dimalonic acid. Under irradiation of 660 nm red light, singlet oxygen with cytotoxicity can be generated, a stable photothermal effect can also be generated, and excellent tumor efficient light treatment potential is shown.

Description

technical field [0001] The invention relates to the preparation and basic properties of an organic compound NS-STPA with photodynamic / photothermal therapeutic potential, and belongs to the field of tumor treatment. Background technique [0002] At present, surgery, radiotherapy and chemotherapy are the routine methods of cancer treatment. However, such treatment methods often have problems such as high operational difficulty, easy to cause complications, low bioavailability of anti-tumor drugs and serious side effects. In recent years, phototherapy is becoming an effective method for the clinical treatment of cancer due to its non-invasive, fast-response, and highly sensitive properties. Phototherapy mainly involves photodynamic therapy (PDT) and photothermal therapy (PTT). PDT usually refers to a non-toxic sensitizer (PS) that is excited by a light source and reaches the triplet state through the intersystem crossing (ISC) process, and converts the surrounding Triple-line ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06A61K41/00A61P35/00
CPCC07D417/06A61K41/0057A61K41/0052A61P35/00
Inventor 杨昌英王逸飞范於菟王慧敏陆爽刘含孙玉东
Owner CHINA THREE GORGES UNIV