Novel photosensitizer as well as preparation method and application thereof

A photosensitizer, a new type of technology, applied in the field of photosensitizers, can solve problems such as high oxygen dependence, and achieve the effect of outstanding universality and high-efficiency treatment

Pending Publication Date: 2022-04-12
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the above-mentioned technical problems, the present invention provides a novel photosensitizer and its preparation method and application, so as

Method used

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  • Novel photosensitizer as well as preparation method and application thereof
  • Novel photosensitizer as well as preparation method and application thereof
  • Novel photosensitizer as well as preparation method and application thereof

Examples

Experimental program
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Example Embodiment

[0044] Example 1

[0045]

[0046] (1) Synthesis of Compound I

[0047]D-biotin (300 mg, 1.23 mmol) of 10 ml of methanol suspension was added to sulfoxide (0.3 mL, 4.0 mmol), stirred at room temperature overnight until the reaction liquid clarified and transparent. The white solid was obtained under reduced pressure. It was dispersed into 10 mL of methanol and slowly dripped the hydrated sac (0.48 mL, 10 mmol) while stirring, heated to 70 ° C, and the reaction was 12 h. Cooled to room temperature, distilled under reduced pressure, poured into a large amount of ice-cold methanol, filtered, washed three times with methanol to give a white powder-shaped compound I.

[0048] (2) Compound IIIA synthesis

[0049] In a nitrogen atmosphere, Compound IIA (DCF-TFM, 20.4 mg, 0.025 mmol) was dissolved in 5 mL anhydrous DMF, 0 ° C, add 1- (3-dimethylaminopropyl) -3-ethyl carbon two Asia Amine hydrochloride (EDCI) (24 mg, 0.125 mmol), 1-hydroxybenzene triazole (HOBT) (17 mg, 0.125 mmol) and N...

Example Embodiment

[0050] Example 2

[0051]

[0052] (1) Synthesis of Compound I as in Example 1.

[0053] (2) Synthesis of Compound IIIB

[0054] In a nitrogen atmosphere, compound IIB (Fl, 50 mg, 0.065 mmol) was dissolved in 5 ml of anhydrous DMF, and 1- (3-dimethylaminopropyl) -3-ethyl carbide hydrochloric acid was added at 0 ° C. Salt (EDCI) (62.8 mg, 0.33 mmol), 1-hydroxybenzene triazole (HOBT) (44 mg, 0.33 mmol) and N, N-diisopropylidelamine (DIEA) (32 μL, 0.2 mmol) reaction 2H After the addition, Compound I (33.5 mg, 0.13 mmol) was added, and stirred at room temperature for 24 h. Decompression distillation was purified by column chromatography (methanol / dichloromethane = 1 / 8) to obtain a photosensitizer compound IIIb. The high distortion of the compound IIIb and the nuclear magnetic resonance spectrometry table show respectively image 3 and Figure 4 Indicated.

Example Embodiment

[0055] Example 3

[0056]

[0057] (1) Synthesis of Compound I as in Example 1.

[0058] (2) Synthesis of Compound IIIC

[0059] In a nitrogen atmosphere, Compound IIC (PPIX, 30 mg, 0.053 mmol) was dissolved in 3 ml anhydrous DMF, and 1- (3-dimethylaminopropyl) -3-ethyl carbide hydrochloric acid was added at 0 ° C. Salt (EDCI) (10.56 mg, 0.053 mmol), 1-hydroxybenzene triazole (HOBT) (7.43 mg, 0.053 mmol) and N, N-diisopropylamine (DIEA) (8.75 μL, 0.053 mmol) After 2 h, Compound I (15.3 mg, 0.05 mmol) was added, and stirred at room temperature for 24 h. Decapression was purified, and the photosensitizer compound was obtained after purification using column chromatography (methanol / dichloromethane = 1 / 8). The high distortion mass spectrometry of Compound IIIC and the nuclear magnetic resonance spectrum pattern are shown. Figure 5 and Image 6 Indicated.

[0060] Figure 7 For the absorption of photosensitizer compound IIIA and compound IIA in ethanol, Figure 8 For the absorption ...

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Abstract

The invention discloses a novel photosensitizer and a preparation method and application thereof, and the preparation method comprises the following steps: adding thionyl chloride into a methanol suspension of D-biotin, stirring overnight at room temperature until a reaction solution is clear and transparent, and carrying out reduced pressure distillation to obtain a white solid; dispersing into methanol, slowly dropwise adding hydrazine hydrate while stirring, heating, and reacting for 10-18 hours; cooling to room temperature, carrying out reduced pressure distillation, pouring methanol, carrying out suction filtration, and washing with methanol for several times to obtain a white powdery compound I; the preparation method comprises the following steps: dissolving a photosensitizer compound II with carboxyl at a terminal in anhydrous DMF in a nitrogen atmosphere, adding EDCI, HOBt and DIEA at 0 DEG C, reacting for 2 hours, adding a compound I, and stirring at room temperature for 24 hours; and performing reduced pressure distillation and purification to obtain a compound III. The novel photosensitizer prepared by the invention can solve the problem of high dependence on oxygen in photodynamic therapy, and has a good treatment effect in both normal oxygen and hypoxic states.

Description

technical field [0001] The invention relates to the technical field of photosensitizers, in particular to a novel photosensitizer and its preparation method and application. Background technique [0002] Malignant tumors have become a major threat to human life and health today. How to effectively diagnose and treat cancer is a hot topic that relevant scholars have been working on. Photodynamic therapy (Photodynamic Therapy, PDT), as a new type of non-invasive treatment method, has the advantages of tumor targeting, low dark toxicity, short treatment time and high reproducibility. [0003] Photosensitizers (Photosensitizers, PS) can convert light energy into reactive oxygen species (ROS) to induce apoptosis and tissue damage. According to different photochemical reaction processes, there are two main types of PDT: type I PDT and type II PDT. Among them, the latter is the dominant mechanism of most photosensitizers at present. However, based on the generated 1 o 2 The ty...

Claims

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Application Information

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IPC IPC(8): A61K47/54A61K41/00A61P35/00
Inventor 宋锋玲
Owner SHANDONG UNIV
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