A type I hemicyanine photosensitizer, a type I targeted photosensitizer, and preparation methods and applications thereof

By preparing an activatable type I targeted photosensitizer and using alkaline phosphatase to enrich it in the tumor area, the problems of type I photosensitizer's high oxygen dependence and severe damage to normal cells in the treatment of hypoxic tumors were solved, achieving precise imaging and efficient treatment of tumors.

CN116730992BActive Publication Date: 2025-09-16SUZHOU UNIV
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Patent Information

Application Number
CN202310742723.8
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-06-21
Publication Date
2025-09-16
Estimated Expiration
2043-06-21

AI Technical Summary

Technical Problem

Existing type I photosensitizers have the problems of high dependence on oxygen and severe damage to normal cells in the treatment of hypoxic tumors, and lack of specificity, resulting in poor treatment effects and obvious side effects.

Method used

A type I hemicyanine photosensitizer was designed and an activatable type I targeted photosensitizer was prepared by reacting with phosphorus oxychloride. It can be enriched in the tumor area under the action of alkaline phosphatase and produce O2·-, realizing precise tumor imaging and treatment.

Benefits of technology

This photosensitizer can efficiently produce O2·- under hypoxic conditions, reducing toxicity to normal cells and improving the specificity and effectiveness of tumor treatment. It also has ultra-sensitivity through alkaline phosphatase response and a low detection limit, and in vivo experiments have shown excellent anti-tumor effects.

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Abstract

The present invention discloses a type I semi-cyanine photosensitizer, a type I targeted photosensitizer, and a preparation method and application thereof. The semi-cyanine photosensitizer can rapidly generate a large amount of O2 under light and hypoxic conditions. ·‑ , thereby achieving the effect of photodynamic therapy, and having good biocompatibility and biodegradability, it is an effective type I photosensitizer. In addition, the above-mentioned type I photosensitizer is reacted with phosphorus oxychloride in the presence of water to prepare a type I photosensitizer with tumor targeting. It can specifically target alkaline phosphatase, a biomarker highly expressed in tumors. Under the action of alkaline phosphatase, the photosensitizer can be enriched in the tumor area, thereby achieving precise tumor imaging and photodynamic therapy, which can effectively reduce the side effects of the photosensitizer and improve the inhibitory effect of the photosensitizer on tumors.
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Claims

1. A type I hemicyanine photosensitizer, characterized in that The type I hemicyanine photosensitizer is a compound represented by the following formula (I) or formula (II): 、 ， Where R is I.

2. Use of the type I hemicyanine photosensitizer according to claim 1 in the preparation of photodynamic therapy drugs.

3. A type I targeted photosensitizer, characterized in that: The type I targeted photosensitizer is a compound represented by the following formula (III) or formula (IV): 、 ， Among them, R is I, R 1 It is -P(O)(OH)2.

4. The type I targeted photosensitizer according to claim 3, characterized in that The type I targeted photosensitizer targets alkaline phosphatase.

5. A method for preparing the type I targeted photosensitizer according to claim 3 or 4, characterized in that: The type I hemicyanine photosensitizer represented by formula (I) or formula (II) described in claim 1 is reacted with phosphorus oxychloride in an aqueous solvent under stirring to obtain the type I targeting photosensitizer.

6. The preparation method according to claim 5, characterized in that The molar ratio of the type I hemicyanine photosensitizer to phosphorus oxychloride is 1:2-5.

7. The preparation method according to claim 5, characterized in that The stirring reaction temperature is -10~30°C, and the stirring reaction time is 10~20 hours.

8. Use of the type I targeted photosensitizer according to claim 3 or 4 in the preparation of photodynamic therapy drugs.

9. Use of the type I targeted photosensitizer according to claim 3 or 4 in the preparation of a liver tumor imaging drug.

Citation Information

Patent Citations

  • Preparation method and application of near-infrared alkaline phosphatase fluorescence probe

    CN106753341A

  • Near-infrared hemicyanine-based fluorescent probe for detecting butyrylcholinesterase, preparation method and applications thereof

    CN108192597A

  • I-type photosensitizer as well as preparation method and application thereof

    CN116621819A

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