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Application of a water-soluble porphyrin in the preparation of photodynamic therapy drugs

A water-soluble, porphyrin technology, applied in the application field of water-soluble porphyrin in the preparation of photodynamic therapy drugs, can solve the problems such as being unsuitable for wide popularization and expensive

Inactive Publication Date: 2019-06-25
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, at present, the detection of G-quadruplex is mainly done by instruments, such as circular dichroism, nuclear magnetic resonance and other methods, which have high requirements for instruments, operation level, skills, etc., are expensive, and are not suitable for widespread use.

Method used

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  • Application of a water-soluble porphyrin in the preparation of photodynamic therapy drugs
  • Application of a water-soluble porphyrin in the preparation of photodynamic therapy drugs
  • Application of a water-soluble porphyrin in the preparation of photodynamic therapy drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) G-quadruplex photocleavage.

[0029] (A) Sample preparation under simulated physiological conditions: 5 μL of 100 μM G-quadruplex (Hum51, ordered by Sangon), 8 μL of 250 mM Tris- HCl (pH=7.4) buffer solution, 10 μL of 1M KCl solution, and ultrapure water were used so that the concentration of Hum51 was 5 μM, the concentration of Tris-HCl buffer solution was 20 mM, and the concentration of KCl was 100 mM. Shake and shake the centrifuge tube well, centrifuge the solution to the bottom, place it in a PCR-type gene amplification thermocycler at 95°C for 5 minutes, and cool down.

[0030] (B) Contrast between light and dark conditions:

[0031] Add 40 μL of ultrapure water into the centrifuge tube numbered 1, shake, shake well, centrifuge and place in the dark at 25°C for 2 hours;

[0032] Add 40 μL of ultrapure water into the centrifuge tube numbered 2, oscillate, shake well, and centrifuge, then irradiate with sunlight at 25°C for 2 hours;

[0033] Add 40 μL of 100 ...

Embodiment 2

[0057] A kind of preparation of water-soluble porphyrin (I):

[0058] The chemical name of the water-soluble porphyrin (I) is: 5,10,15,20-tetrakis{4-[2-(1-methyl-1-piperidine)ethoxy]phenyl}porphyrin tetraiodide. (referred to as TMPipEOPP)

[0059] (The preparation of this embodiment is to enable those skilled in the art to understand the present invention better, but does not make any limitation to the present invention, the water-soluble porphyrin (I) that other synthetic methods obtain, all can be used in the present invention )

[0060] (1) Synthesis of four (p-hydroxyporphyrin) (II)

[0061] Add 100mM p-hydroxybenzaldehyde and 120mL propionic acid into a four-neck flask, stir, add pyrrole 100mM dropwise under reflux (127°C-132°C), drop it in 15min, and reflux for 120min. Pour it into a beaker while it was hot, stir and cool to room temperature, filter with suction, wash the filter cake with propionic acid, and dry in vacuo to obtain a blue-purple crude product, which wa...

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Abstract

The invention discloses application of water-soluble porphyrin in preparing photodynamic therapy medicine. The chemical name of water-soluble porphyrin is tetraiodide 5, 10, 15, 20-tetra {4-[2-(1-methyl-1-piperidine)ethyoxyl][phenyl}porphyrin, water-soluble porphyrin (I) has quite strong recognition effect on G-quadruplex and is high in targeting performance when being applied in photodynamic therapy. TMPipEOPP almost has no cutting activity to G-quadruplex in darkness but presents quite high photosensitive cutting activity to G-quadruplex under light by generating 1O2 and .OH. This shows that TMPipEOPP can serve as a PDT photosensitizer of G-quadruplex under physiological conditions. In addition, cytotoxicity experiments show that TMPipEOOP almost has no dark toxicity or is extremely low in dark toxicity but has quite high photoinduced cytotoxicity, and this also shows that TMPipEOOP is a PDT photosensitizer with quite low dark toxicity.

Description

technical field [0001] The invention belongs to the fields of photodynamic therapy, chemical analysis and biochemistry, and in particular relates to the application of a water-soluble porphyrin in the preparation of photodynamic therapy drugs. Background technique [0002] At present, in the treatment of cancer, traditional methods such as radiotherapy and chemotherapy have some disadvantages. In the course of treatment, it not only kills cancerous tissues and cells, but also causes serious side effects due to loss of function of normal organs, and long-term drug use can lead to multi-drug and drug resistance of tumors. Photodynamic therapy, however, is promising because it selectively destroys malignant cells (produces therapeutic effects only in the illuminated areas) without harming normal tissues. References can be found such as J.P.Celli, Chem.Rev.2010, 110, 2795-2838; A.P.Castano, Nat.Rev.Cancer, 2006, 6, 535-545; L.Benov, Med.Princ.Pract.2015, 24 (suppl 1 ), 14-28. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K41/00A61P35/00
CPCA61K41/0071
Inventor 朱莉娜石珊
Owner TIANJIN UNIV
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