Photodynamically active platinum compound with near-infrared absorption, preparation method and application thereof

A technology of photodynamics and compounds, applied in the direction of organic active ingredients, chemical instruments and methods, compounds containing elements of group 8/9/10/18 of the periodic table, etc., can solve serious drug resistance, toxic and side effects and other problems , to achieve the effects of reducing toxic and side effects, good biocompatibility, and enhancing tumor targeting

Active Publication Date: 2017-11-28
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in clinical use, serious drug resistance and side effects have appeared (Rabik C.A., Dolan M.E., Molecular mechanisms of resistance and toxicity associated with platinating agents, Cancer Treat. Rev. 2007, 33, 9-23.)

Method used

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  • Photodynamically active platinum compound with near-infrared absorption, preparation method and application thereof
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  • Photodynamically active platinum compound with near-infrared absorption, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] (1) Preparation of fluoroborate dipyrrole derivatives: according to figure 1 As shown in the first step in the reaction equation, the fluoroboron dipyrrole derivative is prepared by a conventional method.

[0042] (2) Preparation of fluoroboron dipyrrole extended conjugate: according to figure 1 As shown in the second step in the reaction equation, weigh 130 mg of fluoroborate dipyrrole derivatives prepared in (1) and 147 mg of p-Hydroxybenzaldehyde dissolved in toluene with a volume ratio of 100-300 times, and add 1 ml of ice Acetic acid and 1 ml of piperidine were heated to reflux under nitrogen atmosphere for 20 hours, and then ice-bathed for 30 minutes. The resulting solid product was washed several times with toluene, and then spin-dried by a rotary evaporator to obtain a crude product. Then, the crude product was separated by silica gel chromatography, and the eluent was acetone-petroleum ether system to obtain the purified fluorobodipyrrole extended conjugate wi...

Embodiment 2

[0046] (1) Preparation of fluoroborate dipyrrole derivatives: according to figure 1 As shown in the first step in the reaction equation, the fluoroboron dipyrrole derivative is prepared by a conventional method.

[0047] (2) Preparation of fluoroboron dipyrrole extended conjugate: according to figure 1 Shown in the second step in the reaction equation, weigh 305 mg of the obtained fluoroborate dipyrrole derivatives prepared in (1) and 420 mg of p-Hydroxybenzaldehyde dissolved in toluene with a volume ratio of 100-300 times, and add 0.1 ml of ice Acetic acid and 1 ml of piperidine were heated to reflux under nitrogen atmosphere for 10 hours, and then ice-bathed for 60 minutes. The resulting solid product was washed several times with toluene, and then spin-dried by a rotary evaporator to obtain a crude product. Then, the crude product was separated by silica gel chromatography, and the eluent was acetone-petroleum ether system to obtain the purified fluorobodipyrrole extended ...

Embodiment 3

[0051] (1) Preparation of fluoroborate dipyrrole derivatives: according to figure 1 As shown in the first step in the reaction equation, the fluoroboron dipyrrole derivative is prepared by a conventional method.

[0052] (2) Preparation of fluoroboron dipyrrole extended conjugate: according to figure 1 As shown in the second step in the reaction equation, weigh 30 mg of the obtained fluoroborate dipyrrole derivative prepared in (1) and 47 mg of p-Hydroxybenzaldehyde dissolved in toluene with a volume ratio of 100-300 times, and add 0.5 ml of ice Acetic acid and 0.5 ml of piperidine were heated to reflux under nitrogen atmosphere for 10 hours, then ice-bathed for 40 minutes, and the resulting solid product was washed several times with toluene, and then spin-dried by a rotary evaporator to obtain a crude product. Then, the crude product was separated by silica gel chromatography, and the eluent was acetone-petroleum ether system to obtain the purified fluorobodipyrrole extende...

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Abstract

The invention relates to a photodynamically active platinum compound with near-infrared absorption, a preparation method and an application thereof. Structurally, this platinum compound has a large conjugated system and has strong absorption and emission in the near-infrared region. The combination of cisplatin molecular fragments and fluoroborate dipyrrole dye molecular fragments constructs a single molecular structure with dual therapeutic effects, that is, chemotherapy within a single molecule and photodynamic therapy in the near-infrared region. The present invention finds that the introduction of cisplatin molecular fragments significantly improves the singlet oxygen generation efficiency of fluoroboron dipyrrole dye molecules under near-infrared light irradiation through spectral means, and confirms its photodynamic therapy effect at the cell and animal levels. In addition, the combination of intramolecular photodynamic therapy and platinum-based chemotherapy greatly reduces the lethal dose of tumor cells, thereby effectively avoiding the disadvantages of traditional high-dose platinum-based drugs.

Description

technical field [0001] The invention relates to a platinum compound, a preparation method and its application, in particular to a platinum compound with near-infrared absorption and photodynamic activity, a preparation method and its application. Background technique [0002] Tumor is gradually threatening the quality of life of people all over the world, and it is the most difficult medical problem to be overcome in this century. In medicine, tumor detection techniques and treatment methods are improved to fight against the disasters that tumors bring to human beings. In clinical practice, the commonly used methods for tumor detection are mainly imaging technology and pathological technology, while the treatment methods are mainly surgical treatment. Chemotherapy, radiation therapy and emerging photodynamic therapy and photothermal therapy. However, a single diagnosis and treatment method is difficult to achieve the desired effect. Effective combination of multiple diagno...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K31/555A61K41/00A61K49/00A61P35/00
Inventor 郭正清陈华兵邹烨璘何慧饶佳明
Owner SUZHOU UNIV
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