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Novel phosphorescent ruthenium compound as well as preparation method and application thereof

A ruthenium complex, a new technology, applied in the field of phosphorescent ruthenium complexes and its preparation, can solve the problems of aggravating hypoxic state, limiting therapeutic effect, insufficient oxygen supply, etc., and achieve the effect of guaranteed effect, simple process and abundant raw materials

Active Publication Date: 2018-12-18
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to rapid tumor growth and insufficient oxygen supply, the native microenvironment of solid tumors is a hypoxic environment
In addition, the rapid amount of oxygen consumption during PDT, which will further aggravate the hypoxic state and limit the therapeutic effect, has become the main obstacle of PDT

Method used

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  • Novel phosphorescent ruthenium compound as well as preparation method and application thereof
  • Novel phosphorescent ruthenium compound as well as preparation method and application thereof
  • Novel phosphorescent ruthenium compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Preparation of auxiliary ligand

[0030]

[0031] Preparation of Compound 2: Compound 1 (180mg, 1mmol) and iodine oxide 41mg (1.3mmol) were stirred at room temperature, then 2.5mL of acetic acid was added, heated to reflux for 3h to obtain a purple-black solution, cooled to room temperature, added to deionized water to settle, room temperature Stand overnight, vacuum filter to obtain a yellow solid, then dissolve into chloroform to obtain a dark red solution, and then wash with saturated NaHCO 3 and saturated Na 2 S 2 o 3 Washed, the organic phase was dried with anhydrous sodium sulfate, and finally rotary evaporated to obtain dark brown solid compound 2, yield: 93%.

[0032] 1 H NMR (400MHz, CDCl 3 )8.89(dd, J=2Hz,1.6Hz,1H),8.69(dd,J=0.8Hz,0.4Hz,1H),8.41(dd,J=2Hz,2Hz,1H),8.20(dd,J=1.2 Hz,0.8Hz,1H), 7.83-7.78(m,1H),7.59(dt,J=1.2Hz,8.8Hz,1H),7.43(dd,J=4.8Hz,4.8Hz, 1H).

[0033] Preparation of Compound 4: Compound 2 (833mg, 0.8mmol), ammonium aceta...

Embodiment 2

[0037] Embodiment 2: the preparation of Ru1, Ru2 and Ru3

[0038]

[0039] Preparation of Compound Ru1: Compound 5 (100 mg), Compound 4 (92 mg), 1 mL of triethylamine, stirred with 3 mL of ethylene glycol at room temperature, reacted at 120 °C in the dark for 24 h, cooled to room temperature, added potassium hexafluorophosphate solution and stirred for 2 h After that, ethylene glycol and triethylamine were distilled off under reduced pressure, settled with ethyl acetate, purified by column chromatography, the polarity was dichloromethane: acetonitrile ratio of 10:1, and then recrystallized three times with dichloromethane and ether to obtain the complex Ru1, 26% yield.

[0040] 1 H NMR (400MHz, (CD 3 ) 2 SO)8.77(d,J=8Hz,1H),8.70-8.61(m,4H),8.58(d,J=8Hz,1H),8.15-8.09(m,3H),7.96-7.94(m,1H) ,7.92-7.90(m,1H),7.87-7.78(m,6H),7.74(dd,J=1.2Hz,5.2Hz,1H),7.61-7.58(m,1H),7.45(dd,J=2.6 Hz, 8.4Hz,1H),7.42-7.39(m,1H),7.37-7.33(m,4H),7.29-7.24(m,1H),7.22-7.18(m, 3H),7.12-7.09(m, 8H...

Embodiment 3

[0045] Embodiment 3: the ultraviolet-visible absorption spectrum test of Ru1, Ru2 and Ru3

[0046] The spectrum test concentration adopted in the present invention is 10 μM, and the test solvent is methanol solution.

[0047] Absorption spectra of Ru1, Ru2 and Ru3 as figure 1 As shown, 240-325nm is the ππ* transition centered on the N^N ligand, 325-425nm is the ππ* transition centered on the C^N ligand, and 425-650nm is the charge of the Ru center and the N^N ligand transfer (MLCT) transition.

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PUM

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Abstract

The invention discloses a novel phosphorescent ruthenium compound as well as a preparation method and application thereof. The compound is prepared from polypyridine ligands, metal centers and auxiliary ligands containing donor functional groups. The donor groups in the compound have high electron donating capability, low oxidization potential, high reduction performance and strong electron loss cavity; C^N ligands for electron ring metalation improves the dp(Ru) orbital energy; the electron transfer capability is obviously improved. The biological toxicity of the synthesized ruthenium compound is low; the ruthenium compound can be used for type I photodynamic treatment in anaerobiousanoxia environment; the photodynamic treatment effect is improved; important application prospects are realized in an aspect of the photodynamic treatment. In addition, the synthesis method of the compound is simple; the synthesis conditions are mild; the compound is suitable for being used for mass production.

Description

technical field [0001] The invention belongs to the technical fields of organic photoelectricity and biomaterials. In particular, it relates to a kind of phosphorescent ruthenium complex with type I photodynamic therapy effect and its preparation method and application. Background technique [0002] Photodynamic therapy (PDT) is a safe and effective non-invasive treatment method developed in recent years. This method has little tissue damage, no obvious and long-term adverse reactions, and it is easy to operate, economical and easy to accept for most patients. . [0003] During the process of PDT chemical reaction, the photosensitizer that absorbs light of a specific wavelength can be excited from the ground state to a singlet state with a very short lifetime, and the singlet state can release energy by radiating fluorescence to return to the ground state. Or through the intersystem transition to the triplet state. Due to the longer lifetime of triplet excitons, the inter...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06A61K41/00G01N21/64
CPCA61K41/0057C07F15/0046C09K11/06C09K2211/185G01N21/6486
Inventor 刘淑娟赵强刘雪谢明娟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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