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

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

Example Embodiment

[0029] Example 1: Preparation of auxiliary ligand

[0030]

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

[0032] 1 H NMR(400MHz, CDCl 3 ) 8.89 (dd, J = 2Hz, 1.6 Hz, 1H), 8.69 (dd, J = 0.8 Hz, 0.4 Hz, 1H), 8.41 (dd, J = 2 Hz, 2 Hz, 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: compo...

Example Embodiment

[0037] Example 2: Preparation of Ru1, Ru2 and Ru3

[0038]

[0039] Preparation of compound Ru1: compound 5 (100mg), compound 4 (92mg), 1mL of triethylamine, stirred with 3mL of ethylene glycol at room temperature, reacted at 120℃ in the dark for 24h, cooled to room temperature, added potassium hexafluorophosphate solution and stirred for 2h After removing the ethylene glycol and triethylamine by distillation under reduced pressure, sedimentation with ethyl acetate, purification by column chromatography, the polarity is dichloromethane: acetonitrile 10:1, and then recrystallized with dichloromethane and ether three times to obtain the complex Ru1, the yield is 26%.

[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). 13...

Example Embodiment

[0045] Example 3: UV-Vis absorption spectrum test of Ru1, Ru2 and Ru3

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

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

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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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