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Ruthenium coordination compound with near-infrared fluorescence, preparation method and application thereof

A ruthenium complex, near-infrared technology, applied in the field of medicine, can solve the problems of large toxic and side effects, large surgical trauma, affecting the quality of life of patients, etc., and achieve the effect of great application prospects.

Active Publication Date: 2021-10-19
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, surgical treatment has disadvantages such as large trauma, limited scope of application, and inability to completely remove cancer cells; the biggest problem with chemotherapy and radiotherapy is that it produces relatively large toxic and side effects, which affects the quality of life of patients

Method used

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  • Ruthenium coordination compound with near-infrared fluorescence, preparation method and application thereof
  • Ruthenium coordination compound with near-infrared fluorescence, preparation method and application thereof
  • Ruthenium coordination compound with near-infrared fluorescence, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The structural formula of the ruthenium complex with near-infrared fluorescence is as follows figure 1 shown. Its synthesis method is as follows:

[0047] S1. Formation of bnp ligand by reaction of 2,6-diacetylpyridine with 2-amino-3-pyridinecarbaldehyde

[0048] 2,6-diacetylpyridine (1.6317g, 10mmol) and 2-amino-3-pyridinecarbaldehyde (2.4426g, 20mmol) and sodium hydroxide (0.4g, 10mmol) were heated to 95°C in ethanol (100ml), After 12 hours of reflux reaction, the reaction was cooled to room temperature and the solid was filtered out. The filtered solid was washed with ethanol and dried in vacuum to obtain 3.2886 g of yellow solid bnp with a yield of 98.06%. The above chemical reaction equation is as follows:

[0049]

[0050] Mass spectrum: 336.2, [M+H] + ,358.2,[M+Na] + ;

[0051] H NMR spectrum: 1 H NMR (400MHz, CDCl 3 ):δ9.19(s,2H),9.01(d,J=8.4Hz,4H),8.40(d,J=8.5Hz,2H),8.28(d,J=7.6Hz,2H),8.13(s ,1H), 7.55(s,2H).

[0052] S2. Reaction of 2-acetylpyridi...

Embodiment 2

[0066] Dark stability and photostability of the near-infrared fluorescent ruthenium complex obtained in Example 1

[0067] The dark stability and photostability properties of ruthenium complexes were analyzed by H NMR spectroscopy. The ruthenium complex is made into a solution (control sample) with dimethyl sulfoxide-d6 and added to the NMR tube to record its proton NMR spectrum; after that, it is placed in the dark at room temperature for 72 hours, or 465nm light radiation (39mW / cm 2 ) After 5 minutes, record the H NMR spectrum of the solution after the light and dark treatment and contrast the H NMR spectrum of the control sample to analyze its dark and photostability properties. Such as figure 2 As shown, the spectrum of the ruthenium complex does not change significantly under the conditions of dark and light treatment, and it can be seen that the ruthenium complex has good dark stability and light stability.

Embodiment 3

[0069] Absorbance and fluorescence intensity measurements of the near-infrared fluorescent ruthenium complex obtained in Example 1 in different solvents

[0070] 1. Absorbance of ruthenium complexes in different solvents

[0071] Using dichloromethane, ethyl acetate, acetonitrile, N,N-dimethylformamide, methanol, ethylene glycol, dimethyl sulfoxide, and water as solvents, the metal ruthenium complex was formulated into a 10 μM sample solution, using A double-beam UV-Vis spectrophotometer records the UV absorption spectrum of the ruthenium complex, such as image 3 Shown represents its absorbance in different solvents. It can be seen from the figure that due to the introduction of the bnp ligand, the compound of the present invention exhibits good optical properties, and the absorption peak of the metal ruthenium complex is red-shifted in the visible light region compared with most existing ruthenium complexes.

[0072] 2. Fluorescence intensity of ruthenium complexes in diff...

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Abstract

The invention relates to the technical field of medicine, in particular to a ruthenium coordination compound with near-infrared fluorescence, a preparation method and application thereof. After a chromophore-pyrene is introduced, the coordination compound has obvious phototoxicity (IC50 = 0.040 [mu]M) and small dark toxicity (IC50 = 9.402 [mu]M) when applied to cervical cancer (HeLa cells) under the irradiation of 635 nm red light, the photodynamic therapy index (PI) is 235.05, and the photodynamic therapy has a remarkable curative effect. The ruthenium metal coordination compound can generate singlet oxygen under the irradiation of a 635 nm light source, and can photocatalytically oxidize NADH and NADPH. According to the invention, the ruthenium coordination compound has important significance for promoting the research of a high-efficiency novel anti-tumor ruthenium metal coordination compound photosensitizer, can be further used for preparing anti-tumor drugs, and has a relatively great application prospect.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a ruthenium complex with near-infrared fluorescence and a preparation method and application thereof. Background technique [0002] According to GLOBOCAN 2020 statistics, the morbidity and mortality of malignant tumors are rising rapidly all over the world. This is not only related to the aging of the population, social development, industrialization, and urbanization, but also reflects the continuous growth of carcinogenic factors such as the deterioration of the ecological environment. As far as the current situation is concerned, the high incidence of cancer is inevitable. As a country with a population of 1.4 billion, China's new cancer cases account for 23.7% of the world's new cases, about 4.57 million people, and cancer deaths account for 30% of the world's total, about 3 million deaths. The morbidity and mortality are higher than Compared with the global average, China ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06A61K41/00A61P35/00
CPCC07F15/0053C09K11/06A61K41/0057A61P35/00C09K2211/185C09K2211/1029C09K2211/1044C09K2211/1011
Inventor 黄怀义谢宇珍魏思琪卢培莹赖怡敏江颖何赛
Owner SUN YAT SEN UNIV
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