Fullerene polyaza ligand transition metal complex for magnetic resonance imaging and photodynamic therapy, preparation method, use and product

A technology of transition metal and fullerene derivatives, which can be used in photodynamic therapy, preparations for in vivo tests, and medical preparations with inactive ingredients, etc., which can solve the problems of poor magnetic resonance imaging effect and low relaxation rate. problem, to achieve high-efficiency magnetic resonance effect, strong phototoxicity, and the effect of reducing oxidative damage

Active Publication Date: 2020-08-07
BEIJING FUNAKANG BIOTECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the problems of low relaxation rate and poor magnetic resonance imaging effect when the existing fullerene materials are used for magnetic resonance imaging, the present invention provides a fullerene polyaza ligand transition metal complex, and provides The preparation method, application and related products of fullerene polyaza ligand transition metal complexes are disclosed, and the specific adopted scheme is as follows

Method used

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  • Fullerene polyaza ligand transition metal complex for magnetic resonance imaging and photodynamic therapy, preparation method, use and product
  • Fullerene polyaza ligand transition metal complex for magnetic resonance imaging and photodynamic therapy, preparation method, use and product
  • Fullerene polyaza ligand transition metal complex for magnetic resonance imaging and photodynamic therapy, preparation method, use and product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] When F (Fullerene) is C 70 [C(COOH) 2 ] 3 , M is gadolinium (Gd), when n=122, the preparation method of the fullerene polyaza ligand transition metal complex of formula 1-1 comprises:

[0058] (1) 0.12 millimolar of Boc-NH-PEG(2000)-COOH (purchased from Shanghai Yanyi Biotechnology Co., Ltd.), 0.15 millimolar of 2-(7-benzotriazole oxide)-N,N , N', N'-tetramethyluronium hexafluorophosphate (purchased from Alfa; as amidation reaction catalyst), 0.4 millimolar N, N-diisopropylethylamine (purchased from Enoch; as bound Acid agent) was dissolved in 15 ml of N,N-dimethylformamide solvent (purchased from Bailingwei; as an acid-binding agent), protected under argon atmosphere, stirred at 0°C for 30 minutes, and then added 0.1 mmol of 1, 4,7,10-tetraazacyclododecane-1,4,7-tri-tert-butyl triacetate (purchased from Alfa), stirred at room temperature for 24 hours, precipitated in anhydrous ether under ice bath conditions, dried in vacuo , to obtain the compound shown in formula...

Embodiment 2

[0068] The magnetic resonance performance test of the fullerene polyaza ligand transition metal complex obtained in Example 1, the steps and results are as follows:

[0069] (1) Prepare the aqueous solution (a) of the fullerene multi-aza ligand transition metal complex obtained in Example 1 with different concentrations as follows and the fullerene multi-aza ligand transition metal obtained in Example 1 with different concentrations as follows The physiological saline solution (b) of the complex is placed under a magnetic field strength of 0.5T, and the T 1 Its relaxation rate is calculated, and magnetic resonance imaging images are taken. Among them, T 1 is the longitudinal relaxation time, at the same concentration, T 1 The lower the value, the higher the relaxation rate and the better the MRI.

[0070] The aqueous solution (a) (Gd element concentration: 0.0132, 0.0264, 0.0528, 0.1056, 0.2112 mmol / liter) of the fullerene polyaza ligand transition metal complex obtained in...

Embodiment 4

[0077] Dark toxicity test is carried out to the fullerene polyaza ligand transition metal complex obtained in Example 1, the steps and results are as follows:

[0078] (1) Resuscitate A549 cells (Cell Resource Center, Shanghai Institute of Biology, Chinese Academy of Sciences), and adjust the cell density to 5×10 when the cells enter the logarithmic phase and grow stably. 4 / ml, seeded into 96-well plate, 37°C, 5% CO 2 , incubated for 24 hours;

[0079] (2) After the cells adhere to the wall, replace the DMEM solution (Corning R10-013-CV, purchasing company: Baierdi) with 200 microliters containing C 70 [C(COOH) 2 ] 3 The DMEM solution of the fullerene polyazaligand transition metal complex obtained in Example 1 with effective concentrations of 0, 3.6, 10.8, 18.0, 25.2, and 36.0 micromole / liter respectively, at 37° C., 5% CO 2 , incubated for 24 hours;

[0080] (3) Discard the DMEM solution containing the fullerene polyazaligand transition metal complex obtained in Exampl...

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Abstract

The present invention discloses a fullerene polyaza ligand transition metal complexe for magnetic resonance imaging and photodynamic therapy, a preparation method, application and products. The fullerene polyaza ligand transition metal complex in the present invention is obtained according to the following steps: performing a reaction by taking Boc-NH-PEG-COOH and tri-t-butyl-1,4,7,10-tetraazacyclododeca as raw materials, removing the Boc group in the obtained intermediate, then complexing the treated intermediate and a transition metal compound, and then reacting the obtained complex with a fullerene derivative to obtain the fullerene polyaza ligand transition metal complex. The fullerene polyaza ligand transition metal complex has a high relaxation rate, high-efficiency magnetic resonance effect and high-accuracy magnetic resonance imaging diagnosis and photodynamic therapeutic effect, can be used for preparing magnetic resonance imaging contrast agents, antioxidants, photodynamic therapy agents and drug carriers, and have important clinical value for achieving targeted drug delivery, live-animal tracking, drug therapy, and prognosis monitoring.

Description

technical field [0001] The invention relates to the field of fullerene materials and their medical applications, in particular to fullerene polyaza ligand transition metal complexes, preparation methods, uses and products for magnetic resonance imaging and photodynamic therapy. Background technique [0002] Because malignant tumors are invasive, easy to transfer, and easy to relapse, traditional cancer treatment methods are difficult to cure tumors and improve the quality of life of patients. Traditional surgical treatment will cause functional disturbance to the remaining normal tissue. If the resection is incomplete, it will easily lead to metastasis, while long-term radiotherapy and radiotherapy will cause damage to normal tissue and cells and new lesions. In addition, early lesions may not be accurately detected during single treatment, reducing the therapeutic effect. At the same time, the detection of lesion treatment after treatment cannot evaluate the therapeutic eff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/323C08G65/328C08G65/333A61K49/10A61K41/00A61P35/00C07D257/02A61K47/54
CPCA61K41/0057A61K49/108C07D257/02C08G65/323C08G65/328C08G65/33396C08G2650/04Y02P20/55
Inventor 王春儒赵佳佳舒春英关密荣
Owner BEIJING FUNAKANG BIOTECH CO LTD
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