A kind of gadolinium-based metal fullerene water-soluble nitrene derivative and its preparation method and application

A technology of metallofullerenes and fullerenes, which is applied in the field of carbon nanomaterials, can solve the problems of lack of new paramagnetic gadolinium-based metallofullerene water-soluble derivatives and other problems, and achieve easy large-scale industrial preparation and good smoothness. The effect of magnetic properties and simple purification and separation methods

Active Publication Date: 2021-08-13
HENAN AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is a bottleneck in the application of paramagnetic gadolinium-based metallofullerene derivatives as nano-diagnostic reagents. The key lies in the lack of economical and reasonable large-scale preparation of new paramagnetic gadolinium-based metallofullerene water-soluble derivatives. It is difficult to provide sufficient products for subsequent biological effect studies

Method used

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  • A kind of gadolinium-based metal fullerene water-soluble nitrene derivative and its preparation method and application
  • A kind of gadolinium-based metal fullerene water-soluble nitrene derivative and its preparation method and application
  • A kind of gadolinium-based metal fullerene water-soluble nitrene derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Preparation of Gd@C 82 With the water-soluble derivative of azidopropionic acid Gd@C 82 (NCH 2 COOH) 22

[0050] 10mg Gd@C 82 with liquid N 3 CH 2 CH 2 COOH was sequentially fed into the three-necked reaction flask according to the stoichiometric ratio of 1:500, protected by nitrogen, and stirred; first, the temperature was slowly raised to 60°C at a heating rate of 2°C / min, kept for 1 hour, and then raised to 120°C at a heating rate of 0.5°C / min ℃, keep warm for 48 hours, stop heating; add ethyl acetate to wash and filter, the residue is extracted repeatedly with deionized water until it is colorless, the extract is filtered and dried to obtain a solidified crude product; redissolve in deionized water, use MW= Dialysis with 3500 dialysis bags, membrane filtration, and freeze-drying to obtain pure paramagnetic Gd@C 82 A solid product of a water-soluble derivative of polyalanine.

[0051] Such as figure 1 As shown, the ion peak at m / z 1142 in MALDI-T...

Embodiment 2

[0054] Example 2: Preparation of Gd@C 82 With the water-soluble derivative of azidoacetic acid Gd@C 82 (NCH 2 COOH) 24

[0055] 10mg Gd@C 82 with liquid N 3 CH 2 COOH is sequentially fed into the three-necked reaction flask, protected by nitrogen, and stirred; first, the temperature is slowly raised to 80°C at a heating rate of 2°C / min, and kept for 2 hours, and then raised to 120°C at a heating rate of 0.5°C / min, kept for 48 hours, and the heating is stopped. Add ether for washing, and all the other conditions are the same as in Example 1 of the present invention. Get pure paramagnetic Gd@C 82 Solid product of polyglycine water-soluble derivatives. Thermogravimetric analysis characterized its average molecular formula as Gd@C 82 (NCH 2 COOH) 24 .

Embodiment 3

[0056] Example 3: Preparation of Gd@C 82 The water-soluble derivative Gd@C with azidoethylamine 82 (NCH 2 CH 2 NH 2 ) 20

[0057] 10mg Gd@C 82 with liquid N 3 CH 2 CH 2 NH 2 Feed into the three-necked reaction flask in sequence, under nitrogen protection, and stir; first, slowly raise the temperature to 60°C at a heating rate of 2°C / min, keep it for 2 hours, then raise it to 125°C at a heating rate of 0.5°C / min, keep it for 48 hours, and stop heating Add ethyl acetate to wash; All the other conditions are the same as Example 1 of the present invention. Get pure paramagnetic Gd@C 82 Polyethylenediamine water-soluble derivative Gd@C 82 (NCH 2 CH 2 NH 2 ) 20 solid products.

[0058] Such as Figure 4 As shown, the infrared spectrum is at 3385cm -1 The strong absorption peak at is attributed to N-H stretching vibration, 1388cm -1 The absorption peak is attributed to NH bending vibration, 1037cm -1 Belonging to C-NH 2 Stretching vibration at 2935, 2850cm -1 T...

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Abstract

The invention discloses a water-soluble nitrobene derivative of gadolinium-based metal fullerene, a preparation method and application thereof. The gadolinium-based metal fullerene water-soluble nitrobene derivative is made of paramagnetic gadolinium-based metal fullerene Gd a N b @C 2n with azide N 3 (CH 2 ) m NH 2 or N 3 (CH 2 ) m‑1 COOH is prepared by nitrobin reaction, and its general structural formula is as follows: Gd a N b @C 2n [N(CH 2 ) m NH 2 ] x or Gd a N b @C 2n [N(CH 2 ) m‑ 1 COOM] x In the general structural formula above, a=1~3; b=0~3; n=30~45; m=2~6; x=8~30; M is H, NH 4 , Na or K. The invention provides a method for preparing gadolinium-based metal fullerene water-soluble nitrene derivatives through nitrene reaction. The gadolinium-based metallofullerene water-soluble nitrene derivatives have good water solubility and good paramagnetic properties, and can be used as magnetic resonance imaging contrast agents. When used in MRI imaging, the contrast enhancement effect is very significant. Medical diagnosis and treatment, especially in MRI image-guided diagnosis and treatment, has an important application prospect.

Description

technical field [0001] The invention belongs to the field of carbon nanomaterials, and relates to a class of paramagnetic gadolinium-based metal fullerene water-soluble nitrene derivatives and a preparation method and application thereof. The gadolinium-based metal fullerene water-soluble nitrene derivatives can be used as Magnetic resonance imaging (MRI) contrast agents. Background technique [0002] have a high longitudinal relaxation rate (R 1 ), paramagnetic metallofullerenes with low biotoxicity T 1 Type MRI contrast agents have been developed for nearly 20 years. Among them, gadolinium-based metal fullerene MRI contrast agents as molecular imaging probes are most commonly reported in the literature. These MRI probes are Gd@C modified by hydroxylation, amination, Bingel-Hirsch or Prato reactions in one or more steps. 60 、Gd@C 82 、Sc x Gd 3-x N@C 80 、Gd 3 N@C 80 、Gd 3 N@C 84 derivative. Among these derivatives, Gd@C 82 (OH) 40 Labeling cells as molecular p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/10C08G69/26C08G69/28
CPCA61K49/103C08G69/26C08G69/28
Inventor 何睿毋青男刘艳杰王合中臧振锋王朝霞
Owner HENAN AGRICULTURAL UNIVERSITY
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