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Fitc-labeled vitamin b12 derivatives and their synthesis and application

A VB12-FITC, vitamin technology, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of high cost of vitamin B12 imaging and difficult operation, and achieve good application prospects and low toxicity of raw materials. , the effect of mild preparation conditions

Inactive Publication Date: 2019-09-20
NANFANG HOSPITAL OF SOUTHERN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The first object of the present invention is to provide a FITC-labeled vitamin B12 derivative. The fluorescently-labeled VB12 can activate its low-reactivity group at room temperature under the premise of maintaining the original structure of VB12, thereby solving the current problem. Nuclides and positron-labeled vitamin B12 imaging have problems such as high cost and difficult operation

Method used

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  • Fitc-labeled vitamin b12 derivatives and their synthesis and application
  • Fitc-labeled vitamin b12 derivatives and their synthesis and application
  • Fitc-labeled vitamin b12 derivatives and their synthesis and application

Examples

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Embodiment 1

[0029] Embodiment 1: Preparation of VB12-FITC according to the present invention

[0030] (A) Dissolve 200mg of vitamin B12 in 4ml of dehydrated dimethyl sulfoxide (DMSO) under nitrogen protection, add 200mg of activator N,N'-carbonyldiimidazole (CDI), and protect from light at 20°C After activation for 12 hours, 400 mg of di-1,8-amino-3,6-dioxahexane was added, and the reaction was continued at 20° C. for 6 hours. Precipitate the reaction product with 500ml of acetone, centrifuge at 10000r / min for 10min to separate the reaction product, and dry it in vacuum at 20°C to obtain aminated vitamin B12.

[0031] (B) Weigh 150ng of the aminated vitamin B12 obtained in step A and dissolve it in 4ml of dimethyl sulfoxide (DMSO) that has been treated with water removal, add 0.1ml of catalyst triethylamine, and add FITC in a ratio of 1:1, After reacting in the dark at 20°C for 6 hours, the reaction product was precipitated and separated, and vacuum-dried at 20°C to obtain FITC-labeled v...

Embodiment 2

[0032] Embodiment 2: the preparation of VB12-FITC described in the present invention

[0033] (A) Dissolve 200mg of vitamin B12 in 4ml of dehydrated dimethyl sulfoxide (DMSO) under nitrogen protection, add 300mg of activator N,N'-carbonyldiimidazole (CDI), and protect from light at 22°C After activation for 12 hours, 600 mg of 1,8-diamino-3,6-dioxahexane was added, and the reaction was continued at 22° C. for 6 hours. The reaction product was precipitated with 500 ml of acetone, centrifuged at 10,000 r / min for 10 min to separate the reaction product, and vacuum-dried at 22° C. to obtain aminated vitamin B12.

[0034] (B) Weigh 150ng of the aminated vitamin B12 obtained in step A and dissolve it in 4ml of dimethyl sulfoxide (DMSO) that has been treated with water removal, add 0.1ml of catalyst triethylamine, and add FITC at a ratio of 1:1.25, After reacting in the dark at 22°C for 6 hours, the reaction product was precipitated and separated, and vacuum-dried at 22°C to obtain ...

Embodiment 3

[0035] Embodiment 3: the preparation of VB12-FITC described in the present invention

[0036] (A) Dissolve 200mg of vitamin B12 in 4ml of dehydrated dimethyl sulfoxide (DMSO) under nitrogen protection, add 400mg of activator N,N'-carbonyldiimidazole (CDI), and protect from light at 25°C After activation for 12 hours, 800 mg of di-1,8-amino-3,6-dioxahexane was added, and the reaction was continued at 25° C. for 6 hours. Precipitate the reaction product with 500ml of acetone, centrifuge at 10000r / min for 10min to separate the reaction product, and vacuum dry at 20°C to obtain aminated vitamin B12.

[0037] (B) Weigh 150ng of the aminated vitamin B12 obtained in step A and dissolve it in 4ml of dimethyl sulfoxide (DMSO) that has been treated with water removal, add 0.1ml of catalyst triethylamine, and add FITC at a ratio of 1:1.5, After reacting in the dark at 25°C for 6 hours, the reaction product was precipitated and separated, and vacuum-dried at 20°C to obtain FITC-labeled v...

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Abstract

The invention relates to a novel fluorescence-marked vitamin B12 derivative, and concretely relates to a vitamin B12 derivative marked with fluorescein isothiocyanate (FITC), and the derivative is called a VB12-FITC for short. A preparation method of the VB12-FITC comprises the following steps: a diamino group is coupled with a low-reaction-activity hydroxyl group in a VB12 structure, and then the obtained aminated VB12 is reacted with an isothiocyanate radical of the FITC, so that the VB12-FITC derivative is synthesized. The advantages of the FITC-marked VB12 derivative are as follows: preparation conditions are gentle (the preparation can be performed at room temperature), raw materials are low in toxicity, the operation method is simple and convenient, the synthetic efficiency is high, the properties of reaction products are stable, and the FITC-marked VB12 derivative has good a fluorescence imaging effect. The FITC-marked VB12 derivative provided by the invention has a tumor-uptake targeting property and an important value in research of VB12 absorption and metabolic pathways, tumor imaging therapy and the like.

Description

technical field [0001] The present invention relates to a vitamin B12 derivative, in particular to a novel fluorescently labeled vitamin B12 derivative, referred to as VB12-FITC, and a synthesis method and application of the derivative. Background technique [0002] Vitamin B12, also known as methylcobalamin, is an essential water-soluble vitamin that cannot be synthesized in the body itself, and can only be ingested through food and stored in the liver. In the absence of continuous supplementation of exogenous vitamin B12 in the human body, the total amount of vitamin B12 stored in the liver will be exhausted within 3-6 months. In the methylation of human cell metabolism, maintaining the metabolism and function of nerve myelin sheath, promoting the development and maturation of red blood cells, participating in the synthesis of deoxynucleic acid (DNA), the metabolism of fat and carbohydrates, the synthesis of nucleic acid and protein, etc. Links, are inseparable from the p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H23/00C07H1/00C09K11/06A61K49/00G01N15/14G01N21/31
Inventor 胡彦锋郭伟洪李国新林填刘浩余江李团结陈豪陈新华
Owner NANFANG HOSPITAL OF SOUTHERN MEDICAL UNIV
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