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A kind of Dendrobium polysaccharide fluorescent marker for near-infrared imaging and its synthesis method

A technology of near-infrared imaging and fluorescent markers, which is applied in the direction of chemical instruments and methods, luminescent materials, etc., can solve the problems of unfriendly environment, expensive synthesis and disposal of radioactive compounds, health hazards of nuclide marker imaging, etc., and achieve high Sensitivity and specificity, efficient and fast response, efficient and gentle response

Active Publication Date: 2019-12-20
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] In view of the above defects or improvement needs of the prior art, the object of the present invention is to provide a dendrobium polysaccharide fluorescent marker for near-infrared imaging and a synthesis method thereof, wherein by improving the specific structure of the dendrobium polysaccharide derivatives, obtained Dendrobium polysaccharide derivatives with a specific structure, and correspondingly design the overall process flow of the synthesis method, and control the reaction conditions and parameters (types and proportions of reaction raw materials, etc.) of each step, so that the obtained Dendrobium polysaccharide derivatives can be used as Dendrobium polysaccharide fluorescent markers are used for near-infrared imaging, which can effectively solve the problem that natural plant polysaccharides often need to be labeled and traced in in vivo and in vitro experiments, and nuclide marker imaging has potential health hazards, is not friendly to the environment, and expensive synthesis and disposal of radioactive compounds

Method used

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  • A kind of Dendrobium polysaccharide fluorescent marker for near-infrared imaging and its synthesis method
  • A kind of Dendrobium polysaccharide fluorescent marker for near-infrared imaging and its synthesis method
  • A kind of Dendrobium polysaccharide fluorescent marker for near-infrared imaging and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The specific steps can be as follows: the first step, in the round bottom flask (50ml), add dendrobium polysaccharide (50mg), p-mercaptobenzoic acid (2mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodi Imine hydrochloride (2mg) and 4-dimethylaminopyridine (2mg), add DMSO, in N 2 Under the system, stir the reaction, the reaction temperature is 25°C, and the reaction time is 12h. After the reaction is complete, add ethanol to the reaction system until no precipitation occurs. The reaction system is centrifuged at a speed of 6000r / min to obtain a precipitation. Dissolve the precipitation in water. Use the dialysis bag of 900Da to dialysis freeze-dry, obtain white solid intermediate I yield and be 98%; Second step, add intermediate I (10mg), Cy7.5-maleimide (1mg) in reaction vessel, Add DMSO at N 2 Under the system, the reaction was stirred, the reaction temperature was 25°C, and the reaction time was 12 hours. After the reaction was complete, it was dialyzed and freeze-dried w...

Embodiment 2

[0052] The specific steps can be as follows: the first step, in the round bottom flask (50ml), add dendrobium polysaccharide (100mg), p-mercaptobenzoic acid (5mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodi Imine hydrochloride (39mg) and 4-dimethylaminopyridine (390mg), add DMF, in N 2 Under the system, stir the reaction, the reaction temperature is 50°C, and the reaction time is 24h. After the reaction is complete, add ethanol to the reaction system until no precipitation occurs. The reaction system is centrifuged at a speed of 10,000r / min to obtain a precipitate, which is dissolved in water. Use the dialysis bag of 3500Da to dialysis freeze-dry, obtain white solid intermediate I yield and be 96%; Second step, add intermediate I (100mg), Cy7.5-maleimide (5mg) in reaction vessel, Join DMF, at N 2 Under the system, the reaction was stirred, the reaction temperature was 50°C, and the reaction time was 24 hours. After the reaction was complete, it was dialyzed and freeze-dried usi...

Embodiment 3

[0054] The specific steps can be as follows: the first step, in the round bottom flask (50ml), add dendrobium polysaccharide (150mg), p-mercaptobenzoic acid (10mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodi Imine hydrochloride (7.6mg) and 4-dimethylaminopyridine (38mg), add DMSO, in N 2 Under the system, stir the reaction, the reaction temperature is 25°C, and the reaction time is 24h. After the reaction is complete, add ethanol to the reaction system until no precipitation occurs. The reaction system is centrifuged at a speed of 7500r / min to obtain a precipitation. Dissolve the precipitation in water. Use 2200Da dialysis bag dialysis freeze-drying, obtain white solid intermediate I yield and be 98%; Second step, add intermediate I (120mg), Cy7.5-maleimide (1mg) in reaction container, Add DMSO at N 2 Under the system, the reaction was stirred, the reaction temperature was 25°C, and the reaction time was 12 hours. After the reaction was complete, it was dialyzed and freeze-drie...

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Abstract

The invention discloses a dendrobium polysaccharide fluorescent marker for near-infrared imaging and a synthesis method thereof, wherein the dendrobium polysaccharide fluorescent marker near-infraredimaging is of a structure as shown in the formula (II). The dendrobium polysaccharide fluorescent marker and the synthesis method have the advantages that through improvement in the specific structureof a dendrobium polysaccharide derivative, the dendrobium polysaccharide derivative for near-infrared imaging can be obtained; through the corresponding design of the overall process flow of the synthesis method, reaction conditions and parameters of each step are controlled, so that the obtained dendrobium polysaccharide derivative can particularly serve as the dendrobium polysaccharide fluorescent marker for near-infrared imaging, and the problem that natural plant polysaccharides often need to be marked and traced for in-vivo and in-vitro experiments can be effectively solved. (The formula(II) are shown in the description.).

Description

technical field [0001] The invention belongs to the field of polysaccharide fluorescent markers, and more specifically relates to a dendrobium polysaccharide fluorescent marker for near-infrared imaging and a synthesis method thereof. Background technique [0002] As one of the three types of biomacromolecules, polysaccharides, especially the structure and pharmacological activity of plant polysaccharides, which are natural macromolecules, have always been a hot spot in the current research field. Due to the lack of easy-to-detect luminescent groups and complex spatial structures, it is difficult to study plant polysaccharides. Therefore, in the in vivo and in vitro experiments of polysaccharide compounds, it is often necessary to label and trace them, so as to clearly understand their absorption distribution in vivo and in vitro and the mechanism of their pharmacological activity. [0003] According to domestic and foreign literature reports, many polysaccharides are label...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/00C09K11/06
CPCC08B37/00C09K11/06C09K2211/1466
Inventor 王凯平张玉聂刚王红静汪汉香刘亚鸽吴止境杨夏雯程芳
Owner HUAZHONG UNIV OF SCI & TECH
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