Structure for remarkably improving luminous intensity of fluorescent dye and synthesis method
By designing a new fluorescent dye structure and synthesis method and combining it with the labeled substance in the form of ester, the problem of low luminescence intensity of fluorescent dyes was solved, the fluorescent signal was significantly improved, and the detection sensitivity was increased.
Patent Information
- Application Number
- CN202510813120.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-06-18
- Publication Date
- 2025-10-17
AI Technical Summary
The luminescence intensity of existing fluorescent dyes is low, resulting in insufficient sensitivity in detecting trace amounts of substances, making it difficult to detect harmful cells in the human body in a timely manner.
A new fluorescent dye structure design and synthesis method is used to combine with the labeled substance in the form of ester to increase the fluorescence signal intensity. The specific steps include the addition of the compound and reaction treatment to form a green solid powder product.
The luminescence intensity of the fluorescent dye is significantly improved, so that the fluorescence signal detected by the same amount of substrate increases by 11 times, thereby improving the sensitivity of the detection.
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Figure CN120794899A_ABST
Abstract
Description
TECHNICAL FIELD
[0001] The present application relates to the field of fluorescent dyes, and in particular to a structure and a synthesis method for significantly improving the light emission intensity of fluorescent dyes. BACKGROUND
[0002] Currently, the light emission intensity of the existing fluorescent dyes is low, and the weak signal cannot distinguish trace substances: Conventional labeling: fluorescent probes, molecular probes, nucleic acid / protein labeling, and cell detection per unit labeling synthesis is combined in proportion by amide bond, disulfide bond, etc.
[0003] Detection sensitivity: conventional labeling cannot be detected when the detected substance is extremely small, such as the initial detection of harmful cells in the human body, which is easily missed and cannot be discovered in time. SUMMARY
[0004] In order to solve the technical problems existing in the prior art, the purpose of the present application is to provide a structure and a synthesis method for significantly improving the light emission intensity of fluorescent dyes, and the fluorescence signal of equal amount of substrate is increased by 11 times.
[0005] To solve the above-mentioned technical problems, one of the purposes of the present application is achieved by using the following technical solutions: A structure for significantly improving the light emission intensity of fluorescent dyes, comprising the following synthesis structure:
[0006] Further, X is a fluorescent dye, and the fluorescent dye is any one of fluorescein, rhodamine, and cyanine.
[0007] Further, the structure of the fluorescein dye is as follows:
[0008] Further, the structure of the rhodamine dye is as follows:
[0009] Further, the structure of the cyanine dye is as follows:
[0010] Further, the reaction formula for synthesizing E is as follows:
[0011] Further, the reaction formula for synthesizing compound K is as follows:
[0012] Further, the chemical formula of the synthesis reaction solution is as follows:
[0013] A synthesis method of a structure for significantly improving the light emission intensity of a fluorescent dye, comprising the following steps: S1, synthesis of compound K; S2, in a 5ML round bottom flask, compound H (45.7mg, 0.1mmol) was added, 200ul DMSO was stirred at room temperature for 5 minutes, and after complete dissolution, TSTU CAS: 105832-38-0 (30.1mg, 0.1mmol) and TEA CAS: 121-44-8, (15.3ul, 0.11mmol) were added, the reaction was detected after 30 minutes at room temperature, and the reaction was complete. S3, the reaction solution was used in the next step.
[0014] A synthesis method of a structure for significantly improving the light emission intensity of a fluorescent dye, the synthesis steps of Y-type double dyes are as follows: To the reaction solution of the previous step, compound J (21.7mg, 0.05mmol) was added, and then TEA (30.6ul, 0.1mmol) was added, and stirred at room temperature for 1.5 hours, the reaction conversion was 85%, the reaction was stopped, the reaction was poured into ether to precipitate, filtered, separated on a chloroform / methanol silica gel column, and 29mg of the final pure product was obtained, which was a green solid powder.
[0015] Compared with the prior art, the beneficial effects of the present application are: (1) Label synthesis: all in the form of dye activated ester combined with the labeled substance, without changing the labeling method. Dye combination doubled: the amount of traditional dye labeling increased by one time. Signal improvement: compared with the traditional signal, the fluorescence signal of the same amount of substrate increased by 11 times. BRIEF DESCRIPTION OF DRAWINGS
[0016] Figure 1 The fluorescence intensity spectrum in the present application is a schematic diagram, series 1 is the fluorescence intensity spectrum of the present embodiment, and series 2 is the fluorescence intensity spectrum of ordinary fluorescent dyes. DETAILED DESCRIPTION
[0017] In the following, the present application is further described in combination with the drawings and specific embodiments, and it should be noted that the following described embodiments or technical features can be combined in any manner to form new embodiments without conflict.
[0018] In the description of the present application, it should be understood that the terms "up", "down", "left", "right", etc. indicate the orientation or positional relationship shown in the drawings, and are only for the convenience of describing the present application and simplifying the description, and do not indicate or imply that the devices or elements referred to must have a particular orientation, be constructed and operated in a particular orientation, and therefore cannot be understood as a limitation on the present application.
[0019] The terms "first", "second", and the like in this application are used to distinguish similar objects, and are not used to describe a particular order or sequence. It should be understood that the data used in this way can be interchanged under appropriate circumstances, so that the embodiments of the present application can be implemented in an order other than those illustrated or described herein, and the objects distinguished by "first", "second", etc. are generally a class, not limited to the number of objects, for example, the first object can be one or more. In addition, "and / or" in the specification and claims indicates at least one of the connected objects, and the character " / ", generally indicates that the objects before and after are in a "or" relationship.
[0020] Embodiment 1: A structure for significantly improving the light emission intensity of fluorescent dyes, comprising the following synthetic structure:
[0021] Further, X is a fluorescent dye, and the fluorescent dye is any one of fluorescein, rhodamine, and cyanine.
[0022] Further, the structure of the fluorescein dye is as follows:
[0023] Further, the structure of the rhodamine dye is as follows:
[0024] Further, the structure of the cyanine dye is as follows:
[0025] Further, the reaction formula for synthesizing E is as follows:
[0026] Further, the reaction formula for synthesizing compound K is as follows:
[0027] Further, the chemical formula of the synthesis reaction solution is as follows:
[0028] A synthesis method of a structure for significantly improving the light emission intensity of fluorescent dyes, comprising the following steps: S1, synthesizing compound K; S2, in 5ML round bottom flask, add compound H (45.7mg, 0.1mmol), 200ul DMSO, stir at room temperature for 5 minutes, after complete dissolution, add TSTU CAS: 105832-38-0 (30.1mg, 0.1mmol) and TEA CAS: 121-44-8, (15.3ul, 0.11mmol), after 30 minutes reaction at room temperature, the reaction is complete; S3, the reaction solution is used in the next step.
[0029] A method for synthesizing a structure that significantly improves the light intensity of fluorescent dyes, the synthesis steps of Y-type double dyes are as follows: Add compound J (21.7mg, 0.05mmol) to the reaction solution of the previous step, then add TEA (30.6ul, 0.1mmol), stir at room temperature for 1.5 hours, detect the reaction conversion of 85%, stop the reaction, pour the reaction into ether to precipitate, filter, separate on a chloroform / methanol silica gel column to obtain 29mg of the final pure product, which is a green solid powder. This synthesis method is to combine the dye activated ester form with the label, without changing the labeling method, and the amount of traditional dye labeling is doubled, and compared with the traditional signal, the fluorescence signal of the same amount of substrate is increased by 11 times.
[0030] The above embodiments are only preferred embodiments of the present application, and cannot be used to limit the scope of protection of the present application. Any non-essential changes and substitutions made by those skilled in the art on the basis of the present application are within the scope of the present application.
Claims
1. A structure that significantly improves the luminescence intensity of a fluorescent dye, characterized in that: Includes the following synthetic structures:
2. The structure for significantly improving the luminescence intensity of a fluorescent dye according to claim 1, characterized in that: X is a fluorescent dye, and the fluorescent dye is any one of fluorescein, rhodamine, and cyanine.
3. The structure for significantly improving the luminous intensity of a fluorescent dye according to claim 2, characterized in that: The structure of fluorescein dyes is as follows:
4. The structure for significantly improving the luminous intensity of a fluorescent dye according to claim 3, wherein: The structure of rhodamine dyes is as follows:
5. The structure for significantly improving the luminous intensity of a fluorescent dye according to claim 4, characterized in that: The structure of cyanine dyes is as follows:
6. The structure for significantly improving the luminous intensity of a fluorescent dye according to claim 5, characterized in that The reaction formula for synthesizing E is as follows:
7. The structure for significantly improving the luminous intensity of a fluorescent dye according to claim 6, characterized in that: The reaction formula for synthesizing compound K is as follows:
8. The structure for significantly improving the luminous intensity of a fluorescent dye according to claim 7, characterized in that: The chemical formula of the synthetic reaction solution is as follows:
9. A method for synthesizing a structure for significantly improving the luminous intensity of a fluorescent dye according to claim 1, characterized in that: The steps include: S1, synthesis of compound K; S2, compound H (45.7 mg, 0.1 mmol) and 200 μl DMSO were added to a 5 mL round-bottom flask, stirred at room temperature for 5 minutes, and then TSTU CAS: 105832-38-0 (30.1 mg, 0.1 mmol) and TEA CAS: 121-44-8 (15.3 μl, 0.11 mmol) were added after complete dissolution. The reaction was incubated at room temperature for 30 minutes and the reaction was complete. S3, the reaction solution is used in the next step.
10. The method for synthesizing a structure for significantly improving the luminescence intensity of a fluorescent dye according to claim 8, characterized in that: The synthesis steps of Y-type double dye are as follows: Compound J (21.7 mg, 0.05 mmol) was added to the reaction solution in the previous step, followed by TEA (30.6 μl, 0.1 mmol). The mixture was stirred at room temperature for 1.5 hours. When the reaction conversion was 85%, the reaction was stopped and poured into ether for precipitation. The mixture was filtered and separated by a chloroform / methanol silica gel column to obtain 29 mg of the final pure product as a green solid powder.