CN112759945A - Fluorescent dye based on quantum dot FRET and application thereof - Google Patents
Fluorescent dye based on quantum dot FRET and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
Abstract
The invention provides a fluorescent dye based on quantum dot FRET, which comprises: quantum dot subunits, organic fluorescent dye subunits, linker subunits, and biological binding site subunits. The fluorescent dye absorbs excitation light energy through quantum dots serving as donor groups, transfers the energy to acceptor fluorescent groups through intramolecular Fluorescence Resonance Energy Transfer (FRET), and excites excitation light with different wavelengths, so that excitation with one excitation wavelength and multi-color fluorescence detection are realized. The fluorescent signal amplification effect can be realized by connecting a plurality of organic fluorescent dye molecules on the surface of the quantum dot. The invention also provides application of the fluorescent dye.
Description
Technical Field
The invention relates to the field of molecular diagnosis, in particular to a fluorescent dye based on quantum dot FRET and application of the fluorescent dye.
Background
Quantum dots are semiconductor nanostructures that can confine excitons in three dimensions. The light emitting principle is that when the particle diameter of the quantum dot is smaller than or close to the Bohr radius of the exciton, the exciton is limited to move in a three-dimensional space, so that a discontinuous electron energy level structure similar to an atom is generated, electrons and holes are confined by the quantum, and after the electrons and the holes are excited, light with different wavelengths can be emitted by different sizes and atom structures. Compared with an organic luminescent material, the quantum dot material has the characteristics of easily adjustable wavelength interval, wide absorption, narrow emission, large Stokes displacement, small filtering loss, strong bleaching resistance, long fluorescence life and the like. And thus has become one of the research hotspots in the direction of biosensor and bio-imaging in recent years.
In recent years, with the development of molecular diagnostic techniques, there is an increasing demand for multiple fluorescent labeling techniques. At present, the commercial multiple fluorescent marker adopts an organic fluorescent material, and the excitation light with different wavelengths is obtained under the excitation of a single wavelength by designing a receptor material. However, the fluorescence quantum efficiency of the material is low, the fluorescence intensity is weak, and the material is easily interfered by the background, so that the detection sensitivity of the material is influenced. The quantum dot Fluorescent Resonance Energy Transfer (FRET) fluorescent dye is adopted, a plurality of organic fluorescent groups can be connected to the surface of the quantum dot, and compared with an organic fluorescent material, the quantum dot material has higher fluorescence quantum efficiency.
Disclosure of Invention
At least one embodiment of the present disclosure provides a quantum dot FRET-based fluorescent dye, which includes: quantum dot subunits, organic fluorescent dye subunits, linker subunits, and biological binding site subunits.
For example, in at least one embodiment of the present disclosure, a quantum dot FRET fluorescent dye, the quantum dot subunit of the fluorescent dye is of a core-shell structure, the surface of the quantum dot subunit contains ligand groups, wherein the core structure is selected from at least one of cadmium sulfide, cadmium selenide, cadmium telluride, indium phosphide, zinc oxide, cadmium selenide telluride, cadmium selenide sulfide, cadmium zinc selenide, cadmium zinc sulfide, indium arsenide, zinc selenide, zinc telluride, copper indium disulfide, lead sulfide, and lead selenide, the shell structure can be selected from at least one of zinc sulfide, cadmium sulfide and zinc selenide, and the ligand can be selected from at least one of hexanedithiol, octanedioic acid, hexamethylenediamine, polymaleic anhydride, polyacrylic acid, terminal carboxyl-functionalized polyethylene glycol, thioglycolic acid, mercaptoethylamine, mercaptopropionic acid, mercaptobutyric acid, mercaptohexanoic acid, mercaptopropionic acid, mercaptobutylamino and mercaptohexanoamino.
For example, in at least one embodiment of the present disclosure, in a quantum dot FRET-based fluorescent dye, an organic fluorescent dye subunit in the fluorescent dye is one of the following units:
wherein denotes the attachment site of the organic fluorescent dye unit.
At least one embodiment of the present disclosure provides a fluorescent dye of this type, wherein the linker subunit is one of the following units:
wherein n is a natural number of 1-6, represents a connecting site with the organic fluorescent dye, and ﹏ represents a connecting site with the quantum dot.
At least one embodiment of the present disclosure provides such a fluorescent dye, wherein the biological binding site subunit may be one of the following units:
streptavidin, biotin, oligonucleotide probes, peptide nucleotide probes, amino-modified antigens/antibodies, aptamers.
At least one embodiment of the disclosure also provides a preparation method of the fluorescent dye.
For example, in a manufacturing method provided in at least one embodiment of the present disclosure, the manufacturing method includes the steps of:
(1) reacting organic fluorescent dye with succinimidyl ester with ethylenediamine with tert-butyloxycarbonyl (Boc) protection on one side to form an amino functional group with Boc protection at the tail end;
(2) carrying out amino deprotection on the product in the step (1) by using a 1:1 trifluoroacetic acid aqueous solution to obtain a fluorescent dye group with amino;
(3) carrying out amidation reaction on the product obtained in the step (2) and a cadmium selenide quantum dot material with a thioglycollic acid ligand on the surface in 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC)/N-hydroxysuccinimide (NHS);
(4) and (3) reacting the product obtained in the step (3) with ddNTP (ddNTP refers to one of ddATP \ ddUTP \ ddCTP \ ddGTP) with an amino group at the tail end to obtain a final product.
At least one embodiment of the disclosure also provides application of the fluorescent dye in a fluorescence in situ hybridization technology, a Sanger sequencing technology, multiple immunofluorescence labeling, a gene sequencing technology and a multivariate quantitative detection technology.
For example, in at least one embodiment of the present disclosure, the multiplex quantitative detection is a quantitative detection of one or more detection targets, and the detection targets include at least one of proteins and nucleic acid molecules.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings of the embodiments will be briefly described below, and it is apparent that the drawings in the following description only relate to some embodiments of the present invention and are not limiting on the present invention.
Fig. 1 is a schematic view of a quantum dot structure provided in an embodiment of the present disclosure;
FIG. 2 is a schematic diagram of a quantum dot FRET fluorescent dye structure provided in an embodiment of the present disclosure;
FIG. 3 is a graph of fluorescence spectra of quantum dot FRET-based fluorescent dyes in an embodiment of the disclosure.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the drawings of the embodiments of the present invention. It is to be understood that the embodiments described are only a few embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the described embodiments of the invention, belong to the scope of protection of the invention.
Unless defined otherwise, technical or scientific terms used herein shall have the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs. The word "comprising" or "comprises", and the like, means that the element appearing before the word covers the element appearing after the word and its equivalents, without excluding other elements.
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified. Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The fluorescence spectrometer in the following examples was designated as Hitachi F7000, the magnetic stirrer in the examples was designated as Hadaofu MR Hei-standard heating magnetic stirrer, and the high-speed centrifuge in the examples was designated as Shanghai Hotan HERRYTECH TG 18G.
In the field of molecular diagnostics, the most mature and widespread technique for labeling and detecting biomolecules is fluorescence labeling. The traditional marking method adopts organic dye molecules, and the material has weak fluorescence intensity, short fluorescence life and easy fluorescence quenching, so that the material has the problems of low sensitivity, easy interference of biological background and the like when being applied to biomolecule detection. As a new luminescent material, the quantum dot material has the characteristics of wide absorption, narrow emission, long fluorescence life, high fluorescence quantum efficiency and the like, so that the quantum dot material is often used as a biomarker molecule to be applied to related research work of biosensors and biological imaging.
In this embodiment, the inorganic semiconductor quantum dot material and the organic fluorescent dye are combined, and the fluorescent signal amplification can be realized by connecting a plurality of organic fluorescent dye molecules on the surface of the quantum dot. In addition, the Fluorescence Resonance Energy Transfer (FRET) between the quantum dots and the organic material can realize the functions of single-wavelength excitation and multicolor fluorescence labeling, so that the fluorescent probe has great potential in the detection of various biomarkers and the application of multicolor fluorescence labeling.
The quantum dot material structure in this embodiment is shown in fig. 1, and the ligand of the cadmium selenide/zinc sulfide core-shell structure is thioglycolic acid, which is available from scintillation corporation under the trade designation CdSe/ZnS-525-25. Aminopropargyl ddATP, Aminopropargyl ddUTP, Aminopropargyl ddCTP, Aminopargyl ddGTP were purchased from AAT biordequest with corresponding code numbers 17070, 17074, 17072, 17076, respectively. The fluorochrome molecules Bodipy FLNHS ester, Bodipy 550NHS ester, Rhodamine NHS ester, 6-ROX NHS ester were purchased from Sammerfei Biotech, corresponding to the respective product numbers D2184, D2187, R6160, C6126. Other chemicals were purchased from Beijing Yinocyke technology, Inc., unless otherwise specified.
The chemical synthesis steps used in this example are all mature amidation reaction steps, and the specific synthetic route used in this example is as follows, and the synthesis steps will be described below with reference to the examples.
EXAMPLE Synthesis of a Compound 7 ddATP-Bodipy FL
(1) Synthesis of Compound 3 Bodipy FL-EDA-Boc
A5 ml clean double-mouth round bottom reaction bottle is taken, a magnetic stirrer is added, 10mg of the raw material 1 Bodipy-FLNHS Ester is added, and the reaction bottle is sealed and protected from light and nitrogen. Dissolving 10 microliters of N, N-diisopropylethylamine in 1 milliliter of anhydrous N, N-Dimethylformamide (DMF), injecting the solution into a reaction bottle, fully stirring until the raw material 1 is completely dissolved, then adding 2100 microliters of compound at one time, and reacting for 2 hours at room temperature in a dark place. After the reaction is finished, dropwise adding the reaction solution into a mixed solution of acetone/petroleum ether with the volume ratio of 1:1 to separate out a product, and centrifuging to obtain a solid product with the yield of 92%.
(1) Synthesis of Compound 4Bodipy FL-EDA
Adding the product 3 obtained in the step (1) into a reaction bottle protected by nitrogen, adding 1 ml of ice water/trifluoroacetic acid solution with the volume ratio of 1:1, and reacting for 1 hour in a dark place. The solution after the reaction is dripped into an ether solvent, and the compound 4 trifluoroacetate is obtained by centrifugation with the yield of 88 percent and is directly reacted in the next step.
(2) Synthesis of Compound 6 QD-Bodipy FL
50 microliter of quantum dot 5 aqueous solution (1.5X 10)-5M) in a 5 ml double-mouth reaction bottle, 100 microliters of EDC aqueous solution (0.1M) and 100 microliters of NHS aqueous solution (0.1M) are added, the pH of the reaction solution is adjusted to 8.0 under the protection of nitrogen, the mixture is stirred, and the reaction is carried out for 30 minutes at room temperature in a dark place. And (3) adding 0.02 micromole of the compound 4Bodipy FL-EDA obtained in the step (2) into the reaction solution, fully stirring, reacting for 2 hours at 37 ℃ in a dark place, dropping the reaction solution into ether after the reaction is finished to separate out a product, and directly using the product in the next reaction in the dark place.
(3) Synthesis of compound 7 ddATP-Bodipy FL
Dissolving the compound 6 obtained in the step (3) in 500 microliters of anhydrous DMF, adding 50 microliters of N, N-diisopropylethylamine, stirring for dissolving, and protecting with nitrogen and keeping out of light. Dissolving 5. mu.M Aminopropargyl ddATP in 0.5 mL NaHCO pH 8.53/NaCO3The resulting solution was added dropwise to the reaction mixture three times, reacted for 4 hours, and then the resulting solution was added dropwise to an ether solvent to obtain 7 ddATP-Bodipy FL as a solid product.
Example the synthetic procedure for the compound ddUTP-Bodipy 550 was similar to that for the compound 7 ddATP-Bodipy FL.
Example the synthesis procedure of ddCTP-Rhodamine is similar to that of 7 ddATP-Bodipy FL.
EXAMPLE the synthetic procedure for the four compound, ddGTP-6-ROX, was similar to the synthetic procedure for the compound 7 ddATP-Bodipy FL.
Examples one to four compounds prepared have the following structures:
test example
Dissolving compounds ddATP-Bodipy FL, ddUTP-Bodipy 550, ddCTP-Rhodamine and ddGTP-6-ROX in water to prepare 10-8At a concentration of mol per liter, the sample is put into a quartz cuvette, water is used as a reference sample, the excitation wavelength is 488nm, and the emission peaks of the compounds ddATP-Bodipy FL, ddUTP-Bodipy 550, ddCTP-Rhodamine and ddGTP-6-ROX are 530nm, 558nm, 625nm and 640nm respectively after the measured fluorescence spectrum data are normalized as shown in figure 3.
The embodiment of the invention provides a design and synthesis method of a novel fluorescent dye based on quantum dot FRET, and the fluorescent dye can be applied to the field of molecular diagnosis. Has at least one of the following beneficial effects:
(1) in the fluorescent dye provided by at least one embodiment of the present disclosure, a single wavelength of 488nm excitation can be adopted to realize light emission at four different wavelengths, and the 488nm laser is matched with the excitation wavelength used by the current Sange sequencing instrument, and can be used as a fluorescent marker in multiple marker detection and multi-color fluorescent marking technologies;
(2) in the fluorescent dye provided by at least one embodiment of the present disclosure, quantum dots are used as FRET donors, and multiple fluorescent dyes can be connected to the surfaces of the quantum dots, so that the fluorescent signal amplification effect is realized, and the improvement of the sensitivity of detection signals is facilitated;
(3) in the fluorescent dye provided by at least one embodiment of the present disclosure, the synthesis steps are mature amidation reaction steps, the synthesis is simple, and the synthesis yield is high;
(4) in the fluorescent dye provided by at least one embodiment of the present disclosure, quantum dots are used as donor materials in FRET, and compared with organic donor materials, the fluorescent quantum efficiency is higher.
The following points need to be explained:
(1) the drawings of the embodiments of the invention only relate to the structures related to the embodiments of the invention, and other structures can refer to common designs.
(2) Without conflict, embodiments of the present invention and features of the embodiments may be combined with each other to arrive at new embodiments.
The above description is only an embodiment of the present invention, but the scope of the present invention is not limited thereto, and the scope of the present invention should be subject to the scope of the claims.
Claims (10)
1. A quantum dot FRET-based fluorescent dye, comprising: quantum dot subunits, organic fluorescent dye subunits, linker subunits, and biological binding site subunits.
2. The fluorescent dye according to claim 1, wherein the quantum dot subunits have a core-shell structure and the surface of the quantum dot subunits contains a ligand group.
3. The fluorescent dye according to claim 2, wherein the core structure is selected from at least one of cadmium sulfide, cadmium selenide, cadmium telluride, indium phosphide, zinc oxide, cadmium selenide telluride, cadmium selenide sulfide, cadmium zinc selenide, cadmium zinc sulfide, indium arsenide, zinc selenide, zinc telluride, copper indium disulfide, lead sulfide, lead selenide;
the shell structure is selected from at least one of zinc sulfide, cadmium sulfide and zinc selenide;
the ligand is selected from at least one of hexanedithiol, suberic acid, hexamethylenediamine, polymaleic anhydride, polyacrylic acid, terminal carboxyl functionalized polyethylene glycol, thioglycolic acid, mercaptoethylamine, mercaptopropionic acid, mercaptobutyric acid, mercaptohexanoic acid, mercaptopropylamine, mercaptobutylamine and mercaptohexylamine.
4. The fluorescent dye of claim 1, wherein the organic fluorescent dye subunit is selected from any one of the following units:
wherein denotes the attachment site of the organic fluorescent dye unit.
5. The fluorescent dye of claim 1, wherein the linker subunit is selected from any one of the following units:
wherein n is a natural number of 1-6, represents a connecting site with the organic fluorescent dye, and ﹏ represents a connecting site with the quantum dot.
6. The fluorescent dye according to claim 1, wherein the biological binding site subunit is selected from any one of the following units:
7. the fluorescent dye according to claim 1, wherein the biological binding site subunit is selected from any one of streptavidin, biotin, an oligonucleotide probe, a peptide nucleotide probe, an amino-modified antigen/antibody, and an aptamer.
8. The fluorescent dye according to any one of claims 1 to 7, wherein the fluorescent dye is selected from any one of the following compounds:
9. use of a fluorescent dye according to any one of claims 1 to 8 in fluorescence in situ hybridization techniques, Sanger sequencing techniques, multiplex immunofluorescent labelling, gene sequencing techniques, multiplex quantitative detection techniques.
10. The use of claim 9, wherein the multiplex quantitative determination is a quantitative determination of one or more detection targets, and the detection targets comprise at least one of proteins and nucleic acid molecules.
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| CN101638579A (en) * | 2009-08-21 | 2010-02-03 | 天津城市建设学院 | Quantum dot-cyanine dye-folic acid biological probe and preparation method thereof |
| CN107238708A (en) * | 2017-05-31 | 2017-10-10 | 重庆高圣生物医药有限责任公司 | A kind of method based on the homogeneous immune detection CEA of quantum dot |
| CN108929692A (en) * | 2018-09-05 | 2018-12-04 | 南方科技大学 | A kind of quantum dot fluorescence material and preparation method thereof for detecting heavy metal ion |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070212746A1 (en) * | 2006-03-10 | 2007-09-13 | David Bauer | Quantum dot nanoparticle-based universal neurotoxin biosensor |
| CN101638579A (en) * | 2009-08-21 | 2010-02-03 | 天津城市建设学院 | Quantum dot-cyanine dye-folic acid biological probe and preparation method thereof |
| CN107238708A (en) * | 2017-05-31 | 2017-10-10 | 重庆高圣生物医药有限责任公司 | A kind of method based on the homogeneous immune detection CEA of quantum dot |
| CN108929692A (en) * | 2018-09-05 | 2018-12-04 | 南方科技大学 | A kind of quantum dot fluorescence material and preparation method thereof for detecting heavy metal ion |
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