CN109097027B - Application of pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles in hypochlorite ion detection - Google Patents

Application of pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles in hypochlorite ion detection Download PDF

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CN109097027B
CN109097027B CN201811027838.4A CN201811027838A CN109097027B CN 109097027 B CN109097027 B CN 109097027B CN 201811027838 A CN201811027838 A CN 201811027838A CN 109097027 B CN109097027 B CN 109097027B
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tetrastyrene
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pyrrolo
pyrrole
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CN109097027A (en
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刘正春
聂凯旋
梁波
石环环
董波
朝乐蒙
龙孟秋
徐慧
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Central South University
Changsha University of Science and Technology
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Abstract

The invention discloses an application of a pyrrolopyrrole diketone compound/tetrastyrene compound composite nanoparticle in hypochlorite ion detection, wherein the composite particle has a Fluorescence Resonance Energy Transfer (FRET) effect and good water solubility, can realize high-sensitivity and selectivity ratio type detection of ClO - in a water system or fluorescence imaging of ClO - in cells, and can be widely applied to the fields of biological detection, imaging and the like.

Description

Application of pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles in hypochlorite ion detection
Technical Field
the invention relates to a fluorescent energy transfer nanoparticle, in particular to a composite nanoparticle with fluorescence resonance energy transfer effect (FRET) assembled by a pyrrolopyrrole diketone compound and a tetrastyrene compound, which is used for ClO - detection or intracellular environment imaging in a water body and a method for realizing efficient ClO - detection, and belongs to the field of biological detection.
Background
The small molecules of bioactive oxide have important roles in physiological and pathological aspects, and the concentration level reflects the physiological and pathological states of cells, wherein hypochlorite, an important active oxide in a living body, plays an important role in a plurality of physiological processes in the living body, but excessive hypochlorous acid causes various tissue injuries and diseases including cardiovascular diseases, lung injuries and the like, and since hypochlorous acid in the living body has weak acidity (pK a ═ 7.63), the activity in the physiological environment is high and the existence time is short, so that it is of great significance to design a fluorescent probe for recognizing hypochlorite with high selectivity.
Different from a monomolecular fluorescent probe, the fluorescent nano-probe has the advantages of good photobleaching resistance, high fluorescence quantum efficiency, good water solubility, easy functionalization and the like, and is gradually favored by researchers. The fluorescent nano probe with Fluorescence Resonance Energy Transfer (FRET) effect can realize ratio type detection on an analyzed substance, effectively reduce interference of biological environment background fluorescence, and is a probe construction form with good application prospect. At present, FRET nano-probes are prepared by using inorganic heavy metal materials, and the potential safety threat is an inevitable problem. The preparation of pure organic FRET nanoprobes is limited by the aggregate fluorescence quenching (ACQ) effect of organic fluorescent materials.
disclosure of Invention
The pyrrolopyrrole diketone compound/tetrastyrene compound composite nanoparticles have the specific recognition capability on ClO - by utilizing pyrrolopyrrole diketone molecules, and have the characteristics of strong fluorescence emission and two-photon induced fluorescence emission, while the tetrastyrene molecules can be used as energy donors of the FRET nanoparticles, so that the high-sensitivity and selectivity ratio-type detection or ratio-type two-channel cell imaging of ClO - is realized.
In order to achieve the technical purpose, the invention provides application of the pyrrolopyrrole diketone compound/tetra-styrene compound composite nanoparticles, which are used as fluorescent probes for detecting or imaging hypochlorite ions.
in a preferable scheme, the pyrrolopyrrole diketone compound/tetrabenzene compound composite nano particle is formed by molecular self-assembly of pyrrolopyrrole diketone compound and tetrabenzene compound;
The tetrastyrene compound has the structure of formula 1:
The pyrrolopyrrole dione compound has a structure of formula 2:
Wherein the content of the first and second substances,
R and R 1 are independently selected from hydrophilic groups;
r 2 and R 3 are independently selected from the group consisting of thienyl, thiophene derivative group, furyl, furan derivative group, phenyl, benzene derivative group, pyridyl, and pyridine derivative group.
Preferably, R and R 1 are independently selected from alkoxy chains, sugar groups or other water-solubilizing groups, and R 2 and R 3 are thienyl, furyl, phenyl or pyridyl R and R1 function primarily to increase the hydrophilicity of pyrrolopyrrolediones and tetrastyrenes, ideally all hydrophilic groups are sufficient, as exemplified by hydrophilic groups commonly found in the art.
in the pyrrolopyrrole diketone compound, R 2 and R 3 are mainly a conjugated system for increasing molecules, so that common aryl or aromatic heterocyclic groups meet the requirements, and the common substituent groups which are easy to obtain are listed.
The pyrrolopyrrole diketone compound and the tetrabenzyle compound are synthesized and purchased according to the conventional method reported in the prior literature.
in the pyrrolopyrroledione compound/tetrabenzene compound composite nano particle, the pyrrolopyrroledione compound is used as an energy donor, and the tetrabenzene compound is used as an energy receptor. The pyrrolopyrroledione derivative of the present invention is easily decomposed by hypochlorite oxidation, while the fluorescent molecule (FRET energy donor) of the tetrastyrene compound does not change.
In a preferable scheme, the pyrrolopyrrole diketone compound/tetrabenzene compound composite nano particle is formed by molecular self-assembly of pyrrolopyrrole diketone compound and tetrabenzene compound according to a molar ratio of 1: 3-5.
in a preferable scheme, the pyrrolopyrrole diketone compound/tetrastyrene compound composite nano particle is applied to ratio type detection of hypochlorite ions in a water system or ratio type imaging analysis of hypochlorite ions in an intracellular environment.
The pyrrolo-pyrrole diketone compound/tetra-styrene compound composite nano particle has a dual fluorescence emission function.
The preparation method of the pyrrolopyrrole diketone compound/tetrabenzene compound composite nano particle comprises the steps of adding the pyrrolopyrrole diketone compound and the tetrabenzene compound into water and carrying out ultrasonic treatment to obtain the pyrrolopyrrole diketone compound/tetrabenzene compound composite nano particle.
In a preferable scheme, the mol ratio of the pyrrolopyrrole diketone compound to the tetrabenzyl compound is 1: 3-5.
In a preferable scheme, the total concentration of the pyrrolopyrrole diketone compound and the tetrabenzene compound in water is 30-60 mu M/L.
according to the technical scheme, the stable FRET fluorescent nanoparticles are obtained through self-assembly of hydrophilic modified tetrabenzyl molecules and hydrophilic modified pyrrolopyrrole diketone molecules, wherein the tetrabenzyl molecules are typical Aggregation Induced Emission (AIE) molecules, and a FRET energy donor of the tetrabenzyl molecules is introduced to serve as a recognition unit of ClO - , so that a ratio-type nano sensor is constructed and can be used for ratio-type detection of ClO - .
Compared with the prior art, the technical scheme of the invention has the beneficial technical effects that:
The pyrrolopyrrole diketone molecules in the pyrrolopyrrole diketone compound/tetrastyrene compound composite nanoparticles have the specific recognition capability on ClO - , are easy to be selectively oxidized and decomposed by ClO - , have strong fluorescence emission and two-photon induced fluorescence emission, and the tetrastyrene molecules are used as energy donors of FRET nanoparticles, so that high-selectivity and sensitivity ratio-type detection and ratio-type two-channel cell imaging of ClO - can be realized.
In the FRET nano particle, the tetrastyrene molecules and the pyrrolopyrrole diketone molecules are assembled together to form the micelle, and the tetrastyrene molecules play a role in maintaining the stable structure of the nano micelle and can keep the stability of the multifunctional nano particle.
The preparation method of the pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nano particle is simple, low in cost and beneficial to large-scale production and application.
drawings
FIG. 1 is a schematic diagram of self-assembly of pyrrolopyrrole dione compounds and tetrastyrene compounds into FRET nanoparticles;
FIG. 2 is a graph showing the particle size and fluorescence spectrum of FRET nanoparticles;
Fig. 3 is a fluorescence emission spectrum of FRET nanoparticles with different concentrations of ClO - added;
FIG. 4 is a bar graph of fluorescence response of FRET nanoparticles to different reactive oxygen species;
Fig. 5 is a ClO - fluorescence imaging of FRET nanoparticles used in hela cells.
Detailed Description
For a better understanding of the contents of the present patent, the technical solutions of the present invention are further described below by specific examples and figures. However, these examples do not limit the present invention.
Example 1
Preparation of FRET nanoparticles based on thienylpyrrolopyrroledione derivatives. As shown in fig. 1, this example uses two alkoxy (oligo-polyethylene glycol) modified fluorescent molecules (NDPP and TPE1, both formula shown in fig. 1) as raw materials to prepare FRET nanoparticles. Two fluorescent compounds were added to water at a ratio of NDPP to TPE1 of 1:4 to give a total concentration of 50. mu.M/L. And (3) preparing the required composite nano particles after ultrasonic treatment for 1 minute. As shown in fig. 2, the left graph shows the FRET nanoparticle size morphology measured by Transmission Electron Microscopy (TEM), which indicates that regular particles with spherical shape can be obtained by co-assembling NDPP and TPE 1. The right panel in fig. 2 is a graph of the fluorescence emission of the nanoparticles. By comparison, the fluorescence intensity of TPE1 particles was about 87% less after mixing with NDPP than before, indicating that there is a strong FRET effect between the two molecules.
Example 2
The fluorescence emission spectrum of the FRET nanoparticle responding to ClO - is shown in figure 3. in aqueous solution, the FRET nanoparticle has emission peaks at 490nM and 554nM, which respectively correspond to the characteristic fluorescence emission of TPE1 and NDPP. with the addition of ClO - , the fluorescence of TPE1 is gradually enhanced, and the fluorescence intensity of NDPP is gradually reduced. the detection limit of the FRET nanoparticle on ClO - in water can reach 92nM as calculated by the slope of the fitting curve obtained by the right graph in figure 3, and the method can be used for real-time monitoring of ClO - in water environment.
Example 3
Specific observation of the response of FRET nanoparticles to ClO - is shown in FIG. 4. an aqueous solution of 8 parts of FRET nanoparticles, numbered 1-8, was prepared with PBS buffer, and water, H 2 O 2 OH, &lTtTtransition = 9668; 861 8620C, 96581: 9668861/\\\/8620, (8 &/&tTt9668; 861861861861/\\ 8620, (96581,96689j \\/86120j, 9658 &lTtTtTtG O 2 · - , t-BuOOH and ClO - . the maps indicate that other active oxygen has little effect on the fluorescence emission of the solution in addition to ClO - . this comparative experiment indicates that the nanoparticles have good selectivity in the ClO - assay in the present invention.
Example 4
as shown in figure 5, the FRET nano-particles can well enter the Hela cells, fluorescence pictures obtained by two channels can clearly show cytoplasm and cell nucleus, the fluorescence signal of a blue channel (420 and 520nm) in the cells is gradually enhanced, and the fluorescence signal of a green channel (530 and 650nm) in the cells is gradually weakened along with the increase of the concentration of the sodium hypochlorite solution, so that the ratio type fluorescence imaging of ClO - in the cells can be basically realized.

Claims (4)

1. The application of the composite nano particle of the pyrrolopyrrole diketone compound/the tetrastyrene compound is characterized in that: the fluorescent probe is applied to the detection or imaging of hypochlorite ions; said use is non-disease diagnostic or disease therapeutic;
The pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles are formed by molecular self-assembly of a pyrrolo-pyrrole-dione compound and a tetra-styrene compound;
The tetrastyrene compound has the structure of formula 1:
the pyrrolopyrrole dione compound has a structure of formula 2:
Wherein the content of the first and second substances,
R and R 1 are independently selected from hydrophilic groups;
r 2 and R 3 are independently selected from the group consisting of thienyl, thiophene derivative group, furyl, furan derivative group, phenyl, benzene derivative group, pyridyl, and pyridine derivative group.
2. The application of the pyrrolopyrrole diketone compound/tetrastyrene compound composite nanoparticle according to claim 1, wherein the pyrrolopyrrole diketone compound/tetrastyrene compound composite nanoparticle is characterized in that:
R and R 1 are independently selected from alkoxy chains, saccharide groups or other water-soluble groups;
R 2 and R 3 are thienyl, furyl, phenyl or pyridyl.
3. the application of the pyrrolopyrrole diketone compound/tetrastyrene compound composite nanoparticle according to claim 1, wherein the pyrrolopyrrole diketone compound/tetrastyrene compound composite nanoparticle is characterized in that: the pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles are formed by molecular self-assembly of a pyrrolo-pyrrole-dione compound and a tetra-styrene compound according to a molar ratio of 1: 3-5.
4. The application of the pyrrolopyrrole dione compound/tetrastyrene compound composite nanoparticles according to any one of claims 1 to 3, wherein the applications comprise: the method is applied to ratio-type detection of hypochlorite ions in a water system or ratio-type imaging analysis of hypochlorite ions in an intracellular environment; the use is non-disease diagnostic or disease therapeutic.
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