CN109097027A - Application of the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle in hypochlorite ion detects - Google Patents
Application of the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle in hypochlorite ion detects Download PDFInfo
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Abstract
The invention discloses a kind of application of the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle in hypochlorite ion's detection, the compound particle has fluorescence resonance energy transfer effect (FRET) and good aqueous solubility, it can be achieved that ClO in aqueous systems‑High sensitivity and optional ratio's type detection or intracellular ClO‑Fluorescence imaging, can be widely applied to the fields such as biological detection, imaging.
Description
Technical field
The present invention relates to one kind to have fluorescence energy transfer nanoparticle, in particular to one kind is by dione pyrrolo-pyrrole
The composite nano-granule for having fluorescence resonance energy transfer effect (FRET) that compound and tetraphenyl ethylene class compound assemble
Son, for ClO in water body-Detection or intracellular environment imaging, realize ClO-The method of efficient detection, belongs to field of biological detection.
Background technique
Bioactive oxidation object small molecule plays a significant role in terms of physiology and pathology, and concentration level reflects cell
Physio-pathological condition, wherein hypochlorite participates in the intracorporal many of biology as important activating oxide a kind of in organism
Physiology course plays a very important role to health tool, but excessive hypochlorous acid can cause various tissue damages and disease packet
Include cardiovascular disease and injury of lungs etc..Since the intracorporal hypochlorous acid of biology is at faintly acid (pKa=7.63), active in physiological environment
It is high and short there are the time.Therefore the fluorescence probe for designing a kind of highly selective identification hypochlorite has critically important meaning
Justice.The fluorescence probe of detection hypochlorite is based primarily upon hypochlorous strong oxidizing property and is designed at present, including hypochlorous acid induction
Sulphur/selenolite, oxime oxidation, the oxidation of electron rich radical oxidation, double bond and spirolactams oxidation etc., but most of probes have
Quantum efficiency is low, it is anti-light it is Bleachability it is poor, autofluorescence is strong, poorly water-soluble and the deficiencies of poor selectivity, therefore there is an urgent need to design
The good hypochlorous acid fluorescence probe of fast response time, selectivity out.
Different from single molecular fluorescence probe, it is anti-light Bleachability good that fluorescent nano probe has, and fluorescence quantum efficiency is high, water-soluble
Property it is good and the advantages that be easy to functionalization gradually by the favor of researcher.Wherein, there is fluorescence resonance energy transfer
(FRET) fluorescent nano probe of effect can realize the Ratio-type detection to analyte, can be effectively compared with atom environmental background
The interference of fluorescence is a kind of probe building form with applications well prospect.Currently, the preparation of FRET nano-probe is mostly used
Inorganic heavy metal material, potential security threat are an inevitable problems.The preparation of pure organic FRET nano-probe
The then yoke by aggregation fluorescent quenching (ACQ) effect of organic fluorescence materials.
Summary of the invention
In view of the defects existing in the prior art, the purpose of the invention is to provide a kind of dione pyrrolo-pyrrole chemical combination
Object/tetraphenyl ethylene class compound composite nanoparticle is as ClO-The application of the FRET Ratio-type probe of detection.Pyrrolopyrrole
Cyclohexadione compounds/tetraphenyl ethylene class compound composite nanoparticle has using dione pyrrolo-pyrrole molecule to ClO-'s
Specific recognition ability, while having the characteristics that strong fluorescent emission and two-photoninduced fluorescence transmitting, and tetraphenyl ethylene class
Molecule can be used as the characteristics of energy donor of FRET nanoparticle, realize ClO-High sensitivity and optional ratio's type detection
Or Ratio-type binary channels cell imaging.
In order to achieve the above technical purposes, the present invention provides a kind of dione pyrrolo-pyrrole compound/tetraphenyl ethylenes
The application of class compound composite nanoparticle is applied to the detection or imaging of hypochlorite ion as fluorescence probe.
Preferred scheme, the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle by
Dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound are formed by molecular self-assembling;
The tetraphenyl ethylene class compound has 1 structure of formula:
The dione pyrrolo-pyrrole compound has 2 structure of formula:
Wherein,
R and R1It is independently selected from hydrophilic radical;
R2And R3It is independently selected from thienyl, thiophene derivant group, furyl, furan derivatives group, phenyl, benzenesulfonamide derivative
Object group, pyridyl group and pyridine derivate group.
Preferred scheme, R and R1It is independently selected from alkoxy chain, carbohydrate group or other water soluble groups, R2And R3For thiophene
Base, furyl, phenyl or pyridyl group.R and R1 main function is to increase dione pyrrolo-pyrrole compound and tetraphenyl ethylene class
The hydrophily of compound, theoretically for, all hydrophilic radicals are all satisfied requirement, and enumerated is the common parent in this field
Water base group.
R in dione pyrrolo-pyrrole compound of the invention2And R3Mainly increase the conjugated system of molecule, therefore one
As aryl or aromatic heterocyclic be all satisfied requirement, it is above-mentioned to illustrate several frequently seen, to be easily obtained substituent group.
Dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound of the invention is according to existing literature report
Conventional method synthesis is commercially available.
Pyrroledione in dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle
Class compound is as energy donor, and tetraphenyl ethylene class compound is as energy acceptor.Pyrrolo-pyrrole-dione of the invention is derivative
Object is easy to by hypochlorite oxygenolysis, and tetraphenyl ethylene class compound fluorescent molecule (FRET energy donor) does not change.
Preferred scheme, the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle by
Dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound are formed 1:3~5 in molar ratio by molecular self-assembling.
Preferred scheme, dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle are applied to
In aqueous systems hypochlorite ion Ratio-type detection or intracellular environment in hypochlorite ion Ratio-type imaging analysis.
Dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle has double fluorescence
Emission function.
Dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle preparation side
Method, this method are to be added to the water dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound, ultrasonic treatment to get.
Preferred scheme, dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound 1:3~5 in molar ratio.
Preferred scheme, the total concentration of dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound in water are 30
~60 μM/L.
Technical solution of the present invention is by the pyrrolo-pyrrole-dione of the tetraphenyl ethylene class molecule of hydrophilic modification and hydrophilic modification
Class molecule obtains stable FRET fluorescent nano particle by self assembly.Tetraphenyl ethylene class molecule itself is a kind of typical poly-
Collect induced luminescence (AIE) molecule, by its FRET energy donor, while introducing a kind of dione pyrrolo-pyrrole fluorescent molecule conduct
ClO-Recognition unit can be used for ClO to construct a kind of nano-sensor of Ratio-type-Ratio-type detection.
Compared with the prior art, technical solution of the present invention bring advantageous effects:
Pyrrolo- in dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle
Pyrrole-dione molecule has to ClO-Specific recognition ability, be easy to by ClO-Selective oxidation decomposes, while having strong
Fluorescent emission and two-photoninduced fluorescence transmitting, and energy donor of the tetraphenyl ethylene class molecule as FRET nanoparticle, from
And ClO may be implemented-The detection of highly selective and sensitivity Ratio-type and Ratio-type binary channels cell imaging.
Tetraphenyl ethylene class molecule and dione pyrrolo-pyrrole molecule assemble to be formed altogether in FRET nanoparticle of the invention
Micella, tetraphenyl ethylene class molecule play the role of maintaining the rock-steady structure of nano-micelle, are able to maintain the steady of multifunctional nanoparticle
It is qualitative.
Dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle preparation method letter
Single, low cost, is conducive to large-scale production and application.
Detailed description of the invention
[Fig. 1] is that dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound are self-assembled into FRET nanoparticle
Schematic diagram;
[Fig. 2] is the partial size and fluorescence pattern of FRET nanoparticle;
[Fig. 3] is with various concentration ClO-Addition, the fluorescence emission spectrogram of compound of FRET nanoparticle;
[Fig. 4] is fluorescence response histogram of the FRET nanoparticle to different activities oxygen;
[Fig. 5] is FRET nanoparticle for the ClO in HeLa cell-Fluorescence imaging.
Specific embodiment
The content of patent for a better understanding of the present invention further illustrates this below by specific example and legend
The technical solution of invention.But these embodiments are not intended to limit the present invention.
Embodiment 1
The preparation of FRET nanoparticle based on thienyl Diketopyrrolopyrrolederivative derivative.As shown in Figure 1, this embodiment
Fluorescent molecule (NDPP and TPE1, the two molecular formula are as shown in Figure 1) with two kinds of alkoxies (oligomeric polyethylene glycol) modification is original
Material is to prepare FRET nanoparticle.In water, two kinds of fluorescent chemicals are added in the ratio that NDPP:TPE1 is 1:4, keep it total dense
Degree is 50 μM/L.Ultrasound was prepared into required composite nanometer particle after 1 minute.As shown in Fig. 2, left figure show transmission electron microscope
(TEM) the FRET nano particle diameter pattern measured illustrates that NDPP and TPE1 assemble the regular particle that can get spherical shape altogether.Fig. 2
Middle right figure is the fluorescent emission figure of nano particle.After comparing it is found that mixing with NDPP, the fluorescence intensity of TPE1 particle is compared
In less before about 87%, this illustrates that there are strong FRET effects between two molecules.
Embodiment 2
FRET nanoparticle is to ClO-The fluorescence emission spectrum of response is as shown in Figure 3.In aqueous solution, FRET nanoparticle
FRET nanoparticle has emission peak in 490nm and 554nm, corresponds respectively to the characteristic fluorescence transmitting of TPE1 and NDPP.With
ClO-Addition, the fluorescence of TPE1 gradually increases, and the fluorescence intensity of NDPP gradually weakens.It is fitted as obtained by right figure in Fig. 3
Slope of a curve can calculate, the FRET nanoparticle in water FRET nanoparticle to ClO-Detection limit can reach 92nM,
It can be used for ClO in water environment-Real time monitoring.
Embodiment 3
FRET nanoparticle is to ClO-The specificity of response is investigated as shown in Figure 4.8 parts of FRET are prepared with PBS buffer solution to receive
The aqueous solution of rice corpuscles, number 1-8.Then water, H are separately added into 1-8 sample2O2,·OH,1O2,NO·,ONOO-,t-BuOOH
And ClO-.Map shows: removing ClO-Outside, other active oxygens have little effect the fluorescent emission of solution.The comparative test explanation
FRET nanoparticle in the present invention is in ClO-It is had good selectivity in detection.
Embodiment 4
FRET nanoparticle is to ClO in cell-The application of fluorescence imaging is as shown in Figure 5.Cultured with suitable thin
In the culture dish of born of the same parents' concentration, the FRET nanoparticle DPBS solution that 50 μM/L is added is incubated for 0.5 hour.Training is washed away with DPBS solution
After supporting the FRET nanoparticle in ware, cell is imaged using confocal fluorescent microscopic.As shown in figure 5, FRET nanometers
Particle can enter HeLa cell well, and fluorescence picture obtained by two kinds of channels can clearly show cytoplasm and nucleus.With
The increase of liquor natrii hypochloritis's concentration, the fluorescence signal of intracellular blue channel (420-520nm) gradually increase, and green is logical
The fluorescence signal in road (530-650nm) gradually weakens.This can realize intracellular ClO substantially-Ratio-type fluorescence imaging.
Claims (5)
1. a kind of application of dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle, feature exist
In: it is applied to the detection or imaging of hypochlorite ion as fluorescence probe.
2. a kind of dione pyrrolo-pyrrole compound according to claim 1/tetraphenyl ethylene class compound composite Nano
The application of particle, it is characterised in that: the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle
It is formed by dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound by molecular self-assembling;
The tetraphenyl ethylene class compound has 1 structure of formula:
The dione pyrrolo-pyrrole compound has 2 structure of formula:
Wherein,
R and R1It is independently selected from hydrophilic radical;
R2And R3It is independently selected from thienyl, thiophene derivant group, furyl, furan derivatives group, phenyl, benzene derivative base
Group, pyridyl group and pyridine derivate group.
3. a kind of dione pyrrolo-pyrrole compound according to claim 1/tetraphenyl ethylene class compound composite Nano
The application of particle, it is characterised in that:
R and R1It is independently selected from alkoxy chain, carbohydrate group or other water soluble groups;
R2And R3For thienyl, furyl, phenyl or pyridyl group.
4. a kind of dione pyrrolo-pyrrole compound according to claim 2/tetraphenyl ethylene class compound composite Nano
The application of particle, it is characterised in that: the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle
By dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound, 1:3~5 are formed by molecular self-assembling in molar ratio.
5. a kind of dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound according to any one of claims 1 to 4
The application of composite nanoparticle, it is characterised in that: applied to the Ratio-type detection of hypochlorite ion in aqueous systems or intracellular
The Ratio-type imaging analysis of hypochlorite ion in environment.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN114213338A (en) * | 2021-12-30 | 2022-03-22 | 深圳市质量安全检验检测研究院 | Method for preparing pH sensing compound and method for preparing metal coating piece |
WO2022114573A1 (en) * | 2020-11-25 | 2022-06-02 | 경희대학교 산학협력단 | Fluorescent probe for detecting adenosine triphosphate and use thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104818013A (en) * | 2015-03-20 | 2015-08-05 | 中南大学 | Application of diketopyrrolopyrrole derivative in detection of Hg<2+> |
CN106478458A (en) * | 2015-08-31 | 2017-03-08 | 香港科技大学深圳研究院 | Schiff base compound based on tetraphenylethylene and Maleic nitrile and its preparation method and application |
CN107502344A (en) * | 2017-09-12 | 2017-12-22 | 中南大学 | Based on dione pyrrolo-pyrrole compound and the multi-functional organic fluorescence nano particle of tetraphenyl ethylene class compound and preparation and application |
CN107677659A (en) * | 2017-09-27 | 2018-02-09 | 中南大学 | Application of the dione pyrrolo-pyrrole dyestuff in the detection of trace bivalent cupric ion |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104818013A (en) * | 2015-03-20 | 2015-08-05 | 中南大学 | Application of diketopyrrolopyrrole derivative in detection of Hg<2+> |
CN106478458A (en) * | 2015-08-31 | 2017-03-08 | 香港科技大学深圳研究院 | Schiff base compound based on tetraphenylethylene and Maleic nitrile and its preparation method and application |
CN107502344A (en) * | 2017-09-12 | 2017-12-22 | 中南大学 | Based on dione pyrrolo-pyrrole compound and the multi-functional organic fluorescence nano particle of tetraphenyl ethylene class compound and preparation and application |
CN107677659A (en) * | 2017-09-27 | 2018-02-09 | 中南大学 | Application of the dione pyrrolo-pyrrole dyestuff in the detection of trace bivalent cupric ion |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022114573A1 (en) * | 2020-11-25 | 2022-06-02 | 경희대학교 산학협력단 | Fluorescent probe for detecting adenosine triphosphate and use thereof |
CN114213338A (en) * | 2021-12-30 | 2022-03-22 | 深圳市质量安全检验检测研究院 | Method for preparing pH sensing compound and method for preparing metal coating piece |
CN114213338B (en) * | 2021-12-30 | 2023-12-22 | 深圳市质量安全检验检测研究院 | preparation method of pH sensing compound and preparation method of metal coating piece |
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