CN101021537A - Fluorescent probe for detecting cell hydroxyl radical, and synthesis method and use - Google Patents
Fluorescent probe for detecting cell hydroxyl radical, and synthesis method and use Download PDFInfo
- Publication number
- CN101021537A CN101021537A CN 200710013008 CN200710013008A CN101021537A CN 101021537 A CN101021537 A CN 101021537A CN 200710013008 CN200710013008 CN 200710013008 CN 200710013008 A CN200710013008 A CN 200710013008A CN 101021537 A CN101021537 A CN 101021537A
- Authority
- CN
- China
- Prior art keywords
- solution
- hydroxyl radical
- fluorescence probe
- fluorescence
- room temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Abstract
The invention provides a fluorescence probe, the synthetic method and the use which is to test the cell hydroxyl free radical. The process is: a. heat and chloroauric acid of 150.0 weight concentration and back flow, with mixing, the sodium citrate of 5.0-7.0 is added into the solution to back flow for 10-20min, then to cool in room temperature to get the golden nanometer particle solution; b. mix the particle with the DNA single chain with 5'end modified fluorescein and 3'end modified sulfydryl according to 1:200-500, then to set in room temperature for 1224h, last to adjust the pH by the phosphoric buffer; next to mix the mixture with the 0.5-5mol/L NaCl according to 1:0.1-0.3(V/V) which is set in room temperature for 35-45h; last to centrifugate to remove the upper solution and the deposition is solved in the 0.1-0.3mol/L phosphoric buffer which is the fluorescence probe solution.
Description
Technical field:
The invention belongs to Measurement for Biotechnique and clinical medicine detection range, relate to the fluorescence probe that detects cell hydroxyl radical; The synthetic method that relates to this fluorescence probe simultaneously; In addition, the purposes that also relates to this fluorescence probe.
Background technology:
Produce various free radicals in the metabolic process of vital movement, the aging of biosome and the generation of numerous disease and free radical all have important relationship.Free radical can mediate the many important course of reaction of vital movement, participate in cellular immune function, histiocytic chemical constitution is taken place by destructive the modification, the form and film function (the Witz G. of damage normal tissue cell, Proc.Soc.Exp.Biol.Med.1991,198:675; Feig D.I., Reid T.M., Leob L.A., Cancer Res.1994,54:1890s; Finkl T., Hol brook N.J., Nature 2000,408:239).Hydroxy radical is the very strong free radical of a kind of oxidability, various organism of its oxidation at an easy rate and inorganics, the oxidation efficiency height, reaction rate is fast, be to cause the active oxygen of organizing lipid peroxidation, nucleic acid fracture, protein and polysaccharide to decompose, relevant (de Lara C.M., JennerT.J., Townsend K.M.S. with aging, tumour, radiation damage and the cytophagy of body, Marsden S.J., O ' Neill P., Radiat.Res.1995,144:43; StadtmanE.R., Annu.Rev.Biochem.1993,62:797; Tien M., Svingen B.A., Arch.Biochem.Biophys.1982,216:142).
Radical life is short, content is low, kind is many, is one of the most difficult problem of life science and chemical analysis field to its detection.Hydroxyl radical free radical as produce in a kind of vital movement process present oneself know the free radical that oxidisability is the strongest, its detection is particularly important.The main method of the detection hydroxy radical of domestic and foreign literature report has electron spin resonance (Huycke M.M., Moore D.R., Free Rad.Bio.Med.2002,33:818), high performance liquid chromatography (Kaur H., Hsllinell B., Anal.Biochem.1994,220:11), fluorescence method (Ou B., Hampsch-Woodill, M., Flanagan J., Deemer E.K., Prior R.L., Huang D., J.Agric.Food Chem.2002,50:2772; Shinichiro T., Hideaki I., Shota T., TatsuyaS., Fumiaki H., Mitsunobu N., Tetsuo N., Neurosci Res.2005,53:304).Fluorescence detection is highly sensitive, selectivity good, response speed is fast, demonstrates stronger superiority than other method, in conjunction with the burnt micro-imaging technique of copolymerization, can realize the detection of active somatic cell and in-house active oxygen " real-time, visible, quantitative ".Reported at present and be used for fluorescence probe (Sasaki E., Kojima H., Nishimatsu H., the Urano Y. that cell intracellular nitric oxide and hydrogen peroxide are detected as picture, Kikuchi K., Hirata Y., Nagano T., J.Am.Chem.Soc.2005,127,3684; Xu K H., Tang B., Huang H., Yang G.W., Chen Z.Z., Li P., An L.G., Chem.Commun.2005,48,5974), and be used for the fluorescence probe that hydroxyl radical free radical in the cell is detected as picture based on the FRET (fluorescence resonance energy transfer) principle and do not appear in the newspapers as yet.
Summary of the invention:
It is short that one of purpose of the present invention provides a kind of response time, measure highly sensitive, the good penetrability of pair cell, toxic and side effect is little, the fluorescence oligonucleotide probe that is applicable to that hydroxyl radical free radical detects in the biosome based on the golden quencher of FRET (fluorescence resonance energy transfer) principle, be the hydroxyl radical free radical detection of low content in the biological sample, inquire into human diseases and the mechanism that wears out and the early diagnosis and the prevention of some major disease, good supplementary means is provided; Two of purpose provides the synthetic method of simple this fluorescence probe of a kind of technology; Three of purpose provides the purposes of this fluorescence probe.
One of purpose of the present invention can realize by following technical measures:
The carrier that fluorescence probe of the present invention selects DNA oligonucleotide chain strand to take place as FRET (fluorescence resonance energy transfer), 5 ' terminal modified fluorescein (the excitation wavelength 490nm, emission wavelength 520nm) as energy donor, 3 ' the terminal modified sulfydryl bonding golden nanometer particle is as energy acceptor, and this probe has following structural formula:
In the formula
AGGGTTAGGG:DNA oligonucleotide chain strand, any base sequence, the base number is 2-30;
Fluorescein: X
1, X
2=F, Cl, CH
3, OCH
3
Golden nanometer particle: diameter is 3-32nm.
Two of purpose of the present invention can realize by following technical measures:
This synthetic method is carried out as follows:
A. getting weight concentration is the chlorauric acid solution 150.0 parts by volume reflux of 0.01-0.02%, stirring down, the adding weight concentration is the citric acid three sodium solution 5.0-7.0 parts by volume of 1.0-2.0%, continue backflow 10-20 minute, place cooling under the room temperature, get solution of gold nanoparticles;
B. with the dna single chain of the solution of gold nanoparticles and 5 ' terminal modified fluorescein 3 ' the terminal modified sulfydryl according to 1: 200-500 amount of substance proportioning mixing, placed 12-24 hour under the room temperature, transfer pH=7.0-7.8 with phosphate buffer again; The sodium chloride solution that will be 0.5-5mol/L through the mixed liquor and the amount of substance concentration of adjust pH is by 1 then: 0.1-0.3 parts by volume proportioning mixing, placed 35-45 hour under the room temperature; After centrifugal, remove supernatant liquor, resolution of precipitate is in the phosphate buffer solution of 0.1-0.3mol/L in amount of substance concentration, fluorescence probe solution.
Three of purpose of the present invention can realize by following technical measures:
Described fluorescence probe is used for chemical system, the detection of chemical simulation living things system hydroxyl radical free radical, the detection of the fluorescence imaging of the hydroxyl radical free radical in biological living cells and the living tissue, and the detection of hydroxyl radical free radical in the pathological tissues on the clinical medicine.For inquiring into human diseases and the mechanism that wears out and the early diagnosis and the prevention of some major disease, provide good supplementary means.
The fluorescence oligonucleotide probe of golden quencher of the present invention is synthetic at aqueous phase, adds in the suitable damping fluid that contains cell and tissue usually and tests.
The present invention is based on the FRET (fluorescence resonance energy transfer) principle, utilize the interior hydroxy radical of fluorescence oligonucleotide probe selectivity identification living cells of golden quencher.Probe selects DNA oligonucleotides strand as the carrier that FRET (fluorescence resonance energy transfer) takes place, and 5 ' the terminal modified fluorescein is as energy donor, and 3 ' the terminal modified sulfydryl bonding golden nanometer particle is as energy acceptor.Golden nanometer particle has high extinction coefficient makes fluorescence probe have low blank fluorescence signal; Hydroxyl radical free radical causes that the DNA bound rupture causes the FRET (fluorescence resonance energy transfer) phenomenon to disappear, and the fluorescence of golden nanometer particle quench fluorescence element is restored thereupon, realizes the detection of the cell hydroxyl radical of nanomole level concentration in view of the above.
The conventional method that hydroxyl radical free radical detects in the cell is with cultured cell separated into two parts, a part stimulates with the stimulant phorbol ester, make and produce a large amount of ultra-oxygen anion free radicals in the cell, free chain reaction afterwards can generate hydroxyl radical free radical, after the nutrient solution flushing, carry out the laser co-focusing micro-imaging.Stimulated cells does not obtain blank contrast images with the laser confocal microscope imaging.
Fluorescence probe of the present invention has important use and is worth, and this probe response time is short, measures highly sensitive, the good penetrability of pair cell, toxic and side effect is little, makes this class probe as the reagent of hydroxyl radical free radical in the mensuration biosome good actual value be arranged.
The concrete feature of fluorescence probe of the present invention is as follows:
1, the design of fluorescence probe of the present invention is based on the FRET (fluorescence resonance energy transfer) principle, and golden nanometer particle has high extinction coefficient, brings into play outstanding fluorescence quenching in the FRET (fluorescence resonance energy transfer) that fluorescein-golden nanometer particle is formed for acceptor centering.Hydroxy radical makes DNA oligonucleotides strand discharge free base to the oxidative attack meeting of ribodesose part, cause DNA bound rupture and abasic site, hydroxy radical causes that the DNA bound rupture causes the FRET (fluorescence resonance energy transfer) phenomenon to disappear, the fluorescence of golden nanometer particle quench fluorescence element is restored thereupon, realizes the mensuration of hydroxyl radical free radical.Fluorescence probe shows good selectivity, and the glutathione that exists in the active oxygen of other kind that exists in the body and the body does not cause interference to detection.
2, fluorescence probe of the present invention is 8.0 * 10 to the sensing range of hydroxyl radical free radical
-9-1.0 * 10
-6Mol/L can detect hydroxyl radical free radical in the cell of nanomolar concentration.Laser confocal microscope imaging experiment proof probe molecule can permeates cell membranes enters cell interior and catches hydroxyl radical free radical, and itself does not have toxic and side effect pair cell, and the hydroxyl radical free radical content of nanomole level detects in can pair cell.
3, fluorescence probe of the present invention is selected the acceptor of golden nanometer particle as FRET (fluorescence resonance energy transfer), has the wide range absorption at ultraviolet region and visible region, can effectively avoid the interference of cell autofluorescence, improve the selectivity and the sensitivity of detection method, minimizing helps live body and detects the damage of life entity.
Description of drawings:
Fig. 1 is the emission spectrogram of system after the hydroxyl radical free radical effect of fluorescence probe of the present invention and variable concentrations, the scavenger dimethyl sulfoxide (DMSO) that comprises hydroxyl radical free radical in the spectrogram is used for further confirming the practicality of probe, horizontal ordinate is wavelength (Wavelength/nm), and ordinate is fluorescence intensity (Counts);
Fig. 2 is the fluorescence intensity of system after fluorescence probe of the present invention and the hydroxyl radical free radical effect and the relation in reaction time, and horizontal ordinate is time (Time), and ordinate is relative intensity of fluorescence (Counts);
Fig. 3 is fluorescence probe contrast hydroxyl radical free radical of the present invention (OH) and hydrogen peroxide (H
2O
2), peroxide nitroso-negative ion (ONOO), ultra-oxygen anion free radical (O
2-.), singlet oxygen (
1O
2), glutathione (GSH), sodium hypochlorite (NaClO), nitric oxide free radical (NO), the fluorescence response of fat peroxy radical (ROO), horizontal ordinate are various free radicals and biologic artifact, ordinate is corresponding fluorescence intensity (Counts);
Fig. 4 is the laser co-focusing micro-imaging of fluorescence probe research mouse macrophage of the present invention (RAW 264.7);
Fig. 5 is the fluorescence probe fundamental diagram.
Probe is selective to the hydroxyl free base:
Contrasted the fluorescence response of probe to hydroxyl free base and other free radical and biologic artifact. Final concentration The hydrogen peroxide of 1umol/L, peroxynitrite, ultra-oxygen anion free radical, singlet oxygen, the paddy Guang is sweet Peptide, clorox, the nitric oxide free radical, the fat peroxy radical is added to the phosphoric acid buffer that contains probe pH=7.4 In the solution, the probe excitation wavelength is 490nm, and emission wavelength is 520nm, and test result is shown among Fig. 3. From Can see among the figure that compound has very high sensitivity to the hydroxyl free base, the adding of hydroxyl free base produces phase To strong fluorescence signal, and the interference of the active oxygen fluorescence background of other kind is extremely low, has shown that probe for hydroxyl certainly Good selectivity by base.
Cell is cultivated:
RAW 264.7 cells are cultivated by the DMEM in high glucose nutrient solution, before the imaging, cell attachment on Cover Glass, a part Cell stimulated 30 minutes or 1 hour with stimulant phorbol ester (2ng/ml), and the cell that does not stimulate is as blank, then Add the probe buffer solution, hatched 30 minutes in 37 ℃, carry out Laser scanning confocal microscopy.
Laser confocal imaging
As can be seen from Figure 3, the macrophage inside that stimulates without the stimulant phorbol ester contain amount very little, Be difficult to carry out fluorescent imaging (macrophage of Fig. 4 a), hatching through probe stimulated respectively 30 minutes through phorbol ester and Send strong fluorescence (Fig. 4 b and Fig. 4 c) after 1 hour, show that the hydroxyl free base that the cell internal stimulus generates cuts off The dna single chain causes the FRET phenomenon to disappear, and the fluorescein fluorescence signal recovers. Fig. 4 d is thin under the bright field Born of the same parents' image.
Embodiment
Embodiment 1:
Synthesizing of probe
In the formula
AGGGTTAGGG:DNA oligonucleotide chain strand, any base sequence, the base number is 2-30;
Fluorescein: X
1, X
2=F, Cl, CH
3, OCH
3
SH: sulfydryl
Golden nanometer particle: diameter is 3-32nm.
A. get weight concentration and be 0.01% chlorauric acid solution 150.0mL in the conical flask of 250mL, reflux, the adding weight concentration is 2.0% citric acid three sodium solution 5.0mL under stirring, and continues to reflux 20 minutes, at room temperature place cooling, obtain the peony solution of gold nanoparticles; The transmission electron microscope result shows that the mean grain size of particle is 15.5nm, and by the complete reaction estimation, particle concentration is 1.2 * 10
15/ L.
B. with the dna single chain of the solution of gold nanoparticles and 5 ' terminal modified fluorescein 3 ' the terminal modified sulfydryl according to 1: 200 amount of substance proportioning mixing, placed 24 hours under the room temperature, transfer pH=7.0 with phosphate buffer again; The sodium chloride solution that will be 5mol/L through the mixed liquor and the amount of substance concentration of adjust pH was placed 45 hours under the room temperature by 1: 0.1 parts by volume proportioning mixing then; After centrifugal, remove supernatant liquor, resolution of precipitate is in the phosphate buffer solution of 0.1mol/L in amount of substance concentration, fluorescence probe solution.
Embodiment 2:
A. get weight concentration and be 0.02% chlorauric acid solution 150.0mL in the conical flask of 250mL, reflux, the adding weight concentration is 1.0% citric acid three sodium solution 7.0mL under stirring, and continues to reflux 10 minutes, at room temperature place cooling, obtain the peony solution of gold nanoparticles; The transmission electron microscope result shows that the mean grain size of particle is 15.9nm, and by the complete reaction estimation, particle concentration is 1.2 * 10
15/ L.
B. with the dna single chain of the solution of gold nanoparticles and 5 ' terminal modified fluorescein 3 ' the terminal modified sulfydryl according to 1: 500 amount of substance proportioning mixing, placed 12 hours under the room temperature, transfer pH=7.8 with phosphate buffer again; The sodium chloride solution that will be 0.5mol/L through the mixed liquor and the amount of substance concentration of adjust pH was placed 35 hours under the room temperature by 1: 0.3 parts by volume proportioning mixing then; After centrifugal, remove supernatant liquor, resolution of precipitate is in the phosphate buffer solution of 0.3mol/L in amount of substance concentration, fluorescence probe solution.
Embodiment 3:
A. get weight concentration and be 0.015% chlorauric acid solution 150.0mL in the conical flask of 250mL, reflux, the adding weight concentration is 1.5% citric acid three sodium solution 6.0mL under stirring, and continues to reflux 15 minutes, at room temperature place cooling, obtain the peony solution of gold nanoparticles; The transmission electron microscope result shows that the mean grain size of particle is 15.7nm, and by the complete reaction estimation, particle concentration is 1.2 * 10
15/ L.
B. with the dna single chain of the solution of gold nanoparticles and 5 ' terminal modified fluorescein 3 ' the terminal modified sulfydryl according to 1: 350 amount of substance proportioning mixing, placed 18 hours under the room temperature, transfer pH=7.5 with phosphate buffer again; The sodium chloride solution that will be 3mol/L through the mixed liquor and the amount of substance concentration of adjust pH was placed 40 hours under the room temperature by 1: 0.2 parts by volume proportioning mixing then; After centrifugal, remove supernatant liquor, resolution of precipitate is in the phosphate buffer solution of 0.2mol/L in amount of substance concentration, fluorescence probe solution.
Claims (3)
1, detect the fluorescence probe of cell hydroxyl radical, it is characterized in that this fluorescence probe has following structural formula:
In the formula
AGGGTTAGGG:DNA oligonucleotide chain strand, any base sequence, the base number is 2-30;
Fluorescein: X
1, X
2=F, Cl, CH
3, OCH
3
Golden nanometer particle: diameter is 3-32nm.
2, detect the synthetic method of the fluorescence probe of cell hydroxyl radical, it is characterized in that this method carries out as follows:
A. getting weight concentration is the chlorauric acid solution 150.0 parts by volume reflux of 0.01-0.02%, stirring down, the adding weight concentration is the citric acid three sodium solution 5.0-7.0 parts by volume of 1.0-2.0%, continue backflow 10-20 minute, place cooling under the room temperature, get solution of gold nanoparticles;
B. with the dna single chain of the solution of gold nanoparticles and 5 ' terminal modified fluorescein 3 ' the terminal modified sulfydryl according to 1: 200-500 amount of substance proportioning mixing, placed 12-24 hour under the room temperature, transfer pH=7.0-7.8 with phosphate buffer again; The sodium chloride solution that will be 0.5-5mol/L through the mixed liquor and the amount of substance concentration of adjust pH is by 1 then: 0.1-0.3 parts by volume proportioning mixing, placed 35-45 hour under the room temperature; After centrifugal, remove supernatant liquor, resolution of precipitate is in the phosphate buffer solution of 0.1-0.3mol/L in amount of substance concentration, fluorescence probe solution.
3, the purposes of the fluorescence probe of the detection cell hydroxyl radical of claim 1, it is characterized in that described fluorescence probe is used for the detection of chemical system, chemical simulation living things system hydroxyl radical free radical, the fluorescence imaging of the hydroxyl radical free radical in biological living cells and the living tissue detects, and the detection of hydroxyl radical free radical in the pathological tissues on the clinical medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710013008 CN101021537A (en) | 2007-01-04 | 2007-01-04 | Fluorescent probe for detecting cell hydroxyl radical, and synthesis method and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710013008 CN101021537A (en) | 2007-01-04 | 2007-01-04 | Fluorescent probe for detecting cell hydroxyl radical, and synthesis method and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101021537A true CN101021537A (en) | 2007-08-22 |
Family
ID=38709373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200710013008 Pending CN101021537A (en) | 2007-01-04 | 2007-01-04 | Fluorescent probe for detecting cell hydroxyl radical, and synthesis method and use |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101021537A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101424642B (en) * | 2008-11-14 | 2010-08-25 | 中国科学院上海应用物理研究所 | Target molecule detecting method based on nanometer aurum and nucleic acid structure |
| CN102127445A (en) * | 2010-12-23 | 2011-07-20 | 江南大学 | Preparation method of self-assembled nano material provided with chiral signal |
| CN102127542A (en) * | 2010-12-27 | 2011-07-20 | 江南大学 | Preparation method of self-assembly material having surface-enhanced Raman activity |
| CN102259834A (en) * | 2011-06-27 | 2011-11-30 | 江南大学 | Method for manufacturing asymmetric tetrahedron assembly structure with chiral signal |
| CN102286371A (en) * | 2011-07-04 | 2011-12-21 | 福建医科大学 | Alternating current impedance type deoxyribonucleic acid (DNA) electrochemical sensor based on probe DNA control assembly interface |
| CN103698374A (en) * | 2013-12-23 | 2014-04-02 | 邢士超 | Electrochemical sensor of DNA (deoxyribonucleic acid) probe based on fluorescein and sulfydryl modification |
| CN103740363A (en) * | 2014-01-16 | 2014-04-23 | 东南大学 | In-situ rapid synthesis gold and silver fluorescence nanometer material based on biomolecules such as nucleosides, preparation method and application of nanometer material |
| CN103760143A (en) * | 2014-01-17 | 2014-04-30 | 上海交通大学 | Manufacture method of nitrogen oxide fluorescent probe based on necklace type gold nanoparticle self-assembling system |
| CN103760145A (en) * | 2014-01-27 | 2014-04-30 | 同济大学 | Ratio fluorescent probe for detecting hydroxyl radical and synthesis method and application of ratio fluorescent probe |
| CN103954565A (en) * | 2014-05-14 | 2014-07-30 | 江南大学 | Method for establishing intracellular plasma chiral platform based on discrete gold nanoparticle dimer |
| CN106610372A (en) * | 2015-10-23 | 2017-05-03 | 清华大学 | Probe and method for detecting catechol and/or hydroquinone |
| CN107389621A (en) * | 2017-06-28 | 2017-11-24 | 中南民族大学 | A kind of hydrogen peroxide and peroxide enzyme assay method based on modified nano gold |
| CN107924580A (en) * | 2015-09-03 | 2018-04-17 | 西门子保健有限责任公司 | The visualization of surface volume mixing module in medical imaging |
| CN110202128A (en) * | 2019-06-25 | 2019-09-06 | 重庆科技学院 | A kind of gold and silver composite Nano cluster, preparation process and the application in biological thiol detection |
| CN112872362A (en) * | 2021-01-12 | 2021-06-01 | 青岛大学 | Gold-loaded tin telluride nanobelt, and preparation method and application thereof |
-
2007
- 2007-01-04 CN CN 200710013008 patent/CN101021537A/en active Pending
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101424642B (en) * | 2008-11-14 | 2010-08-25 | 中国科学院上海应用物理研究所 | Target molecule detecting method based on nanometer aurum and nucleic acid structure |
| CN102127445A (en) * | 2010-12-23 | 2011-07-20 | 江南大学 | Preparation method of self-assembled nano material provided with chiral signal |
| CN102127445B (en) * | 2010-12-23 | 2013-02-27 | 江南大学 | Preparation method of self-assembled nano material provided with chiral signal |
| CN102127542A (en) * | 2010-12-27 | 2011-07-20 | 江南大学 | Preparation method of self-assembly material having surface-enhanced Raman activity |
| CN102259834A (en) * | 2011-06-27 | 2011-11-30 | 江南大学 | Method for manufacturing asymmetric tetrahedron assembly structure with chiral signal |
| CN102286371A (en) * | 2011-07-04 | 2011-12-21 | 福建医科大学 | Alternating current impedance type deoxyribonucleic acid (DNA) electrochemical sensor based on probe DNA control assembly interface |
| CN102286371B (en) * | 2011-07-04 | 2013-07-17 | 福建医科大学 | Alternating current impedance type deoxyribonucleic acid (DNA) electrochemical sensor based on probe DNA control assembly interface |
| CN103698374A (en) * | 2013-12-23 | 2014-04-02 | 邢士超 | Electrochemical sensor of DNA (deoxyribonucleic acid) probe based on fluorescein and sulfydryl modification |
| CN103740363B (en) * | 2014-01-16 | 2015-09-09 | 东南大学 | A kind of original position Fast back-projection algorithm gold and silver fluorescent nano material based on biomolecule such as nucleosides and its preparation method and application |
| CN103740363A (en) * | 2014-01-16 | 2014-04-23 | 东南大学 | In-situ rapid synthesis gold and silver fluorescence nanometer material based on biomolecules such as nucleosides, preparation method and application of nanometer material |
| CN103760143A (en) * | 2014-01-17 | 2014-04-30 | 上海交通大学 | Manufacture method of nitrogen oxide fluorescent probe based on necklace type gold nanoparticle self-assembling system |
| CN103760143B (en) * | 2014-01-17 | 2015-12-09 | 上海交通大学 | Based on the method for making of the nitric oxide fluorescent probe of item chain gold nano grain self-assembly system |
| CN103760145A (en) * | 2014-01-27 | 2014-04-30 | 同济大学 | Ratio fluorescent probe for detecting hydroxyl radical and synthesis method and application of ratio fluorescent probe |
| CN103954565A (en) * | 2014-05-14 | 2014-07-30 | 江南大学 | Method for establishing intracellular plasma chiral platform based on discrete gold nanoparticle dimer |
| CN107924580A (en) * | 2015-09-03 | 2018-04-17 | 西门子保健有限责任公司 | The visualization of surface volume mixing module in medical imaging |
| CN107924580B (en) * | 2015-09-03 | 2021-04-23 | 西门子保健有限责任公司 | Visualization of surface-volume blending modules in medical imaging |
| CN106610372A (en) * | 2015-10-23 | 2017-05-03 | 清华大学 | Probe and method for detecting catechol and/or hydroquinone |
| CN107389621A (en) * | 2017-06-28 | 2017-11-24 | 中南民族大学 | A kind of hydrogen peroxide and peroxide enzyme assay method based on modified nano gold |
| CN110202128A (en) * | 2019-06-25 | 2019-09-06 | 重庆科技学院 | A kind of gold and silver composite Nano cluster, preparation process and the application in biological thiol detection |
| CN112872362A (en) * | 2021-01-12 | 2021-06-01 | 青岛大学 | Gold-loaded tin telluride nanobelt, and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101021537A (en) | Fluorescent probe for detecting cell hydroxyl radical, and synthesis method and use | |
| Kang et al. | A near-infrared fluorescent probe for ratiometric imaging peroxynitrite in Parkinson's disease model | |
| CN110437199B (en) | Selenium cysteine near-infrared fluorescent probe and preparation method and application thereof | |
| CN109395079B (en) | Multifunctional nano probe and preparation method and application thereof | |
| CN108117544A (en) | A kind of reversible sulfur dioxide/sulfurous acid（Hydrogen）The fluorescence probe of salt | |
| CN105802611A (en) | Ratio-type nano silicon quantum dot fluorescence probe and preparation method and application thereof | |
| Zhu et al. | A novel highly sensitive fluorescent probe for bioimaging biothiols and its applications in distinguishing cancer cells from normal cells | |
| CN106749034A (en) | Ratio-type fluorescent labeling reagent and its synthetic method and application are answered to bisulfite and hypochlorite double-bang firecracker | |
| CN104949946B (en) | A kind of application of fluorescence probe in hydrogen peroxide molecule detection | |
| CN109053700A (en) | A kind of hypochlorous acid ratio fluorescent probe and its application | |
| CN112062755B (en) | Near-infrared fluorescent molecular probe for detecting aspartyl aminopeptidase, preparation method and application | |
| CN106404726B (en) | A kind of fluorescence probe based on double-stranded DNA protection and the application in preparing detection plasmodium falciparum lactic dehydrogenase drug | |
| CN108440476A (en) | One kind is used for while detecting hydrazine hydrate and sulfurous acid（Hydrogen）Fluorescence probe of salt and its preparation method and application | |
| CN110615786B (en) | Near-infrared fluorescent compound for detecting viscosity and preparation and application thereof | |
| CN110128414A (en) | A kind of preparation and application of the anoxic fluorescence probe based on hemicyanine dye | |
| CN106544007B (en) | Hypochlorous fluorescence probe and its application in a kind of detection biosystem | |
| WO2015106466A1 (en) | Gold/silver fluorescent nanomaterial synthesized rapidly in-situ on basis of biomolecules such as nucleosides, and preparation method and use for said material | |
| CN105503768B (en) | The preparation method of the fluorescence of alpha ketoglutaric acids/ultraviolet molecular probe and its application in biological specimen | |
| CN107286173A (en) | Rhodol analog derivatives and its preparation method and application | |
| CN114181204A (en) | Near-infrared fluorescent probe for detecting viscosity and preparation and application thereof | |
| CN108640902A (en) | The fluorescence probe of sulfur dioxide and its application in a kind of identification pure aquatic system | |
| CN114478513B (en) | Glutathione fluorescent probe and application thereof | |
| CN111560033A (en) | Synthesis method of light controlled release compound and application of light controlled release compound in tumor treatment | |
| CN108276991B (en) | Two-photon fluorescent probe for detecting pneumonia marker activity and synthetic method | |
| CN110407873A (en) | A kind of tumor microenvironment H2O2Respond cross-linking type near-infrared molecular probe and its application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20070822 |