CN105693654B - A kind of preparation and its application of fluorescence probe HSeSeH - Google Patents
A kind of preparation and its application of fluorescence probe HSeSeH Download PDFInfo
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Abstract
A kind of preparation and its application of fluorescence probe HSeSeH.The present invention provides one kind can be used for selective enumeration method H2The fluorescence probe of S, primary synthetic methods are as fluorescent parent using diselenide, and introducing 2 (2 hydroxy phenyl) benzothiazoles (2 (2 hydroxyphenyl) benzothiazole) generating structure formula is on diselenide parentCompound, utilize the difference of photoluminescent property before and after reaction, indicate H2The presence of S or quantitative determination H2The concentration of S is used especially for detecting intracellular H2S。
Description
Technical field
The present invention relates to fluorescence probe fields, and in particular to a kind of fluorescence probe available for selective enumeration method hydrogen sulfide.
2- (2- hydroxy phenyls) benzothiazole (2- (2-hydroxyphenyl) is introduced in diselenide fluorescent parent
Benzothiazole), two selenium keys and ester bond are chain carrier, probe and H2Apparent enhancing occurs for fluorescence after S effects,
To realize to H2The selective enumeration method of S, the H being particularly applicable in detection biosystem2S。
Background technology
Hydrogen sulfide (H2S it is) a kind of toxic gas being widely present in mammal body, in addition to toxicity, vulcanization
Hydrogen also has protection cell, the function of conducted signal.Whether its Metabolism of Normal with heart disease, hypertension, Down's syndrome, old
A variety of diseases such as dementia disease are associated.Also therefore, how timely and accurately to detect the metabolic condition of intracellular hydrogen sulfide for
It is just particularly important for physiology and pathology.
Fluorescence probe is one of means of hydrogen sulfide in effective detection life entity.One fluorescence probe with application prospect
Should have many advantages, such as that change in fluorescence is apparent, fast to target molecule response, selectivity is good, synthesis is simple before and after effect.In recent years, energy
The fluorescence probe of hydrogen sulfide is not within minority in enough living cells applied to detection, but most synthesis responses are slower, and visible
It is still very few for detecting the fluorescence probe of hydrogen sulfide (smaller to be injured to biological tissue) in the longer section in light area.
The content of the invention
The present invention addresses the above problem, provides a kind of fluorescence that can be used for selective enumeration method intracellular hydrogen sulfide
Probe.Such fluorescence probe, itself has weaker fluorescence, with H2Fluorescence enhances after S effects, and fluorescence intensity direct ratio
In H2S concentration, so as to indicate H2The presence of S or quantitative determination H2The concentration of S.It is particularly applicable to detect intracellular H2S。
The present invention adopts the following technical scheme that：Using diselenide as fluorescent parent, introduced on diselenide parent
2- (2- hydroxy phenyls) benzothiazole (2- (2-hydroxyphenyl) benzothiazole) utilizes photoluminescent property before and after reaction
Difference, indicate H2The presence of S or quantitative determination H2The concentration of S is used especially for detecting intracellular H2S。
Under the structural formula such as structural formula I of the fluorescence probe：
Structure code name：HSeSeH.
The preparation method of the fluorescence probe is：Using diselenide as fluorescent parent, introduced on diselenide parent
2- (2- hydroxy phenyls) benzothiazole (2- (2-hydroxyphenyl) benzothiazole), specific preparation process is as follows：
1) preparation of diazol：Ortho-aminobenzoic acid is taken to be made into weak solution with dilute hydrochloric acid and water, 5 are cooled to ice salt bath
DEG C, sodium nitrite solution is added in into weak solution, is reacted, obtains corresponding diazol；
2) preparation of two selenizing disodiums：Selenium powder and sodium borohydride solution are stirred to react at room temperature to selenium powder and dissolved, is obtained
To reaction solution alkalized with sodium hydrate aqueous solution, obtain two selenizing disodium accordingly；
3) preparation of diphenyl disenenide：The two selenizing disodiums obtained in step 2 are cooled with an ice bath to 5 DEG C, by step 1)
In obtained diazol be added thereto, stir when being added dropwise, to ensure the temperature of solution during dropwise addition below 10 DEG C, drop
Continue to stir 3h for 60 DEG C after adding, then continue to stir 3h under room temperature, reaction solution is acidified afterwards, filter, consolidate
Body to solid washing, removal of impurities, further after acidifying, is obtained by filtration solid and is washed with water to neutrality, drying obtains
4) preparation of acyl chlorides：Diphenyl disenenide and benzene is taken to mix, 80 DEG C is heated to, adds in thionyl chloride thereto, is continued
80 DEG C are heated with stirring to, until raw material is completely dissolved, vacuum is spin-dried for mixed liquor, and product is recrystallized using dichloromethane,
Obtain acyl chlorides；
5) preparation of probe：It will be under the acyl chlorides obtained by step 4) and 2- (2 '-hydroxy phenyl) benzothiazole, triethylamine room temperature
10h is reacted in methylene chloride, obtains corresponding fluorescence probe.
The molar ratio of ortho-aminobenzoic acid and sodium nitrite addition described in step 1) is 1：1；
The molar ratio of selenium powder and sodium borohydride addition described in step 2) is 1：1, the sodium hydroxide and selenium powder of addition
Molar ratio be 1.9：1；
The molar ratio of diazol and two selenizing disodium additions is 1 in step 3)：1；
The molar ratio of diphenyl disenenide and benzene addition is 1 in step 4)：60, the thionyl chloride and diphenyl disenenide of addition
Ratio be 2.5：1；
The molar ratio of acyl chlorides and 2- (2 '-hydroxy phenyl) benzothiazole, triethylamine described in step 5) is 1：2.5：2.
The fluorescence probe HSeSeH can be used for the qualitative or quantitative detection of hydrogen sulfide.
It is compound of the generation with structure I I and structure III when the fluorescence probe is applied to detection hydrogen sulfide,
So as to cause change in fluorescence；
The title of structure II：2- (2- hydroxy benzenes) benzothiazole；
The title of structure III：Five-membered ring of the benzene ortho position containing selenium and thioester bond；
When the fluorescence probe is for quantitatively detecting hydrogen sulfide, fluorescence probe at 460nm with after hydrogen sulfide effect, measuring
Fluorescence intensity be proportional to the concentration of hydrogen sulfide.
The fluorescence probe can be used for Endogenous Hydrogen Sulfide in detection active somatic cell, while can also detect exogenous sulphur
Change hydrogen.
Beneficial effects of the present invention：The compound is in H2Fluorescence significantly increases in the presence of S, available for it is highly selective,
High sensitivity it is qualitative and quantitatively detect H2S.Especially, which can be used for H in biosystem2The detection of S, this is for depth
Enter to study H2Physiology and the kinetics mechanism of pathologic process are of great significance S in vivo.
Description of the drawings
The principle schematic of Fig. 1 fluorescence probe detection hydrogen sulfide provided by the invention；
The probe that Fig. 2 present invention synthesizes1H NMR spectras；
The probe that Fig. 3 present invention synthesizes13C NMR spectras；
The spectrogram of fluorescence probe in Fig. 4 embodiments 2：Ultraviolet-visible absorption spectroscopy (a), fluorescence emission spectrum (b)；
Fluorescence probe is to the selective schematic diagram of hydrogen sulfide in Fig. 5 embodiments 3；
Fluorescence probe is to the detects schematic diagram of excessive vulcanized sodium in Fig. 6 embodiments 4；
Quantitative detection of the fluorescence probe to vulcanized sodium in Fig. 7 embodiments 5；
Fluorescence intensity of the fluorescence probe under different pH conditions in Fig. 8 embodiments 6；
The dynamics schematic diagram of fluorescence probe in Fig. 9 embodiments 7；
Fluorescence probe imaging schematic diagram in RAW264.7 cells in Figure 10 embodiments 8.
Specific embodiment
Embodiment 1 (synthesis of probe)：
The preparation of ortho-aminobenzoic acid：
Take 30.11g (0.2mol) methyl anthranilate, 200mL methanol, 100mL tetrahydrofurans, containing 9.12g hydrogen
The 100mL aqueous solutions of lithia, 41 DEG C of reactions, are tracked with TLC, use ethyl acetate：Petroleum ether=1:1 is chased after as solvent
Track, until reaction terminates.Solution becomes light yellow liquid from the liquid of water white transparency, and after the completion of reaction, solvent is spin-dried for.With
Water three times, is mutually adjusted to PH=4 or so with the hydrochloric acid of 1M, filtered by 50mL water and the extraction of 30mL ether, drying.It is shallow to obtain 26.3g
Yellow solid ortho-aminobenzoic acid, yield 96%.The synthesis of probe：
(1) synthesis of diazol：18.00g (0.130mol) ortho-aminobenzoic acid is added to by the hydrochloric acid of 38mL 36%
In the weak solution being made into 100mL water, 5 DEG C are cooled to ice salt bath；The 30mL water of 8.99g sodium nitrites (0.130mol) will be contained
Solution is added dropwise thereto, is stirred when being added dropwise, and when reaction solution liquid clear for khaki, stops stirring, obtains corresponding
Diazol.
(2)Na2Se2Synthesis：In N2Under protection, into the there-necked flask containing 35mL water and 5.10g (0.065mol) selenium powder
The aqueous solution 100mL containing 4.45g (0.130mol) sodium borohydride is added dropwise.Selenium powders dissolving is waited, another part 5.13g is added portionwise
(0.065mol) selenium powder.Obtained reaction mixture continues to stir and heats 30min to ensure that selenium powder is completely dissolved.The palm fibre of generation
Red reaction solution is alkalized with the sodium hydrate aqueous solution that 25mL concentration is 10mol/L, obtains corresponding Na2Se2。
3) preparation of diphenyl disenenide：The reaction solution obtained in step 2) is cooled with an ice bath to less than 5 DEG C, by step 1)
Obtained diazol is all added drop-wise to Na2Se2In reaction solution, during dropwise addition, have to ensure dropwise addition slowly, reaction
Temperature must be controlled below 10 DEG C, and bubble can be generated during dropwise addition, it is necessary to assure can continue to drip after bubble collapse
Add.Continue to stir after being added dropwise, bronzing is presented in reaction solution, continue at 60 DEG C stirring 3 it is small when, then stirring 3 is small under room temperature
When.Treat that after reaction, mixed liquor is acidified with dilute hydrochloric acid so that then the PH of mixed liquor is filtered in 3-4.Brownish red is obtained to consolidate
Body is washed with water, and is then dissolved with sodium bicarbonate aqueous solution, is filtered to remove insoluble impurity, the dilute salt of obtained brown liquid
Acid is acidified to PH<1.The solid of the brownish red of filtering is fully washed with water to neutrality.Ultraviolet drying, obtained corresponding brownish red
Solid diphenyl disenenide 9.86g, yield 37.92%.It is 285 DEG C to measure fusing point with melting point apparatus.
4) in N2Under protection, above-claimed cpd 2.5g (6.22mmol) is taken to add in 33mL benzene as in 100mL there-necked flasks,
85 DEG C are heated to, after benzene reflux, 1.85g (15.68mmol) thionyl chloride is slowly added dropwise, continues agitating and heating, until raw material
It is completely dissolved.After reaction, reaction mixture is spin-dried under vacuum conditions.Product is tied again using dichloromethane
Crystalline substance obtains the crystal acyl chlorides of light yellow diamond shape.
5) probeSynthesis：
In N2Under protection, the crystal 1.96g (4.47mmol) of diamond shape is taken, adds in 0.90g (8.95mmol) triethylamine, 17mL
Dichloromethane adds in 2.54g (11.2mmol) 2 (2- hydroxy phenyls) benzothiazole, reacts at room temperature, TLC trackings, dichloromethane
Alkane：Petroleum ether=2：The solvent separation of 1 (volume ratio).Lily solid powder probe HSeSeH1.57g is obtained, yield is
43%, fusing point is 295 DEG C.Probe obtained1HNMR and13CNMR is as follows：
1HNMR(400MHz,d6-DMSO)δ(ppm):8.53-8.48(d,1H),8.37-8.32(d,1H),8.15-8.08
(d,1H),7.81-7.77(d,1H),7.77-7.74(d,1H),7.75-7.69(d,1H),7.66-7.62(d,2H),7.61-
7.55 (m, 2H), 7.54-7.48 (t, 1H), 7.48-7.41 (t, 1H) (such as Fig. 2).
13CNMR(d6-DMSO,500MHz)δ(ppm):170.45,157.97,145.98,142.74,142.39,
141.28,130.66,128.91,127.53,124.82,122.86,117.33,110.83,98.76,48.70,38.84,
28.02,24.70,21.82,17.68,12.42 (such as Fig. 3).
Embodiment 2 (absorption of probe HSeSeH and transmitting spectrogram)：
Probe solution storing solution (the pure DMF of probe solution) is dissolved in 0.1M PB:DMSO=1:(PB phosphate delays 1 (volume)
It rushes in solution (pH=7.40) buffer solution, is configured to the solution of 100uM；Vulcanized sodium is configured to the solution of 1000uM.Take 20uL
Probe solution, 96 hole elisa Plates that 20uL sodium sulfide solutions is taken to be added in the multi-functional readout instrument of full wavelength scanner formula are surveyed
Amount, it is 1 separately to take 160uL volume ratios:1 0.1MPB and DMSO is also added in corresponding porous plate, measures the purple of the working solution
Outer visible absorption spectra (a), fluorescence emission spectrum (b)；As shown in figure 4, maximum excitation wavelength after probe response be 320nm,
Maximum emission wavelength is 460nm.
Embodiment 3 (probe HSeSeH is to the selectivity of hydrogen sulfide)：
Each reaction is in the PB (PH=7.4) of 160ul 0.1M：DMSO volume ratios 1:Add 20ul probes in 1 buffer solution
0.1M PB, 10mMKSCN, 100mM cysteine, the 100mMKCl, 10mM Na of (100uM) and 20ul2S2O3,10mMH2O2,
100mM sodium citrates, 100mMNa2HPO4,100mMNa2SO4,1000uMNa2S, 10mM glutathione, 100mM KI, using complete
The multi-functional readout instrument of length scanning formula and 96 hole elisa Plates measure.Measure the fluorescence emission spectrum of the working solution, λ ex=
320nm, raster width 5nm, λ em=460nm.Probe is to H2The selective experimental result of S is as shown in Figure 5, and ordinate represents
Fluorescence intensity, abscissa represent the variation of time.Fluorescence intensity changes significantly as time increases.Fig. 5 shows probe
To H2S has good selectivity, and system fluorescence significantly increases.Under determination condition, compared to H2S, fluorescence caused by other substances
Enhancing can be ignored.
Embodiment 4 (detections of the probe HSeSeH to excess hydrogen sulfide)：
By the probe stock concentrations gradient dilution of 1000uM, each reaction is in PB buffer solutions (0.1M, PH=of 160uL
7.4) sodium sulfide solution of 20uL probe solutions (100uM) and 20uL various concentrations (0uM-1000uM) is added in.Use all-wave
The multi-functional readout instrument of long scan formula and 96 hole elisa Plates measure.Measure the fluorescence emission spectrum of the working solution, λ ex=
320nm, raster width 5nm, λ em=460nm.The results show：Such as Fig. 6, with the growth of vulcanization na concn, fluorescence intensity is gradual
Increase.
Embodiment 5 (quantitative detections of the probe HSeSeH to vulcanized sodium)：
Each reaction in the PB buffer solutions (0.1M, PH=7.4) of 160ul plus 20uL probe solutions (100uM) and
The sodium sulfide solution of 20uL various concentrations (0uM-400uM).Use the multi-functional readout instrument of full wavelength scanner formula and 96 hole elisa Plates
It measures.Measure the fluorescence emission spectrum of the working solution, λ ex=320nm, raster width 5nm, λ em=460nm.By attached
It can see in Fig. 7, when the final test concentration of vulcanized sodium is in below 40uM, the fluorescence intensity of probe and the concentration of vulcanized sodium
Now good linear positive correlation.Corresponding equation of linear regression is F460nm=5.281* [vulcanized sodium]+40.526, it is linear
Related coefficient is R=0.9406.
Embodiment 6 (influences of the different PH to probe HSeSeH fluorescence intensities)
Probe is configured to the storing solution of 100uM, 160uL 0.1MPB are separately added into 96 hole elisa Plates：DMSO volumes
Than for 1:1 buffer solution adds in the 1000uM sodium sulfide solutions of 20uL, adds in the probe storing solution of the 100uM of 20uL.Wherein
The PH of 0.1MPB is respectively 1.5,2.5,3.5,4.5,5.5,6.5,7.5,8.5,9.5,10.5.Utilize the more work(of full wavelength scanner formula
Energy readout instrument puts carry out simple scan at the same time to the reaction solution under this ten different pH conditions respectively, with different ten
A PH is drawn as ordinate using different fluorescence intensities as abscissa, show Fig. 8.
Fig. 8 illustrates that under the conditions of pH is 1.5 to 10.5 pH the fluorescence of probe can significantly increase under hydrogen sulfide effect
By force, pH has an impact the probe, and fluorescence intensity is stronger under the physiology PH of PH=7.4 or so.Also illustrate the fluorescence probe compared with
It is suitably applied in organism to carry out biological detection.
Embodiment 7 (the dynamics schematic diagram of fluorescence probe HSeSeH)：
160uL 0.1MPB are separately added into 96 hole elisa Plates：DMSO volume ratios are 1:1 buffer solution, adds in 20uL's
0,10,25,50,100,200,400,800,1000uM sodium sulfide solution adds in the probe storing solution of the 100uM of 20uL.Complete
The fluorescence emission spectrum of the working solution, λ ex=320nm, raster width 5nm, λ are measured under the multi-functional readout instrument of length scanning formula
Em=460nm monitors its fluorescence intensity change situation.The results show：Such as Fig. 9, growth at any time, fluorescence intensity presents gradual
Incremental trend is finally reached platform, i.e., the reaction was complete.
Embodiment 8 (probe is used for the detection of hydrogen sulfide in RAW264.7 cells)：
RAW264.7 cells are cultivated according to American type Tissue Culture Collection regulations.
It is inoculated in cultivate in the culture dish of 35mm × 12mm and is allowed to adherent for 24 hours.Culture solution is discarded using preceding, three are washed with 0.01M PBS
It is secondary.Using Laser Scanning Confocal Microscope Olympus FV1000 (Ex.405nm, Em.425-525nm) camera lenses (× 100) observed with
And Image Acquisition, a, blanc cell carry out an Image Acquisition；B, adding the PBS solutions of 10uM probes, (PBS buffer solution concentration is
0.01M, pH 7.4) it is incubated a 30min Image Acquisition of progress；C first adds in 100uM sodium sulfide solutions and is incubated 20min, then adds
Enter probe and be incubated a 30min Image Acquisition of progress.The results show：Such as Figure 10, in RAW264.7 cells, fluoroscopic image brightness ratio
More c>b>a.The experiment proves that probe can be used for the detection of Endogenous Hydrogen Sulfide in cell and detection /V is normal into the cell
Hydrogen sulfide under horizontal, can also detect exogenous hydrogen sulfide.
Claims (7)
1. a kind of fluorescence probe, which is characterized in that the structure of the fluorescence probe is shown in structure I：
Structure code name：HSeSeH.
2. a kind of preparation method of fluorescence probe described in claim 1, it is characterised in that：Comprise the following steps：
1) preparation of diazol：Ortho-aminobenzoic acid is taken to be made into weak solution with dilute hydrochloric acid and water, 5 DEG C are cooled to ice salt bath, to
Sodium nitrite solution is added in weak solution, is reacted, obtains corresponding diazol；
2) preparation of two selenizing disodiums：Selenium powder and sodium borohydride solution are stirred to react at room temperature to selenium powder dissolving, obtained
Reaction solution is alkalized with sodium hydrate aqueous solution, obtains two selenizing disodium accordingly；
3) preparation of diphenyl disenenide：The two selenizing disodiums obtained in step 2) are cooled with an ice bath to 5 DEG C, will be obtained in step 1)
To diazol be added thereto, while be added dropwise while stir, be added dropwise after 60 DEG C continue stirring 3h, then continue to stir under room temperature
3h is afterwards acidified reaction solution, and filtering obtains solid, to solid washing, removal of impurities, further after acidifying, is obtained by filtration solid
Body is washed with water to neutrality, and drying obtains
4) preparation of acyl chlorides：Diphenyl disenenide and benzene is taken to mix, 80 DEG C is heated to, adds in thionyl chloride thereto, continue to stir
80 DEG C are heated to, until raw material is completely dissolved, vacuum is spin-dried for mixed liquor, and product is recrystallized using dichloromethane, is obtained
Acyl chlorides；
5) preparation of probe：By under the acyl chlorides obtained by step 4) and 2- (2 '-hydroxy phenyl) benzothiazole, triethylamine room temperature two
10h is reacted in chloromethanes, obtains corresponding fluorescence probe.
3. the preparation method of fluorescence probe according to claim 2, it is characterised in that：
The molar ratio of ortho-aminobenzoic acid and sodium nitrite addition described in step 1) is 1：1；
The molar ratio of selenium powder and sodium borohydride addition described in step 2) is 1：1, the sodium hydroxide of addition and rubbing for selenium powder
You are than being 1.9：1；
The molar ratio of diazol and two selenizing disodium additions is 1 in step 3)：1；
In step 4)Molar ratio with benzene addition is 1：60, the thionyl chloride of addition and diphenyl disenenide
Molar ratio is 2.5：1；
The molar ratio of acyl chlorides and 2- (2 '-hydroxy phenyl) benzothiazole, triethylamine described in step 5) is 1：2.5：2.
4. a kind of application in fluorescence probe described in claim 1, it is characterised in that：The fluorescence probe is for non-diagnostic
Or the qualitative or quantitative detection of the hydrogen sulfide of therapeutic purposes.
5. application according to claim 4, it is characterised in that：When the fluorescence probe is applied to detection hydrogen sulfide,
It is compound of the generation with structure I I and structure III, so as to cause change in fluorescence；
II title of structure：2- (2 '-hydroxy phenyl) benzothiazole；
III title of structure：Five-membered ring of the benzene ortho position containing selenium and thioester bond.
6. application according to claim 4, which is characterized in that when the fluorescence probe is for quantitatively detecting hydrogen sulfide,
After fluorescence probe is acted on hydrogen sulfide, the fluorescence intensity measured at 460nm is proportional to the concentration of hydrogen sulfide.
7. the application of fluorescence probe according to claim 4, which is characterized in that the fluorescence probe can be put to detect
Endogenous Hydrogen Sulfide in active somatic cell, while exogenous hydrogen sulfide can also be detected.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005036169A2 (en) * | 2003-10-03 | 2005-04-21 | Cumbre Inc. | Fluorescent probes for ribosomes and method of use |
| CN103571457A (en) * | 2012-08-02 | 2014-02-12 | 中国科学院大连化学物理研究所 | Fluorescent probe and application thereof in dynamic detection of mercaptan |
| CN103848787A (en) * | 2012-12-06 | 2014-06-11 | 中国科学院大连化学物理研究所 | Fluorescence probe and application thereof in reversible detection of hypochlorous acid |
-
2014
- 2014-11-26 CN CN201410696719.3A patent/CN105693654B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005036169A2 (en) * | 2003-10-03 | 2005-04-21 | Cumbre Inc. | Fluorescent probes for ribosomes and method of use |
| CN103571457A (en) * | 2012-08-02 | 2014-02-12 | 中国科学院大连化学物理研究所 | Fluorescent probe and application thereof in dynamic detection of mercaptan |
| CN103848787A (en) * | 2012-12-06 | 2014-06-11 | 中国科学院大连化学物理研究所 | Fluorescence probe and application thereof in reversible detection of hypochlorous acid |
Non-Patent Citations (4)
| Title |
|---|
| A flurescent probe for rapid detection of thiols and imaging of thiols reducing repair and H2O2 oxidative stress cycles in living cells;Zhangrong Lou，等;《Chem.Commun.》;20131231;第49卷(第4期);第391-393页 * |
| A near-infrared reversible and ratiometric fluorescent probe based on Se-BODIPY for the redox cycle mediated by hypobromous acid and hydrogen sulfide in living cells;Bingshuai Wang，等;《Chem.Commun.》;20131231;第49卷(第51期);第5790-5792页 * |
| A Near-IR Reversible Fluorescent Probe Modulated by Selenium for Monitoring Peroxynitrite and Imaging in living Cells;Fabiao Yu，等;《Journal of the American Chemistry Society》;20110627;第133卷(第29期);第11030-11033页 * |
| 含硒、碲有机荧光探针研究进展;杨志广，等;《化学试剂》;20140630;第36卷(第6期);第508-512页 * |
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