CN105602547A - Water-soluble fluorescent probe based on glucoside, synthesis and application - Google Patents
Water-soluble fluorescent probe based on glucoside, synthesis and application Download PDFInfo
- Publication number
- CN105602547A CN105602547A CN201410599185.2A CN201410599185A CN105602547A CN 105602547 A CN105602547 A CN 105602547A CN 201410599185 A CN201410599185 A CN 201410599185A CN 105602547 A CN105602547 A CN 105602547A
- Authority
- CN
- China
- Prior art keywords
- fluorescence probe
- fluorescence
- glycoside
- fluorescent probe
- water soluble
- 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.)
- Granted
Links
- 239000007850 fluorescent dye Substances 0.000 title abstract description 12
- 229930182478 glucoside Natural products 0.000 title abstract description 3
- 150000008131 glucosides Chemical class 0.000 title abstract description 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 14
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 14
- 238000002372 labelling Methods 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 239000000523 sample Substances 0.000 claims description 40
- 229930182476 C-glycoside Natural products 0.000 claims description 18
- 150000000700 C-glycosides Chemical class 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 14
- 150000001450 anions Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000004458 analytical method Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 claims description 5
- WSOYRJWLBCFOAL-UHFFFAOYSA-N benzaldehyde;n-ethylethanamine Chemical compound CCNCC.O=CC1=CC=CC=C1 WSOYRJWLBCFOAL-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 2
- -1 carbon glycoside Chemical class 0.000 abstract description 18
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 229930182470 glycoside Natural products 0.000 abstract description 15
- 229910052799 carbon Inorganic materials 0.000 abstract description 14
- 239000002585 base Substances 0.000 abstract description 8
- 238000001514 detection method Methods 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 238000002331 protein detection Methods 0.000 abstract description 2
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000003586 protic polar solvent Substances 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- 238000007039 two-step reaction Methods 0.000 abstract 1
- 229940125782 compound 2 Drugs 0.000 description 13
- 239000000126 substance Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 1
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 229930182474 N-glycoside Natural products 0.000 description 1
- 241000736199 Paeonia Species 0.000 description 1
- 235000006484 Paeonia officinalis Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 230000000215 hyperchromic effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000010148 water-pollination Effects 0.000 description 1
Landscapes
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention discloses a water-soluble fluorescent probe compound based on glucoside, synthesis and application thereof. The fluorescent probe is obtained through two-step reaction, and has the characteristics of cheap and easily-obtained reaction raw materials, few reaction steps, high yield and the like. The invention discloses multiple applications of the sugar-based carbon glycoside fluorescent probe, which comprises the following steps: 1. analyzing the pH value, namely analyzing the pH value by utilizing the characteristics of an acid-base switch of the fluorescent probe because the fluorescent probe does not have fluorescence under the acid condition and the fluorescence is kept under the alkali condition; 2. sulfhydryl anion detection, namely selectively detecting sulfhydryl by utilizing the characteristics of alpha, beta-unsaturated ketone (namely, the property of providing electrophilic center); 3. protein labeling is used for labeling proteins and enhancing the sensitivity of protein detection by utilizing the characteristic that the fluorescent compound has weak or no fluorescence in a protic solvent, but generates fluorescence after adding the proteins into an aqueous solution of the compound.
Description
Technical field
The present invention relates to a kind of new type water-solubility fluorescence probe based on C-glycoside and its production and use, specifically, relate to a kind of synthetic and application of the sugar charcoal glycoside fluorescent probe compounds with lignocaine benzaldehyde structure.
Background technology
At present the relevant fluorescence probe based on sugared obtains after by glycosidic bond combination by glycan molecule and fluorescent chemicals (as rhodamine, cumarin) mostly, thereby different fluorescent chemicalses are carried out to modification, but little with the research of the fluorescence probe of C-glycoside. Carbon glycosides, because it is for natural O-and N-glycosides, has chemistry and biology stability preferably, and resistance to acids and bases and the stability to glycosidase, attracting domestic and international numerous scholars' concern.
In protein, sulfydryl part is the functional group most with reactivity relevant with enzymatic activity, therefore seems particularly important for the detection of sulfhydryl compound. Mainly by colorimetric owing to detecting sulfydryl at present, electrochemistry, the methods such as mass spectrum, but these method complex operations, high to the purity requirement of detection thing, sensitivity is low. Therefore, fluoroscopic examination means have high sensitivity because of it, excellent specific property easy and simple to handle and become gradually the emphasis about-SH compound test. Particularly, in protein detection, fluorescence probe can strengthen the sensitivity of detection, and to the mensuration of protein content, the research of protein structure has great importance.
Summary of the invention
Inventor's object is to provide synthesizing of a kind of water soluble fluorescence probe based on C-glycoside and preparation method thereof.
Another object of the present invention is this kind of fluorescence probe to be applied to sulfydryl anion detect, acid-base value analysis, protein labeling aspect.
Realizing technical solution of the present invention is: a kind of water soluble fluorescence probe based on C-glycoside, and described fluorescence probe has following structure:
Synthesizing of a kind of water soluble fluorescence probe based on C-glycoside, comprise the steps:
(1) by 3-acetyl group-5-C-(2,3-dihydroxy-1,4-dehydration-D-erythro furyl glycosyl)-2-methylfuran and 4-N, TMSDEA N diethylamine benzaldehyde is dissolved in alcohol solvent, and add catalyst sodium hydrate aqueous solution in reactor, stirring at room temperature reaction, TLC plate is followed the tracks of to react to raw material and is disappeared;
(2), except desolventizing, silicagel column is purified, and obtains the thick target product of bronzing.
3-acetyl group-5-C-(2 described in step (1); 3-dihydroxy-1; 4-dehydration-D-erythro furyl glycosyl)-2-methylfuran, 4-N; the mol ratio of TMSDEA N diethylamine benzaldehyde and catalyst sodium hydrate aqueous solution (mass fraction is 10%) is 1:1.5:1.25, and the stirring at room temperature reaction time is 6h.
An application for water soluble fluorescence probe based on C-glycoside, detects the fluorescence probe of above-mentioned preparation and protein labeling for acid-base value analysis, sulfydryl anion.
Principle of the present invention is:
This fluorescence probe is divided into three parts by the present invention: binding site, by glycosylation, strengthens this fluorescent chemicals hydrophily and biocompatibility; Signaling switch, this zone similarity, in the bridge of fluorescence transfer part, can, by nucleopilic reagent attack, destroy conjugated system, and fluorescence is disappeared; Hyperchromic group, by increase this region to electronics, can strengthen fluorescence and the UV absorption intensity of compound entirety, improve the sensitivity of this compound in the time of application, strengthen using value and the feasibility of this compound for multi-field fluoroscopic examination.
The present invention compared with prior art, its remarkable advantage: (1) this fluorescent chemicals has good water-soluble. (2) this fluorescent chemicals fluorescence in proton solvent disappears or weakens, and in aprotic solvent, fluorescence strengthens. (3) this fluorescent chemicals has stronger adhesive ability to protein, and after protein combination, sends green fluorescence. (4) range of application of this fluorescent chemicals is wider, can detect for anion acid-base value analysis, the fields such as protein labeling.
Brief description of the drawings
The ultraviolet spectrogram of the fluorescence probe series compound 2 of Fig. 1 based on carbon glycosides sugar under different solvents.
The fluorescence spectrum figure of the fluorescence probe series compound 2 of Fig. 2 based on carbon glycosides sugar under different solvents.
The fluorescence spectrum change in concentration figure of the fluorescence probe series compound 2 of Fig. 3 based on carbon glycosides sugar.
The anion of the fluorescence probe series compound 2 of Fig. 4 based on carbon glycosides sugar detects analysis chart.
Fig. 5 is during anion detects, and relative fluorescence probe 2 adds the percentage that fluorescence reduces and fluorescence strengthens after different anions.
The Acidity of Aikalinity of the fluorescence probe series compound 2 of Fig. 6 based on carbon glycosides sugar detects analysis chart.
The fluorescence probe series compound 2 of Fig. 7 based on carbon glycosides sugar detects analysis chart with BSA protein combination concentration and fluorescence intensity.
The fluorescence probe series compound 2 and BSA protein combination concentration and fluorescence intensity graph of a relation of Fig. 8 based on carbon glycosides sugar.
Detailed description of the invention
Below provide the synthetic of a kind of fluorescent chemicals based on C-glycoside of the present invention and in acid-base value analysis, sulfhydryl compound detects, the application testing of protein labeling aspect.
The synthetic route of the compounds of this invention is as follows, and first glucose obtains compound 1 through Lewis acid catalysis and acetylacetone,2,4-pentanedione condensation, then reacts with aromatic aldehyde, obtains compound 2, and its two steps productive rate can reach 55%.
Embodiment 1
The preparation of compound 2
By 3-acetyl group-5-C-(2 of 0.226g (1mmol), 3-dihydroxy-1, 4-dehydration-D-erythro furyl glycosyl)-2-methylfuran 1 is (wherein, 3-acetyl group-5-C-(2, 3-dihydroxy-1, 4-dehydration-D-erythro furyl glycosyl) preparation of-2-methylfuran is referring to document: Xiang Yanfei, local records outstanding person, Li Longxia, CoCl26H2O, AlCl36H2O is at the synthetic C-pyrroles's glucosides of aqueous catalysis, chemical research and application, 2013, 25 (10): 1426-1429.) be dissolved in 4mL ethanol, add 4-N to moving liquid in reaction system, TMSDEA N diethylamine benzaldehyde 0.266g (1.5mmol) and 10%NaOH aqueous solution 0.15mL, under room temperature, stir 8h, follow the tracks of with TLC, after reaction finishes, decompression distillation is except desolventizing, and extract with 15mL ethyl acetate, saturated NaCl solution 20mL washing three times, anhydrous sodium sulfate drying organic layer, filter, decompression distillation obtains thick product, silica gel column chromatography separating-purifying (benzinum: ethyl acetate=3:1), obtain peony paste liquid 0.343g, productive rate is 89%.
1HNMR(500MHz,CDCl3)δ7.62(d,J＝15.4Hz,1H),7.42(d,J＝8.6Hz,2H),6.90(d,J＝15.4Hz,1H),6.70(s,1H),6.56(t,J＝9.1Hz,2H),4.70(d,J＝5.9Hz,1H),4.35(d,J＝15.7Hz,3H),4.27–4.13(m,2H),3.88(d,J＝10.0Hz,1H),3.34(dd,J＝13.9,6.9Hz,5H),2.54(s,3H),1.13(t,J＝7.0Hz,6H).
13CNMR(CDCl3):δ186.5,159.0,149.9,149.7,145.1,130.9,122.7,121.3,117.6,111.2,109.3,76.9,74.7,73.1,71.0,44.4,14.6,12.5.
ESI-MSm/z:386.1(M+H)+.
Embodiment 2
The ultraviolet of different solvents on this fluorescence probe and the impact of fluorescence spectrum.
The difference of solvent, can have a certain impact to the fluorescence intensity of fluorescence probe and maximum absorption wavelength. Fig. 1 and Fig. 2 provide the ultraviolet of fluorescence probe 2 under different solvents and the change of properties of fluorescence spectrum of carbon glycosides sugar. As can be seen from Figure 1, this compound ultraviolet maximum absorption wavelength changes little, in Fig. 2, the variation of fluorescence maximum absorption wavelength is comparatively obvious, by calculating the stokes displacement of this fluorescence probe 2, and compared with other fluorescence probes (most of fluorescent material stokes displacement is between 50-70nm), this fluorescent chemicals has larger stokes displacement (86nm, solvent is acetonitrile). This compound is at DMF, CH3In CN isopolarity aprotic solvent, fluorescent absorption is stronger, and in polar aprotic solvent, the basic cancellation of fluorescence.
Embodiment 3
The fluorescence intensity of the fluorescent probe compounds 2 of C-glycoside and change in concentration relation.
Fig. 3 provides fluorescence intensity and the concentration curve figure of the fluorescence probe series compound 2 of carbon glycosides sugar, from collection of illustrative plates, can obtain, and compound 2 is in acetonitrile solvent, when concentration reaches 4 × 10-5Time, its fluorescence intensity is the highest, and in the time that concentration continues to increase, fluorescence starts to weaken gradually.
Embodiment 4
The detection of the fluorescent probe compounds 2 of C-glycoside to sulfydryl anion.
By screening common anion, can obtain being adapted to the anion that this detects based on carbon glycosides sugar fluorescence probe system. The anion that Fig. 4 has provided the fluorescent probe compounds 2 of carbon glycosides sugar detects analysis chart, and Cl has been selected in test-，NO2 -，H2PO4 -，HSO3 -，I-，F-,-SH ion and group, this compound has higher susceptibility to sulfydryl as can be drawn from Figure 5. When compound is in the time that sulfhydryl compound is combined, the fluorescence of compound disappears.
Embodiment 5
The fluorescence probe of C-glycoside detects acid-base value.
Due to the detection of fluorescence probe and the Acidity of Aikalinity of environment closely related, Fig. 6 provides the acid-base value detection case of the fluorescent probe compounds 2 of carbon glycosides sugar, from figure, can obtain, under acid condition system fluorescence disappear, alkali condition fluorescence keep.
Embodiment 6
The fluorescence probe of C-glycoside is to protein labeling.
In addition,, in order to analyze the mark situation of this fluorescence probe to protein, Fig. 7 and Fig. 8 have provided compound 2 and have detected analysis chart with BSA protein combination concentration and fluorescence intensity, with 4x10-4The compound 2 of mol/L is primary standard substance, tests. Configuration concentration is respectively 0.1,0.2, and 0.4,0.6,0.8,1.0,1.2,1.4,1.6,1.8, the concentration of 2.0mg/mL is analyzed, and finds that its fluorescence intensity reaches peak in the time that concentration reaches 1.6mg/mL, and in the time continuing to improve BSA concentration, fluorescence intensity is substantially constant.
Claims (6)
1. the water soluble fluorescence probe based on C-glycoside, is characterized in that, described fluorescence probe has following structure:
。
2. the water soluble fluorescence probe based on C-glycoside as claimed in claim 1 is synthetic, it is characterized in that, comprises the steps:
(1) by 3-acetyl group-5-C-(2,3-dihydroxy-1,4-dehydration-D-erythro furyl glycosyl)-2-methylfuran and 4-N, TMSDEA N diethylamine benzaldehyde is dissolved in alcohol solvent, and add catalyst sodium hydrate aqueous solution in reactor, stirring at room temperature reaction, TLC plate is followed the tracks of to react to raw material and is disappeared;
(2), except desolventizing, silicagel column is purified, and obtains the thick target product of bronzing.
3. the water soluble fluorescence probe based on C-glycoside as claimed in claim 2 is synthetic; it is characterized in that; 3-acetyl group-5-C-(2 described in step (1); 3-dihydroxy-1; 4-dehydration-D-erythro furyl glycosyl)-2-methylfuran, 4-N, the mol ratio of TMSDEA N diethylamine benzaldehyde and catalyst NaOH is 1:1.5:1.25.
4. the water soluble fluorescence probe based on C-glycoside as claimed in claim 2 is synthetic, it is characterized in that, the stirring at room temperature reaction time described in step (1) is 6h.
5. the water soluble fluorescence probe based on C-glycoside as claimed in claim 2 is synthetic, it is characterized in that, the mass fraction of the sodium hydrate aqueous solution described in step (1) is 10%.
6. the application of the water soluble fluorescence probe based on C-glycoside as described in as arbitrary in claim 1-5, is characterized in that, fluorescence probe is detected and protein labeling for acid-base value analysis, sulfydryl anion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410599185.2A CN105602547B (en) | 2014-10-30 | 2014-10-30 | Water-soluble fluorescent probe based on glucoside, synthesis and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410599185.2A CN105602547B (en) | 2014-10-30 | 2014-10-30 | Water-soluble fluorescent probe based on glucoside, synthesis and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105602547A true CN105602547A (en) | 2016-05-25 |
| CN105602547B CN105602547B (en) | 2017-09-29 |
Family
ID=55982915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410599185.2A Expired - Fee Related CN105602547B (en) | 2014-10-30 | 2014-10-30 | Water-soluble fluorescent probe based on glucoside, synthesis and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105602547B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108003145A (en) * | 2016-11-02 | 2018-05-08 | 南京理工大学 | A kind of water-soluble carbon glycosides coumarin fluorescent probe, synthetic method and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102533249A (en) * | 2010-12-17 | 2012-07-04 | 中国科学院生态环境研究中心 | Preparation of water soluble saccharide fluorescent molecular probe and rapid detection for iron ions in water and biological tissue |
| CN102533250A (en) * | 2010-12-17 | 2012-07-04 | 中国科学院生态环境研究中心 | Preparation of water-soluble fluorescence probe and rapid detection of iron ion by use of the same |
-
2014
- 2014-10-30 CN CN201410599185.2A patent/CN105602547B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102533249A (en) * | 2010-12-17 | 2012-07-04 | 中国科学院生态环境研究中心 | Preparation of water soluble saccharide fluorescent molecular probe and rapid detection for iron ions in water and biological tissue |
| CN102533250A (en) * | 2010-12-17 | 2012-07-04 | 中国科学院生态环境研究中心 | Preparation of water-soluble fluorescence probe and rapid detection of iron ion by use of the same |
Non-Patent Citations (4)
| Title |
|---|
| ABDULLAH M. ASIRI 等: "(2E)-3-(4-Dimethylaminophenyl)-1-(2,5-dimethylfuran-3-yl)-prop-2-en-1-one prop-2-en-1-one", 《MOLBANK》 * |
| SAMY A.EL-DALY等: "Spectroscopic studies and laser acivity of 3-(4-dimethylamino-phenyl)-1-(2,5-dimethyl-furan-3-yl)-propenone (DDFP)：A new green laser dye", 《JOURNAL OF LUMINESCENCE》 * |
| WAEL A. EL-SAYED 等: "C-Furyl glycosides, I: Synthesis and antimicrobial evaluation of C-furyl glycosides and chalcones derived therefrom", 《MONATSH CHEM》 * |
| WAEL A. EL-SAYED等: "C-Furyl glycosides, II: synthesis and antimicrobial evaluation of C-furyl glycosides bearing pyrazolines, isoxazolines, and 5,6-dihydropyrimidine-2(1H)-thiones", 《MONATSH CHEM》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108003145A (en) * | 2016-11-02 | 2018-05-08 | 南京理工大学 | A kind of water-soluble carbon glycosides coumarin fluorescent probe, synthetic method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105602547B (en) | 2017-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Li et al. | Determination of trace patulin in apple-based food matrices | |
| Zhang et al. | Detection of saccharides by reactive desorption electrospray ionization (DESI) using modified phenylboronic acids | |
| Kurzyna-Szklarek et al. | Analysis of the chemical composition of natural carbohydrates–an overview of methods | |
| CN107082785B (en) | A kind of fluorescence probe and its synthesis and methods for using them of detection cyanide ion | |
| Sutariya et al. | A simple and rapid creatinine sensing via DLS selectivity, using calix [4] arene thiol functionalized gold nanoparticles | |
| Wang et al. | Spectrophotometric determination of nitrate and nitrite in water and some fruit samples using column preconcentration | |
| CN105548109A (en) | A fluorescence detecting system for heavy metal cadmium and a fluorescence detecting method | |
| CN104962278B (en) | Palladium ion fluorescent probe, and preparation method and applications thereof | |
| CN103342697B (en) | A kind of for detecting hypochlorous difunctional near-infrared fluorescent molecular probe and preparation method thereof | |
| CN110117282A (en) | A kind of zinc ion fluorescent compound and the preparation method and application thereof | |
| CN106866460A (en) | A kind of Schiff bases Multifunction fluorescent probe and preparation method and application | |
| Peng et al. | Simultaneous ligand fishing and identification of human serum albumin binders from Eucommia ulmoides bark using surface plasmon resonance-high performance liquid chromatography–tandem mass spectrometry | |
| CN106749093A (en) | One kind is for detecting palladium ion fluorescence probe, preparation method and application | |
| CN106749362A (en) | A kind of manganese and the fluorescence probe of copper double ion response and preparation method thereof | |
| CN103387830B (en) | Chromium-ion ratio type fluorescence probe as well as preparation method and application thereof | |
| You et al. | Detection of carbohydrates using new labeling reagent 1-(2-naphthyl)-3-methyl-5-pyrazolone by capillary zone electrophoresis with absorbance (UV) | |
| Zuo et al. | Ratiometric fluorescence sensing of formaldehyde in food samples based on bifunctional MOF | |
| Hu et al. | A novel solid fluorescence method for the fast determination of quercetin in biological samples based on the quercetin–Al (III) complex imprinted polymer | |
| CN107629036A (en) | A kind of fluorescence probe of visual detection copper ion and its preparation method and application | |
| CN105602547B (en) | Water-soluble fluorescent probe based on glucoside, synthesis and application | |
| Li et al. | Current analytical strategies for the determination of resveratrol in foods | |
| CN104132920A (en) | Method for measuring Ag<+> or F<-> through fluorescence quenching | |
| CN103822916A (en) | Double-schiff-base based on naphthol, synthesis thereof and application thereof as fluorinion sensor molecular | |
| CN105439948A (en) | Small molecule fluorescent probe for quantitative detection of nitrite and nitrosomercaptan | |
| Wang et al. | A Ca2+ controlled thioether linked bichromophoric squaraine foldamer for “turn on” fluorescent sensing of oxalate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20170929 Termination date: 20201030 |