CN102391855A - Fluorescent probe for detecting hypochlorous acid based on part cyanine, and preparation method thereof - Google Patents
Fluorescent probe for detecting hypochlorous acid based on part cyanine, and preparation method thereof Download PDFInfo
- Publication number
- CN102391855A CN102391855A CN2011102847004A CN201110284700A CN102391855A CN 102391855 A CN102391855 A CN 102391855A CN 2011102847004 A CN2011102847004 A CN 2011102847004A CN 201110284700 A CN201110284700 A CN 201110284700A CN 102391855 A CN102391855 A CN 102391855A
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- detection
- cyanines
- hypochlorous
- probe
- 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
- HZAYYQUNZCJLRD-UHFFFAOYSA-O CC1(C)c2ccccc2[N+](CCCCS(O)(=O)=O)=C1/C=C/c(cc1)ccc1O Chemical compound CC1(C)c2ccccc2[N+](CCCCS(O)(=O)=O)=C1/C=C/c(cc1)ccc1O HZAYYQUNZCJLRD-UHFFFAOYSA-O 0.000 description 1
- HZAYYQUNZCJLRD-UHFFFAOYSA-N CC1(C)c2ccccc2[N+](CCCCS(O)(=O)=O)=C1/C=C/c(cc1)ccc1[O-] Chemical compound CC1(C)c2ccccc2[N+](CCCCS(O)(=O)=O)=C1/C=C/c(cc1)ccc1[O-] HZAYYQUNZCJLRD-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention provides a fluorescent probe for detecting hypochlorous acid based on part cyanine, and a preparation method thereof, and relates to a fluorescent probe. The invention provides a fluorescent probe which is high in sensitivity and selectivity and is used for detecting the hypochlorous acid based on the part cyanine, and a preparation method thereof. The fluorescent probe is dimethylamino-sulfo-methoxycarbonyl part cyanine compound which contains a part cyanine fluorophore structure and takes dimethylamino-sulfo-formoxyl as a phenolic hydroxyl protecting group. The preparation method of the fluorescent probe comprises the steps of: firstly synthesizing intermediate A, then synthesizing intermediate B, and finally synthesizing the target product fluorescent probe which is used for detecting the hypochlorous acid based on the part cyanine. The fluorescent probe for detecting the hypochlorous acid based on the part cyanine can be applied to detecting HClO in water solution in a fluorescent way under the neutral condition.
Description
Technical field
The present invention relates to a kind of fluorescent probe, especially relate to a kind of with the dimethylin thioformyl be the phenolic hydroxyl group blocking group, to spend cyanines with portion be fluorescent probe and the preparation thereof of fluorophore and the application during the hypochlorous acid fluorescent method detects in the aqueous solution under neutrallty condition.
Background technology
Hypochlorous acid (HClO) is that the organism myeloperoxidase (myeloperoxidase, MPO) play an important role in multiple physiology, pathologic process by a kind of important active oxygen species of mediation generation.Design is synthetic to have high sensitivity, HClO fluorescent probe that specificity is strong; Foundation is applied to the fluorescent microscopic imaging method of HClO in the cell; Realize that target molecule is real-time, the spike of original position; Be molecule relevant in postgraduate's object and cell incident, and the drug screening and the evaluation of relevant disease provide authentic communication with it, have important scientific meaning and application prospect with HClO.This field has become one of focus of people's research.
In recent years, reported several fluorescent probes to HClO, as DCFH, DHR (referring to document: A.Bizyukin, et al; Bull.Exp.Biol.Med.1995,119,347.), APF (referring to document: T.Nagano, et al; J.Biol.Chem.2003,278,3170.), MitoAR is (referring to document: T.Nagano; Et al, J.Am.Chem.Soc.2007,129; 10324.) etc., but above probe be except can detecting HClO, and other active oxygen species is also had fluorescence response in various degree.Because every kind of active oxygen all has its unique separately physiologically active, therefore the demand to the strong HClO fluorescent probe of specificity seems particularly urgent.In the other HClO probe of having reported, the need that have under the severe condition of strong basicity (like pH 12), use (referring to document: H.M.Ma, et al; Chem.Eur.J.2008,14,4719.); Or poorly water-soluble is (referring to document: W.Tan et al, Chem.Eur.J.2009,15; 2305.), can't really be applied in the living things system.At present, it is few to be applied under the neutrallty condition fluorescent probe that HClO detects in the aqueous solution, and need expensive preparation under loaded down with trivial details exacting terms and get (referring to document: T.Nagano, et al, J.Am.Chem.Soc.2007,129,7313.; Document: J.Tae, et al, Org.Lett.2009,11, (4), 859.; Document: R.Weissleder, P.Libby, et al, Chem.Biol.2007,14,1221.).
Summary of the invention
The objective of the invention is to existing deficiency of various HClO fluorescent probes and the defective reported, hypochlorous fluorescent probe of detection of spending cyanines based on portion of one type of highly sensitive, highly selective and preparation method thereof is provided.
Said based on portion spend cyanines the hypochlorous fluorescent probe of detection (below be designated as probe
1) molecular structural formula following:
Said based on portion spend the hypochlorous fluorescent probe of detection of cyanines be contain portion spend cyanines fluorophore structure, be the dimethylin sulfo-formicester base portion flower cyanine compound of phenolic hydroxyl group protection base with the dimethylin thioformyl.
The synthetic route of the said hypochlorous fluorescent probe of detection of spending cyanines based on portion is as follows:
The step of its compound method is:
1) intermediate A is synthetic: in container, add 1.0 parts sodium hydride in molar ratio, N
2Add DMF under the atmosphere, the dry DMF solution that will be dissolved with 1.0 parts of PARA HYDROXY BENZALDEHYDEs after ice bath stirs down splashes into wherein, keeps N
2Atmosphere stirs the recession deicing and bathes, at N
2Under the atmosphere mixture is added the dry DMF solution that another is dissolved with 1.0 parts of dimethylin sulfo-formyl chlorides in advance; Reaction mixture is with 1.0～2.0 times of methylene dichloride dilutions; The gained organic phase is successively with saturated sodium-chloride and water washing; Rotary evaporation is drained methylene dichloride, separates with column chromatography, gets white intermediate A;
2) intermediate B is synthetic: in container, add 1.0 part 2,3 in molar ratio, 3-trimethyl-3H-indole; And 3.0 part 1,4-butane sultone dissolves in the orthodichlorobenzene solvent; Reflux stirs in the oil bath under nitrogen atmosphere, pours in the freezing acetone after the reaction mixture cooling, has the dark red solid to separate out; With freezing washing with acetone, get the intermediate B of pinkiness powder;
3) title product is spent the hypochlorous fluorescent probe of detection synthetic of cyanines based on portion: add intermediate A and intermediate B in the medium mol ratio of container, with dissolve with ethanol, add 1.0～3.0 parts of piperidines again; Mixture reacts under nitrogen atmosphere, and rotary evaporation is drained solvent again, and solid residue separates with column chromatography, gets orange-yellow title product is spent cyanines based on portion the hypochlorous fluorescent probe of detection.
In step 1), the massfraction of said sodium hydride can be 55%～65%; Said at N
2Under the atmosphere mixture is added the dry DMF solution that another is dissolved with 1.0 parts of dimethylin sulfo-formyl chlorides in advance, treat that preferably temperature natural rises to room temperature after, at N
2Under the atmosphere mixture is added the dry DMF solution that another is dissolved with 1.0 parts of dimethylin sulfo-formyl chlorides in advance; Said successively with saturated sodium-chloride and water washing, preferably earlier with saturated sodium-chloride wash 3 times, again to wash 1 time; Said column chromatography can adopt methylene dichloride/sherwood oil=1: 3.
In step 2) in, the temperature of said oil bath can be 120 ℃.
In step 3), said alcoholic acid add-on can be 10.0mL; Said column chromatography can adopt methylene dichloride/ethanol=20: 3.
Saidly spend the hypochlorous fluorescent probe of detection of cyanines to can be applicable to the fluoroscopic examination of HClO in the aqueous solution under the neutrallty condition based on portion.
The invention provides fluorescence/colour developing probe of HClO in a kind of aqueous solution of excellent performance; Detection HClO method proposed by the invention depends on following chemical reaction mechanism: spend the blocking group of phenolic hydroxyl group on the phthalocyanine molecule with the dimethylin thioformyl as hyperfluorescence property fluorescence regiment headquarters, the compound that is obtained is a probe
1, probe
1 Present hypofluorescence.Probe
1, under the HClO effect, slough (the going protection) of dimethylin thioformyl blocking group taken place, discharge portion again and spend phthalocyanine molecule with hyperfluorescence character, realize the rapid variation of the signal of fluorescence from " nothing " to " having ".Reaction process is as follows:
Compared with prior art, useful technique effect of the present invention is following:
Is the fluorescent probe molecule that the phenolic hydroxyl group blocking group designs based on novelty with the dimethylin thioformyl;
No fluorescence of this probe self or fluorescent signal very a little less than, significantly strengthen with HClO effect back fluorescence, so detection is highly sensitive;
The aqueous solution of this probe self is colourless, only with after the HClO effect manifests red-purple, has the colour developing effect;
This probe is strong for the specificity of HClO effect.
Description of drawings
Fig. 1 is a probe
1With the fluorescence spectrum after the hypochlorous acid effect of different concns.In Fig. 1, X-coordinate is wavelength (nm), and ordinate zou is a relative intensity of fluorescence; In the pH of 0.01mol/L 7.4 phosphate buffer solutions (acetone=1/9, the ratio of volume), probe
1Concentration is 20.0 μ mol/L, and NaClO concentration (from bottom to top) is respectively: 0,0.1,0.3,0.5,0.7,0.9,2.0,3.0,4.0,5.0,6.0,7.0,9.0,10.0 μ mol/L; Excitation wavelength: 503nm.
* annotate: NaClO is that spontaneous generation acid moves and produce HclO in the aqueous solution under neutrallty condition, and remainder together.
Fig. 2 is a probe
1In the pH of 0.01mol/L 7.4 phosphoric acid buffers (acetone=1/9, the ratio of volume), the fluorescence spectrum under acting on respectively for various active oxygen species.In Fig. 2, X-coordinate is wavelength (nm), and ordinate zou is a relative intensity of fluorescence; Probe
1Concentration is 20.0 μ mol/L, and various activity keto concentrations are 20 μ mol/L; Excitation wavelength: 503nm.
Fig. 3 is a probe
1Fluorescent method detects the working curve diagram of NaClO in the aqueous solution of pH7.4.In Fig. 3, X-coordinate is a NaClO concentration, and ordinate zou is a relative intensity of fluorescence.
Embodiment
Following examples will combine accompanying drawing that the present invention is described further, but the present invention is not limited by the strictness of the following example.
Embodiment 1: the preparation method of probe
Synthesizing of intermediate A: in 25mL exsiccant round-bottomed flask, add the sodium hydride (content 55%～65%) of 0.33g (8.20mmol), N
2With the dry DMF dissolving of 2.0mL, the dry DMF solution that will be dissolved with 1.2g (9.84mmol) PARA HYDROXY BENZALDEHYDE under the ice bath behind the stirring 10min in advance splashes into wherein, keeps N under the atmosphere
2Atmosphere, 0 ℃ is stirred 30min; Remove ice bath, treat that temperature natural rises to room temperature after, N
2Under the atmosphere this mixture is slowly splashed into the dry DMF solution of the 5.0mL that is dissolved with 1.01g (8.20mmol) dimethylin sulfo-formyl chloride in advance, react 12h under the room temperature; Reaction mixture dilutes with an amount of methylene dichloride, and organic phase is given a baby a bath on the third day after its birth inferior respectively with saturated sodium-chloride, and washing once; Rotary evaporation is drained methylene dichloride; Separate with column chromatography (methylene dichloride/sherwood oil=1: 3), get the intermediate A 0.89g of white solid, productive rate 52.0%.
Synthesizing of intermediate B: in 25mL exsiccant round-bottomed flask; Add 2,3 respectively, 3-trimethyl-3H-indole (1.6g; 10.06mmol) and 1; 4-butane sultone (4.5g 33.09mmol) fully dissolves it in the 12mL orthodichlorobenzene, under the nitrogen atmosphere in 120 ℃ of oil baths reflux stirred 12 hours; Pour in the freezing acetone after the cooling of question response mixture, have the dark red solid to separate out, it is inferior to give a baby a bath on the third day after its birth with freezing acetone, obtains the intermediate B 2.0g of pink powder shape, productive rate 67.39%.
The title product probe
1Synthetic: in the round-bottomed flask of 25mL, add 0.20g (0.96mmol) intermediate B and 0.38g (1.29mmol) intermediate A,, add 200 μ L piperidines again with the dry dissolve with ethanol of 10.0mL; Mixture is normal-temperature reaction 6h under nitrogen atmosphere and vigorous stirring; Rotary evaporation is drained solvent, and solid residue separates with column chromatography (methylene dichloride/ethanol=20: 3), gets orange/yellow solid (title product, i.e. probe
1) 0.20g..Productive rate 43.01%.
ESI-MS：C
25H
30N
2O
4S
2，m/z：487.65(M+1)
+。
1H?NMR：(400MHz，CH
3OH-d6，ppm)δ8.44(d，J＝16.08，1H)，8.15(d，J＝7.45，2H)，7.88(d，J＝4.18，1H)7.62-1.75(m，4H)7.24(d，J＝6.90，2H)4.71(t，J＝6.54，2H)3.40(s，3H)3.35(s，3H)2.90-2.93(m，2H)2.15-2.18(m，2H)2.00(t，J＝6.50，2H)1.84(s，6H)
13C?NMR：(100MHz，CH
3OH-d6，ppm)δ187.92，183.96，159.71，155.64，145.34，142.21，133.33，132.05，131.15，130.73，126.30，124.13，116.45，113.44，64.34，54.12，51.20，48.02，43.57，39.13，28.25，26.65，24.70，23.34
Embodiment 2: probe
1Detect the description of the fluorescence property of HClO in the aqueous solution
(1) preparation steps of test fluid:
In the 10mL cuvette, add 1.0mL phosphate buffer solution (pH 7.4) successively, the standardized solution of the 0.001mol/L Youxiaolin of different volumes, 1.0mL acetone is diluted to scale with deionized water again, shakes up; The concentration that adds 0.2mL is 1.0 * 10
-3The probe of mol/L
1The methyl alcohol storing solution, shake up once more; After placing 10min, measure fluorescence intensity in the 553nm place.As above operation, but do not add the probe of HClO or other active oxygens
1Solution is the preparation of blank test solution.
(2) probe
1Spectral response curve and detect performance.In conjunction with marginal data.
Fig. 1 is a probe
1Under neutrallty condition in the aqueous solution to hypochlorous fluorescence response.Fig. 1 shows, probe
1In pH is 7.4 phosphate buffer solution, present hypofluorescence at the 553nm place, along with hypochlorous adding, the fluorescence at 553nm place significantly strengthens.This phenomenon shows, probe
1HClO had sensitivity and fluorescent signal response rapidly.
Fig. 2 is a probe
1Fluorescence response spectrogram under acting on respectively for various active oxygen species with isoconcentration.Curve 1 is a probe
1Itself and with 2 normal H
2O
2, OH, ONOO
-, NO
2 -Fluorescence spectrum under the difference concurrent conditions; Curve 2 is a probe
1With the fluorescence spectrum under the 2 normal NaClO concurrent conditionses; Curve 3 is a probe
1With 2 normal Hg
2+Fluorescence spectrum under the concurrent conditions.
Fig. 2 shows, has hypochlorous acid only and can cause probe
1The remarkable enhancing of fluorescence intensity at the 553nm place; And the existence of other active oxygen does not all cause the tangible fluorescence enhancing signal of system.This result shows, probe
1The selectivity that hypochlorous fluorescence sense is had height.
Fig. 3 is a probe
1In the phosphate buffer solution of pH7.4, detect the working curve diagram of NaClO.Result of study shows that the fluorescence intensity of system is 0.1 * 10
-6Mol/L～10 * 10
-6Present good linear relationship with NaClO concentration in the concentration range of mol/L.
Experimental result shows, probe
1The aqueous solution of self is closely colourless, has hypochlorous acid only and can cause probe
1Aqueous solution displaing amaranth; And the existence of other active oxygen does not all cause probe
1The aqueous solution manifest red-purple.This result shows, probe
1The colour developing selectivity that hypochlorous acid is had height.
Claims (10)
1. spend the hypochlorous fluorescent probe of detection of cyanines based on portion, it is characterized in that its molecular structural formula is following:
Said based on portion spend the hypochlorous fluorescent probe of detection of cyanines be contain portion spend cyanines fluorophore structure, be the dimethylin sulfo-formicester base portion flower cyanine compound of phenolic hydroxyl group protection base with the dimethylin thioformyl.
2. the compound method of spending the hypochlorous fluorescent probe of detection of cyanines based on portion as claimed in claim 1 is characterized in that the steps include:
1) intermediate A is synthetic: in container, add 1.0 parts sodium hydride in molar ratio, N
2Add DMF under the atmosphere, the dry DMF solution that will be dissolved with 1.0 parts of PARA HYDROXY BENZALDEHYDEs after ice bath stirs down splashes into wherein, keeps N
2Atmosphere stirs the recession deicing and bathes, at N
2Under the atmosphere mixture is added the dry DMF solution that another is dissolved with 1.0 parts of dimethylin sulfo-formyl chlorides in advance; Reaction mixture is with 1.0～2.0 times of methylene dichloride dilutions; The gained organic phase is successively with saturated sodium-chloride and water washing; Rotary evaporation is drained methylene dichloride, separates with column chromatography, gets white intermediate A;
2) intermediate B is synthetic: in container, add 1.0 part 2,3 in molar ratio, 3-trimethyl-3H-indole; And 3.0 part 1,4-butane sultone dissolves in the orthodichlorobenzene solvent; Reflux stirs in the oil bath under nitrogen atmosphere, pours in the freezing acetone after the reaction mixture cooling, has the dark red solid to separate out; With freezing washing with acetone, get the intermediate B of pinkiness powder;
3) title product is spent the hypochlorous fluorescent probe of detection synthetic of cyanines based on portion: add intermediate A and intermediate B in the medium mol ratio of container, with dissolve with ethanol, add 1.0～3.0 parts of piperidines again; Mixture reacts under nitrogen atmosphere, and rotary evaporation is drained solvent again, and solid residue separates with column chromatography, gets orange-yellow title product is spent cyanines based on portion the hypochlorous fluorescent probe of detection.
3. the compound method of spending the hypochlorous fluorescent probe of detection of cyanines based on portion as claimed in claim 2 is characterized in that in step 1) the massfraction of said sodium hydride is 55%～65%.
4. as claimed in claim 2ly spend the compound method of the hypochlorous fluorescent probe of detection of cyanines, it is characterized in that in step 1) based on portion, said at N
2Under the atmosphere mixture being added the dry DMF solution that another is dissolved with 1.0 parts of dimethylin sulfo-formyl chlorides in advance, is after treating that temperature natural rises to room temperature, at N
2Under the atmosphere mixture is added the dry DMF solution that another is dissolved with 1.0 parts of dimethylin sulfo-formyl chlorides in advance.
5. as claimed in claim 2ly spend the compound method of the hypochlorous fluorescent probe of detection of cyanines, it is characterized in that in step 1) based on portion, said successively with saturated sodium-chloride and water washing, be earlier with saturated sodium-chloride wash 3 times, again to wash 1 time.
6. the compound method of spending the hypochlorous fluorescent probe of detection of cyanines based on portion as claimed in claim 2 is characterized in that in step 1) said column chromatography employing methylene dichloride/sherwood oil=1: 3.
7. the compound method of spending the hypochlorous fluorescent probe of detection of cyanines based on portion as claimed in claim 2 is characterized in that in step 2) in, the temperature of said oil bath is 120 ℃.
8. the compound method of spending the hypochlorous fluorescent probe of detection of cyanines based on portion as claimed in claim 2 is characterized in that in step 3) said alcoholic acid add-on is 10.0mL.
9. the compound method of spending the hypochlorous fluorescent probe of detection of cyanines based on portion as claimed in claim 2 is characterized in that in step 3) said column chromatography employing methylene dichloride/ethanol=20: 3.
10. as claimed in claim 1ly spend the hypochlorous fluorescent probe of detection of cyanines to be applied to the fluoroscopic examination of HClO in the aqueous solution under the neutrallty condition based on portion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011102847004A CN102391855A (en) | 2011-09-22 | 2011-09-22 | Fluorescent probe for detecting hypochlorous acid based on part cyanine, and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011102847004A CN102391855A (en) | 2011-09-22 | 2011-09-22 | Fluorescent probe for detecting hypochlorous acid based on part cyanine, and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102391855A true CN102391855A (en) | 2012-03-28 |
Family
ID=45859241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011102847004A Pending CN102391855A (en) | 2011-09-22 | 2011-09-22 | Fluorescent probe for detecting hypochlorous acid based on part cyanine, and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102391855A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102977131A (en) * | 2012-12-21 | 2013-03-20 | 天津理工大学 | Hemicyanine borate molecular fluorescence probe, and preparation method and application thereof |
| CN102977130A (en) * | 2012-12-21 | 2013-03-20 | 天津理工大学 | Molecular fluorescent probe for detecting hypochlorite and preparation and application thereof |
| 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 |
| CN107936011A (en) * | 2016-10-12 | 2018-04-20 | 南开大学 | A kind of four substituted olefine probes of high selectivity detection hypochlorite ion |
| CN110174397A (en) * | 2019-06-15 | 2019-08-27 | 贵州医科大学 | A kind of application of colorimetric probe |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050130059A1 (en) * | 2003-12-15 | 2005-06-16 | Ting Tao | Infrared absorbing N-alkylsulfate cyanine compounds |
| WO2008110063A1 (en) * | 2007-03-12 | 2008-09-18 | Versitech Limited | Reagents for detection of hypochlorous acid |
| WO2010121163A2 (en) * | 2009-04-17 | 2010-10-21 | Li-Cor, Inc. | Fluorescent imaging with substituted cyanine dyes |
-
2011
- 2011-09-22 CN CN2011102847004A patent/CN102391855A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050130059A1 (en) * | 2003-12-15 | 2005-06-16 | Ting Tao | Infrared absorbing N-alkylsulfate cyanine compounds |
| WO2008110063A1 (en) * | 2007-03-12 | 2008-09-18 | Versitech Limited | Reagents for detection of hypochlorous acid |
| WO2010121163A2 (en) * | 2009-04-17 | 2010-10-21 | Li-Cor, Inc. | Fluorescent imaging with substituted cyanine dyes |
Non-Patent Citations (3)
| Title |
|---|
| D. K. BARMA等: "Dimethylthiocarbamate (DMTC): An", 《ORG. LETT.》, 19 November 2003 (2003-11-19), pages 4755 - 4757 * |
| XIAOHUA LI等: "A near-infrared fluorescent probe for monitoring tyrosinase activity", 《CHEM.COMM.》, vol. 46, 11 March 2010 (2010-03-11), pages 2560 - 2562 * |
| 王淑萍: "基于部花菁染料的光化学传感器的设计研究", 《厦门大学硕士学位论文》, 6 November 2009 (2009-11-06) * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN102977131A (en) * | 2012-12-21 | 2013-03-20 | 天津理工大学 | Hemicyanine borate molecular fluorescence probe, and preparation method and application thereof |
| CN102977130A (en) * | 2012-12-21 | 2013-03-20 | 天津理工大学 | Molecular fluorescent probe for detecting hypochlorite and preparation and application thereof |
| CN102977131B (en) * | 2012-12-21 | 2014-11-19 | 天津理工大学 | Hemicyanine borate molecular fluorescence probe, and preparation method and application thereof |
| CN102977130B (en) * | 2012-12-21 | 2014-11-19 | 天津理工大学 | Molecular fluorescent probe for detecting hypochlorite and preparation and application thereof |
| CN107936011A (en) * | 2016-10-12 | 2018-04-20 | 南开大学 | A kind of four substituted olefine probes of high selectivity detection hypochlorite ion |
| CN110174397A (en) * | 2019-06-15 | 2019-08-27 | 贵州医科大学 | A kind of application of colorimetric probe |
| CN110174397B (en) * | 2019-06-15 | 2020-05-19 | 贵州医科大学 | Application of colorimetric probe |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Guo et al. | Recognition and sensing of various species using boronic acid derivatives | |
| CN105542756B (en) | A kind of fluorescence probe for detecting formaldehyde and preparation method and application | |
| CN102382641B (en) | Fluorescent probe for detecting hypochlorous acid and preparation method thereof | |
| CN102391855A (en) | Fluorescent probe for detecting hypochlorous acid based on part cyanine, and preparation method thereof | |
| CN103342697B (en) | A kind of for detecting hypochlorous difunctional near-infrared fluorescent molecular probe and preparation method thereof | |
| CN102746313A (en) | Rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit, preparation method and application thereof | |
| CN104017568B (en) | -Application of fluorescent probe containing rhodamine in detecting Hg2+ | |
| CN103436253A (en) | Rhodamine fluorescent probe for detecting ferrous ion, and preparation method thereof | |
| CN104910070A (en) | Rapid high-selectivity hypochloric acid fluorescence probe and application thereof | |
| CN107033158B (en) | A kind of colorimetric fluorescence probe and preparation method thereof of hypersensitive analysis mercury ion | |
| CN105622624A (en) | Rhodamine B derivative, preparation method and application of rhodamine B derivative serving as fluorescent probe | |
| Song et al. | Ratiometric chemosensing of Mg2+ ions by a calix [4] arene diamide derivative | |
| CN107382981A (en) | A kind of fluorescence probe based on the double hydazone derivatives of pyrroles's cumarin and its preparation method and application | |
| CN108658838B (en) | Heptamethine indocyanine-based formaldehyde fluorescent probe and preparation method and use method thereof | |
| US20180215773A1 (en) | Homoallylamines as formaldehyde-responsive triggers | |
| CN109400563B (en) | Hypochlorous acid fluorescent probe and preparation method and application thereof | |
| Yang et al. | Dual–channel colorimetric fluorescent probe for determination of hydrazine and mercury ion | |
| Zhang et al. | A novel near-infrared fluorescent probe based on the dicyanoisophorone for the selective detection of Cu2+ in real water samples | |
| CN105985291B (en) | A kind of colorimetric fluorescence probe of quick high-selectivity analysis fluorine ion | |
| CN109912581B (en) | Hypochlorous acid fluorescent probe based on coumarin and styrylpyridinium and application thereof | |
| CN101439191B (en) | Synthesizing method of visible light induced zinc ion fluorescence angiographic reagent capable of being applied in cell/tissue/living body | |
| CN102503875B (en) | Fluorescent probe for detecting copper ions and preparation method thereof | |
| CN110818703A (en) | Pyrrole-part cyanine derivative fluorescent probe and preparation method and application thereof | |
| CN105331358A (en) | Dirhodamine-based Sn4+ fluorescent probe molecule and preparation method and application thereof | |
| CN113956274B (en) | Fluorescent probe design and synthesis method for dual response to viscosity and peroxynitrite change in epileptic diseases |
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 |
Application publication date: 20120328 |