CN103436254B - Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof - Google Patents
Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof Download PDFInfo
- Publication number
- CN103436254B CN103436254B CN201310362261.3A CN201310362261A CN103436254B CN 103436254 B CN103436254 B CN 103436254B CN 201310362261 A CN201310362261 A CN 201310362261A CN 103436254 B CN103436254 B CN 103436254B
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- probe
- preparation
- methylene dichloride
- ethanol
- 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.)
- Expired - Fee Related
Links
- 0 *c1cc(*)nc(CNCc2cc(*)cc(*)n2)c1 Chemical compound *c1cc(*)nc(CNCc2cc(*)cc(*)n2)c1 0.000 description 1
- SPNLSRAQTVGSRO-UHFFFAOYSA-N Oc1ccnc(CN(C=C2N3C=CC(O)=C2)C3=S)c1 Chemical compound Oc1ccnc(CN(C=C2N3C=CC(O)=C2)C3=S)c1 SPNLSRAQTVGSRO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention discloses a functional multi-nitrogen heterocyclic ring fluorescent probe, and a preparation method and an application of the functional multi-nitrogen heterocyclic ring fluorescent probe, wherein the general structural formula of the functional multi-nitrogen heterocyclic ring fluorescent probe is shown in the specification, wherein R1, R2, R3 and R4 respectively and independently represent hydrophilic groups. The preparation method of the fluorescent probe comprises the following steps: taking bipyridine dimethylamine as a molecular skeleton, rearranging bipyridine dimethylamine after bipyridine dimethylamine is reacted with carbon disulfide to increase the molecular rigidity, and obtaining the organic probe giving out green fluorescence. The fluorescent probe is high in stability and is not easily photobleached. The fluorescent strength and the color of the probe are changed under the action of hypochlorous acid, so that the probe can be used to quantitatively and qualitatively detect the hypochlorous acid, the limit of detection is as low as 0.43 micrometer, and very high selectivity is acquired.
Description
One, technical field
The present invention relates to a kind of organic fluorescence molecular probe, the specifically polynary aza ring fluorescent probe of a kind of functionalization, Its Preparation Method And Use, fluorescent probe of the present invention can be used for the qualitative and quantitative detection of hypochlorous acid or hypochlorite.
Two, background technology
In the last few years, fluorescence sense technology had more and more been applied to the analyzing and testing of biological micromolecule.With respect to other analysis and detection technology, UV-Visible absorption spectrum for example, electrochemical process and colorimetry etc., fluorescence spectroscopy technique has advantages of that it is unique, as highly sensitive, highly selective, response is fast, the most important is that fluorescence spectroscopy technique can be used for the real-time detection of the imaging of organism inner cell and target compound.The fluorescent probe of having developed at present mainly includes machine molecule, biomolecules and nano material etc.
Utilizing fluorescent spectroscopy technology to detect target compound is mainly that variation based on fluorescence intensity and wavelength realizes, and always has three kinds of patterns, comprises fluorescent quenching, and fluorescence strengthens and ratio fluorescent.Wherein fluorescent quenching and fluorescence enhancing are all the fluorescence intensity changes based on single, so concentration and probe concentration, and the factors such as Instrument working state and envrionment conditions are disturbed larger to gathered signal, and ratio fluorescent can be avoided this defect largely.
So-called ratio fluorescent is exactly two kinds of colour mixture fluorescence that the different fluorescence of luminous intensity forms, and the ratio of two fluorescence intensities is referred to as ratio fluorescent.Ratio fluorescent is with different variation of different or same target product concentration of target product, and namely observable ratio fluorescent is different.The outstanding advantages that ratio fluorescent detects is exactly by the variation of intensity rate, to improve the scope of dynamic response, by setting up interior mark, greatly weaken the interference of other factors, realize the detection by quantitative to target analytes, greatly improved the tolerance range and the sensitivity that detect.
Because hypochlorous acid has strong oxidizing property, in life, be used as conventional disinfection of tap water agent.In addition,, as a kind of important biological activity oxygen small molecules, hypochlorous acid has participated in many physiological processs, is mainly bringing into play the effect of anti-inflammatory sterilization.Yet too much hypochlorous acid can damage body itself, a kind of therefore seek efficient and sensible the hypochlorous method of detection is all extremely important for environmental and biological materials.Yet up to the present Exploitation Rate fluorescent probe detects hypochlorous acid and yet there are no bibliographical information.
Three, summary of the invention
The present invention aims to provide the polynary aza ring fluorescent probe of a kind of functionalization, Its Preparation Method And Use, and technical problem to be solved is that the design by controlled polynary nitrogen heterocyclic organic fluorescence molecular structure realizes the detection to hypochlorous highly sensitive highly selective.
The polynary aza ring fluorescent probe of functionalization of the present invention (abbreviation fluorescent probe) has the polynary nitrogen heterocyclic structure of conjugation, is connected with and has certain chemically active thioketones group on heterocycle, and its general structure is:
R wherein
1, R
2, R
3, R
4difference is expression-H ,-OH independently, the hydrophilic radicals such as-COOH, sulfonic group or phosphate.
The preparation method of the polynary aza ring fluorescent probe of functionalization of the present invention operates according to the following steps:
By R
1r
2r
3r
4(Py)
2(CH
2)
2nH and ammoniacal liquor add in the mixed solvent of methylene dichloride and ethanol, precooling half an hour under ice bath, then drip dithiocarbonic anhydride solution, after dripping off, in ice bath, react 1 hour, then remove ice bath, at room temperature lucifuge continues stirring reaction 8-10 hour, after reaction finishes, revolves steaming except desolventizing can obtain crude product, and crude product can be obtained to target product after silica gel chromatographic column separating-purifying;
Described dithiocarbonic anhydride solution is that dithiocarbonic anhydride is dissolved in the mixed solvent of methylene dichloride and ethanol and is obtained;
R wherein
1r
2r
3r
4(Py)
2(CH
2)
2the proportioning of NH, ammoniacal liquor and dithiocarbonic anhydride is counted 1:1:1-1.5 by molar weight, and the molar weight of ammoniacal liquor is with NH
3h
2o meter.
Ammoniacal liquor the effect is here to provide alkaline environment so that R
1r
2r
3r
4(Py)
2(CH
2)
2nH reacts completely as far as possible, and concentration there is no impact, without being particularly limited.
In described mixed solvent, the volume ratio of methylene dichloride and ethanol is 1:1.
Reaction process of the present invention is as follows:
The polynary aza ring fluorescent probe of functionalization of the present invention detects in hypochlorous process the application as ratio fluorescent probe in fluorescent spectroscopy.
Concrete operation step of the present invention is as follows:
1, fluorescent probe is synthetic
By R
1r
2r
3r
4(Py)
2(CH
2)
2nH and ammoniacal liquor add in the mixed solvent of methylene dichloride (DCM) and ethanol (EtOH), precooling half an hour under ice bath, then drip dithiocarbonic anhydride solution, after dripping off, in ice bath, react 1 hour, then remove ice bath, at room temperature lucifuge continues stirring reaction 8-10 hour, reaction is revolved after finishing to steam and can be obtained crude product except desolventizing, thick product is dissolved in a small amount of as far as possible methylene dichloride, then successively with methylene dichloride, the methylene chloride/methanol mixing solutions of volume ratio 100:1 obtains target product as eluent by silica gel chromatographic column separating-purifying.
2, hypochlorous detection in solution
Fluorescent probe of the present invention is dissolved in to N, in dinethylformamide (DMF), prepare fluorescent probe storing solution, when fluoroscopic examination, get a certain amount of fluorescent probe storing solution and be distributed in ethanol/phosphate buffer soln, obtaining ultimate density is the fluorescent probe solution of 1.0 μ M.Described ethanol/phosphate buffer soln be by ethanol and phosphate buffer soln (PBS) by volume the ratio of 1:3 be mixed to get, wherein the pH value of phosphate buffer soln is 7.4.
In the fluorescent probe solution of preparation, add and contain hypochlorous testing sample, continuous increase along with testing sample concentration, increasing fluorescent probe molecule and hypochlorous acid react, cause fluorescence intensity and the fluorescence peak position of fluorescent probe to change gradually, green fluorescence peak intensity constantly reduces, blue-fluorescence peak intensity raises gradually simultaneously, and other biological activity oxygen small molecules does not produce obvious impact to the fluorescence intensity of probe and wavelength.Under ultraviolet lamp auxiliary, by naked eyes, can be observed before and after hypochlorous acid adds, the fluorescence of fluorescent probe obviously becomes blueness from green, and this colour-change can be used as hypochlorous acid qualitative detection foundation.Set up ratio between these two fluorescence peak intensity and the linear relationship curve of hypochlorous acid concentration, thereby realize hypochlorous detection by quantitative.
Fluorescent probe of the present invention has the polynary nitrogen heterocyclic structure of conjugation, and on heterocycle, be connected with and there is certain chemically active thioketones group, when reacting with hypochlorous acid, the material that the oxidized generation of thioketones key is new, meanwhile, fluorescence intensity and color change.The fluorescence excitation peak of fluorescent probe of the present invention has two, and an excitation peak wavelength is 300nm, and another excitation peak is wider, and wavelength is 365-390nm, emission peak wavelength 500-510nm.
In fluorescent probe solution of the present invention, add after hypochlorous acid, the fluorescence color of fluorescent probe of the present invention presents by green to blue ratio vary, and present linear dependence between its fluorescence intensity change and hypochlorous concentration, thereby qualitative and quantitative detection that can realize target thing.
It is less that fluorescent probe of the present invention is affected by potential of hydrogen, both can realize hypochlorous qualitative and quantitative detection, also can realize the qualitative and quantitative detection to hypochlorite.
Compared with the prior art, beneficial effect of the present invention is embodied in:
The present invention is the polynary nitrogen heterocyclic organic fluorescence probe of synthetic sulfur-bearing ketone groups first, and utilizes this fluorescent probe to realize hypochlorous ratio test, and detectability can reach 0.43 μ M, highly sensitive, and selectivity is good.
Fluorescent probe of the present invention can be avoided the use of large-scale instrument to a certain extent, and what only need a hand-held ultraviolet lamp just can realize hypochlorous qualitative detection, simple to operate, fast and easy, and effect is remarkable; Fluorescent probe of the present invention can effectively be avoided the interference of other impurity in sample, and selectivity is good, does not also need preprocessing process simultaneously, has greatly improved detection efficiency.
Four, accompanying drawing explanation
Fig. 1 is the fluorescence spectrum figure of fluorescent probe of the present invention.As can be seen from Figure 1, this fluorescent probe maximum excitation wavelength is 300nm, and its maximum emission wavelength is positioned at 505nm place.
Fig. 2 is the light stability figure of fluorescent probe of the present invention.As can be seen from Figure 2, under ultraviolet lamp, after continuous agitation 300 times, the fluorescence intensity of fluorescent probe of the present invention still remains 93% of initial value, and after placing 30 days, the fluorescence intensity of fluorescent probe of the present invention is also without considerable change, so this fluorescent probe stability is very good.
Fig. 3 is change in fluorescence and the linear relationship chart that in solution, hypochlorous acid detects.As can be seen from Figure 3, along with hypochlorous, add, the fluorescence generation considerable change of fluorescent probe of the present invention, the fluorescence intensity at 505nm place reduces gradually, 428nm place fluorescence intensity raises gradually, and linear between the logarithm of two fluorescence peak intensity rates and the hypochlorous acid concentration that adds, therefore can be used as hypochlorous detection by quantitative.
Fig. 4 is the visual photo that in solution, hypochlorous acid detects.As can be seen from Figure 4, before not adding hypochlorous acid, fluorescent probe transmitting green fluorescence of the present invention under ultra violet lamp, and add after hypochlorous acid, the color of fluorescence obviously becomes blueness from green, and the variation of this kind of fluorescence color can be used as hypochlorous qualitative detection.
Fig. 5 is the visual photo that in solution, hypochlorous acid selectivity detects.Hydrogen peroxide (the H that is followed successively by from left to right control group and has added respectively equivalent
2o
2), tertbutyl peroxide (TBHP), hydroxyl radical free radical (OH), hypochlorite (ClO
-), super-oxide (O
2 -), sulfide (S
2-) and nitrite (NO
2 -) after the fluorescence photo of this fluorescent probe.Control group is with joining gained in this fluorescent probe solution with the isopyknic PBS buffered soln of other solution of additive.As can be seen from Figure 5, only can there is obvious change in this fluorescence probe color after adding hypochlorous acid, and other materials are not observed considerable change after adding, illustrate that with this probe, detecting hypochlorous acid has extraordinary selectivity.
Five, embodiment
Further with non-limiting examples, be described below now:
Embodiment 1: fluorescent probe R
1r
2r
3r
4(Py)
2cH
2cHNCS(R
1, R
2, R
3, R
4be-H) preparation
The single necked round bottom flask of 10mL is placed in to ice-water bath, to the methylene dichloride that adds 1mL in round-bottomed flask, the ethanol of 1mL, (Py) of 1.0mmol
2(CH
2)
2the ammoniacal liquor of NH and 1.0mmol, the molar weight of ammoniacal liquor is with NH
3h
2o meter, stirs 30 minutes, then drips CS
2solution, described CS
2solution is the CS by 1.1mmol
2be dissolved in 1mL ethanol and 1mL methylene dichloride and obtain, after dripping off in ice-water bath stirring reaction 1 hour, remove ice bath, under room temperature, continue reaction 9 hours, whole reaction process lucifuge is carried out; Reaction finishes rear rotary evaporation and obtains crude product except desolventizing, crude product dissolves with the methylene dichloride of minute quantity, then through column chromatography for separation, purify, first take methylene dichloride after eluent wash-out for some time, with methyl alcohol, adjust polarity (methyl alcohol: methylene chloride volume is than being 1:100) again and continue wash-out, thereby obtain target product, productive rate is 82%.
The fluorogram of fluorescent probe prepared by the present embodiment is shown in Fig. 1.
Mass spectroscopy: ESI-MS:m/z (%): 242.07 (M
++ 1)
Nmr analysis:
1h NMR (CDCl
3, 400MHz) δ: 8.58 (d, J=5.2Hz, 1H), 8.28 (dd, J=7.6Hz, J=1.2Hz, 1H), 7.66 (td, J=7.6Hz, J=1.6Hz, 1H), 7.45 (d, J=8.0Hz, 1H), 7.23 (q, J=4.8Hz, 1H), 7.18 (s, 1H), 7.11 (d, J=9.2Hz, 1H), 6.73 (q, J=6.0Hz, 1H), 6.52 (td, J=7.2Hz, J=1.2Hz, 1H), 5.66 (s, 2H).
13C NMR(CDCl
3,400MHz)δ:155.02,153.77,149.52,137.07,127.50,125.36,123.39,123.15,122.36,117.31,112.19,106.91,52.97.
Embodiment 2: fluorescent probe R
1r
2r
3r
4(Py)
2cH
2cHNCS(R
1=R
4=-H, R
2=R
3=-OH) preparation
The single necked round bottom flask of 10mL is placed in to ice-water bath, to the methylene dichloride that adds 1mL in round-bottomed flask, the ethanol of 1mL, (Py) of 1.0mmol
2(CH
2)
2(OH)
2the ammoniacal liquor of NH and 1.0mmol, the molar weight of ammoniacal liquor is with NH
3h
2o meter, stirs 30 minutes, then drips CS
2solution, described CS
2solution is the CS by 1.1mmol
2be dissolved in 1mL ethanol and 1mL methylene dichloride and obtain, after dripping off in ice-water bath stirring reaction 1 hour, remove ice bath, under room temperature, continue reaction 9 hours, whole reaction process lucifuge is carried out; Reaction finishes rear rotary evaporation and obtains crude product except desolventizing, crude product dissolves with the methylene dichloride of minute quantity, then through column chromatography for separation, purify, first take methylene dichloride after eluent wash-out for some time, with methyl alcohol, adjust polarity (methyl alcohol: methylene chloride volume is than being 1:100) again and continue wash-out, thereby obtain target product, productive rate is 81.5%.
Mass spectroscopy: ESI-MS:m/z (%): 274.06 (M
++ 1)
Nmr analysis:
1h NMR (CDCl
3, 400MHz) δ: 10.50 (s, 1H), 9.26 (s, 1H), 8.06 (dd, J=7.6Hz, J=1.6Hz, 1H), 7.95 (d, J=8.0Hz, 1H), 7.30 (d, J=4.8Hz, 1H), 7.22 (s, 1H), 7.10 (s, 1H), 6.73 (d, J=6.0Hz, 1H), 6.52 (s, 1H), 5.66 (s, 2H).
13C NMR(CDCl
3,400MHz)δ:158.51,153.62,150.0,146.36,136.20,123.30,116.91,110.12,105.42,104.55,92.76,80.89,53.31.
Embodiment 3: fluorescent probe R
1r
2r
3r
4(Py)
2cH
2cHNCS(R
1=R
4=-H, R
2=-OH, R
3=-COOH) preparation
The single necked round bottom flask of 10mL is placed in to ice-water bath, to the methylene dichloride that adds 1mL in round-bottomed flask, the ethanol of 1mL, (Py) of 1.0mmol
2(CH
2)
2the ammoniacal liquor of OHNHCOOH and 1.0mmol, the molar weight of ammoniacal liquor is with NH
3h
2o meter, stirs 30 minutes, then drips CS
2solution, described CS
2solution is the CS by 1.1mmol
2be dissolved in 1mL ethanol and 1mL methylene dichloride and obtain, after dripping off in ice-water bath stirring reaction 1 hour, remove ice bath, under room temperature, continue reaction 9 hours, whole reaction process lucifuge is carried out; Reaction finishes rear rotary evaporation and obtains crude product except desolventizing, crude product dissolves with the methylene dichloride of minute quantity, then through column chromatography for separation, purify, first take methylene dichloride after eluent wash-out for some time, with methyl alcohol, adjust polarity (methyl alcohol: methylene chloride volume is than being 1:100) again and continue wash-out, thereby obtain target product, productive rate is 79.1%.
Mass spectroscopy: ESI-MS:m/z (%): 302.05 (M
++ 1)
Nmr analysis:
1h NMR (CDCl
3, 400MHz) δ: 11.24 (s, 1H), 10.56 (s, 1H), 8.52 (dd, J=7.6Hz, J=1.6Hz, 1H), 7.96 (s, 1H), 7.53 (d, J=4.8Hz, 1H), 7.25 (d, J=8.0Hz, 1H), 7.16 (s, 1H), 6.73 (s, 1H), 5.34 (d, J=6.0Hz, 1H), 5.05 (s, 2H).
13C NMR(CDCl
3,400MHz)δ:162.42,157.12,153.3,151.62,147.36,144.84,125.22,121.31,117.12,116.05,106.80,94.32,83.1,55.72.
Embodiment 4: fluorescent probe R
1r
2r
3r
4(Py)
2cH
2cHNCS(R
1=R
4=-H, R
2=R
3=-COOH) preparation
The single necked round bottom flask of 10mL is placed in to ice-water bath, to the methylene dichloride that adds 1mL in round-bottomed flask, the ethanol of 1mL, (Py) of 1.0mmol
2(CH
2)
2nH (COOH)
2with the ammoniacal liquor of 1.0mmol, the molar weight of ammoniacal liquor is with NH
3h
2o meter, stirs 30 minutes, then drips CS
2solution, described CS
2solution is the CS by 1.1mmol
2be dissolved in 1mL ethanol and 1mL methylene dichloride and obtain, after dripping off in ice-water bath stirring reaction 1 hour, remove ice bath, under room temperature, continue reaction 9 hours, whole reaction process lucifuge is carried out; Reaction finishes rear rotary evaporation and obtains crude product except desolventizing, crude product dissolves with the methylene dichloride of minute quantity, then through column chromatography for separation, purify, first take methylene dichloride after eluent wash-out for some time, with methyl alcohol, adjust polarity (methyl alcohol: methylene chloride volume is than being 1:100) again and continue wash-out, thereby obtain target product, productive rate is 79.1%.
Mass spectroscopy: ESI-MS:m/z (%): 330.05 (M
++ 1)
Nmr analysis:
1h NMR (CDCl
3, 400MHz) δ: 14.12 (s, 1H), 11.54 (s, 1H), 8.93 (dd, J=7.6Hz, J=1.6Hz, 1H), 8.16 (s, 1H), 7.93 (d, J=4.8Hz, 1H), 7.45 (d, J=8.0Hz, 1H), 7.36 (s, 1H), 6.50 (s, 1H), 5.52 (d, J=6.0Hz, 1H), 5.04 (s, 2H).
13C NMR(CDCl
3,400MHz)δ:160.22,159.32,154.8，153.3,151.62,146.63,137.74,128.22,128.01,121.31,117.80,116.35,110.42,107.32,60.72.
With the prepared fluorescent probe of embodiment 1, carry out hypochlorous detection below.Other fluorescent probe application same methods, in this not narration one by one.
Embodiment 5: hypochlorous detection in ethanol/phosphate buffer soln
1, get the prepared fluorescent probe of 2.42mg embodiment 1 and be dissolved in 10mL DMF, mix, obtaining concentration is the fluorescent probe storing solution of 1mmol/L, keeps in Dark Place.
2, clorox is dissolved in in phosphate buffer soln, to be mixed with concentration be 5 * 10
-4the clorox storing solution of mol/L, standby.
3, the fluorescent probe storing solution of getting 3 μ L is distributed in the cuvette that fills 3mL ethanol/phosphate buffered saline buffer (the volume ratio 1:3 of ethanol and phosphate buffered saline buffer), and obtaining ultimate density is the fluorescent probe solution of 1 μ mol/L.
4, in the fluorescent probe solution of step 3 preparation, add the different clorox storing solutions of measuring, make ClO
-ultimate density reach respectively 0 μ M, 0.5 μ M, 1 μ M, 2 μ M, 3 μ M, 4 μ M, 5 μ M, 6 μ M, 7 μ M.Along with ClO in fluorescent probe solution
-the continuous increase of concentration, the photoluminescent property of fluorescent probe changes gradually, finally from green fluorescence, becomes blue-fluorescence.Thereby can realize hypochlorous qualitative and quantitative detection according to the linear relationship of setting up between the variation of fluorescence color and two peak-to-peak log-of-ratio of fluorescence and hypochlorous acid concentration.ClO
-when concentration is 0.5 μ M, just there is response, detect very sensitively, see Fig. 3, Fig. 4.
The pH value of the phosphate buffer soln using in embodiment is 7.4.
Claims (4)
1. the polynary aza ring fluorescent probe of functionalization, is characterized in that its general structure is:
R in formula
1, R
2, R
3, R
4difference is expression-H ,-OH independently ,-COOH, sulfonic group or phosphate.
2. a preparation method for the polynary aza ring fluorescent probe of functionalization claimed in claim 1, is characterized in that:
By R
1r
2r
3r
4(Py)
2(CH
2)
2nH and ammoniacal liquor add in the mixed solvent of methylene dichloride and ethanol, precooling half an hour under ice bath, then drip dithiocarbonic anhydride solution, after dripping off, in ice bath, react 1 hour, then remove ice bath, at room temperature lucifuge continues stirring reaction 8-10 hour, after reaction finishes, revolves steaming except desolventizing can obtain crude product, and crude product can be obtained to target product after silica gel chromatographic column separating-purifying;
Described dithiocarbonic anhydride solution is that dithiocarbonic anhydride is dissolved in the mixed solvent of methylene dichloride and ethanol and is obtained;
R wherein
1r
2r
3r
4(Py)
2(CH
2)
2the proportioning of NH, ammoniacal liquor and dithiocarbonic anhydride is counted 1:1:1-1.5 by molar weight, and the molar weight of ammoniacal liquor is with NH
3h
2o meter;
Described R
1r
2r
3r
4(Py)
2(CH
2)
2the structural formula of NH is:
3. preparation method according to claim 2, is characterized in that:
In described mixed solvent, the volume ratio of methylene dichloride and ethanol is 1:1.
4. a purposes for the polynary aza ring fluorescent probe of functionalization claimed in claim 1, is characterized in that: in fluorescent spectroscopy, detect in hypochlorous process the application as ratio fluorescent probe.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310362261.3A CN103436254B (en) | 2013-08-19 | 2013-08-19 | Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310362261.3A CN103436254B (en) | 2013-08-19 | 2013-08-19 | Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103436254A CN103436254A (en) | 2013-12-11 |
| CN103436254B true CN103436254B (en) | 2014-10-08 |
Family
ID=49689974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310362261.3A Expired - Fee Related CN103436254B (en) | 2013-08-19 | 2013-08-19 | Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103436254B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR099890A1 (en) * | 2014-03-31 | 2016-08-24 | Epitherapeutics Aps | HISTONE DEMETILASE INHIBITORS |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008085008A1 (en) * | 2007-01-11 | 2008-07-17 | Mogam Biotechnology Research Institute | T-cell inhibiting compounds and their use for the treatment of t-cell-mediated diseases |
| CN102382641B (en) * | 2011-09-22 | 2013-07-24 | 厦门大学 | Fluorescent probe for detecting hypochlorous acid and preparation method thereof |
-
2013
- 2013-08-19 CN CN201310362261.3A patent/CN103436254B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN103436254A (en) | 2013-12-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhong et al. | A simple H2S fluorescent probe with long wavelength emission: application in water, wine, living cells and detection of H2S gas | |
| Zhang et al. | A highly sensitive and rapidly responding fluorescent probe based on a rhodol fluorophore for imaging endogenous hypochlorite in living mice | |
| Dai et al. | Simultaneous monitoring of polarity changes of lipid droplets and lysosomes with two-photon fluorescent probes | |
| CN107188876B (en) | It is a kind of for detecting the synthesis and application of the near infrared fluorescent probe of hydrogen polysulfide | |
| CN108003869B (en) | Fluorescent probe for detecting hypochlorite with high sensitivity and synthesis method and application thereof | |
| Li et al. | A new mechanism-based fluorescent probe for the detection of ClO− by UV–vis and fluorescent spectra and its applications | |
| CN102206223A (en) | Optical probe film and special-purposed organic dye for micro determination of copper ion content in water sample | |
| CN107021953A (en) | A kind of coumarin fluorescent probe and preparation method and its application on detection hypochlorite ion | |
| Zheng et al. | Two quenching groups are better than one: A robust strategy for constructing HOCl fluorescent probe with minimized background fluorescence and ultra-high sensitivity and its application of HOCl imaging in living cells and tissues | |
| Zhang et al. | A new naphthalimide-picolinohydrazide derived fluorescent “turn-on” probe for hypersensitive detection of Al3+ ions and applications of real water analysis and bio-imaging | |
| Aziz et al. | Design of a highly sensitive and selective bulk optode based on fluorescence enhancement of N, N′-bis-(1-hydroxyphenylimine) 2, 2′-pyridil Schiff base: Monitoring of zinc (II) ion in real samples and DFT calculation | |
| Yang et al. | pH-sensitive fluorescent salicylaldehyde derivative for selective imaging of hydrogen sulfide in living cells | |
| Jin et al. | Construction of DCM-based NIR fluorescent probe for visualization detection of H2S in solution and nanofibrous film | |
| Chen et al. | A novel fluorescent probe for cascade detection of hydrogen sulfide and hypochlorous acid and its application in bioimaging | |
| CN110172070A (en) | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide | |
| CN106397319A (en) | Fluorescent probe for proportionally detecting hydrazine, method for synthesizing fluorescent probe and application thereof | |
| CN106518763A (en) | High-selectivity fluorescence probe for detecting cyanide ions in ratio mode and synthesis method and application thereof | |
| CN103436254B (en) | Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof | |
| Xu et al. | Screening of aggregation-induced emission and multi-response acrylonitrile-bridging fluorescent molecules tailored for rapid turn-on detection of HClO as well as ratiometric visualizing of extreme basicity | |
| CN110878085B (en) | Rapid high-selectivity hypobromous acid fluorescent probe, preparation method and application | |
| CN110669503B (en) | Preparation and application of carbon monoxide near-infrared fluorescent probe | |
| CN105778897B (en) | PH sensitive fluorescence dyes and its preparation method and application | |
| Luo et al. | A novel dual-activatable ultrasensitive chemiluminescent probe for mercury (II) monitoring: From rational design to multiple application | |
| CN105622540A (en) | CO probe and preparation method and application thereof | |
| CN110407849A (en) | A kind of detection method of naphthalene fluorescent molecule and preparation method thereof and tyrosinase |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| 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: 20141008 Termination date: 20180819 |