CN103664735A - Fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and application thereof - Google Patents
Fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and application thereof Download PDFInfo
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Abstract
The invention relates to a fluorescent probe for detecting hydrogen sulfide (H2S), and specifically relates to a fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and an application thereof. The fluorescent probe takes a hemicyanine dye or a cyanine dye as a fluorescent matrix, and m-nitrophenylamine or m-nitrophenol is introduced to the matrix. The fluorescent probe is used for detecting hydrogen sulfide inside and outside a water body or a living body. According to these compounds of the fluorescent probe for detecting hydrogen sulfide, corresponding fluorescence intensity changes in presence of hydrogen sulfide, so that the fluorescent probe can be used for detecting hydrogen sulfide, thereby greatly reducing interference of outer conditions and improving the detection accuracy. In particular, these compounds used as the fluorescent probe can be used for detecting intracellular hydrogen sulfide, thereby having an important significance for lucubrating the dynamic mechanism of hydrogen sulfide which is generated, conveyed, accumulated and the like in the living body and further understanding the physiological and toxicological effects of hydrogen sulfide.
Description
Technical field
The present invention relates to for detection of hydrogen sulfide (H
2s) fluorescent probe, specifically a kind of fluorescent probe and application thereof that detects hydrogen sulfide in cell based on nitroreduction.
Background technology
For centuries, hydrogen sulfide (H
2s) aspect environmental toxicity and murder by poisoning impact, causing a lot of attentions.In the time of among human body is exposed to exogenous hydrogen sulfide, thereby this gas can promptly be absorbed and be entered blood circulation by lung, then in human body, produces toxic action.Generally believe now that sulfide produces physiology toxicity with mode inhibited oxidation enzyme like Cyanides.Yet recently relevant life entity endogenous H
2its some physiological functions are all devoted in the research work of S.After nitrogen protoxide (NO) and carbon monoxide (CO), H
2s is confirmed as the 3rd and has bioactive gas, is called as gasotransmitter or gas amboceptor.H
2s is distributed widely in whole body everywhere, and the scope of its physiology related concentrations is not from nmole level to mmole level level etc. according to estimates.Under physiological concentration level, hydrogen sulfide participates in a series of physiological process, comprises and regulates antiotasis, myocardial contraction, nerve conduction, insulin secretion etc.Once cell can not maintain the interior level of the physiological range of its hydrogen sulfide, just can cause the diseases such as artery and pulmonary hypertension, Alzheimer's disease, gastric mucosa injury, liver cirrhosis.In addition, hydrogen sulfide also shows as the anti-oxidant scavenging agent as active oxygen species and active nitrogen species.In addition much research also demonstrates three gasotransmitters, H
2s, NO and CO, between also have various interactions indicating the Health and Disease of human body.Therefore, to the research interest of organism Endogenous Hydrogen Sulfide, also steady-state growth is in the ascendant in recent years.
Fluorescent probe is effectively to detect H in life entity
2one of means of S.A fluorescent probe with application prospect should have that change in fluorescence obviously before and after effect, fast to target molecule response, selectivity is good, can be used for the advantages such as real-time reversible detection.Christopher J.Chang etc. discloses a class and in order to detect fluorescent probe SF1 and the SF2(structure of hydrogen sulfide, has seen Fig. 1, C.J.Chang et.al, J. Am.Chem.Soc., 2011,133,10078), with H
2after S effect, thereby fluorescence strengthens detection H
2the existence of S.But this class fluorescent probe, can not be for detecting H rapidly to hydrogen sulfide low-response
2s.Binghe Wang etc. discloses a kind of detection H
2the fluorescent probe DNS-Az(structure of S is shown in Fig. 1, B.Wang et.al, Angew.Chem.Int.Ed., 2011,50,9672), but the excitation-emission wavelength of this probe is positioned at ultraviolet region, can not effectively avoid the interference of biological autofluorescence, UV-light is very large to organism photobleaching simultaneously, is easy to damage biological sample.Above-mentioned probe is all fluorescence enhancement type probe, there is no the variation of wavelength, cannot realize detection by quantitative.For reaching, be fully penetrated into organization internal and avoid cell autofluorescence to disturb object, greatly reduce the interference of outside atmosphere, realize detection by quantitative, still need exploitation to there is the operability fluorescent probe of longer excitation-emission wavelength.Therefore, exploitation has good selectivity, can carry out H in detection of biological system in near-infrared region
2the fluorescent probe of S is significant.
Summary of the invention
The object of the invention is to, a kind of fluorescent probe and application thereof that detects hydrogen sulfide in cell based on nitroreduction is provided.
The technical solution used in the present invention is for achieving the above object:
Based on nitroreduction, detect a fluorescent probe for hydrogen sulfide in cell, fluorescent probe is to using hemicyanine dye or cyanine dye as fluorescence parent, and on parent, introduces m-nitraniline or/and m-nitrophenol.
Described fluorescent probe is to using hemicyanine dye or cyanine dye as fluorescence parent, and on parent, introduces m-nitraniline or m-nitrophenol, as shown in structural formula I, II;
Formula I
Formula II
In formula I,
R
1for phenyl or allyl group;
R
2, R
3for C
1-5alkyl, phenyl or benzyl;
R
4, R
5for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen or sulfonic group;
Y is N, O or S;
In formula II,
R
1for phenyl or allyl group;
R
2for C
1-5alkyl, phenyl or benzyl;
R
3for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen or sulfonic group;
R
4for C
1-5alkyl, phenyl or benzyl;
X is halogen, N, O or S;
Y is N, O or S.
Based on nitroreduction, detect the application of the fluorescent probe of hydrogen sulfide in cell, described fluorescent probe is for the detection of water body or the inside and outside hydrogen sulfide of organism.
Described fluorescent probe is for detection of hydrogen sulfide in living things system, and carries out the fluorescence imaging of cell or tissue.
Thereby the hydrogen sulfide inside and outside formula I or II and water body to be determined or organism is caused to the change of fluorescence intensity, the compound of gained general formula III, IV structure;
General formula III
General formula I V.
Beneficial effect of the present invention: the present invention visits this compounds of hydrogen sulfide fluorescent probe, under hydrogen sulfide exists, corresponding fluorescence intensity changes, and can be used for the detection of hydrogen sulfide, greatly reduces the interference of external conditions, improves accuracy in detection.Especially, this compounds is as fluorescent probe, can be used for the detection of hydrogen sulfide in cell, this kinetics mechanism to the further investigation hydrogen sulfide processes such as generation, conveying and accumulation in vivo, physiology and the toxicological effect of further understanding hydrogen sulfide are significant.
Accompanying drawing explanation
The published hypochlorous acid fluorescent probe structural representation of lifting in Fig. 1 background technology;
The probe synthetic route schematic diagram that Fig. 2 provides for the embodiment of the present invention;
The probe in detecting principle schematic that Fig. 3 provides for the embodiment of the present invention;
The impact of the temperature that Fig. 4 provides for the embodiment of the present invention on detection rates;
The fluorescence intensity change curve of the fluorescent probe that under the different pH that Fig. 5 provides for the embodiment of the present invention, probe adopts;
The selectivity schematic diagram of the fluorescent probe adopting that Fig. 6 provides for the embodiment of the present invention to hydrogen sulfide;
The linear fit curve that the fluorescent probe 789nm fluorescence intensity adopting that Fig. 7 provides for the embodiment of the present invention and concentration of hydrogen sulfide change
The fluorescent probe Cy-NO adopting that Fig. 8 provides for the embodiment of the present invention
2laser Scanning Confocal Microscope imaging for detection of hydrogen sulfide in cell.
The fluorescent probe Cy-NO adopting that Fig. 9 provides for the embodiment of the present invention
2laser Scanning Confocal Microscope photo for the thin inner cellular localization of probe.
Embodiment
The general formula of fluorescent probe is:
Formula I
General formula II
In formula I,
R
1for phenyl, allyl group;
R
2, R
3for C
1-5alkyl, phenyl, benzyl;
R
4, R
5for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen, sulfonic group;
Y is N, O, S;
In general formula II,
R
1for phenyl, allyl group;
R
2for C
1-5alkyl, phenyl, benzyl;
R
3for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen, sulfonic group;
R
4for C
1-5alkyl, phenyl, benzyl;
X is halogen, N, O, S;
Y is N, O, S.
Work as R
1for phenyl, when Y is O, the general formula of described fluorescent probe is:
General formula V
In general formula V:
R
2, R
3for C
1-5alkyl, phenyl, benzyl;
R
4, R
5for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen, sulfonic group;
Work as R
1for phenyl, when Y is N, the general formula of described fluorescent probe is:
General formula VI
In general formula VI:
R
1for phenyl, allyl group;
R
2for C
1-5alkyl, phenyl, benzyl;
R
3for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen, sulfonic group;
R
4for C
1-5alkyl, phenyl, benzyl;
X is halogen, N, O, S;
The term using in the present invention " alkyl " comprises straight chained alkyl and branched-chain alkyl.As mentioned, single alkyl is as " propyl group ", only refers in particular to straight chained alkyl, as mentioned, single branched-chain alkyl is as " sec.-propyl ", only refers in particular to branched-chain alkyl.For example, " C
1-6alkyl " comprise C
1-4alkyl, C
1-3alkyl, methyl, ethyl, n-propyl, sec.-propyl and the tertiary butyl.Other group that similarly rule is also applicable to use in this specification sheets.
The term using in the present invention " halogen " comprises fluorine, chlorine, bromine and iodine.
Refer to-CH of the term using in the present invention " benzyl "
2-Ph group.When modifying benzyl with " optionally replacing ", refer to that this benzyl can unsubstituted form exist, or can in any suitable position, be replaced by suitable substituting group.Suitable substituting group includes but not limited to H, C
1-18alkyl, CN, COOH, NH
2, NO
2, OH, SH, C
1-6alkoxyl group, C
1-6alkylamino, C
1-6amido, halogen or C
1-6haloalkyls etc., as long as the final compound forming has the character of the present invention's expectation.Preferably benzyl is by COOH, NH
2, OH, C
1-6alkoxyl group, halogen optionally replace.
By general formula V, VI structure applications is in detecting H
2during S, it is and H
2after S effect, generate and there is the compound of general formula VII, VIII structure, thereby cause the change of fluorescence intensity;
General formula VII
General formula VIII
General formula VII, VIII can be to H
2s carries out qualitative, quantitative detection.
Embodiment
Embodiment is used for further illustrating the present invention, but the invention is not restricted to embodiment.
Synthesizing of compound shown in the concrete formula I of embodiment 1..
The structure code name Cy-NO of the probe compound that as shown in Figure 2, the concrete formula I of embodiment adopts
2represent
0.696g m-nitrophenol and 0.0524-0.173g sodium hydride are dissolved in 30mL dry DMF, add 0.5g cyanine dye Cy7-Cl, room temperature reaction 24h under nitrogen protection.After reaction finishes, vacuum is removed DMF, and silica gel chromatographic column is purified, and eluent is ethyl acetate and methyl alcohol, obtains deep green product 0.425 g, productive rate 73.2%.
1H?NMR(500MHz,CDCl
3-D
1)δ(ppm):1.25-2.09(m,20H),2.63-2.65(q,4H),4.17-4.22(q,4H),6.08-6.17(d,2H),7.04-7.98(m,12H),8.01-8.09(d,2H).
13C?NMR(500MHz,CDCl
3-D
1)δ(ppm):171.4,162.2,159.7,141.7,141.1,131.7,129.9,128.8,125.3,122.3,122.2,117.4,110.7,110.5,110.2,100.7,77.3,77.0,76.8,49.0,40.0,28.4,27.8,24.8,21.0,12.4,12.3.LC-MS(API-ES):m/z?C
40H
44N
3O
3 +Calcd?614.3,found[M
+]614.5.Elemental?analysis?calcd(%)for?C
40H
44IN
3O
3:C,64.77;H,5.98;N,5.67;O,6.47;found:C,64.76;H,5.99;N,5.68;O,6.48.
Synthesizing of compound shown in the concrete formula II of embodiment 2
The structure code name mCy-NO of the probe compound that as shown in Figure 2, the concrete formula I of embodiment adopts
2represent
0.696g m-nitraniline is dissolved in 30mL dry DMF, adds triethylamine, after stirring at room 15min, then adds 0.50g cyanine dye Cy7-Cl, under nitrogen protection, in 60-90 ℃, reacts 24h.After reaction finishes, vacuum is removed DMF, with silica gel chromatographic column, purifies, and eluent is ethyl acetate and methyl alcohol.Obtain mazarine product 0.274g, productive rate 47.3%.
1HNMR(400MHz,CDCl
3-D
1,0.1%CD
3COOD-D
4)δ(ppm):8.00(s,1H),7.30-7.15(m,8H),6.50(s,1H),5.84(s,1H),5.28(s,1H),4.02(m,2H),2.96(s,2H),2.88(s,2H),2.79(s,1H),1.87-1.58(m,10H).
13C?NMR(100MHz,CDCl
3-D
1)δ(ppm):168.8,162.6,142.4,140.7,140.1,128.5,127.7,123.8,122.2,122.0,121.5,120.0,109.2,105.54,96.3,59.2,54.6,45.5,39.3,32.9,29.6,29.3,28.6,25.1,24.4,22.7,22.0,20.1,12.1,11.0ppm.LC-MS(API-ES):m/z?C
30H
42ClN
3O
+Calcd?462.1943,found?492.2000.Elemental?Analysis:Calcd?C,70.04;H,6.31;N,9.08,found?C,70.06;H,6.30;N,9.09.
Each compound in its general formula, can take the synthetic of probe that hemicyanine dye is parent according to above-mentioned synthetic method.
Embodiment 3
Compound C y-NO shown in concrete formula I
2temperature effective to hydrogen sulfide response
For simulating as far as possible physiological condition, the following detects effect experiment and all under pH=7.4 condition, carries out (HEPES buffered soln, concentration is 40mM), and concentration and probe concentration adopts 10 μ M.
PH adopts HEPES buffered soln to control.In 10ml colorimetric cylinder, add Compound C y-NO shown in the concrete formula I of 10 μ M
2, then add 40mM HEPES, then add 350 μ M Na
2s, ultrapure water constant volume, to 10ml, shakes up solution, at 25,37,45,60 ℃, after balance 50min, above-mentioned working fluid is added in fluorescence ware and measures fluorescence spectrum.。Fluorescence intensity variation with temperature as shown in Figure 4.Fig. 4 shows Cy-NO
2and H
2the speed of reaction temperature influence of S.In order to realize the object applied in organism, we are 37 ℃ by temperature optimization.
Embodiment 4
Compound C y-NO shown in concrete formula I
2selectivity to hydrogen sulfide
PH adopts HEPES buffered soln to control.In 10ml colorimetric cylinder, add Compound C y-NO shown in the concrete formula I of 10 μ M
2, then adding 20mM HEPES, ultrapure water constant volume, to 10ml, shakes up solution, after balance 50min, above-mentioned working fluid is added in fluorescence ware and measures fluorescence spectrum at 37 ℃.Fluorescence intensity F with the variation of pH as shown in Figure 5.Fig. 5 shows that F does not have considerable change in the scope of pH 4.0～9.0,, in the system of pH 4.0～9.0, can use Cy-NO
2detect hydrogen sulfide.
In 10ml colorimetric cylinder, add 10 μ M probes, then add 40mM HEPES pH 7.4, then add ultrapure water to 5ml, shake up, then add various determinands, finally use ultrapure water constant volume to 10ml.Shake up solution, balance 50min, pours working fluid into fluorescence ware and measures fluorescence spectrum.Cy-NO
2to the selectivity of hydrogen sulfide as shown in Figure 6.Fig. 6 shows Cy-NO
2hydrogen sulfide is had to good selectivity, after hydrogen sulfide effect, Cy-NO
2corresponding fluorescence strengthens.Na under condition determination
2s, HSO
3 -, SO
3 2-, S
2o
3 2-, S
2o
4 2-, S
2o
5 2-, NO, H
2o
2at 300 μ M.Cl
-, Br
-, I
-, N
3 -, NO
2 -, OAc
-, Lipoic acid, citrate, glutathione, cysteine, S-nitrosoglutathione and 2-mercaptoethanol etc. can not make fluorescence probe change.
Embodiment 5
Compound C y-NO shown in concrete formula I
2detection by quantitative to hydrogen sulfide in the aqueous solution and serum
In 10ml colorimetric cylinder, add 10 μ M Cy-NO
2, then add 40mM HEPES pH 7.4, then add ultrapure water to 5ml, shake up, then add different concns hydrogen sulfide, finally use ultrapure water/serum constant volume to 10ml.Shake up solution, balance 50min, pours working fluid into fluorescence ware and measures fluorescence spectrum, gets each 789nm place fluorescence spectrum value, and Input Software OriginPro 8.0, obtains linear work curve.
Peroxidation nitrosyl concentration after constant volume: 0,50,100,150,200,250,300,350 μ M.
Fig. 7 red line and blue line represent with H
2the variation of the variation system fluorescence intensity of S concentration, shows the increase with concentration of hydrogen sulfide, and system 789nm absorption intensity is in obvious enhancing.
Fig. 7 blue line is illustrated in the fluorescence intensity of 789nm in the aqueous solution and the linear fit curve that concentration of hydrogen sulfide changes, and the linear regression constant of linear fit curve is 0.992, shows the mensuration ONOO that probe can be quantitative
-concentration.
Fig. 7 red line is illustrated in the fluorescence intensity of 789nm in serum and the linear fit curve that concentration of hydrogen sulfide changes, and the linear regression constant of linear fit curve is 0.996, shows the mensuration ONOO that probe can be quantitative
-concentration.
Embodiment 6
Compound C y-NO shown in concrete formula I
2detection for hydrogen sulfide in cell
RAW264 cell is cultivated according to American type Tissue Culture Collection regulation.10uM Cy-NO as shown in Figure 8
2hatch RAW264 cell 30 minutes, with substratum washing 3 times, be placed under confocal fluorescent microscope and take pictures.Separately get 4 groups of cells, add 10uM Cy-NO
2hatch RAW264 cell 3 minutes, then add (b) 50 μ M, (c) 150 μ M, (d) 250 μ M, and (e) 350 μ M Na
2s incubated cell 30 minutes, with substratum washing 3 times, Laser Scanning Confocal Microscope is taken pictures, and as shown in Figure 9, fluorescence intensity obviously raises result; Then add 1uM Hoechest to hatch RAW264 cell 10 minutes, with substratum washing 3 times, be placed under confocal fluorescent microscope and take pictures, after 9a and 9b stack, result is as shown in Fig. 9 c.Fig. 9 c shows that probe mainly dyes to tenuigenin.
In the present invention, designed all hydrogen sulfide probes are the fluorescent probe of fluorescent switch type, and after the operation of the different fluorescence parents of conversion, the Fluorescence behaviour of all probes is all similar to embodiment.Namely on parent, introduce after m-nitrophenol or m-nitro amine groups, parent fluorescence is by quencher, and when adding after hydrogen sulfide is amino by nitroreduction, the fluorescence of fluorescence parent recovers.
Above content is in conjunction with concrete preferred implementation further description made for the present invention, can not assert that specific embodiment of the invention is confined to these explanations.For general technical staff of the technical field of the invention, without departing from the inventive concept of the premise, can also make some simple deduction or replace, all should be considered as belonging to protection scope of the present invention.It as fluorescence dye, is a kind of purposes of new compound of the present invention; can not assert that compound of the present invention is only for fluorescence dye; for general technical staff of the technical field of the invention; under the consideration as the same function mechanism of fluorescence dye based on the compounds of this invention; can also make some simple inferences; draw other application purpose of compound of the present invention, all should be considered as belonging to protection scope of the present invention.
Claims (5)
1. based on nitroreduction, detect a fluorescent probe for hydrogen sulfide in cell, it is characterized in that: fluorescent probe is for usining hemicyanine dye or cyanine dye as fluorescence parent, and on parent, introduce m-nitraniline or/and m-nitrophenol.
2. by the fluorescent probe that detects hydrogen sulfide in cell based on nitroreduction claimed in claim 1, it is characterized in that: described fluorescent probe is for usining hemicyanine dye or cyanine dye as fluorescence parent, and on parent, introduce m-nitraniline or m-nitrophenol, as shown in structural formula I, II;
Formula I
Formula II
In formula I,
R
1for phenyl or allyl group;
R
2, R
3for C
1-5alkyl, phenyl or benzyl;
R
4, R
5for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen or sulfonic group;
Y is N, O or S;
In formula II,
R
1for phenyl or allyl group;
R
2for C
1-5alkyl, phenyl or benzyl;
R
3for H, C
1-20alkyl, hydroxyl, alkoxyl group, cyano group, alkyl secondary amine base, nitro, halogen or sulfonic group;
R
4for C
1-5alkyl, phenyl or benzyl;
X is halogen, N, O or S;
Y is N, O or S.
3. an application that detects the fluorescent probe of hydrogen sulfide in cell based on nitroreduction claimed in claim 1, is characterized in that: described fluorescent probe is for the detection of water body or the inside and outside hydrogen sulfide of organism.
4. by the application that detects the fluorescent probe of hydrogen sulfide in cell based on nitroreduction claimed in claim 3, it is characterized in that: described fluorescent probe is for detection of hydrogen sulfide in living things system, and carry out the fluorescence imaging of cell or tissue.
5. by the application based on the fluorescent probe of hydrogen sulfide in nitroreduction detection cell described in claim 3 or 4, it is characterized in that: thus the hydrogen sulfide inside and outside general formula I or II and water body to be determined or organism is caused to the change of fluorescence intensity, the compound of gained general formula III, IV structure;
General formula III
General formula I V.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN105001857A (en) * | 2015-07-23 | 2015-10-28 | 中国科学院烟台海岸带研究所 | Fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof |
| CN105017128A (en) * | 2014-04-28 | 2015-11-04 | 中国科学院烟台海岸带研究所 | Cyanine compound and application thereof |
| CN105038763A (en) * | 2015-06-04 | 2015-11-11 | 济南大学 | Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof |
| CN105295899A (en) * | 2015-09-21 | 2016-02-03 | 山东大学 | Ratiometric fluorescent probe for detecting hydrogen sulfide and application of ratiometric fluorescent probe |
| CN106588906A (en) * | 2016-12-14 | 2017-04-26 | 南开大学 | Near infrared fluorescent probe and preparation method and application of near infrared fluorescent probe |
| CN107286186A (en) * | 2016-04-12 | 2017-10-24 | 中国科学院化学研究所 | Hydrogen sulfide fluorescence probe and its preparation method and application |
| CN107400080A (en) * | 2017-07-27 | 2017-11-28 | 中国科学院烟台海岸带研究所 | A kind of application of organic compound and its intermediate based on flower cyanines |
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| CN112694431A (en) * | 2019-10-23 | 2021-04-23 | 中国医学科学院药物研究所 | Nitroreductase in hypersensitive fluorescent probe detection bacteria and application in bacterial infection |
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| CN105017128A (en) * | 2014-04-28 | 2015-11-04 | 中国科学院烟台海岸带研究所 | Cyanine compound and application thereof |
| CN105017128B (en) * | 2014-04-28 | 2017-09-15 | 中国科学院烟台海岸带研究所 | A kind of cyanine compound and its application |
| CN104098500A (en) * | 2014-07-08 | 2014-10-15 | 中国科学院烟台海岸带研究所 | Organic compound based on gallocyanine and application of organic compound |
| CN104098500B (en) * | 2014-07-08 | 2016-03-16 | 中国科学院烟台海岸带研究所 | Based on organic compound and the application thereof of cyanine |
| CN105038763A (en) * | 2015-06-04 | 2015-11-11 | 济南大学 | Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof |
| CN105001857A (en) * | 2015-07-23 | 2015-10-28 | 中国科学院烟台海岸带研究所 | Fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof |
| CN105001857B (en) * | 2015-07-23 | 2017-01-18 | 中国科学院烟台海岸带研究所 | Fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof |
| CN105295899B (en) * | 2015-09-21 | 2017-05-10 | 山东大学 | Ratiometric fluorescent probe for detecting hydrogen sulfide and application of ratiometric fluorescent probe |
| CN105295899A (en) * | 2015-09-21 | 2016-02-03 | 山东大学 | Ratiometric fluorescent probe for detecting hydrogen sulfide and application of ratiometric fluorescent probe |
| CN107286186A (en) * | 2016-04-12 | 2017-10-24 | 中国科学院化学研究所 | Hydrogen sulfide fluorescence probe and its preparation method and application |
| CN106588906A (en) * | 2016-12-14 | 2017-04-26 | 南开大学 | Near infrared fluorescent probe and preparation method and application of near infrared fluorescent probe |
| CN107400080A (en) * | 2017-07-27 | 2017-11-28 | 中国科学院烟台海岸带研究所 | A kind of application of organic compound and its intermediate based on flower cyanines |
| CN107400080B (en) * | 2017-07-27 | 2020-03-31 | 中国科学院烟台海岸带研究所 | Organic compound based on cyanine and application of intermediate thereof |
| CN107954920A (en) * | 2017-11-28 | 2018-04-24 | 中国科学院烟台海岸带研究所 | A kind of organic compound and application based on flower cyanines |
| CN109232360A (en) * | 2018-12-17 | 2019-01-18 | 中国科学院烟台海岸带研究所 | A kind of fluorescent probe compounds and preparation method thereof for polysulfide detection |
| CN110498758A (en) * | 2019-08-14 | 2019-11-26 | 华中科技大学 | The near infrared fluorescent probe of glutathione and its preparation and application for identification |
| CN112694431A (en) * | 2019-10-23 | 2021-04-23 | 中国医学科学院药物研究所 | Nitroreductase in hypersensitive fluorescent probe detection bacteria and application in bacterial infection |
| CN112694431B (en) * | 2019-10-23 | 2022-09-16 | 中国医学科学院药物研究所 | Nitroreductase in hypersensitive fluorescent probe detection bacteria and application in bacterial infection |
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