CN108148057A - Prepare for detect cysteine fluorescence probe method - Google Patents
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- CN108148057A CN108148057A CN201810155917.7A CN201810155917A CN108148057A CN 108148057 A CN108148057 A CN 108148057A CN 201810155917 A CN201810155917 A CN 201810155917A CN 108148057 A CN108148057 A CN 108148057A
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- JJOPQMAMJLOGFB-UHFFFAOYSA-N Oc1c(C=O)cccc1C=O Chemical compound Oc1c(C=O)cccc1C=O JJOPQMAMJLOGFB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Oc1ccccc1 Chemical compound Oc1ccccc1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The present invention relates to prepare for detect cysteine fluorescence probe method.Probe prepared by the method for the present invention can act on, and have the characteristics that high sensitivity and selectivity with cysteine, can be applied in cysteine high sensitivity and highly selective identification or its can in determination sample cysteine concentration.
Description
Technical field
The present invention relates to prepare for detect cysteine fluorescence probe method.Probe prepared by the present invention can be with
It is acted on cysteine, and there is high sensitivity and selectivity, it can be in cysteine high sensitivity and highly selective
Applied in identification or its can in determination sample cysteine concentration.
Background technology
There are many kinds of the types of mercaptan, but there are three types of small molecule biological thiols, respectively homocysteine, glutathione
And cysteine.And wherein cysteine is present in many small molecules and protein of biological tissue cell, is to form them
Important substance, and cysteine played in mammal regulating system adjusts a variety of physiology and pathologic process it is quite important
Effect, mainly by the reproducibility speciality of cysteine can be oxidized to oxidisability substance maintain cellular environment in
Redox equilibrium.Homocysteine plays an important role in organism, it is methionine in some reactions
Intermediate product, it is rear there are two types of outlet once being formed, first, methionine is re-converted into, second is that the shape under the catalysis of some substances
Into cysteine.Glutathione is non-protein sulfydryl most abundant in human body, in the cell there are many function, including removing toxic substances
Free radical and peroxide adjust the function of cell growth and protein and safeguard immune function, so, glutathione it is dense
Degree can be as assessment redox state and the index in biologic detoxication state status in organism.But cysteine is in people
It is to play one of vital amino acid in body, it can change the disulfide bond between protein molecule to weaken protein sky
Between structure, so as to which protein be enable to extend.In addition cysteine also have removing toxic substances, anti-aging, change inflammation and in advance
Anti- treatment radiation disease.A large amount of investigation show that the biological thiol beyond normal level has been demonstrated the generation with human diseases
It is related, it such as slowly grows, liver is damaged and skin damage.Cysteine deficiency can lead to many diseases, be damaged including retarded growth, liver
Bad, drowsiness, muscle weakness and fat loss.The homocysteine of human blood middle and high concentration is to cause nerve channel effect, bone
The risk factor of the diseases such as matter osteoporosis and inflammatory bowel disease.
At present, the method for quantitative detection cysteine is varied, and main method includes：Titration method, ultraviolet suction
Receipts method, molecular fluorescent method, emission spectrometry method, mass spectrometry etc..Several method in contrast, utilizes molecular fluorescence
The fluorescence probe of analysis has apparent advantage, including it is highly selective, have it is highly sensitive, can fast reaction, detection in time,
Cell imaging etc..The probe for being used for detecting cysteine at present has very much, but the fluorescence probe of Ratio-type near-infrared and can
Carry out the seldom of bio-imaging.
On the other hand, Ratiometric fluorescent probe can mitigate ambient enviroment using the variable value between two adjacent peaks
Influence to cysteine detection, so the practical value with bigger.
To sum up, the Ratio-type near infrared fluorescent probe that preparation can detect cysteine is very significant.
Invention content
This field is badly in need of preparing a kind of method that high sensitivity and highly selective Ratio-type measure cysteine, so as to
Effectively detection particularly can detect cysteine in the sample.For this purpose, the present invention proposes a kind of novel detection half of preparation
The method of cystine, the probe can be used directly, and not need to do further organic synthesis modification, and can be highly sensitive and high
Optional ratio's type identifies cysteine.Probe of the present invention can be to the carry out high sensitivity of cysteine and highly selective
It measures.
Specifically, the present invention provides prepare for detect cysteine fluorescence probe method, preparation method
It is as follows：
Wherein：R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13For independently selected from by hydrogen atom, straight chain or
The group that branched alkyl, straight or branched alkoxyl, sulfonic group, ester group and hydroxyl form；And R therein1, R2, R3, R4, R5, R6,
R7, R8, R9, R10, R11, R12And R13It can be identical or different.
Preferably, the present invention provides preparation for detecting the method for the fluorescence probe of cysteine, preparation method is such as
Under：
Ratiometric fluorescent probe prepared by the present invention can be acted on cysteine, lead to the variation of fluorescence spectrum,
It is quantitatively detected so as to fulfill the Ratio-type to cysteine.
Specifically, cysteine Ratiometric fluorescent probe prepared by the present invention respectively with Cys, Gly, Pro, Leu,
Val, Thr and Ala, which are acted on, cannot lead to substantially changeing for fluorescence spectrum, so as to fulfill the selectivity to cysteine
Identification, and then can be optionally used for excluding the interference of the quantitative determination of the presence of these amino acid to cysteine.
The stability of cysteine colorimetric probe prepared by the present invention is good, can preserve use for a long time.
Further, the cysteine probe prepared by the present invention being capable of half Guang of highly sensitive and highly selective Ratio-type measure
Propylhomoserin, and do not need to do further organic synthesis modification, be conducive to commercialized popularization and application.
Description of the drawings
Fig. 1：Probe has good response for the cysteine of various concentration.Probe (5 μM) and cysteine (0,
0.1,0.2,0.3 0.4,0.5,0.6,0.7,0.8,0.9,1,1.5,2,2.5,3,3.5,4,4.5,5,5.5,6,6.5,7,
7.5,8 μM) it is put into sepectrophotofluorometer and is detected after reaction 10min.
Fig. 2：Have at a concentration of 0 to 8 μM linear well, detection is limited to 1 μM.Probe (5 μM) and cysteine (0,
0.1,0.2,0.3 0.4,0.5,0.6,0.7,0.8,0.9,1,1.5,2,2.5,3,3.5,4,4.5,5,5.5,6,6.5,7,
7.5,8 μM) it is put into sepectrophotofluorometer and is detected after reaction 10min.
Fig. 3：When other amino acid (Cys, Gly, Pro, Leu, Val, Thr, Ala) are 100 μM a concentration of, probe (5 μM)
The response of probe after cysteine is inside added in their fluorescence response value and again.It is second to detect solution system
Alcohol：Water=5：5 (v/v) are 25 DEG C containing PBS=5mM, pH=7.4, test temperature.
Specific embodiment
The synthetic route and method of the cysteine Ratio-type probe of the present invention are as follows：
Wherein：R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13For independently selected from by hydrogen atom, straight chain or
The group that branched alkyl, straight or branched alkoxyl, sulfonic group, ester group and hydroxyl form；And R therein1, R2, R3, R4, R5, R6,
R7, R8, R9, R10, R11, R12And R13It can be identical or different.
Preferably, heretofore described linear or branched alkyl group, straight or branched alkoxyl are the alkyl or alcoxyl of C1-10
Base.
Preferably, heretofore described linear or branched alkyl group, straight or branched alkoxyl are the alkyl or alcoxyl of C1-5
Base.
Preferably, heretofore described linear or branched alkyl group, straight or branched alkoxyl are the alkyl or alcoxyl of C1-3
Base.
Preferably, heretofore described linear or branched alkyl group for methyl, ethyl, propyl, n-pentyl, 2- methyl butyls,
Isobutyl group or 4- methylheptyls.
Preferably, heretofore described straight or branched alkoxyl is methoxyl group, ethyoxyl or propoxyl group.
Preferably, R in the present invention1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13For independently selected from hydrogen original
Son, methyl, ethyl, propyl, methoxyl group, ethyoxyl or propoxyl group.
Preferably, R in the present invention1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13Selected from hydrogen, methyl, second
Base or propyl；Most preferably, R1, R2, R3, R4, R5,
R6, R7, R8, R9, R10, R11, R12And R13It is H.
It is further preferred that it is in absolute ethyl alcohol that the method for detecting the fluorescence probe of cysteine is prepared in the present invention
As what is carried out under conditions of solvent.
It is further preferred that it is to react 12 at normal temperatures that the method for detecting the fluorescence probe of cysteine is prepared in the present invention
It carries out within a hour.
Preferably still, it is prepared in the present invention in the method for detecting the fluorescence probe of cysteine, 2- formoxyls -6-
The molar ratio of benzothiazole phenol and N- methyl -2- methylquinoline salt is 1:3-3:1, preferably 1:1.
Probe prepared by the present invention can highly sensitive and highly selective Ratio-type measure cysteine and/or in amino
Can quantitative analysis accurately be carried out to cysteine in the presence of acid.
Probe prepared by the method for the present invention has the following advantages that：
1st, there is very good selectivity to cysteine, and for other amino acid then without apparent response；
2nd, the probe response time is 20min, therefore can be as the means of quick detection cysteine；And/or
3rd, the detection of the probe is limited to 1 μM, the cysteine of 1 to 8 μM of detection that can be quantified, and remolding sensitivity is higher.
The probe reacted with cysteine after there are one 170nm blue shift, this detection cysteine Ratio-type it is closely red
It is fewer in the probe of outer class.The present invention also proposes a new method to synthesize a kind of Ratio-type probe.
It below will be by the way that the present invention be described in more detail by following embodiment.Following embodiment is merely illustrative,
It should be understood that the present invention is not limited by following embodiments.
It is prepared by 1 probe of embodiment
2,6- diformyls phenol synthesizes and purification
It weighs in the balance and phenol 940.5mg and hexamethylenetetramine 2.80g is taken to be put into the glass reaction bottle of 100mL, add in
The trifluoroacetic acid of 30mL is put into the small magneton of a wash clean, is heated to reflux later using 84-1 magnetic agitation control-temperature electric heating sets,
Recording reacting time tracks process in reaction process using tlc silica gel plate, about needs reaction 6h, after the reaction was complete, turns off
Reaction.Synthetic reaction is shown in Formulas I：
Prepare the beaker of a 100mL, pour the distilled water of 50mL or so into wherein.Stop in reaction, it, will be anti-after cooling
Solution is answered to be added dropwise in preprepared beaker,
It is stirred evenly with dropper, the liquid in beaker is poured into separatory funnel, then add 20mL's or so wherein
Dichloromethane, fastening plug rock with strength it is several under, separatory funnel is placed on brandreth stands a few minutes later, make liquid point
Layer.Since the density ratio water of dichloromethane is big, so dichloromethane solution is below, our product is organic matter, generally not
Be dissolved in water, so as to extract during be completely dissolved in dichloromethane.The piston of separatory funnel is opened, dichloromethane is made to be flowed from lower part
Go out.Then it adds in the dichloromethane extraction of 20mL or so in remaining liquid in separatory funnel again, is so iteratively repeated 3 to 5
It is secondary, make product completely into dichloromethane.
After having extracted, we are extracted obtained two by the glass reaction bottle of one 25mL of weighing with this flask
Chloromethanes liquid is spin-dried for Rotary Evaporators.Then the substance being spin-dried for a little is taken to add a small amount of two in the centrifuge tube of 4mL
Chloromethanes makes its dissolving, and a little solution is pipetted with capillary glass tube, the contact plate on tlc silica gel plate, later by thin-layer chromatography
Silica gel plate is put into the glass jar containing about 1mL dichloromethane, about waits for 3min quietly, until dichloromethane liquid is soon by thin layer
Tlc silica gel plate is taken out with tweezers when chromatographic silica gel plate all soaks, with the 365nm's in portable uv analyzer
Fluorescent lamp excites, it is observed that a phosphor dot, in the fluorescent lamp excitation of 254nm, without other points, illustrates that extraction is spin-dried for
The solid obtained afterwards is purer, can directly cast single step reaction.It weighs again after waiting flasks cooling, the weight for obtaining product is
976.5mg, yield 65.1%.
The synthesis and purification of 2- formoxyl -6- benzothiazole phenol
Product 2,6- diformyl phenol obtained above is weighed into 450.0mg and near amino thiophenols weigh 375.6mg
It is put into the glass reaction bottle of 100mL, adds 25mL ethanol solutions, be completely dissolved two kinds of drugs, be put into wash clean
Small magneton, glass reaction bottle is placed on the strong magnetic stirring apparatus of 84-B is stirred at room temperature later.It is added in during stirring
37% hydrochloric acid solution of 9mmol is eventually adding 30% hydrogenperoxide steam generator of 18mmol.Continue to be stirred at room temperature
30min or so.Synthetic reaction is shown in Formula II.
Reaction is completed, and solid matter is sucked out using dropper, then filters, is rinsed with absolute ethyl alcohol.
A little upper strata product is pipetted in centrifuge tube, is dissolved in a small amount of dichloromethane, is pipetted a little with capillary glass tube
Solution, the contact plate on tlc silica gel plate put the silica gel plate put into glass wide-mouth containing about 1mL dichloromethane later
In bottle, about wait for 3min quietly, until dichloromethane liquid soon all soaks tlc silica gel plate with tweezers by thin-layer chromatography
Silica gel plate takes out, and is excited with the fluorescent lamp of the 365nm in portable uv analyzer, it is observed that a phosphor dot,
During the fluorescent lamp excitation of 254nm, there are one the stains of very little, illustrate that the solid that suction filtration obtains is purer, since this is not final
Product, purity reach more than 80% and may be used for reacting in next step, so we do not purify further, is directly used in down
Single step reaction.
A period of time is filtered, until after solid parches completely, is pipetted from funnel solid using spoon small to 25mL
It in glass reaction bottle, weighs to small glass reaction bottle, weighs again after being put into product in advance, so as to obtain the weight of product
For 521.6mg, yield 68.2%.
The preparation and purification of N- methyl -2- methylquinoline salt
It weighs in the balance in the glass reaction bottle of 50mL that 300mg 2- methylquinolines is taken to be put into wash clean, pours the iodine of 20mL into
Methane is put into magneton, and or so 4 hours are heated to reflux with 84-1 magnetic agitation control-temperature electric heating sets.Synthetic reaction is shown in formula III.
Flask is removed after having reacted, after cooling, has solid precipitation, is filtered with Suction filtration device, obtain solid,
About 285mg after weighing, yield 98%.
The synthesis and purification of 2- (N- methyl -2- vinyl) quinoline -6- benzothiazole phenol
Weigh product 2- formoxyl -6- benzothiazole phenol 255mg and product N- methyl -2- methylquinoline salt 285mg
It is put into the glass reaction bottle of the 50mL of wash clean, pours the absolute ethyl alcohol of 20mL or so into, be as possible completely dissolved 2 kinds of drugs,
It puts small magneton into later, is heated to reflux with 84-1 magnetic agitation control-temperature electric heating sets, react 12 hours.
After reaction, reaction dissolvent absolute ethyl alcohol is removed by revolving, and the dichloromethane for adding in 15mL makes its dissolving.
Then solution is added dropwise in chromatographic column, obtains the weight of sterling as 108.9mg, yield 20.8%.
1The analysis of H-NMR results
Hydrogen modal data is as follows：1H-NMR(400MHz,DMSO-d6)δ(*10-6):4.23 (s, 3H), 7.16 (t, J=
7.6Hz, 1H), 7.25-7.27 (m, 4H), 7.52 (t, J=7.0Hz, 1H), 7.59 (t, J=7.0Hz, 1H), 7.64 (d, J=
16.9Hz, 1H), 7.90 (d, J=8.0Hz, 1H), 7.99 (d, J=8.0Hz, 1H), 8.10 (d, J=8.0Hz, 1H), 8.15
(d, J=16.9Hz, 1H), 8.20 (d, J=8.0Hz, 1H), 8.22 (d, J=7.6Hz, 1H), 8.83 (d, J=7.6Hz, 1H),
13.32(s,1H).Data above meets the structural formula feature of 2- (N- methyl -2- vinyl) quinoline -6- benzothiazole phenol.
13The analysis of C-NMR results
Carbon modal data is as follows：13C-NMR(100MHz,DMSO-d6)δ(*10-6):46.28,114.26,116.27,
117.19,118.64,119.16,121.32,121.76,123.18,123.53,123.97,124.38,125.47,126.29,
127.62,130.36,131.28,131.38,134.25,144.47,150.18,152.47,155.29,167.36.Above number
According to the structural formula feature for meeting 2- (N- methyl -2- vinyl) quinoline -6- benzothiazole phenol.
2 solution of embodiment is prepared
The final products of 5.22mg are weighed, are configured to the probe mother liquor of 1mM.The cysteine for weighing 12.1mg is configured to
Cysteine (Cys) mother liquor of 10mM.
50 μ L liquid dilutings are pipetted from probe mother liquor to 10mL, are made into 5 μM of probe in detecting liquid.By 10mL probe in detecting
Liquid is divided into two, and adds in the cysteine mother liquor of 25 μ L in portion wherein, a concentration of 50 μM.
The above-mentioned system for being used to prepare solution is ethyl alcohol：Water=5：5 (v/v) are containing PBS=5mM, pH=7.4.
Influence of 3 response time of embodiment to probe identification cysteine
With the probe in detecting liquid that 5 μM are made into described in embodiment 2, rapidly joining cysteine mother liquor later makes its concentration
Be 10 μM, rock it is several under, it is quickly put into sepectrophotofluorometer after making the dispensed materials in solution uniform, set fluorescence
Thus spectrophotometer obtains the response spectrum of different time in every 30 seconds run-downs, recording light spectrogram simultaneously preserves, during detection
Room temperature is 25 DEG C.Detection solution system remains as ethyl alcohol：Water=5：5 (v/v) are containing PBS=5mM, pH=7.4.As a result such as Fig. 1 institutes
Show.Find out that pure probe solution peak value at 700nm is higher from fluorescence spectra, peak is there is no at 530nm, add in
After cysteine, spectrogram slowly reduces for the peak value at 700nm, and the peak value at 530nm slowly increases.
4 probe of embodiment is to the quantitative effect of cysteine
The similary probe in detecting liquid for preparing 5 μM, and probe in detecting liquid is added in colorimetric cylinder and is settled to 10mL.Pipette half Guang
Propylhomoserin solution is sequentially added in colorimetric cylinder, and the concentration for making cysteine is finally：0,0.1,0.2,0.3 0.4,0.5,0.6,
0.7,0.8,0.9,1,1.5,2,2.5,3,3.5,4,4.5,5,5.5,6,6.5,7,7.5,8 μM and it is made to be evenly distributed, detected
Solution system is ethyl alcohol：Water=5：5 (v/v) are existed containing PBS=5mM, pH=7.4 after placing 10min with sepectrophotofluorometer
Excitation wavelength is to be detected under 430nm and keep spectrogram.Room temperature is 25 DEG C during detection.The results are shown in Figure 2.Probe pair
There is good response in the cysteine of various concentration.Have at a concentration of 0 to 8 μM linear well, detection is limited to 1 μM.
It can be seen that the probe synthesized by the present invention can be by comparing the method detection cysteine of the fluorescence intensity at two neighboring peak
And there is good sensitivity.
Anti-interference when 5 probe of embodiment identifies cysteine
Prepare 7 colorimetric cylinders and add in probe solution constant volumes to 10mL, only 10 μM of cysteine of addition in first is remaining
Cys, Gly, Pro, Leu, Val, Thr, Ala are sequentially added, a concentration of 100 μM, then adds 10 μM of cysteine.It is similary quiet
After putting 10min, since the colorimetric cylinder of first, left side, it is sequentially placed into sepectrophotofluorometer and detects, and keep data.Inspection
Survey solution system is ethyl alcohol：Water=5：5 (v/v) are containing PBS=5mM, pH=7.4, and room temperature is 25 DEG C during detection.As a result such as Fig. 3 institutes
Show.
It can be seen from the figure that other thiol solutions being added in probe solution after reaction a period of time, in solution
The fluorescence intensity of probe is not responded to without too big variation, explanation, but after inside cysteine is added in again, probe is just
It will appear the high response of comparison.Therefore, probe has cysteine good selectivity, anti-interference.
Have to cysteine highly selective and resist well dry it can be seen that the probe synthesized by the method for the present invention is one
The probe of immunity.
Although with above embodiments describe the present invention, it should be appreciated that before the spirit without departing substantially from the present invention
It puts, the present invention further can be modified and be changed, and these modifications and variation all belong to the scope of protection of the present invention it
It is interior.
Claims (10)
1. it is a kind of prepare for detect cysteine Ratio-type probe method, synthetic route is as follows：
Wherein：R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13For independently selected from by hydrogen atom, linear chain or branch chain
The group that alkyl, straight or branched alkoxyl, sulfonic group, ester group and hydroxyl form；And R therein1, R2, R3, R4, R5, R6, R7, R8,
R9, R10, R11, R12And R13It can be identical or different.
2. according to the method described in claim 1, wherein described linear or branched alkyl group, straight or branched alkoxyl are C1-10
Alkyl or alkoxy.
3. according to the method described in claim 1, wherein described linear or branched alkyl group, straight or branched alkoxyl are C1-5
Alkyl or alkoxy.
4. according to the method described in claim 1, wherein described linear or branched alkyl group, straight or branched alkoxyl are C1-3
Alkyl or alkoxy.
5. according to the method described in claim 1, wherein described linear or branched alkyl group for methyl, ethyl, propyl, n-pentyl,
2- methyl butyls, isobutyl group or 4- methylheptyls.
6. according to the method described in claim 1, wherein described straight or branched alkoxyl is methoxyl group, ethyoxyl or the third oxygen
Base.
7. according to the method described in claim 1, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13For independence
Ground is selected from hydrogen atom, methyl, ethyl, propyl, methoxyl group, ethyoxyl or propoxyl group.
8. according to the method described in claim 1, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13It is selected from
Hydrogen, methyl, ethyl or propyl；Most preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12And R13It is H.
9. according to the method described in claim 1, wherein, the method is carried out under conditions of absolute ethyl alcohol is as solvent
's.
10. according to the method described in claim 1, wherein, 2- formoxyls -6- benzothiazoles phenol and N- methyl -2- methyl quinolines
The molar ratio of quinoline salt is 1:3-3:1, preferably 1:1.
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| CN201810155917.7A CN108148057B (en) | 2018-02-23 | 2018-02-23 | Prepare the method for detecting the fluorescence probe of cysteine |
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Cited By (2)
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| CN110885312A (en) * | 2019-12-17 | 2020-03-17 | 济南大学 | Golgi-targeted cysteine fluorescent probe, and preparation method and application thereof |
| CN111116574A (en) * | 2019-12-25 | 2020-05-08 | 渤海大学 | Viscosity fluorescent probe with mitochondrial targeting function and preparation method and application thereof |
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| CN106588910A (en) * | 2016-12-07 | 2017-04-26 | 南京工业大学 | Difunctional fluorescent probe, preparation method and application |
| CN106588912A (en) * | 2016-11-30 | 2017-04-26 | 济南大学 | Fluorescent probe capable of separately detecting cysteine/homocysteine, glutathione and sulfuretted hydrogen and preparation method and application of fluorescent probe |
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| CN106588912A (en) * | 2016-11-30 | 2017-04-26 | 济南大学 | Fluorescent probe capable of separately detecting cysteine/homocysteine, glutathione and sulfuretted hydrogen and preparation method and application of fluorescent probe |
| CN106588910A (en) * | 2016-12-07 | 2017-04-26 | 南京工业大学 | Difunctional fluorescent probe, preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110885312A (en) * | 2019-12-17 | 2020-03-17 | 济南大学 | Golgi-targeted cysteine fluorescent probe, and preparation method and application thereof |
| CN110885312B (en) * | 2019-12-17 | 2022-04-12 | 济南大学 | Golgi-targeted cysteine fluorescent probe, and preparation method and application thereof |
| CN111116574A (en) * | 2019-12-25 | 2020-05-08 | 渤海大学 | Viscosity fluorescent probe with mitochondrial targeting function and preparation method and application thereof |
| CN111116574B (en) * | 2019-12-25 | 2022-10-14 | 渤海大学 | Viscosity fluorescent probe with mitochondrial targeting function and preparation method and application thereof |
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