CN104893711B - The fluorescent probe of detection peroxynitrite and preparation and application - Google Patents
The fluorescent probe of detection peroxynitrite and preparation and application Download PDFInfo
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Abstract
The present invention provides the fluorescent probe that a class detects peroxynitrite, and the general structure with Formulas I a or Ib passes through（1）R4Substituted near amino thiophenols or R4Substituted o-aminophenol and R1、R2Substituted benzaldehyde is stirred at room temperature two hours in methanol solution, obtains 1a；（2）R4Substituted near amino thiophenols or o-aminophenol and R2Substituted salicylaldhyde carries out oxidative condensation, obtains benzothiazoles or benzoxazoles class intermediate；The phenolic hydroxyl group of the intermediate is converted into after triflate and R3Substituted para hydroxybenzene tert-butyldimethyl silyl ether or p-aminophenyl tert-butyldimethyl silyl ether are coupled, and Jing aniline nitrogen-atoms methylate, hydroxyl removing silicon ether protection group, obtain Ib.The fluorescent probe that the present invention is provided can generate the product with hyperfluorescence, so as to realize the specific detection to peroxynitrite with peroxynitrite specificity fast reaction.The general structure of probe of the present invention：.
Description
Technical field
The invention belongs to field of biological detection, be related to fluorescent probe of class detection peroxynitrite and preparation method thereof and
Using.
Background technology
Peroxynitrite is a member of active nitrogen family, is one of product of the biological stress of nitrification in vivo, in body
It is interior to be synthesized by nitric oxide free radical and superoxide anion.Due to its strong oxidizing property and strong nucleophilicity, peroxynitrite can be with
With biomolecule numerous in vivo, including the reaction such as protein, metalloenzyme, lipid, nucleic acid, body oxidative damage is caused finally to lead
Cause apoptosis.In fact, peroxynitrite is widely regarded as nitric oxide free radical and superoxide anion is produced at present
The arch-criminal of cytotoxicity, and participate in the generation development of the diseases such as cardiovascular disease, neurodegenerative diseases.And the opposing party
Invasion pathogen in vivo also can be removed as signaling molecule or cellulotoxic effect by report in face, peroxynitrite, so as to send out
Wave positive body protective effect.Recent studies suggest that, peroxynitrite can be joined by nitroprotein matter tyrosine residue
With in tyrosine phosphorylation signal path.At present, people are to peroxynitrite physiology in vivo and pathological role
Still full of dispute.Therefore, develop the method that real-time tracing detection can be carried out to the peroxynitrite in organism, greatly can push away
The related physiopathology research of dynamic peroxynitrite.
The method of traditional detection peroxynitrite relies on substantially product downstream --- 3- nitrotyrosines
Detection.There is poor specificity, be not applied for the both sides such as In vivo detection in this detection method.Fluorescent probe is detected
Method is the new method for growing up in recent years.Oxidisability or nucleophilicity of the method using peroxynitrite, design can be with
The fluorescent probe of peroxynitrite specific reaction, after these fluorescent probes unstressed configuration itself, with peroxynitrite reaction
The product with hyperfluorescence can be generated, thus can be used for the Sensitive Detection of peroxynitrite.As small-molecule fluorescent probe has
Have the advantages that small volume, biological membrane permeability are good, thus fluorescence probe method is except suitable for detecting the mistake blood plasma, tissue homogenate
Oxidation nitroso-group, applies also for the detection of peroxynitrite in living cells even animal tissue.
The content of the invention
It is an object of the present invention to provide the small molecule fluorescent of the new specific detection peroxynitrite of a class is visited
Pin, with the general structure shown in Formulas I a or Ib：
Wherein：
X is sulfur or oxygen atom；
Y is oxygen atom, or alkylamino radical, aryl amine；
R1For hydroxyl, alkyl secondary amine or secondary aryl amine；
R2For hydrogen, fluorine atom or bromine atoms, C1-C4Alkyl, or electron-donating group such as alkoxyl, alkylamino radical etc.；
R3For hydrogen or alkoxyl；
R4For hydrogen, C1-C4Alkyl, or electron-donating group such as alkoxyl, alkylamino radical etc.；
A further object of the present invention is to provide the preparation method of compound shown in Formulas I a and Ib, by following two preparations
Method is realized：
（1）The preparation method of Formulas I a compound：
R4Near amino thiophenols or R that base replaces4Substituted o-aminophenol and R1、R2Substituted benzaldehyde is in methanol
Two hours are stirred at room temperature in solution, sucking filtration obtains final product formula 1a.
（2）The preparation method of Formulas I b compound：
A. R4Near amino thiophenols or R that base replaces4Substituted o-aminophenol and R2Substituted salicylaldhyde
Under conditions of methanol solution, hydrogen peroxide and the common presence of hydrochloric acid, room temperature reaction obtains intermediate II；
B. intermediate II with trifluoromethanesulfonic acid anhydride reactant under conditions of pyridine presence, obtains middle in dichloromethane solution
Body III；
C. intermediate III and R3Substituted para hydroxybenzene tert-butyldimethyl silyl ether or R3The tertiary fourth of substituted p-aminophenyl
Base dimethyl-silicon ether is coupled in the presence of palladium, methylate by aniline nitrogen-atoms, hydroxyl removing silicon ether protection group, obtain Ib
Shown probe.
Wherein：
X is sulfur or oxygen atom；
Y is oxygen atom, or alkylamino radical, aryl amine；
R1For hydroxyl, alkyl secondary amine or secondary aryl amine；
R2For hydrogen, fluorine atom or bromine atoms, C1-C4Alkyl, or electron-donating group such as alkoxyl, alkylamino radical etc.；
R3For hydrogen or alkoxyl；
R4For hydrogen, C1-C4Alkyl, or electron-donating group such as alkoxyl, alkylamino radical etc..
It is also another object of the present invention to provide Formulas I a or the fluorescent probe shown in Ib are in the biological peroxynitrite of detection
In application.The present invention can be realized by following steps by taking the application in living cells as an example：In cell culture medium add Formulas I a or
Fluorescent probe shown in Ib so as to final concentration of 5 μM, is incubated 30 minutes at 37 DEG C, observed and recorded cell fluorescence intensity, this
The fluorescent probe of bright offer is characterised by that itself only has faint fluorescence in physiological environment, but can be with peroxynitrite
Specificity fast reaction, generates the product with hyperfluorescence, realizes 3 times to 600 times of Fluorescence Increasing, so as to realize to peroxidating
Nitroso specific detection and quantitative analyses.
Fluorescent probe according to the present invention has the advantages that：（1）Good stability, can preserve use for a long time；（2）
It is poor with larger absorption launch wavelength（>100nm）, the interference of exciting light can be prevented effectively from；（3）As probe itself is without glimmering
Light, just has fluorescence only after reacting with peroxynitrite, therefore, detection signal-to-noise ratio is high, and sensitivity is good；（4）With outstanding
Selectivity, peroxynitrite can be specifically detected in complex biological sample；（5）It is penetrating with good biomembrane
Property, thus the detection of peroxynitrite in living cells can be used for；（6）With preferable two photon absorption cross section, can be used for double
Observe under photon microscope.
Description of the drawings
Fig. 1 is the change in fluorescence before and after fluorescent probe molecule Ia-1 is reacted with peroxynitrite.
Fig. 2. the change in fluorescence before and after fluorescent probe molecule Ib-1 and peroxynitrite reaction.
Fig. 3. the change in fluorescence before and after fluorescent probe molecule Ib-2 and peroxynitrite reaction.
Fig. 4 is selectivitys of the fluorescent probe molecule Ia-1 to peroxynitrite.
Fig. 5 is selectivitys of the fluorescent probe molecule Ib-1 to peroxynitrite.
Fig. 6 is selectivitys of the fluorescent probe molecule Ib-2 to peroxynitrite.
Fig. 7 is fluorescent probe molecule Ib-2 to peroxynitrite concentration dependent Fluorescence Increasing.
Fig. 8 is peroxynitrite in fluorescent probe molecule Ib-1 detection living cells vascular endothelial cells.
Fig. 9 is that fluorescent probe molecule Ib-1 detects peroxynitrite in 2 kinds of living cells.
Specific embodiment
The present invention will be further described with reference to the accompanying drawings and examples, and below example is not to limit the present invention
Scope.
Embodiment 1：The preparation of fluorescent probe molecule Ia-1
1g near amino thiophenols（8 mMs）With salicylaldhyde（8 mMs）Two are stirred at room temperature in 8mL methanol
Hour, sucking filtration obtains white solid 2-（2,3- dihydrobenzos [d] thiazol-2-yl）Phenol.Obtain final product 1a-1, yield 50%.1H NMR
(500 MHz, DMSO) δ9.85 (s,1H), 7.4 (d,1H), 7.1(t,1H), 6.95(d,1H), 6.75-6.85(m,
3H), 6.65(d,2H), 6.55(t,1H), 6.45(s,1H)。
。
Embodiment 2：The preparation of fluorescent probe molecule Ib-1
Near amino thiophenols（0.5g, 3.6 mMs）With salicylaldhyde（0.438g, 3.5 mMs）It is dissolved in 5mL
In methanol solution, the hydrogen peroxide of Deca 37% under ice bath（15.75 mMs）Then 37% hydrochloric acid of Deca again（9.2 mM）,
Two hour sucking filtration of room temperature reaction, ethyl alcohol recrystallization obtain intermediate 2-（Benzo [d] thiazol-2-yl）Phenol is II-1, yield
70%；Intermediate II -1（0.5g, 2 mMs）First with 20 milliliters of anhydrous methylene chloride stirring and dissolving, nitrogen displacement, under ice bath
The Deca pyridine solution first in reactant liquor（328 L, 4 mMs）, then again to uniform speed slow Deca fluoroform in reactant liquor
Sulphonic acid anhydride（0.863g, 3 mMs）, 3-4 hours are stirred at room temperature.Reaction is finished and is extracted with ethyl acetate, anhydrous sodium sulfate drying,
Column chromatography purification, obtains intermediate 2-（Benzo [d] thiazol-2-yl）Phenyl trifluoromethanesulfonate methanesulfonic acid is III-1；Intermediate III -1
（0.25g, 0.7 mM）With 4-（（T-butyldimethylsilyl）Epoxide）Aniline（0.2g, 0.8 mM）, acetic acid
Palladium（3% mM）、BINAP（4.5% mM）And cesium carbonate（1.4 mM）It is dissolved in 4mL toluene, 80 degrees Celsius of reactions
16 hours, sucking filtration, column chromatography purification.Obtain yellow 2-（Benzo [d] thiazol-2-yl）In the middle of-N- phenylanilines class is crucial, yield
80%, intermediate Jing N- methylate, and dehydroxylation protection group obtains probe molecule 1b-1, yield 68%.1H NMR (500 MHz,
DMSO) δ9.8 (s, 1H), δ8.85 (s, 1H), 8.5(dd,J=10,1H), 8.05 (t, 1H), 7.6 (m,
1H), 7.55 (m, 2H), 6.64 (d, 2H), 6.55 (d, 2H), 3.1 (s, 3H).
。
Embodiment 3：The preparation of fluorescent probe molecule Ib-2
Intermediate 2-（Benzo [d] thiazol-2-yl）Phenyl trifluoromethanesulfonate methanesulfonates（0.25g, 0.7 mM）With 4-（（Uncle
Butyldimethylsilyl）Epoxide）- 3- aminoanisoles（0.25g, 0.8 mM）, palladium（3% mM）、BINAP
（4.5% mM）And cesium carbonate（1.4 mM）It is dissolved in 4mL toluene, 80 degrees Celsius are reacted 16 hours, sucking filtration, column chromatography
Purification.Obtain yellow 2-（Benzo [d] thiazol-2-yl）In the middle of-N- phenylanilines class is crucial, yield 80%；Intermediate Jing N- methyl
Change, dehydroxylation protection group obtains probe molecule 1b-2, yield 65%.1H NMR (500 MHz, DMSO) δ 10.4 (s, 1H),
8.15 (d, 1H), 8.05 (d, 1H), 7.8 (d, 1H), 7.55 (t, 1H), 7.45 (t, 1H), 7.3 (m, 2H),
7.0 (3,1H), 6.85 (3,1H), 6.7 (d, 1H), 6.5 (dd, 1H), 3.85 (s, 3H), 3.8 (s,
3H)。
。
Embodiment 4：The preparation of fluorescent probe molecule Ib-3
Intermediate 2-（Benzo [d] thiazol-2-yl）- 5- fluorophenyl triflates（0.50g, 1.4 mMs）With 4-
（（T-butyldimethylsilyl）Epoxide）- 3- aminoanisoles（0.50g, 1.6 mMs）, palladium（3% mM）、
BINAP（4.5% mM）And cesium carbonate（1.4 mM）It is dissolved in 8mL toluene, 80 degrees Celsius are reacted 16 hours, sucking filtration,
Column chromatography purification.Obtain yellow 2-（Benzo [d] thiazol-2-yl）In the middle of-N- phenylanilines class is crucial, yield 78%；Intermediate Jing
N- methylates, and dehydroxylation protection group obtains probe molecule 1b-2, yield 70%.1H NMR (500 MHz, DMSO) δ 8.52 (dd,
1H), 8.45 (s, 1H), 8.02 (d, 2H), 7.5 (t, 1H), 7.40 (t, 1H), 7.34 (t, 1H), 7.2 (dd,
2H), 6.62 (d, 1H), 6.38(d, 1H), 6.10(dd, 1H), 3.64 (s, 3H),3.16（S, 3H）.
。
Embodiment 5：Change in fluorescence before and after fluorescent probe molecule Ia-1 and peroxynitrite reaction
Probe molecule is dissolved with a small amount of DMSO, the PBS solution of PBS or peroxynitrite is separately added into, is made
Final concentration of 5 M of probe molecule, final concentration of 10 M of peroxynitrite.Reaction 10min after using fluorescence spectrophotometer photometry with
375 nm are excited, and recording solution is in maximum emission wavelength（About 470 nm）Under fluorescence intensity, and then determine probe molecule and mistake
After oxidation nitroso-group reaction, fluorescence intensity strengthens, as shown in Figure 1.
Embodiment 6：Change in fluorescence before and after fluorescent probe molecule Ib-1 and peroxynitrite reaction
Probe molecule is dissolved with a small amount of DMSO, the PBS solution of PBS or peroxynitrite is separately added into, is made
Final concentration of 5 M of probe molecule, final concentration of 10 M of peroxynitrite.Reaction 10min after using fluorescence spectrophotometer photometry with
375 nm are excited, and recording solution is in maximum emission wavelength（About 470 nm）Under fluorescence intensity, and then determine probe molecule and mistake
After oxidation nitroso-group reaction, fluorescence intensity strengthens, as shown in Figure 2.
Embodiment 7：Change in fluorescence before and after fluorescent probe molecule Ib-2 and peroxynitrite reaction
Probe molecule is dissolved with a small amount of DMSO, the PBS solution of PBS or peroxynitrite is separately added into, is made
Final concentration of 5 M of probe molecule, final concentration of 10 M of peroxynitrite.Reaction 10min after using fluorescence spectrophotometer photometry with
375 nm are excited, and recording solution is in maximum emission wavelength（About 470 nm）Under fluorescence intensity, and then determine probe molecule and mistake
After oxidation nitroso-group reaction, fluorescence intensity strengthens, as shown in Figure 3.
Embodiment 8：Selectivitys of the fluorescent probe molecule Ia-1 to peroxynitrite
Probe molecule is dissolved with a small amount of DMSO, PBS is added and is configured to solution, be separately added into PBS
The testing sample of dissolving, makes final concentration of 5 M of probe molecule, and final concentration of 10 M of testing sample.Make after reaction 30min
Excited with 375 nm with fluorescence spectrophotometer photometry, recording solution is in maximum emission wavelength（About 470 nm）Under fluorescence intensity, and then
Determine selectivity of the probe molecule to peroxynitrite, as shown in Figure 4.
Embodiment 9：Selectivitys of the fluorescent probe molecule Ib-1 to peroxynitrite
Probe molecule is dissolved with a small amount of DMSO, PBS is added and is configured to solution, be separately added into PBS
The testing sample of dissolving, makes final concentration of 5 M of probe molecule, and final concentration of 10 M of testing sample.Make after reaction 30min
Excited with 375 nm with fluorescence spectrophotometer photometry, recording solution is in maximum emission wavelength（About 470 nm）Under fluorescence intensity, and then
Determine selectivity of the probe molecule to peroxynitrite, as shown in Figure 5.
Embodiment 10：Selectivitys of the fluorescent probe molecule Ib-2 to peroxynitrite
Probe molecule is dissolved with a small amount of DMSO, PBS is added and is configured to solution, be separately added into PBS
The testing sample of dissolving, makes final concentration of 5 M of probe molecule, and final concentration of 10 M of testing sample.Make after reaction 30min
Excited with 375 nm with fluorescence spectrophotometer photometry, recording solution is in maximum emission wavelength（About 470 nm）Under fluorescence intensity, and then
Determine selectivity of the probe molecule to peroxynitrite, as shown in Figure 6.
Embodiment 11：Fluorescent probe molecule Ib-2 is to peroxynitrite concentration dependent Fluorescence Increasing
Probe molecule is dissolved with a small amount of DMSO, PBS is added and is configured to solution, be separately added into variable concentrations
Peroxynitrite solution, makes final concentration of 5 M of probe molecule, using fluorescence spectrophotometer photometry with 375 nm after reaction 30min
Excite, recording solution is in maximum emission wavelength（About 470 nm）Under fluorescence intensity, and then determine that probe molecule is sub- to peroxidating
Nitro concentration dependent Fluorescence Increasing, as shown in Figure 7.
Embodiment 12：Peroxynitrite in fluorescent probe molecule Ib-1 detection living cells
Vascular endothelial cell EA.hy926 is inoculated on the slide that poly-D-lysine was coated with, containing 10% hyclone
After cultivating 24 hours in DMEM full nutrient solutions, ONOO is added-（60）Or ONOO-Donor SIN-1 (1mM) processes 6h.Subsequently change
Liquid, addition contain 5Fluorescent probe Ib-1（5mM, 1:1000）Culture fluid, be placed in cell culture incubator 37 DEG C of incubations
30min.After 4%PFA fixes 45min, PBS is washed 3 times Cell sheet glass, and 0.1%triton X-100 permeable membrane processes 5min, adds
50 37 DEG C of/ml RANase process 30min and exclude RNA interference, subsequently carry out apoptotic nueleolus PI dyeing, mounting.Using sharp
The over-focusing fluorescence microscope of light, takes pictures.405nm and 543nm optical maser wavelengths are wherein respectively adopted and excite Ib-1 and PI.As a result
Show, fluorescent probe molecule Ib-1 can effective detection to the Peroxynitrite in living cells vascular endothelial cell, as shown in Figure 8.
Additionally, adopting glycosyloxy deprivation model（Oxygen-Glucose deprivation, OGD）Process blood vessel endothelium thin
Whether born of the same parents EA.hy926 and Human Brain Microvascular Endothelial HBMEC, investigating fluorescent probe molecule Ib-1 can effective detection ischemic
ONOO during pathology damage-Accumulation.Jing after OGD processes 3h, such as above-mentioned method adds fluorescent probe molecule incubation to cell, and
It is fixed, permeable membrane, nucleus PI dyeing, mounting, confocal microscopy, takes pictures, as a result as shown in Figure 9.Compared to just
Normal group, the Ib-1 fluorescence intensities of OGD treatment group cells are remarkably reinforced, and show that fluorescent probe molecule Ib-1 effectively monitors cell pathology
ONOO in damage process-Change.
Claims (3)
1. a class detects the fluorescent probe of peroxynitrite, it is characterised in that with the general structure shown in Formulas I b：
Wherein：
X is sulfur or oxygen atom；
Y is oxygen atom, or alkylamino radical, aryl amine；
R2For hydrogen, fluorine atom or bromine atoms, C1-C4Alkyl, alkoxyl, alkylamino radical；
R3For hydrogen or alkoxyl；
R4For hydrogen, C1-C4Alkyl, alkoxyl, alkylamino radical.
2. the preparation method of compound shown in a kind of Formulas I b, it is characterised in that realized by following preparation method：
（1）R4Near amino thiophenols or R that base replaces4Substituted o-aminophenol and R2Substituted salicylaldhyde is in first
Under conditions of alcoholic solution, hydrogen peroxide and hydrochloric acid are present jointly, room temperature reaction obtains intermediate II；
（2）Intermediate II with trifluoromethanesulfonic acid anhydride reactant under conditions of pyridine presence, obtains intermediate in dichloromethane solution
III；
（3）When Y is alkylamino radical, aryl amine, intermediate III and R3Substituted p-aminophenyl tert-butyldimethyl silyl ether is in acetic acid
It is coupled in the presence of palladium, by aniline nitrogen atom or arylation, hydroxyl removing silicon ether protection group, it is alkane to obtain the Y shown in Ib
The compound of amido, aryl amine；
Reaction equation is：
Wherein substituent X, Y, R2 、R3 、R4 Definition with claim 1.
3. application of a kind of fluorescent probe of detection peroxynitrite in the biological peroxynitrite of detection, its feature exist
In,
The fluorescent probe is compound shown in Formulas I a or Formulas I b,
Wherein substituent X, Y, R2 、R3 、R4 Definition with claim 1, R1For hydroxyl, alkyl secondary amine or secondary aryl amine.
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| CN107312068B (en) * | 2017-06-09 | 2021-02-09 | 浙江大学 | Fluorescent probe for detecting activity of proline isomerase, preparation and application thereof |
| CN108409685B (en) * | 2018-02-09 | 2021-06-08 | 华南理工大学 | Light-activated aggregation-induced emission probe with in-situ generation capability and preparation and application thereof |
| CN108570063A (en) * | 2018-05-30 | 2018-09-25 | 泰山医学院 | A kind of small-molecule fluorescent probe that can detect ONOO- and its application |
| CN115974812B (en) * | 2022-12-12 | 2024-03-08 | 渤海大学 | Fluorescent probe for nondestructive monitoring of fish freshness and preparation method and application thereof |
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