CN108484555A - A kind of Cys two-photon fluorescence probes and its preparation method and application - Google Patents
A kind of Cys two-photon fluorescence probes and its preparation method and application Download PDFInfo
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- CN108484555A CN108484555A CN201810538012.8A CN201810538012A CN108484555A CN 108484555 A CN108484555 A CN 108484555A CN 201810538012 A CN201810538012 A CN 201810538012A CN 108484555 A CN108484555 A CN 108484555A
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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Abstract
The present invention provides a kind of two-photon fluorescence probe of detection Cys, chemical names 7（Diethylamino）2 oxo 2H chromenes, 3 base acrylate, structural formula are：.Probe provided by the invention, background interference is small, small, sensitivity and high selectivity are interfered in scattering, can avoid photobleaching and photic malicious phenomenon；Tissue can be penetrated and carry out imaging deep, had broad application prospects in biomolecule detection field.
Description
Technical field
The present invention relates to a kind of intracellular Cys of detection（Cysteine）Two-photon fluorescence probe and its application, belong to raw
Object mercaptan fluorescence probe field.
Background technology
Intracellular mercaptan such as cysteine（Cys）, homocysteine（Hcy）And glutathione（GSH）It is physiologically to rise
Important function matrix, including Redox homeostasis and cell growth.The shortage of Cys can cause many syndromes, such as hair to take off
Color, drowsiness, hepatic injury, DOMS, skin injury and inability.Therefore, exploitation identifies and detects in the biological sample mercaptan life
Object molecule has foreground and meaning.
Although biological thiol and many diseases are closely bound up, present metabolism machine of the medical worker to Cys in vivo
Reason and pathogenic mechanism are still not very clear.This mainly lacks at this stage can be in complicated physiological environment simply, efficiently
The method for monitoring Cys.The method of existing frequently-used detection mercaptan have liquid chromatogram, mass spectrum, electrochemical method, Capillary Electrophoresis and
Colorimetric estimation.These methods need the instrument of complex and expensive and difficult preprocessor, such as separation and purifying mostly.This
Outside, the limitation cumbersome in sample preparation procedure due to them is seldom suitable for intracellular detection in them and grinds in vivo
Study carefully.Therefore these methods are used, real-time monitoring Cys concentration in the biological sample is can not achieve and changes this physiology course.Therefore,
It is particularly important to develop a kind of simple and fast method for testing the Cys contents in living biological samples.Fluorescence probe has operation letter
It is single, possess highly sensitive and selectivity, the advantages that strong antijamming capability, plus the toxicity of itself is very low, therefore with or life
The potential using value of Cys concentration dynamic changes is monitored in object sample in real time.
At this stage, the Cys fluorescence probes reported not are very much, and profound pair penetrated can be carried out by being especially a lack of
Photon Cys fluorescence probes.Therefore, at this stage, some small background interferences, the scattering small, sensitivity of interference and selective higher are developed,
The two-photon Cys fluorescence probes that photobleaching and photic malicious phenomenon generate can be avoided particularly important.
Invention content
The problem of for the profound two-photon Cys fluorescence probes penetrated are lacked in the prior art, the present invention provides a kind of
Background interference is small, small, sensitivity and high selectivity are interfered in scattering, can avoid the two-photon Cys of photobleaching and photic malicious phenomenon
Fluorescence probe.
It is a further object of the present invention to provide a kind of methods easily synthesizing above-mentioned differentiation fluorescence probe.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of two-photon fluorescence probe of detection Cys, chemical name 7-（Diethylamino）- 2- oxo -2H- chromenes -
3- base acrylate, abbreviation Co-Cys, structural formula such as formula（I）It is shown：
Formula（I）.
A kind of synthetic method of above-mentioned fluorescence probe, includes the following steps：
（1）7- diethylin -4 hydroxy coumarin（1）Reaction is heated in HCl solution, synthesis 7- lignocaine -3- hydroxyls are fragrant
Legumin（2）；
（2）By 7- lignocaine -3- Hydroxycoumarins（2）With acryloyl chloride（3）It is stirred to react to obtain final product in methylene chloride,
That is 7-（Diethylamino）- 2- oxo -2H- chromene -3- base acrylate.
The molar ratio of 7- diethylin -4 hydroxy coumarin and HCl are 1:30.
The HCl solution is a concentration of 1-1.5mol/L.
Step（1）In, reaction temperature is 100 DEG C；Reaction time is 3-4h.
The molar ratio of 7- lignocaine -3- Hydroxycoumarins and acryloyl chloride is 1:2.
Step（2）In, reaction temperature is 25 DEG C, reaction time 12h.
Step（2）In further include the steps that product separating-purifying：Reaction solution decompression steams solvent, the solid mistake after drying
Silica gel column chromatography, eluent are dichloromethane/petroleum ether（V/V=5:1）.
Synthetic route is as follows：
；
。
A kind of above-mentioned fluorescence probe detects the application of Cys in solution and cell for single photon or two-photon.
The recognition mechanism of fluorescence probe is as follows in the present invention：
The fluorescence probe Co-Cys of the detection Cys of the present invention itself hales electronics due to methyl acrylate base and tonka bean camphor structure
Ability leads to being quenched for molecular fluorescence, and after probe and Cys molecular actions, compound Co-Cys is reduced into 7- lignocaines-
3- Hydroxycoumarins cause fluorescence intensity to obtain since the strong push-and-pull electronic action of hydroxyl and tonka bean camphor structure makes ICT effects become strong
To significantly being promoted, the identification to Cys is realized in a manner of Fluorescence Increasing.
Identification reaction is as follows：
。
The present invention has the following advantages：
The Co-Cys fluorescence probes of the present invention can sensitively detect the presence of Cys in solution especially cell；It is at low concentrations
It can be reacted with Cys in cell, the interference of anti-various active oxygen, amino acid and compounds containing thiol groups.The Co-Cys fluorescence of the present invention
Probe has two-phpton property, can avoid photobleaching and photic malicious phenomenon；Tissue can be penetrated and carry out imaging deep, in biology point
Sub- detection field has broad application prospects.
Description of the drawings
Fig. 1 is Co-Cys's1H NMR spectras；
Fig. 2 is Co-Cys's13C NMR spectras；
Fig. 3 is selectivity of the Co-Cys fluorescence probes to different molecular or ion；
Fig. 4 be various concentration Cys under Co-Cys fluorescence intensity；
Fig. 5 is the fluorescence intensity with Co-Cys when the Cys differential responses times；
Fig. 6 is Co-Cys to external source Cys cell imaging figures；
Fig. 7 is Co-Cys to slicer external source Cys images.
Specific implementation mode
With reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not limited by following embodiments
System.
The synthesis of 1 Co-Cys fluorescence probes of embodiment
（1）In 100 mL round-bottomed flasks, 7- lignocaine -3- aminocoumarins are added（1）1 mmol, it is a concentration of in 20mL
It is heated to 100 DEG C in the aqueous hydrochloric acid solution of 1.5mol/L, is filtered after the completion of reaction, filter cake is that 7- lignocaine -3- hydroxyls are fragrant
Legumin（2）.Wherein aqueous hydrochloric acid solution is；Reaction time is 4 hours, yield：91 %；1H NMR (400 MHz, DMSO-d 6 ) δ
9.51 (s, 1H), 7.29 (d, J=8,8 Hz, 1H), 7.02 (s, 1H), 6.65 (dd, J 1 =8.8 Hz, J 2 =
2.3 Hz, 1H), 6.51 (d, J=2.3 Hz, 1H), 3.38 (dd, J 1 =14.4 Hz, J 2 =7.4 Hz, 5H),
7.62 (t, J=7.0 Hz, 6H); 13C NMR (126 MHz, DMSO) δ 159.50, 152.02, 148.10,
137.47, 127.55, 117.53, 109.67, 108.86, 97.41, 44.33, 12.79；Product is not purified directly
It carries out in next step：
；
（2）The compound 7- lignocaine -3- Hydroxycoumarins that upper step is obtained（2）With acryloyl chloride（3）2mmol is in 10mL bis-
It is stirred in chloromethanes, reaction temperature is 25 DEG C, reaction time 12h, is evaporated under reduced pressure, vacuum drying, with dichloromethane/petroleum ether
（V/V=5:1）Silica gel column chromatography is carried out for eluent, obtains compound 7-（Diethylamino）- 2- oxo -2H- chromene -3- bases
Acrylate（4）；Yield：67 %.Its1H NMR and13C NMR spectras are as depicted in figs. 1 and 2：
1H NMR (400 MHz, DMSO) δ = 7.93 (s, 1H), 7.45 (d, J=8.9, 1H), 6.77 (dd,J 1 =8.9 Hz, J 2 =2.3 Hz, 1H), 6.61 (m, 1H), 5.99 (ddd, J 1 =22.6 Hz, J 2 =10.7 Hz J 3 =
5.5, 1H), 5.42 (dd, J 1 =17.2 Hz, J 2 =1.4 Hz, 1H), 5.32 (dd, J 1 =10.5 Hz, J 2 =1.0
Hz1H), 4.75 (m, 2H), 3.44 (q, J=7.0, 4H), 1.12 (m, 6H)；
13C NMR (126 MHz, DMSO) δ = 157.35, 154.94, 152.61, 150.84, 133.00,
131.95, 130.40, 129.91, 119.46, 110.09, 106.45, 97.13, 69.63, 44.53, 40.48,
40.31, 40.15, 39.98, 39.81, 39.64, 39.48, 12.72；
。
Selectivity of the 2 Co-Cys fluorescence probes of embodiment to different molecular or ion
Co-Cys fluorescence probes in embodiment 1 are configured to the mother liquor of a concentration of 1 mM.
By following substance：Calcium chloride, magnesium chloride, sodium nitrate, sodium nitrite, sodium hydrogensulfite, vulcanized sodium, sodium sulphate, sulphur
Sour ferrous iron, potassium iodide, sodium bromide, sodium hypochlorite, hydrogen peroxide, tert-butyl hydroperoxide, Sodium Pyruvate, formaldehyde, acetaldehyde, trichlorine
Acetaldehyde, glyoxal, Cys, Hcy and GSH are with phosphate buffer（0.01 mM, pH=7.4）It is configured to the mother of a concentration of 40 mM of 5 mL
Liquid.
Take 22 test tubes, be separately added into the mother liquor of 25 μ L probes mother liquors, 1 mL DMSO and each lewis' acid, control with
Equivalent water replaces interfering substance；Use phosphate buffer（0.01 mM, pH=7.4）5 mL are settled to, the final concentration of interfering substance is made
For 0.1 mM.Each solution shakes up rear 50min and carries out fluoroscopic examination（λex = 400 nm, λem = 496 nm）.With fluorescence intensity
For ordinate, Fig. 3 is made as abscissa using different molecular or ion；Wherein, 1-22 is respectively probe Co-Cys, calcium chloride, chlorination
Magnesium, sodium nitrate, sodium nitrite, sodium hydrogensulfite, vulcanized sodium, sodium sulphate, ferrous sulfate, potassium iodide, sodium bromide, sodium hypochlorite,
Hydrogen peroxide, tert-butyl hydroperoxide, Sodium Pyruvate, formaldehyde, acetaldehyde, trichloroacetaldehyde, glyoxal, Cys, Hcy and GSH.By Fig. 3
It can be found that the addition fluorescence intensity of other lewis' acids has little effect, and the amino acid containing thio-alcohol（Hcy、Cys、
GSH）Addition so that the fluorescence of compound Co-Cys is significantly increased, wherein be added Cys when enhancing it is most notable.
The fluorescence intensity of Co-Cys under the Cys of 3 various concentration of embodiment
The mother liquor of a concentration of 100 mM Cys of 10 mL is prepared, and is diluted with water as 0-55 μM of totally 18 concentration, is control with water.
Co-Cys mother liquors in embodiment 2 are diluted to 5 μM, are separately added into the Cys of various concentration, fluorescence inspection is carried out after reacting 50 min
It surveys（λex = 400 nm, λem = 496 nm）, fluorescence intensity in each system is detected, curve is made with fluorescence intensity-Cys concentration,
As shown in Figure 4.As seen from the figure, with the increase of Cys concentration, the enhancing of reaction system fluorescence intensity, a concentration of 2.5-50 μM of Cys
When, there is preferable fluorescence intensity-concentration linear relationship；When Cys concentration reaches 55 μM, reaction system fluorescence intensity reaches saturation
State.
The fluorescence intensity of embodiment 4 and Co-Cys when the Cys differential responses times
Prepare the mother liquor of a concentration of 100 mM Cys of 10 mL.It takes Co-Cys mother liquors in embodiment 2 and above-mentioned Cys mother liquors, dilution
To contain 5 μM of probe；Cys concentration is respectively 0,10,25 and 55 μM of solution, carries out fluoroscopic examination（λex = 400 nm, λem
= 496 nm）, fluorescence intensity in each system is tested every 5 min, 50 min is tested, curve is made with fluorescence intensity-action time,
As shown in Figure 5.As seen from the figure, with the increase in Cys reaction time, 45 min are about reacted in the enhancing of reaction system fluorescence intensity,
Reaction system fluorescence intensity reaches saturation state.
5 Co-Cys fluorescence probe exogenous Cys cell imagings of embodiment
Fluorescence probe Co-Cys of the present invention is applied to carry out fluorescence imaging in HeLa cells, obtains Fig. 6,1-3 arranges small figure difference
For light field, single photon, both superimposed image, concrete operation step is as follows：
（1）It is 3 × 10 by 3 parts of density5The HeLa cells of a/mL are 37 DEG C in temperature, CO2In the incubator of a concentration of 5 %
Culture is adherent to cell；
（2）Sample preparation is imaged after a cell is incubated 30min under old terms；
（3）A cell is taken, 5 μM of Co-Cys is added to be incubated 30 min, cell is rinsed 3 times with PBS buffer solution, in fluorescence after sample preparation
Light field, single photon, the two stacking image are distinguished under microscope, excitation wavelength is 405 nm, emission band 450-500nm；
（4）Another cell is taken, 5 μM of Co-Cys is added to be incubated 30 min, after 30 min of Cys incubations are added, is rushed with PBS buffer solution
It washes cell 3 times, is imaged in fluorescence microscope after sample preparation, condition is same as above.
Cell is set to send out intense fluorescence it will be appreciated from fig. 6 that fluorescence probe Co-Cys can be reacted with intracellular exogenous Cys.
The Cys imagings exogenous to slicer of 6 Co-Cys fluorescence probes of embodiment
Fluorescence probe Co-Cys of the present invention is applied to carry out two-photon fluorescence imaging in mouse liver, obtains Fig. 7, wherein figure A is
Probe is incubated imaging, and figure B is that probe is incubated imaging altogether with Cys；It is as follows to be incubated concrete operation step：
（1）After kunming mice cervical dislocation is put to death, solution takes liver, and liver section is made；
（2）A part of liver section is immersed in the tissue culture medium containing a concentration of 30 μM of probe solutions, incubator is cultivated
90min；
（3）Another part tumor biopsy is immersed in the tissue culture medium containing a concentration of 30 μM of probe solutions, incubator training
It educates；After 30min, tissue culture medium is siphoned away, the tissue culture medium containing 100 μM of Cys is replaced with and is incubated 60 min again；
（4）The tissue culture medium of two groups of experimental groups is siphoned away, is rinsed 3 times with PBS buffer solution, is carried out under the conditions of two-photon successively
Fluorescence imaging（Excitation wavelength：760 nm, emission band：500-550 nm）.
As shown in Figure 7, the fluorescence that the histotomy for the experimental group that addition Cys culture solutions impregnate is sent out is significantly stronger, wears
Saturating ability has reached 130 μm.
Claims (9)
1. a kind of two-photon fluorescence probe of detection Cys, chemical name 7-（Diethylamino）- 2- oxo -2H- chromenes -3-
Base acrylate, structural formula such as formula（I）It is shown：
Formula（I）.
2. a kind of synthetic method of two-photon fluorescence probe as described in claim 1, which is characterized in that include the following steps：
（1）7- diethylin -4 hydroxy coumarin heats reaction in HCl solution, synthesizes 7- lignocaine -3- hydroxyl tonka-beans
Element；
（2）7- lignocaine -3- Hydroxycoumarins and acryloyl chloride are stirred to react to obtain final product, i.e. 7- in methylene chloride
（Diethylamino）- 2- oxo -2H- chromene -3- base acrylate.
3. synthetic method according to claim 2, which is characterized in that 7- diethylin -4 hydroxy coumarin and HCl's rubs
You are than being 1:30.
4. synthetic method according to claim 2, which is characterized in that the HCl solution is a concentration of 1-1.5mol/L.
5. synthetic method according to claim 2, which is characterized in that step（1）In, reaction temperature is 100 DEG C；When reaction
Between be 3-4h.
6. synthetic method according to claim 2, which is characterized in that 7- lignocaine -3- Hydroxycoumarins and acryloyl
The molar ratio of chlorine is 1:2.
7. synthetic method according to claim 2, which is characterized in that step（2）In, reaction temperature is 25 DEG C, when reaction
Between be 12h.
8. synthetic method according to claim 2, which is characterized in that step（2）In further include to product separating-purifying
Step：Reaction solution decompression steams solvent, and the solid after drying crosses silica gel column chromatography, and eluent is dichloromethane/petroleum ether（V/V=
5:1）.
9. a kind of two-photon fluorescence probe as described in claim 1 is in single photon or two-photon detection solution and cell
The application of Cys.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134441A (en) * | 2018-10-11 | 2019-01-04 | 贺州学院 | A kind of novel fluorescence probe and its preparation method and application detecting cysteine |
| CN111499604A (en) * | 2020-03-30 | 2020-08-07 | 山西大学 | Lysosome targeted Cys near-infrared fluorescent probe and preparation method and application thereof |
| CN113999218A (en) * | 2021-12-03 | 2022-02-01 | 德州学院 | Flavonol compound, preparation method and application thereof in detection of biological thiol |
Citations (1)
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|---|---|---|---|---|
| CN105419783A (en) * | 2015-11-24 | 2016-03-23 | 齐鲁工业大学 | Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof |
-
2018
- 2018-05-30 CN CN201810538012.8A patent/CN108484555A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105419783A (en) * | 2015-11-24 | 2016-03-23 | 齐鲁工业大学 | Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| YONGKANG YUE等: ""pH-Dependent Fluorescent Probe That Can Be Tuned for Cysteine or Homocysteine"", 《ORGANIC LETTER》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134441A (en) * | 2018-10-11 | 2019-01-04 | 贺州学院 | A kind of novel fluorescence probe and its preparation method and application detecting cysteine |
| CN111499604A (en) * | 2020-03-30 | 2020-08-07 | 山西大学 | Lysosome targeted Cys near-infrared fluorescent probe and preparation method and application thereof |
| CN111499604B (en) * | 2020-03-30 | 2022-03-18 | 山西大学 | Lysosome targeted Cys near-infrared fluorescent probe and preparation method and application thereof |
| CN113999218A (en) * | 2021-12-03 | 2022-02-01 | 德州学院 | Flavonol compound, preparation method and application thereof in detection of biological thiol |
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