CN107652234A - Detect Cu (II) two-photon fluorescence probe and preparation method and application - Google Patents
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- CN107652234A CN107652234A CN201710823552.6A CN201710823552A CN107652234A CN 107652234 A CN107652234 A CN 107652234A CN 201710823552 A CN201710823552 A CN 201710823552A CN 107652234 A CN107652234 A CN 107652234A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- 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 invention discloses a kind of two-photon fluorescence probe of detection Cu (II) and its production and use, the preparation method of fluorescence probe is as follows：Step 1, by 4 bromines 1,8 naphthalene anhydrides, N (2 amino-ethyl) morpholine are added in round-bottomed flask A, then ethanol is added into addition round-bottomed flask A again, round-bottomed flask A is placed in oil bath, the solution in round-bottomed flask A is stirred with magnetic stirring apparatus, reaction system is filtered while hot to obtain compound A；Step 2, compound A obtained by step 1 and hydroxyethyl piperazine are added in round-bottomed flask B, ethylene glycol monomethyl ether is added until compound A is completely dissolved, round-bottomed flask B is placed in oil bath, and the solution in round-bottomed flask is stirred with magnetic stirring apparatus, obtain solution A；Step 3, chromatography is carried out to solution A with the eluent of dichloromethane and the composition of methanol, produced.Targeting two-photon fluorescence imaging detection applied to Cu (II) in cytase body.
Description
Technical field
The invention belongs to the fluorescent probe technique field of metal ion detection, and in particular to one kind is used to detect Cu's (II)
Two-photon fluorescence probe, the invention further relates to the preparation method and application of the fluorescence probe.
Background technology
Copper is one of trace element basic in organism, as content in human body be in the 3rd transition metal from
Son, important role is played the part of in biological processes.The absorption of breathing, iron in different physiology courses such as mitochondria and a large amount of enzymes
Oxidation-reduction process (including superoxide dismutase and tyrosinase etc.) in play an important role as catalytic cofactor.Cu
(II) the appropriate normal work that there are beneficial to maintaining body in vivo, but excessive Cu (II) knows from experience generation poison to people
Property, cause functional disturbances of gastrointestinal tract and neurogenic disease, such as Wilson's and Alzheimer's syndromes.U.S. environment protection
Cu (II) highest content is 20 μM in office (EPA) regulation drinking water.To sum up, Cu (II) is detected to have very important significance.
The detection side such as XRF and traditional atomic absorption spectrum, plasma light emission spectrum, high performance liquid chromatography
Method is compared, and its is convenient, fast, cost is cheap, is generally also provided with higher sensitivity and selectivity.Developed using XRF
Fluorescence probe, design synthesis is simple, cost is cheap, has higher sensitivity and selectivity.Fluorescence probe is a kind of molecule
Device, its size are mostly molecule scale dimensions.Some live signals, such as fluorescence can be provided when it and analyte interact
Enhancing, quenching or migration (movement of launch wavelength) etc., therefore there is convenient and practical advantage.
Two-photon fluorescence probe is using low energy, the two-photon excitation of long wavelength, when being detected applied to biosystem, than list
Photon light excites the interference that the damage to biological tissue is small, penetration depth is deep, avoids face bias light, so its performance is better than monochromatic light
Sub- fluorescence probe.1,8- naphthalimide absorbing wavelength and fluorescence emission wavelengths are all in " ultraviolet-visible " light area, stocks displacements
Greatly, quantum yield is high, has good two-photon fluorescence property, is that fluorogen can be excellent with preparation property with 1,8- naphthalimides
Two-photon fluorescence probe.
The content of the invention
It is an object of the invention to provide a kind of two-photon fluorescence probe of detection Cu (II), is selected by molecule suitable glimmering
Light probe structure, obtain high selectivity, high sensitivity, lysosome-targeting two-photon fluorescence imaging detection Cu (II) fluorescence and visit
Pin.
It is a further object to provide a kind of preparation method of the two-photon fluorescence probe of detection Cu (II).
The technical solution adopted in the present invention is detection Cu (II) two-photon fluorescence probe, and its structural formula is as follows：
Second technical scheme of the present invention is the preparation method of detection Cu (II) two-photon fluorescence probe,
Specifically include following steps：
Step 1, by bromo- 1, the 8- naphthalene anhydrides of 4-, N- (2- amino-ethyls) morpholines using the amount ratio of material as 1:1 is added to round bottom
In flask A, ethanol then is added into addition round-bottomed flask A again, round-bottomed flask A is placed in oil bath, will with magnetic stirring apparatus
Solution in round-bottomed flask A is stirred at reflux 2 hours, and reaction system is filtered while hot to obtain compound A, compound A structural formula
It is as follows：
Step 2, by the compound A obtained by step 1 and hydroxyethyl piperazine using the amount ratio of material as 1:1 ratio adds round bottom
In flask B, then again into round-bottomed flask B add ethylene glycol monomethyl ether until compound A be completely dissolved, round-bottomed flask B is placed in
In oil bath, and backflow 24 hours is stirred to the solution in round-bottomed flask with magnetic stirring apparatus, reaction system is cooled to room
Temperature, by the ethylene glycol monomethyl ether being evaporated under reduced pressure in removing system, obtain solution A；
Step 3, it is 100~10 with volume ratio:The eluent of 1 dichloromethane and the composition of methanol is to step 2 gained
Solution A carries out chromatography, produces.
The features of the present invention also resides in,
Oil bath temperature wherein in step 1 is 80 DEG C.
Oil bath temperature wherein in step 2 is 125 DEG C.
The invention has the advantages that the two-photon provided by the invention that be used to detect Cu (II) based on naphthalimide is glimmering
Light probe (Probe 1) has the Selective recognition of highly sensitive, high selectivity fluorescent switch type (Off-On) to Cu (II), and
When caused fluorescence intensity and Cu (II) concentration are in the range of 5 μM to 30 μM in good linear relationship, the i.e. probe herein
Scope interior energy quantitatively detects Cu (II) well；In addition, Probe 1 can penetration cell film enter in cell, targeting it is double
Cu (II) in photon fluorescence image checking lysosome.
Brief description of the drawings
Fig. 1 is the excitation and emission spectra figure of present invention detection Cu (II) two-photon fluorescence probe；
Fig. 2 is present invention detection Cu (II) two-photon fluorescence probe for the glimmering of the Selective recognition of different metal ions
Light spectrogram；
Fig. 3 be the present invention detection Cu (II) two-photon fluorescence probe and the probe in the presence of different metal ions in purple
Outer lamp excite under design sketch；
Fig. 4 is fluorescence light when various concentrations Cu (II) being added dropwise into present invention detection Cu (II) two-photon fluorescence probe
Spectrogram；
When Fig. 5 is dropwise addition various concentrations Cu (II) into present invention detection Cu (II) two-photon fluorescence probe at 530nm
The graph of relation of fluorescence intensity and Cu (II) concentration；
Fig. 6 be Cu (II) concentration when in the range of 5-30 μM, the present invention detection Cu (II) two-photon fluorescence probe exist
The linear fit graph of a relation of fluorescence intensity and Cu (II) concentration at 530nm；
Fig. 7 is in CH3CN-H2O(4:1, v/v) in, in present invention detection Cu (II) two-photon fluorescence probe and the probe
Be separately added into 20 μM, 40 μM of Cu (II) when, 365nm uviol lamps excite under image；
Fig. 8 be present invention detection Cu (II) two-photon fluorescence imaging photo of the two-photon fluorescence probe in living cells and
Fluorescence imaging identification Cu (II) image；
Fig. 9 is that lysosome targeting fluorescence imaging of present invention detection Cu (II) two-photon fluorescence probe in living cells is known
Other Cu (II) photo.
Embodiment
The present invention is described in detail with reference to the accompanying drawings and detailed description.
Present invention detection Cu (II) two-photon fluorescence probe, its structural formula are as follows：
。
The preparation method of Cu (II) two-photon fluorescence probe is detected, specifically includes following steps：
Step 1, by bromo- 1, the 8- naphthalene anhydrides of 4-, N- (2- amino-ethyls) morpholines using the amount ratio of material as 1:1 is added to round bottom
In flask A, ethanol then is added into addition round-bottomed flask A again, round-bottomed flask A is placed in 80 DEG C of oil baths, uses magnetic agitation
Solution in round-bottomed flask A is stirred at reflux 2 hours by device, and reaction system is filtered while hot to obtain compound A, compound A knot
Structure formula is as follows：
Step 2, by the compound A obtained by step 1 and hydroxyethyl piperazine using the amount ratio of material as 1:1 ratio adds round bottom
In flask B, then again into round-bottomed flask B add ethylene glycol monomethyl ether until compound A be completely dissolved, round-bottomed flask B is placed in
In 125 DEG C of oil baths, and backflow 24 hours is stirred to the solution in round-bottomed flask with magnetic stirring apparatus, reaction system is cooled down
To room temperature, by the ethylene glycol monomethyl ether being evaporated under reduced pressure in removing system, solution A is obtained；
Step 3, it is 100~10 with volume ratio:The eluent of 1 dichloromethane and the composition of methanol is to step 2 gained
Solution A carries out chromatography, produces the fluorescence probe (Probe1) for being used to detect Cu (II) based on naphthalimide.
Embodiment 1：Fluorescence probe Probe 1 synthesis：
Glacial acetic acid, bromo- 1, the 8- naphthalene anhydrides (2.77g, 0.01mol) of 4-, n-butylamine are added into 100mL round-bottomed flasks A
(4.93mL, 0.05mol).In 80 DEG C of oil baths, magnetic stirrer is flowed back 2 hours, and reaction system is filtered while hot to obtain
Compound A；(1.0132g, 3.06mmol) compound A, (0.39mL, 3.06mmol) hydroxyl second are added into 100mL round-bottomed flasks B
Base piperazine and ethylene glycol monomethyl ether, it is stirred at reflux at 125 DEG C 24 hours, reaction system is cooled to room temperature, vacuum distillation removes second
Glycol methyl ether obtains solution A, is 100~10 with dichloromethane and methanol volume ratio:1 eluent chromatography obtains Probe 1
(yellow powder), 0.71g, yield：61.11%.1H NMR(CDCl3, 400MHz, ppm), δ 8.58 (dt, J=10.5,5.2Hz,
1H), 8.52 (dd, J=8.2,0.9Hz, 1H), 8.40 (d, J=8.6Hz, 1H), 7.69 (t, J=8.5Hz, 1H), 7.23 (d, J
=9.0Hz, 1H), 4.34-4.09 (m, 2H), 3.82-3.60 (m, 2H), 3.33 (s, 3H), 2.89 (s, 3H), 2.81-2.67
(m, 2H), 1.78-1.58 (m, 2H), 1.45 (td, J=15.4,7.5Hz, 2H), 0.98 (dd, J=8.3,7.5Hz, 3H).
ESI-MS:M/z=381.9 [M+H]+, synthetic route is as follows：
Embodiment 2：The fluorescence spectrum test of fluorescence probe：
The fluorescence probe of the present invention is dissolved in CH3CN-H2O(4:1, v/v) in solution, concentration is 10 μM, uses fluorescence spectrum
Instrument detects it and excited and emission spectrum, and (Fig. 1 (a) is Probe 1 exciting light spectrogram, and Fig. 1 (b) is Probe as shown in Figure 1
1 launching light spectrogram)：The maximum excitation wavelength of the fluorescence probe of the present invention is at 385nm, and maximum emission wavelength is at 530nm.
In CH3CN-H2O(4:1, v/v) in solution, Probe 1 (10 μM) is added, then be separately added into 40 μM of Li+、Na+、
K+、Ca2+、Mg2+、Ba2+、Ni2+、Mn2+、Co2+、Ag+And Cu (II) metal salt solution, after fluorescence cuvette is placed in FS5 fluorescence
Spectrometer is tested, to study Selective recognitions of the Probe1 for metal ion, test result such as Fig. 2：Only add 40 μ
During M Cu (II), fluorescence probe system shows obvious Fluorescence Increasing, launches bright orange green fluorescence, and adds other metals
Ion, fluorescence is substantially unchanged, and this change directly can distinguish (such as Fig. 3) by naked eyes.
Embodiment 3：Response test of the fluorescence probe to Cu (II)：
In CH3CN-H2O(4:1, v/v) in, when Cu (II) being gradually added dropwise into the solution containing 10 μM of Probe 1, system
Fluorescence spectra such as Fig. 4, with being continuously added for Cu (II), the fluorescence intensities of Probe 1 constantly strengthen, such as Fig. 5；As Cu (II)
For concentration when in the range of 5-30 μM, the fluorescence intensity of the system and Cu (II) concentration are in good linear relationship, i.e. this hair
Bright fluorescence probe can quantitatively detect Cu (II) (referring to Fig. 6) well within this range.Also, it only with the naked eye just can be seen that, add
When entering 20 μM of Cu (II), fluorescence probe system of the present invention has strengthened than fluorescence when not adding Cu (II), and it is obvious to start display
Yellow green；When adding 40 μM of Cu (II), the fluorescence intensity enhancing of fluorescence probe system of the present invention is more, the Huang that system is presented
Green color is also deeper (as shown in Figure 7).
In CH3CN-H2O(4:1, v/v) in, 40 μM of Li are separately added into the probe+、Na+、K+、Ca2+、Mg2+、Ba2+、
Ni2+、Mn2+、Co2+、Ag+And Cu (II), the probe only show the Selective recognition of Fluorescence Increasing to Cu (II).
Embodiment 4：The two-photon fluorescence property test of fluorescence probe：
10 μM of Probe 1 are only added in HeLa cells, and 10 μM of the μ of Probe 1 and 20 are added in HeLa cells
M Cu (II), is incubated 30min respectively；Then using 770nm as excitation wavelength, cell is observed with confocal laser scanning microscope, CLSM
Cellular morphology and change in fluorescence such as Fig. 8 under light field, details in a play not acted out on stage, but told through dialogues and superimposed field：Only add Probe 1 HeLa cells substantially without
Fluorescence (such as Fig. 8 a2、a3), Fig. 8 a1-a3The two-photon fluorescence imaging photo for being Probe 1 in living cells, wherein a1For under light field
Photo, a2For the photo under details in a play not acted out on stage, but told through dialogues, a3Photo under being superimposed for light and shade field；Fig. 8 b1-b3Cu is identified for the fluorescence imagings of Probe 1
(II) photo, wherein b1For the photo under light field, b2For the photo under details in a play not acted out on stage, but told through dialogues, b3It is the photo under the superimposed field of light and shade field (in figure
Scale is 20 μm)；And the HeLa cells for adding 10 μM of Probe 1 and 20 μM of Cu (II) send bright green fluorescence (such as
Fig. 8 b2、b3).The result shows that Probe 1 can be used as Cu (II) two-photon fluorescence probe.
Embodiment 5：The lysosome targeted imaging test of fluorescence probe：
10 μM of Probe 1 are added in HeLa cells and are incubated 30min, 20 μM of Cu (II) is added and is incubated 30min, afterwards
Add red lysosome tracer (100nM) to continue to be incubated 30min, using 770nm as excitation wavelength, shown with common focus point migration
Micro mirror is observed, and such as Fig. 9, (in fig.9, a is that Probe 1 and lysosome red tracer are added in HeLa cells
(LysoTracker) images under light field, b are that the two-photon fluorescence imagings of Probe 1 that green channel is observed under details in a play not acted out on stage, but told through dialogues shine
Piece, c are the lysosome red tracer two-photon fluorescence imaging photo that red channel is observed under details in a play not acted out on stage, but told through dialogues, and d is b and c under details in a play not acted out on stage, but told through dialogues
Stacking chart, e are the stacking chart of b and c under light field, and g and f are respectively lysosome verification film and corresponding numerical fitting figure, in figure
Scale is 20 μm).Probe 1 green fluorescence (such as Fig. 9 b), red channel under details in a play not acted out on stage, but told through dialogues are observed in green channel under details in a play not acted out on stage, but told through dialogues
It was observed that the red fluorescence (such as Fig. 9 c) of lysosome red tracer (LysoTracker), b and c Overlapping display is under details in a play not acted out on stage, but told through dialogues
Sodium yellow (such as Fig. 9 d), Fig. 9 f are the stacking chart of b and c under light field；Fig. 9 g and Fig. 9 f are respectively lysosome verification film and correspondingly
Numerical fitting figure, draw the overlapping Pearson coefficients 92.69% that Probe1 marks with lysosome tracer, Mander is overlapping
Rate is respectively 95.00%.I.e. Probe 1 can be positioned in lysosome, be successfully applied to the target of Cu (II) in cytase body
Tropism two-photon fluorescence imaging detects.
Claims (6)
1. detect Cu (II) two-photon fluorescence probe, it is characterised in that：Structural formula is as follows：
2. the preparation method of detection Cu (II) two-photon fluorescence probe as claimed in claim 1, it is characterised in that：The probe
Synthetic route it is as follows：
3. the preparation method of detection Cu (II) two-photon fluorescence probe as claimed in claim 2, it is characterised in that：Specific bag
Include following steps：
Step 1, by bromo- 1, the 8- naphthalene anhydrides of 4-, N- (2- amino-ethyls) morpholine with 1:The amount of 1 material is added in round-bottomed flask A,
Then ethanol is added to adding in round-bottomed flask A again, round-bottomed flask A is placed in oil bath, with magnetic stirring apparatus by round-bottomed flask A
In solution be stirred at reflux 2 hours, reaction system is filtered while hot to obtain compound A, compound A structural formula is as follows：
Step 2, by the compound A obtained by step 1 and hydroxyethyl piperazine using the ratio of the amount of material as 1:1 ratio adds round bottom and burnt
Bottle B in, then again into round-bottomed flask B add ethylene glycol monomethyl ether until compound A be completely dissolved, round-bottomed flask B is placed in oil
In bath, and backflow 24 hours is stirred to the solution in round-bottomed flask with magnetic stirring apparatus, reaction system is cooled to room temperature,
By the ethylene glycol monomethyl ether being evaporated under reduced pressure in removing system, solution A is obtained；
Step 3, it is 100~10 with volume ratio:The eluent of 1 dichloromethane and the composition of methanol is to the solution A obtained by step 2
Chromatography is carried out, is produced.
4. the preparation method of the two-photon fluorescence probe of detection Cu (II) according to claim 3, it is characterised in that：It is described
Oil bath temperature in step 1 is 80 DEG C.
5. the preparation method of the two-photon fluorescence probe of detection Cu (II) according to claim 3, it is characterised in that：It is described
Oil bath temperature in step 2 is 125 DEG C.
A kind of 6. purposes of the two-photon fluorescence probe of detection Cu (II) as claimed in claim 1, it is characterised in that：In cell
The application of Cu (II) targeting two-photon fluorescence imaging detection in lysosome.
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Cited By (1)
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| CN108148573A (en) * | 2018-02-01 | 2018-06-12 | 济南大学 | A kind of fluorescence probe for detecting lysosomal pH and its synthetic method and application |
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| 郭祥峰: "亲水性萘酰亚胺阳离子荧光分子探针的设计、合成及性能", 《中国优秀博硕士学位论文全文数据库（博士） 工程科技I辑》 * |
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Application publication date: 20180202 |