CN109115743A - Aluminum ions method in a kind of longwave transmissions fluorescence imaging detection cell - Google Patents
Aluminum ions method in a kind of longwave transmissions fluorescence imaging detection cell Download PDFInfo
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Abstract
Aluminum ions method in a kind of longwave transmissions fluorescence imaging detection cell is with fluorescence probe L, as trace of Al in fluorescence imaging detection cell3+Fluorescence imaging probe, pass through longwave transmissions fluorescence imaging detect cell in trace of Al3+, the chemical structural formula of the fluorescence probe L are as follows:When detection, first enter fluorescence probe L in competent cell with fluorescence probe L solution and cell culture, then the competent cell and Al that there will be fluorescence probe L3+Culture, makes probe and Al3+Reaction generates the compound that can emit characteristic wavelength fluorescence in competent cell, realizes probe to Al in competent cell3+Ionic dyeing imaging, with the competent cell fluorescent image after laser confocal fluorescence microscope observation culture.Advantage is: selectivity and good sensitivity with height, the trace of Al in fluorescence imaging detection cell under longer launch wavelength3+, and tissue penetration is strong, avoids light injury and background fluorescence self-interference.
Description
Technical field
The present invention relates to aluminum ions methods in a kind of longwave transmissions fluorescence imaging detection cell.
Background technique
It is well known that focusing on since the chemical sensor of detection metal ion plays in medicine, life system and environment
It acts on, therefore its development receives the extensive concern of people.Aluminium (Al) is the third-largest most universal and the most abundant gold in the earth's crust
Belong to element, people contact aluminium extensively, because it is dispersed in water process, food additives, store tools or cooker, drug and light conjunction
The fields such as gold.Meanwhile Al3+It is also one of life system indispensable element, but takes in excessive Al3+It will affect intestinal calcium absorption,
Lead to skeleton softening, atrophy even deforms, and influences to absorb the iron in blood, causes anaemia.In addition, Al3+Toxicity to maincenter
Nervous system damages, and leads to neurodegenerative disease, such as Alzheimer disease, Parkinson's disease, malacosteon and renal failure
It exhausts.The World Health Organization (WHO) provides Al3+Average human intake be about 1 day 3-10mg and be limited in potable water concentration
7.41mmol/L.Human body tolerable Al weekly3+Intake estimation is 7mg/Kg.
In recent years, based on identification Al3+The design of fluorescent probe molecule has very much, for example, Biosens Bioelectron
(2015),68,749-756；Spectrochim Acta A Mol Biomol Spectrosc(2018),19,2257-2262；
Sensors and Actuators B:Chemical(2017),247,451-460；Biosens Bioelectron(2017),
77,530-536；Sensors and Actuators B:Chemical(2018),266,95-105；Anal Chim Acta
(2016),942,104-111；TetrahedronLetters(2016),57(8),953-958；These documents are all to a variety of
The detection of cation, is not carried out to Al3+Specific recognition, Sensors and Actuators B:Chemical
(2016),229,138-144；Spectrochim Acta A Mol Biomol Spectrosc(2018),201,185-192；
Analytical Methods(2012),4(7),1906；Sensors and Actuators B:Chemical(2017),
240,916-925；Journal of Photochemistry and Photobiology A:Chemistry(2017),332,
101-111；Sensors and Actuators B:Chemical(2017),238,128-137；Sensors and
Actuators B:Chemical(2018),264,304-311；Although these documents can single-minded identification Al3+, but launch wavelength
It is shorter, it cannot be detected in long wavelength range, be easy to cause light injury to cell or biological living sample, draw to a certain extent
Background fluorescence self-interference is played, and most cell permeabilities are poor, may not apply to identify Al into the cell3+, therefore, design and synthesis
More excellent Al3+Fluorescence probe is of great significance.
Summary of the invention
The technical problem to be solved in the present invention is to provide aluminum ions sides in a kind of longwave transmissions fluorescence imaging detection cell
Method, this method may be implemented in fluorescence imaging under longer launch wavelength and detect Al3+, and tissue penetration is strong, avoids light injury
With background fluorescence self-interference.
The technical solution of the invention is as follows:
Aluminum ions method in a kind of longwave transmissions fluorescence imaging detection cell, be characterized in that is visited with fluorescence
Needle L, as trace of Al in fluorescence imaging detection cell3+Fluorescence imaging probe, pass through longwave transmissions fluorescence imaging detect cell
Middle trace of Al3+, the chemical structural formula of the fluorescence probe L are as follows:
Further, trace of Al in longwave transmissions fluorescence imaging detection cell3+When, it is first glimmering with 5 μm of ol/L-10 μm of ol/L
Light probe L solution and cell culture enter fluorescence probe L in competent cell, then the competent cell and Al that will have fluorescence probe L3+
Culture, makes probe and Al3+Reaction generates the compound that can emit characteristic wavelength fluorescence in competent cell, realizes probe to activity
Intracellular Al3+Ionic dyeing imaging, with the competent cell fluorescent image after laser confocal fluorescence microscope observation culture.
Further, the solvent PBS buffer solution of fluorescence probe L solution.
Further, it under the excitation of 488nm wavelength, is observed with the channel 630nm-650nm, if there is red fluorescence, then
There are Al3+。
Further, the competent cell is HeLa cell, abbreviation HeLa cell.
Further, the fluorescence probe L, specific synthesis mode are as follows:
Using ethyl alcohol as solvent, raw material Isosorbide-5-Nitrae-diethyl -7- hydroxy tetrahydro quinoxaline -6- formaldehydeAnd bigcatkin willow
Benzoyl hydrazineIt feeds intake according to molar ratio 1:1~1:3, heating reflux reaction 8h~12h, reaction terminates
After have yellow solid precipitation, recrystallized with ethyl alcohol, obtain fluorescence probe L
Further, the fluorescence probe L can also in aqueous solvent fluorescence detection Al3+, identify Al3+Solvent be
DMSO and Tris volume of buffer solution ratio 7:3 identifies Al3+Solvent pH=4~10.
Beneficial effects of the present invention:
(1) synthesis fluorescence probe separating-purifying process is easy；Fluorescence probe can in water-bearing media long wavelength (642nm)
Fluorescence enhancement identifies Al3+, selectivity and good sensitivity with height, and may be used on detecting Al in cell3+。
(2) using Isosorbide-5-Nitrae-diethyl -7- hydroxy tetrahydro quinoxaline -6- formaldehyde as substrate, by introducing salicylide benzoyl hydrazine
Extend conjugated system and increases chelating site, Al3+The isomerization of C=N double bond is inhibited in conjunction with after, and keeps molecule coplanar, is increased
Molecular rigidity is added, so that fluorescence enhancement be made to identify Al3+。
Detailed description of the invention
Fig. 1 is the fluorescence probe L that aluminium ion uses in longwave transmissions fluorescence imaging detection cell of the present invention1H H NMR spectroscopy
Figure；
Fig. 2 is the fluorescence probe L that aluminium ion uses in longwave transmissions fluorescence imaging detection cell of the present invention13C H NMR spectroscopy
Figure；
Fig. 3 is the mass spectrogram for the fluorescence probe L that aluminium ion uses in longwave transmissions fluorescence imaging detection cell of the present invention；
Fig. 4 is fluorescence probe L detection Al3+Fluorescence emission spectrogram of compound；
Fig. 5 is that coexistent metallic ion detects Al to fluorescence probe L3+Fluorescence intensity influence diagram；
Fig. 6 is various concentration Al3+To the fluorescence titration spectrogram of probe；
Fig. 7 be in longwave transmissions fluorescence imaging detection cell the fluorescence probe L that uses of aluminium ion to Al3+Detection limit figure；
Fig. 8 be in longwave transmissions fluorescence imaging detection cell the fluorescence probe L that uses of aluminium ion to the toxicity of HeLa cell；
Fig. 9 is and various concentration Al3+The detection photo of HeLa cell fluorescence probe L fluorescence imaging after effect.
Specific embodiment
Technical solution of the present invention is described in more detail combined with specific embodiments below.
Embodiment 1- embodiment 3 is the fluorescence probe that aluminium ion uses in longwave transmissions fluorescence imaging detection cell of the present invention
The specific synthesis of L.
The specific synthetic route of fluorescence probe L is as follows:
Embodiment 1
Compound Isosorbide-5-Nitrae-diethyl -7- hydroxy tetrahydro quinoxaline -6- formaldehyde (234mg, 1mmol) and bigcatkin willow benzoyl hydrazine
(152mg, 1mmol) is dissolved in alcohol reflux 8h, is cooled to room temperature, and yellow solid is precipitated, is purified with ethyl alcohol recrystallization, is obtained
237mg yellow solid is receptor L, yield 64.3%.Fluorescence probe L's1H NMR spectra,13C NMR spectra and mass spectrum spectrum
Figure is as shown in Figs. 1-3.
1H NMR(400MHz,DMSO-d6)δ12.07(s,1H),11.77(s,1H),10.75(s,1H),8.46(s,1H),
7.90 (d, J=7.7Hz, 1H), 7.44 (t, J=7.6Hz, 1H), 6.96 (t, J=8.1Hz, 2H), 6.54 (s, 1H), 6.08
(s, 1H), 3.41 (s, 2H), 3.34 (d, J=7.0Hz, 2H), 3.27-3.17 (m, 2H), 3.11 (s, 2H), 1.09 (td, J=
6.6,2.9Hz,6H).
13C NMR(101MHz,DMSO-d6)δ164.26,159.74,153.26,151.39,140.10,134.09,
128.53,128.32,119.27,117.72,115.77,111.26,97.42,47.11,45.12,10.68,10.15.
HRMS(ESI+)calcd for C20H24N4O3[M+H]+:369.1848,found:369.1910.
Embodiment 2
Compound Isosorbide-5-Nitrae-diethyl -7- hydroxy tetrahydro quinoxaline -6- formaldehyde (234mg, 1mmol) and bigcatkin willow benzoyl hydrazine
(304mg, 2mmol) is dissolved in alcohol reflux 10h, is cooled to room temperature, and yellow solid is precipitated, is purified with ethyl alcohol recrystallization, is obtained
257mg red solid is fluorescence probe L, yield 69.8%.Fluorescence probe L's1H NMR spectra,13C NMR spectra and matter
It is as shown in Figs. 1-3 to compose spectrogram.
Embodiment 3
Compound Isosorbide-5-Nitrae-diethyl -7- hydroxy tetrahydro quinoxaline -6- formaldehyde (234mg, 1mmol) and bigcatkin willow benzoyl hydrazine
(456mg, 3mmol) is dissolved in alcohol reflux 12h, is cooled to room temperature, and yellow solid is precipitated, is purified with ethyl alcohol recrystallization, is obtained
267mg red solid is receptor L, yield 72.5%.Fluorescence probe L's1H NMR spectra,13C NMR spectra and mass spectrum spectrum
Figure is as shown in Figs. 1-3.
Fluorescence probe L detects Al in cell3+:
Longwave transmissions fluorescence imaging detects trace of Al in cell3+When, first the fluorescence probe L with 5 μm of ol/L-10 μm of ol/L is molten
Liquid (solvent is PBS buffer solution) and cell culture enter fluorescence probe L in competent cell, then the activity that will have fluorescence probe L
Cell and Al3+Culture, makes probe and Al3+Reaction generates the compound that can emit characteristic wavelength fluorescence in competent cell, realizes
Probe is to Al in competent cell3+Ionic dyeing imaging, it is glimmering with the competent cell after laser confocal fluorescence microscope observation culture
Light image.Under the excitation of 488nm wavelength, is observed with the channel 630nm-650nm, if there is red fluorescence, then there is Al3+。
We carry out living cells imaging experiment with HeLa cell, and HeLa cell and 10 μm of ol/L fluorescence probe L solution is (molten
Agent is PBS buffer solution) it is cultivated 30 minutes at 37 DEG C, then HeLa cell is washed three times with PBS buffer solution, adds Al3+(10 μM,
50 μM, 100 μM) culture 30 minutes, red fluorescence brightness is observed with Al3+Concentration increase and enhance (see Fig. 9), these the result shows that
Probe L has good cell permeability, the Al being able to detect in HeLa cell3+.It is thin using conventional HeLa in incubation
Born of the same parents' culture solution can be realized.
Fluorescence probe L is to Al3+The detection of selectivity:
DMSO:Tris=7:3 (v/v, pH=7.4) buffer solution of 10 μm of ol/L fluorescence probe L, is separately added into thereto
8 μ L (50mmol/L) cation (Mg2+, Fe2+, Fe3+, Al3+, Mn2+, Pb2+, Na+, Cu2+, Cd2+, Cr3+, Ca2+, K+, Ba2+, Co2 +, Ni2+, Sr2+, Zn2+), the fluorescence emission spectrum variation of solution is detected, as shown in Figure 4.Figure 4, it is seen that when sun is added
When ion, only Al3+It can cause fluorescence intensity significant changes, i.e. addition Al3+The fluorescence intensity at 608nm and 642nm increases afterwards
By force, and other cation additions fluorescence intensity is had not significant impact, it follows that fluorescence probe L is to Al3+There is the choosing of height
Selecting property.
Fluorescence probe L identifies Al3+Anti-interference detection:
DMSO:Tris=7:3 (v/v, pH=7.4) solution of 10 μm of ol/L fluorescence probe L, is separately added into 8 μ L thereto
(50mmol/L) 17 kinds of cation (Mg2+, Fe2+, Fe3+, Al3+, Mn2+, Pb2+, Na+, Cu2+, Cd2+, Cr3+, Ca2+, K+, Ba2+,
Co2+, Ni2+, Sr2+, Zn2+), the fluorescence emission spectrum of solution is detected, is then divided again into above each solution containing cation
The Al of 8 μ L (50mmol/L) is not added3+, the fluorescence emission spectrum of solution is detected, value corresponding to maximum emission wavelength is taken to map,
As shown in figure 5, in the presence of having other cations, Al3+It can result in probe L fluorescence enhancement, illustrate fluorescence probe L to Al3+It is insighted
Not, it is interfered by partial cation.
Fluorescence probe L is to Al3+Titration test:
DMSO:Tris=7:3 (v/v, pH=7.4) buffer solution of the fluorescence probe L of 10 μm of ol/L, it is separately added into 0~
The Al of 20 times (50mmol/L)3+, the fluorescence emission spectrum variation of solution is detected, as shown in Figure 6.From fig. 6 it can be seen that with
Al3+It is continuously added, the emission peak at 640nm gradually rises, as the Al for being added 20 times3+When, the emission peak at 640nm is not
It increases again, illustrates to have reached saturation at this time.
Fluorescence probe L is to Al3+Detection limit test:
In DMSO:Tris=7:3 (v/v, pH=7.4) buffer solution of probe L, the fluorescence of 20 Duplicate Samples is tested
Intensity, according to formula ∑ (Xi-X)2=(X1-X)2+(X2-X)2+……+(Xn-X)2Find out the summation (X of the difference of two squaresiTo survey every time
Receptor fluorescence intensity level itself is measured, X is mean value of fluorescence intensity, and n is testing time, and n is more than or equal to 11), then according to formula S
=[∑ (Xi-X)2/(n-1)]0.5S is found out, limits formula 3S/K further according to detection, K is the slope (note: straight line of selected straight line portion
It is that point diagram is done according to titration, abscissa is ion concentration, and ordinate is fluorescence intensity), finding out detection line is 5.73 × 10-7mol/
L (see Fig. 7), this illustrates that the probe has lower detection to limit, the Al of detectable level low concentration3+, sensitivity with higher,
There is certain practical application value.
Toxicity detection of the fluorescence probe L to HeLa cell:
We, to the toxicity of HeLa cell, cultivate 10 μM of probe L and HeLa cells with DMEM with mtt assay detection probe L
For 24 hours, cell survival rate illustrates probe L (see Fig. 8) very low to the toxicity of HeLa cell still close to 100% for base culture.
The above is only specific embodiments of the present invention, are not intended to restrict the invention, for those skilled in the art
For member, the invention may be variously modified and varied.All within the spirits and principles of the present invention, it is made it is any modification,
Equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (7)
1. aluminum ions method in a kind of longwave transmissions fluorescence imaging detection cell, it is characterized in that: be with fluorescence probe L, as
Fluorescence imaging detects trace of Al in cell3+Fluorescence imaging probe, pass through longwave transmissions fluorescence imaging detect cell in trace of Al3 +, the chemical structural formula of the fluorescence probe L are as follows:
2. aluminum ions method in longwave transmissions fluorescence imaging detection cell according to claim 1, it is characterized in that: long wave
Emit trace of Al in fluorescence imaging detection cell3+When, first with the fluorescence probe L solution of 5 μm of ol/L-10 μm of ol/L and cell culture
Enter fluorescence probe L in competent cell, then the competent cell and Al that there will be fluorescence probe L3+Culture, makes probe and Al3+In work
Property into the cell reaction generate and can emit the compound of characteristic wavelength fluorescence, realize probe to Al in competent cell3+Ionic dyeing at
Picture, with the competent cell fluorescent image after laser confocal fluorescence microscope observation culture.
3. aluminum ions method in longwave transmissions fluorescence imaging detection cell according to claim 2, it is characterized in that: fluorescence
The solvent PBS buffer solution of probe L solution.
4. aluminum ions method in longwave transmissions fluorescence imaging detection cell according to claim 2, it is characterized in that: with swashing
Competent cell fluorescent image after the observation culture of light confocal fluorescent microscopic uses 630nm- under the excitation of 488nm wavelength
, if there is red fluorescence, then there is Al in the observation of the channel 650nm3+。
5. aluminum ions method in longwave transmissions fluorescence imaging detection cell according to claim 2, it is characterized in that: described
Competent cell be HeLa cell.
6. aluminum ions method in longwave transmissions fluorescence imaging detection cell according to claim 1, it is characterized in that: described
Fluorescence probe L, specific synthesis mode are as follows:
Using ethyl alcohol as solvent, raw material Isosorbide-5-Nitrae-diethyl -7- hydroxy tetrahydro quinoxaline -6- formaldehyde and bigcatkin willow benzoyl hydrazine according to mole
It feeds intake than 1:1~1:3, heating reflux reaction 8h~12h has yellow solid precipitation after reaction, carries out weight with ethyl alcohol
Crystallization, obtains fluorescence probe L.
7. aluminum ions method in longwave transmissions fluorescence imaging detection cell according to claim 1, it is characterized in that: described
Fluorescence probe L can also in aqueous solvent fluorescence detection Al3+, identify Al3+Solvent be DMSO and Tris volume of buffer solution
Al is identified than 7:33+Solvent pH=4~10.
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| 钟克利: "肼二腙类多功能长波发射荧光探针的合成及其铜配合物对H2S的识别", 《有机化学》 * |
| 陈虹蓉等: "2-羟基萘甲醛苯甲酰腙衍生物对Al3+的裸眼识别和荧光传感", 《应用化学》 * |
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