CN110498803A - A kind of compound and the preparation method and application thereof based on hydrazide structure in rhodamine - Google Patents
A kind of compound and the preparation method and application thereof based on hydrazide structure in rhodamine Download PDFInfo
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Abstract
The present invention provides a kind of compound and the preparation method and application thereof based on hydrazide structure in rhodamine.Wherein, the structural formula of compound is as follows:Compound based on hydrazide structure in rhodamine of the invention is able to detect Pd2+, and there is universality, i.e., the strategy can be applied to the problem of hydrazide structure detects the metal ion in living cells in rhodamine.Fluorescence probe is in detection Pd2+Application in shown many advantages such as response multiple is high, selectivity is good, and it is successfully applied in the imaging of the confocal fluorescent of living cells, it is a kind of novel imaging tool, detects metal-ion fluorescent probe for Future Development and provide new approaches and new strategy.Value with good practical application.
Description
Technical field
The invention belongs to organic compound synthesis and technical field of fluorescence detection, and in particular to one kind is based on acyl in rhodamine
The compound and the preparation method and application thereof of hydrazine structure.
Background technique
Disclosing the information of the background technology part, it is only intended to increase understanding of the overall background of the invention, without certainty
It is considered as recognizing or implying in any form that information composition has become existing skill well known to persons skilled in the art
Art.
Palladium is a heavy metal species, it is extremely common in life, and is played an important role.Its advantage is embodied in it
With stable property, good biocompatibility and variable chemical property, thus it alloy material, various jewelry,
Medical corona, chemical fuel cell, catalysts and automobile catalyst in be widely applied.
But it is noted that palladium be widely used and meanwhile also to the health care belt of people and other biological come centainly endanger,
Being primarily due to palladium can not be biodegradable.So the palladium in the various product generated in the above various approach may just exist
It is constantly accumulated in food chain.When the accumulation of the amount of palladium to a certain extent when, it is possible to mitochondria in cell and DNA can be made
Degradation, the effect on the other hand also resulting in part enzyme are suppressed.So country is to the palladium taken in the daily food of adult
Amount made certain limitation, this value should be lower than 1.5-15 μ g.So developing a kind of efficiently and to palladium with good choosing
The method of selecting property and low detection limit is very urgent.
The reaction principle of fluorescent molecular probe is clear, and fluorescent switch is easy to control, and has high sensitivity, not by electromagnetic field
Interference, is able to carry out remote real time on-line monitoring.Based on above advantages, fluorescent molecular probe is in life science, chemistry
And the fields such as medicine receive the very big concern of researcher, become a research hotspot, and be widely used in each neck
Domain.However, it is found by the inventors that detecting Pd at present2+The generally existing detection limit for height of method or the bad problem of selectivity, while by
In the compound that detection probe uses often cytotoxicity with higher, limit it when being applied to living cells detection
System.
Summary of the invention
For the above-mentioned prior art, the present invention provides a kind of compound based on hydrazide structure in rhodamine and its preparation side
Method and application, the compound can be used as fluorescence probe, and can be to Pd2+Be imaged, and have high sensitivity, selectivity high and
Convieniently synthesized advantage.Value with good practical application.
The present invention is achieved through the following technical solutions:
The first aspect of the invention provides a kind of formula (I) compound, structural formula are as follows:
The second aspect of the invention provides above-mentioned formula (I) preparation method of compound, and the method includes with rhodamine
B, hydrazine hydrate and 8-hydroxyquinoline -2- formaldehyde are raw material, carry out reaction preparation according to following reaction route:
At least one of the third aspect of the invention provides formula (I) purposes of compound, is following 1) -7):
1) fluorescence probe made of formula (I) compound；
2) application of formula (I) compound in the fluorescence probe as fluorescence probe or as detection palladium ion；
3) contain the optical sensor of formula (I) compound；
4) formula (I) compound is preparing the application in optical sensor or the optical sensor for detecting palladium ion；
5) application of formula (I) compound in detection palladium ion；
6) application of the above-mentioned fluorescence probe 1) in detection palladium ion；
7) application of the above-mentioned optical sensor 3) in detection palladium ion.
Wherein, formula (I) compound, 1) fluorescence probe and 3) optical sensor is used equally for detection palladium ion,
The detection environment can be liquid phase environment, further, can be applied to the detection of palladium ion in living cells.
When formula (I) compound is as fluorescence probe or as optical sensor, Pd is encountered2+When, hydrazide structure in rhodamine B
It is induced open loop, PET effect is prohibited, and fluorescent radiation enhancing embodies the fluorescence signal of off-on type.
The invention has the benefit that
1. being able to detect Pd based on hydrazide structure in rhodamine the present invention provides a kind of2+Layout strategy, be to have
Universality, i.e., the strategy can be applied to the problem of hydrazide structure detects the metal ion in living cells in rhodamine.
2. fluorescence probe is in detection Pd2+Application in shown many advantages such as response multiple is high, selectivity is good, and
It has been successfully applied in the imaging of the confocal fluorescent of living cells, experiment proves that, to other common metals and metalloid
Ion fluorescence responsiveness is extremely low, shows that it is suitable for Pd2+Carry out highly sensitive and highly selective detection, therefore it is as one
The novel imaging tool of kind detects metal-ion fluorescent probe for Future Development and provides new approaches and new strategy.
3. the good biocompatibility of probe of the invention, small to cell and living injury.
Layout strategy of the invention and synthetic route are easy, and raw material be it is cheap and easy to get, be expected to be applied to the marketization
Production, therefore have stronger promotional value and application value.
Detailed description of the invention
The Figure of description for constituting a part of the invention is used to provide further understanding of the present invention, and of the invention shows
Examples and descriptions thereof are used to explain the present invention for meaning property, does not constitute improper limitations of the present invention.
Fig. 1 is the fluorescence emission spectrogram of compound of fluorescence probe prepared by the embodiment of the present invention 1, wherein abscissa is wavelength
(nm), ordinate is fluorescent emission intensity.
Fig. 2 is the UV absorption spectrogram of fluorescence probe prepared by the embodiment of the present invention 1, wherein abscissa is wavelength (nm),
Ordinate is UV absorption intensity.
Fig. 3 is the selective determination figure of fluorescence probe prepared by the embodiment of the present invention 1 and each metal ion species.It has detected
Metal ion is successively from left to right: Zn2+、Sn2+、Pt2+、Ni2+、NH4 +、Na+、Mg2+、Li+、La+、K+、Eu3+、Fe2+、Er3+、
Cs+、Co2+、Cd2+、Ca2+、Cu2+、Al3+、Fe3+、Pd2+, wherein Pd2+Concentration be 50 μM, other ion concentrations are 1mM.
Fig. 4 is toxicity figure of the fluorescence probe to Human umbilical vein endothelial cells of the preparation of the embodiment of the present invention 1；
Fig. 5 be the embodiment of the present invention 1 prepare fluorescence probe in Human umbilical vein endothelial cells to Pd2+It changes over time
Confocal fluorescent image.
Specific embodiment
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the present invention.Unless another
It indicates, all technical and scientific terms used herein has usual with general technical staff of the technical field of the invention
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe specific embodiment, and be not intended to restricted root
According to exemplary embodiments of the present invention.As used herein, unless the context clearly indicates otherwise, otherwise singular
Also it is intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " packet
Include " when, indicate existing characteristics, step, operation, device, component and/or their combination.It should be understood that protection model of the invention
It encloses and is not limited to following specific specific embodiments；It is also understood that term used in the embodiment of the present invention is to retouch
Specific specific embodiment is stated, rather than limiting the scope of protection of the present invention.
As background technique is introduced, in the prior art for detecting Pd2+Fluorescence probe especially for living cells
Interior Pd2+The research of detection probe is less, and in order to solve technical problem as above, the invention proposes a kind of novel based on Luo Dan
Bright interior hydrazide structure detects Pd into the cell2+Fluorescence probe layout strategy and synthetic method.
In an exemplary embodiment of the invention, a kind of formula (I) compound, structural formula are provided are as follows:
In still another embodiment of the invention, above-mentioned formula (I) preparation method of compound is provided, with rhodamine B, water
Closing hydrazine and 8-hydroxyquinoline -2- formaldehyde is raw material, carries out reaction preparation according to following reaction route:
In still another embodiment of the invention, the solvent of rhodamine B and hydrazine hydrate reaction system is ethyl alcohol；Preferably
Dehydrated alcohol.
In still another embodiment of the invention, the mass ratio of the material of rhodamine B and hydrazine hydrate is 1:5-10.
In still another embodiment of the invention, the reaction temperature of rhodamine B and hydrazine hydrate is 75 DEG C -85 DEG C, reaction
Time be 8h-12h.
In still another embodiment of the invention, formula (II) compound and 8-hydroxyquinoline -2- formaldehyde reaction system
Solvent is ethyl alcohol；Preferably dehydrated alcohol.
In still another embodiment of the invention, temperature that formula (II) compound is reacted with 8-hydroxyquinoline -2- formaldehyde
For 75 DEG C -85 DEG C (preferably 80 DEG C), the reaction time is 3-8h (preferably 6h), (makes reaction temperature by optimizing reaction temperature
Close to the boiling point of ethyl alcohol) and the reaction time, to keep reaction more abundant, yield is higher.
In still another embodiment of the invention, the amount of the substance of formula (II) compound and 8-hydroxyquinoline -2- formaldehyde
The ratio between be 1:1.
In still another embodiment of the invention, catalysis that formula (II) compound is reacted with 8-hydroxyquinoline -2- formaldehyde
Agent is acetic acid, can provide a weakly acidic condition, and the alkali generated in neutralization reaction using the catalyst for reaction.
In still another embodiment of the invention, provide formula (I) purposes of compound, be following 1) -7) at least
It is a kind of:
1) fluorescence probe made of formula (I) compound；
2) application of formula (I) compound in the fluorescence probe as fluorescence probe or as detection palladium ion；
3) contain the optical sensor of formula (I) compound；
4) formula (I) compound is preparing the application in optical sensor or the optical sensor for detecting palladium ion；
5) application of formula (I) compound in detection palladium ion；
6) application of the above-mentioned fluorescence probe 1) in detection palladium ion；
7) application of the above-mentioned optical sensor 3) in detection palladium ion.
Wherein, 1) fluorescence probe and 3) optical sensor be used equally for detection palladium ion, the detection environment
It can be liquid phase environment, further, can be the detection applied to palladium ion in living cells.
When formula (I) compound is as fluorescence probe or as optical sensor, Pd is encountered2+When, hydrazide structure in rhodamine B
It is induced open loop, PET effect is prohibited, and fluorescent radiation enhancing embodies the fluorescence signal of off-on type.
Explanation is further explained to the present invention by the following examples, but is not construed as limiting the invention.It should be understood that
These examples are only for illustrating the present invention and are not intended to limit the scope of the present invention.
The synthesis of 1 fluorescence probe of embodiment
Raw material rhodamine B (1.0g) and hydrazine hydrate (0.5ml) is taken to be dissolved in the dehydrated alcohol of 25mL, flow back 12h at 80 DEG C.
After completion of the reaction, rotary evaporation removes solvent.Then use ethyl acetate: petroleum ether=1:1 is purified as eluant, eluent, column chromatography
Compound is up to hydrazides (90%) in white solid intermediate product rhodamine.
Hydrazides (0.944g) and 8-hydroxyquinoline -2- formaldehyde (0.346g) in intermediate product rhodamine are taken, 3ml ethyl alcohol is dissolved in
In, it is added acetic acid (0.01ml), 80 DEG C are heated at reflux 6h.After completion of the reaction, rotary evaporation removes solvent.Then use acetic acid second
Ester: petroleum ether=1:1, column chromatography purification compound obtain yellow powder, as final probe (80%).
Nuclear-magnetism and mass spectral characteristi:
δ=8.67 (s, 1H) 1H NMR (400MHz, CDCl3), 8.03 (dt, J=18.6,8.7,4H), 7.55-7.45
(m, 2H), 7.35 (t, J=7.9,1H), 7.21 (d, J=8.1,1H), 7.15 (d, J=7.2,1H), 7.07 (d, J=7.4,
1H), 6.55 (d, J=8.8,2H), 6.50 (d, J=2.1,2H), 6.25 (dd, J=8.9,2.3,2H), 3.31 (q, J=6.9,
8H), 1.14 (t, J=7.0,12H) .13C NMR (101MHz, CDCl3) δ=165.40,153.15,152.54,152.17,
149.09,146.02,137.54,135.86,133.87,128.68–128.29,128.10,127.89,123.98,123.65,
118.86,117.71,110.10,108.09,105.61,98.06,66.16,44.35,34.14,31.58,29.73,22.30,
14.09,12.63,11.80.LRMS(ESI)m/z:[M+H]calculated for C38H37N5O3,612.29found
612.80
Effect experiment:
In general, dye molecule can be dissolved in physiological saline, buffer or water-soluble organic by acetonitrile, dimethyl sulfoxide etc.
Solvent, is then added appropriate buffer and other organic reagents are tested.It is water-soluble in pH=7.4 buffering that probe is had studied respectively
Liquid and the various photophysical properties that common are in machine reagent are simultaneously used for living cells imaging experiment.The colouring method of living cells
It is that cultured cell is put in the buffer solution containing probe molecule to be incubated for, removes Incubating Solution after being incubated for the regular hour,
Carry out co-focusing imaging experiment.
Probe and Pd2+UV absorption, fluorescent emission and the selectivity experiment of reaction:
Control group: probe (50 μM), PBS buffer solution (10mM), pH=7.4；Experimental group: probe (50 μM), PBS buffering
Solution (10mM), pH=7.4, Pd2+(50μM).Control group and experimental group are all incubated for 30min at 37 DEG C, then respectively with it
Absorption maximum is one-photon excitation wavelength, measures its UV absorption and fluorescence emission spectrogram of compound, spectrogram is shown in Fig. 1 and figure
2.Abscissa is wavelength (nm), and Fig. 1 ordinate is fluorescence intensity, Fig. 2 ordinate is UV absorption intensity.Fig. 3 is probe to more
The response condition of the metal ion of kind, the metal ion detected is successively from left to right: Zn2+、Sn2+、Pt2+、Ni2+、NH4 +、
Na+、Mg2+、Li+、La+、K+、Eu3+、Fe2+、Er3+、Cs+、Co2+、Cd2+、Ca2+、Cu2+、Al3+、Fe3+、Pd2+, wherein Pd2+It is dense
Degree is 50 μM, other ion concentrations are 1mM.As shown in figure 3, only working as Pd2+In the presence of, fluorescence intensity have significant enhancing and
Response multiple is up to 230 times.This explanation is compared with other components in organism, and probe is to Pd2+There is fabulous selectivity, it can be with
In complicated cell and living body biological environment, specific detection Pd2+。
The cytotoxicity experiment of probe:
Human umbilical vein endothelial cells HUVEC is that 3- (4,5- bis- is added in cell by the DMEM culture solution culture of high sugar
Methyl thiazolium mile -2) -2,5- diphenyl, four nitrogen frustrates bromide (MTT), probe is demonstrated by the survival rate of cell to the poison of cell
Property.It is respectively 0.01 μM, 0.1 μM, 1 μM, 10 μM, 20 μM, 50 μM that probe, which has chosen five concentration,.As a result such as Fig. 4, cell are deposited
Motility rate is all 80% or more, and probe is to cytotoxicity very little.The toxicity for thereby confirming probe is very low, can be used for intracellular
Fluorescence detection.
Probe is to living cells confocal fluorescent imaging experiment:
Human umbilical vein endothelial cells HUVEC is by the DMEM culture solution culture of high sugar.It is incubated for carefully for (5 μM) of probe at 37 DEG C
Born of the same parents 30min then rinses cell at least three times with Hepes buffer solution, washes off the extra probe for not entering into cell, to prevent
Interference is generated to imaging.Then Pd is added in the ware of glass bottom2+, concentration is 5 μM, is put into progress laser co-focusing fluorescence under microscope
Imaging.It claps every 5min once, as a result as shown in figure 5, it is observed that the brightness of fluorescence obviously increases with the growth of time
By force, show that probe can detecte Pd in the cell2+.One-photon excitation light is 514nm, and red channel collects 530nm-600nm.
The synthesis of 2 fluorescence probe of embodiment
Raw material rhodamine B (0.8g) and hydrazine hydrate (0.8ml) is taken to be dissolved in the dehydrated alcohol of 15mL, flow back 10h at 85 DEG C.
After completion of the reaction, rotary evaporation removes solvent.Then use ethyl acetate: petroleum ether=1:1 is purified as eluant, eluent, column chromatography
Compound is up to hydrazides (60%) in white solid intermediate product rhodamine.
Hydrazides (0.653g) and 8-hydroxyquinoline -2- formaldehyde (0.478g) in intermediate product rhodamine are taken, 10ml second is dissolved in
In alcohol, it is added acetic acid (0.1ml), 70 DEG C are heated at reflux 4h.After completion of the reaction, rotary evaporation removes solvent.Then use acetic acid second
Ester: petroleum ether=1:1, column chromatography purification compound obtain yellow powder, as final probe (40%).
The synthesis of 3 fluorescence probe of embodiment
Raw material rhodamine B (1.2g) and hydrazine hydrate (0.4ml) is taken to be dissolved in the dehydrated alcohol of 35mL, flow back 8h at 70 DEG C.
After completion of the reaction, rotary evaporation removes solvent.Then use ethyl acetate: petroleum ether=1:1 is purified as eluant, eluent, column chromatography
Compound is up to hydrazides (76%) in white solid intermediate product rhodamine.
Hydrazides (0.944g) and 8-hydroxyquinoline -2- formaldehyde (0.2g) in intermediate product rhodamine are taken, 5ml ethyl alcohol is dissolved in
In, it is added acetic acid (0.001ml), 80 DEG C are heated at reflux 6h.After completion of the reaction, rotary evaporation removes solvent.Then use acetic acid second
Ester: petroleum ether=1:1, column chromatography purification compound obtain yellow powder, as final probe (55%).
It should be noted that above example is only used to illustrate the technical scheme of the present invention rather than is limited.Although ginseng
It is described the invention in detail according to given example, but those skilled in the art can be as needed to this hair
Bright technical solution is modified or replaced equivalently, without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
- Formula 1. (I) compound, structural formula are as follows:
- The preparation method of formula described in claim 1 2. (I) compound, it is characterised in that: with rhodamine B, hydrazine hydrate and 8- hydroxyl Quinoline -2- formaldehyde is raw material, carries out reaction preparation according to following reaction route:
- 3. preparation method according to claim 2, it is characterised in that: the solvent of rhodamine B and hydrazine hydrate reaction system is Ethyl alcohol；Preferably dehydrated alcohol.
- 4. preparation method according to claim 2, it is characterised in that: the molar ratio of rhodamine B and hydrazine hydrate is 1:5-10.
- 5. preparation method according to claim 2, it is characterised in that the temperature of rhodamine B and hydration hydrazine reaction is 75-85 DEG C, the time of reaction is 8-12h.
- 6. preparation method according to claim 2, it is characterised in that: formula (II) compound and 8-hydroxyquinoline -2- formaldehyde The temperature of reaction is 75-85 DEG C, and the time of reaction is 3-8h；Preferably, the temperature that formula (II) compound is reacted with 8-hydroxyquinoline -2- formaldehyde is 80 DEG C, and the time of reaction is 6h.
- 7. preparation method according to claim 2, it is characterised in that: formula (II) compound and 8-hydroxyquinoline -2- formaldehyde The solvent of reaction is ethyl alcohol, preferably dehydrated alcohol；Preferably, the ratio between amount of substance of formula (II) compound and 8-hydroxyquinoline -2- formaldehyde is 1:1；Preferably, the catalyst that formula (II) compound is reacted with 8-hydroxyquinoline -2- formaldehyde is acetic acid.
- 8. a kind of fluorescence probe, which is characterized in that the fluorescence probe is compound described in claim 1；Preferably, described Fluorescence probe is the fluorescence probe for detecting palladium ion.
- 9. a kind of optical sensor, which is characterized in that the optical sensor includes compound described in claim 1；It is preferred that , the optical sensor is the optical sensor for detecting palladium ion.
- 10. optical sensor described in fluorescence probe described in compound, claim 8 described in claim 1 or claim 9 is being examined Survey the application in palladium ion；Preferably, the detection environment is living cells.
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