CN110498803B - Compound based on rhodamine hydrazide structure and preparation method and application thereof - Google Patents
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- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
Abstract
The invention provides a compound based on a rhodamine hydrazide structure, and a preparation method and application thereof. Wherein the compound has the following structural formula:
the compound based on the rhodamine hydrazide structure can detect Pd2+And is universal, i.e. the strategy can be applied to the problem of detecting metal ions in living cells by rhodamine internal hydrazide structure. Detection of Pd by fluorescent probe2+The fluorescent probe shows many advantages of high response multiple, good selectivity and the like, is successfully applied to the imaging of the confocal fluorescence of living cells, is a novel imaging tool, and provides a new idea and a new strategy for developing and detecting the metal ion fluorescent probe in the future. Has good practical application value.
Description
Technical Field
The invention belongs to the technical field of organic compound synthesis and fluorescence detection, and particularly relates to a compound based on a rhodamine hydrazide structure, and a preparation method and application thereof.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
Palladium is a heavy metal, which is extremely common in life and plays an important role. Its advantages are stable nature, high biocompatibility and changeable chemical nature, so it can be widely used in alloy material, jewels, medical crown, chemical fuel cell, reaction catalyst and catalytic converter of car.
It is worth mentioning, however, that the widespread use of palladium also presents certain health risks to humans and other living beings, mainly because palladium cannot be biodegraded. Therefore, the palladium in the various products produced in the above routes may accumulate continuously in the food chain. When the amount of palladium is accumulated to a certain extent, it may cause degradation of mitochondria and DNA in cells, and on the other hand, may cause inhibition of partial enzyme action. Therefore, the country places a limit on the amount of palladium that an adult can ingest per day, which should be less than 1.5-15 μ g. Therefore, it is not uncommon to develop a method that is efficient and has good selectivity for palladium and a low detection limit.
The reaction principle of the fluorescent molecular probe is clear, the fluorescent switch is easy to control, and the fluorescent molecular probe has high sensitivity, is not interfered by an electromagnetic field and can carry out remote real-time online monitoring. Based on the above advantages, fluorescent molecular probes have received great attention from researchers in the fields of life science, chemistry, medicine, and the like, have become a research hotspot, and are widely applied to various fields. However, the inventors found that Pd is currently detected2+The method has the problems of high detection limit or poor selectivity, and the compound used by the detection probe is limited when being applied to living cell detection because the compound usually has high cytotoxicity.
Disclosure of Invention
In view of the above prior artThe invention provides a compound based on a rhodamine hydrazide structure, a preparation method and application thereof2+The method has the advantages of high sensitivity, high selectivity and simple synthesis. Has good practical application value.
The invention is realized by the following technical scheme:
in a first aspect of the invention, there is provided a compound of formula (I) having the formula:
in a second aspect of the present invention, there is provided a process for preparing a compound of formula (I) as described above, said process comprising reacting rhodamine B, hydrazine hydrate and 8-hydroxyquinoline-2-carbaldehyde as starting materials according to the following reaction scheme:
in a third aspect of the invention, there is provided the use of a compound of formula (I) which is at least one of 1) to 7) below:
1) fluorescent probes made from compounds of formula (I);
2) the application of the compound of the formula (I) as a fluorescent probe or a fluorescent probe for detecting palladium ions;
3) an optical sensor comprising a compound of formula (I);
4) the use of a compound of formula (I) in the manufacture of an optical sensor or an optical sensor for the detection of palladium ions;
5) the use of a compound of formula (I) for detecting palladium ions;
6) the fluorescent probe of 1) above is applied to detecting palladium ions;
7) use of the optical sensor of 3) above for detecting palladium ions.
The compound of formula (I), the fluorescent probe of 1) and the optical sensor of 3) can be used for detecting palladium ions, the detection environment can be a liquid phase environment, and further, the method can be applied to detection of palladium ions in living cells.
Pd is encountered when the compounds of formula (I) are used as fluorescent probes or as optical sensors2+In the process, the rhodamine B internal hydrazide structure is induced to open the ring, the PET effect is forbidden, the fluorescence radiation is enhanced, and an off-on fluorescence signal is reflected.
The invention has the beneficial effects that:
1. the invention provides a rhodamine hydrazide structure-based method capable of detecting Pd2+The design strategy of (1) is universal, namely the strategy can be applied to the problem of detecting metal ions in living cells by using rhodamine internal hydrazide structures.
2. Detection of Pd by fluorescent probe2+The fluorescent probe shows many advantages of high response times, good selectivity and the like, is successfully applied to the imaging of confocal fluorescence of living cells, and has extremely low fluorescence responsivity to other common metal and metalloid ions through experimental verification, which shows that the fluorescent probe is suitable for Pd2+The method is used for detecting with high sensitivity and high selectivity, so that the method is used as a novel imaging tool and provides a new idea and a new strategy for developing and detecting the metal ion fluorescent probe in the future.
3. The probe of the invention has good biocompatibility and small damage to cells and living bodies.
The method has simple design strategy and synthesis route, and the raw materials are cheap and easily available, and are expected to be applied to marketized production, so the method has strong popularization value and application value.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a fluorescence emission spectrum of a fluorescent probe prepared in example 1 of the present invention, wherein the abscissa is wavelength (nm) and the ordinate is fluorescence emission intensity.
FIG. 2 is an ultraviolet absorption spectrum of the fluorescent probe prepared in example 1 of the present invention, in which the abscissa is wavelength (nm) and the ordinate is ultraviolet absorption intensity.
FIG. 3 is a graph showing the selectivity of the fluorescent probe prepared in example 1 of the present invention with respect to various metal ions. The detected metal ions are sequentially as follows 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+In which Pd2+The concentration of (3) was 50. mu.M, and the concentration of other ions was 1 mM.
FIG. 4 is a graph showing the toxicity of the fluorescent probe prepared in example 1 of the present invention against human umbilical vein endothelial cells;
FIG. 5 shows the Pd pair in human umbilical vein endothelial cells by the fluorescent probe prepared in example 1 of the present invention2+Confocal fluorescence imaging as a function of time.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise. It is to be understood that the scope of the invention is not to be limited to the specific embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention.
As described in the background, the prior art is directed to detecting Pd2+Especially for Pd in living cells2+The research on detection probes is less, and in order to solve the technical problems, the invention provides a novel intracellular detection method for Pd based on a rhodamine hydrazide structure2+The design strategy and synthesis method of the fluorescent probe.
In one exemplary embodiment of the present invention, there is provided a compound of formula (I) having the structural formula:
in another embodiment of the present invention, there is provided a method for preparing the compound of formula (I), wherein rhodamine B, hydrazine hydrate and 8-hydroxyquinoline-2-carbaldehyde are used as raw materials, and the preparation method comprises the following steps:
in another embodiment of the invention, the solvent of the reaction system of rhodamine B and hydrazine hydrate is ethanol; preferably anhydrous ethanol.
In another embodiment of the present invention, the ratio of the amounts of rhodamine B and hydrazine hydrate is 1: 5-10.
In another embodiment of the invention, the reaction temperature of rhodamine B and hydrazine hydrate is 75-85 ℃, and the reaction time is 8-12 h.
In another embodiment of the present invention, the solvent of the reaction system of the compound of formula (II) and 8-hydroxyquinoline-2-carbaldehyde is ethanol; preferably anhydrous ethanol.
In still another embodiment of the present invention, the reaction temperature of the compound of formula (II) with 8-hydroxyquinoline-2-carbaldehyde is 75-85 deg.C (preferably 80 deg.C), the reaction time is 3-8h (preferably 6h), and the reaction temperature (making the reaction temperature close to the boiling point of ethanol) and the reaction time are optimized, so that the reaction is more complete and the yield is higher.
In yet another embodiment of the invention, the mass ratio of the compound of formula (II) to 8-hydroxyquinoline-2-carbaldehyde is 1: 1.
In yet another embodiment of the present invention, the catalyst for the reaction of the compound of formula (II) with 8-hydroxyquinoline-2-carbaldehyde is acetic acid, and the use of this catalyst can provide a weak acid environment for the reaction and neutralize the base produced in the reaction.
In still another embodiment of the present invention, there is provided a use of the compound of formula (I) as at least one of the following 1) to 7):
1) fluorescent probes made from compounds of formula (I);
2) the application of the compound of the formula (I) as a fluorescent probe or a fluorescent probe for detecting palladium ions;
3) an optical sensor comprising a compound of formula (I);
4) the use of a compound of formula (I) in the manufacture of an optical sensor or an optical sensor for the detection of palladium ions;
5) the use of a compound of formula (I) for detecting palladium ions;
6) the fluorescent probe of 1) above is applied to detecting palladium ions;
7) use of the optical sensor of 3) above for detecting palladium ions.
Wherein, 1) the fluorescent probe and 3) the optical sensor can be used for detecting palladium ions, and the detection environment can be a liquid phase environment, and further can be used for detecting palladium ions in living cells.
Pd is encountered when the compounds of formula (I) are used as fluorescent probes or as optical sensors2+In the process, the rhodamine B internal hydrazide structure is induced to open the ring, the PET effect is forbidden, the fluorescence radiation is enhanced, and an off-on fluorescence signal is reflected.
The invention is further illustrated by the following examples, which are not to be construed as limiting the invention thereto. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
EXAMPLE 1 Synthesis of fluorescent Probe
Raw materials of rhodamine B (1.0g) and hydrazine hydrate (0.5mL) are dissolved in 25mL of absolute ethyl alcohol and refluxed for 12 hours at the temperature of 80 ℃. After the reaction was completed, the solvent was removed by rotary evaporation. Then, the mixture is mixed with ethyl acetate: and (3) using petroleum ether as an eluent, namely 1:1, and purifying the compound by column chromatography to obtain a white solid intermediate rhodamine hydrazide (90%).
The intermediate rhodamine lactohydrazide (0.944g) and 8-hydroxyquinoline-2-formaldehyde (0.346g) are taken and dissolved in 3ml ethanol, acetic acid (0.01ml) is added, and the mixture is heated under reflux at 80 ℃ for 6 h. After the reaction was completed, the solvent was removed by rotary evaporation. Then, the mixture is mixed with ethyl acetate: and (3) purifying the compound by column chromatography to obtain light yellow powder, namely the final probe (80%).
Nuclear magnetic and mass spectrum characterization:
1H NMR(400MHz,CDCl3)δ＝8.67(s,1H),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, the dye molecules can be dissolved in physiological saline, buffer solution or water-soluble organic solvent such as acetonitrile, dimethylsulfoxide, etc., and then added with appropriate buffer solution and other organic reagents for the test. The photophysical properties of the probe in pH 7.4 buffered aqueous solutions and various common organic reagents were studied and used in live cell imaging experiments, respectively. The living cell staining method is to incubate the cultured cells in a buffer solution containing probe molecules, remove the incubation solution after incubation for a certain time, and perform a confocal imaging experiment.
Probe and Pd2+Ultraviolet absorption, fluorescence emission and selectivity experiments of the reaction:
controlGroup (2): probe (50 μ M), PBS buffer (10mM), pH 7.4; experimental groups: probe (50 μ M), PBS buffer (10mM), pH 7.4, Pd2+(50. mu.M). The control group and the experimental group were incubated at 37 ℃ for 30min, and then the ultraviolet absorption and fluorescence emission spectra were measured with the maximum absorption as the single photon excitation wavelength, respectively, and the spectra are shown in fig. 1 and fig. 2. The abscissa is wavelength (nm), the ordinate of fig. 1 is fluorescence intensity, and the ordinate of fig. 2 is ultraviolet absorption intensity. Fig. 3 is a response situation of the probe to various metal ions, and the detected metal ions are sequentially as follows 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+In which Pd2+The concentration of (3) was 50. mu.M, and the concentration of other ions was 1 mM. As shown in fig. 3, only when Pd is present2+When present, there was a significant increase in fluorescence intensity with response times as high as 230. This indicates that the probe is paired with Pd as compared with other components in the body2+Has excellent selectivity, can be used in complex cellular and living biological environments to specifically detect Pd2+。
Cytotoxicity assay of probes:
HUVEC (human umbilical vein endothelial cells) are cultured by a high-sugar DMEM culture solution, 3- (4, 5-dimethyl thiagli-2) -2, 5-diphenyl tetranitrogen bromide (MTT) is added into the cells, and the toxicity of the probe on the cells is verified through the survival rate of the cells. Five concentrations of the probe were selected, 0.01. mu.M, 0.1. mu.M, 1. mu.M, 10. mu.M, 20. mu.M, and 50. mu.M, respectively. As a result, as shown in FIG. 4, the survival rate of the cells was 80% or more, and the toxicity of the probe to the cells was small. Thus, the toxicity of the probe is low, and the probe can be used for intracellular fluorescence detection.
Confocal fluorescence imaging experiment of probes on living cells:
HUVEC (human umbilical vein endothelial cells) are cultured by a DMEM culture solution with high sugar. Probe at 37 ℃: (5 μ M) were incubated for 30min, and then the cells were washed at least three times with Hepes buffer, washing off excess probe that did not enter the cells, to prevent interference with imaging. Then Pd was added to the glass plate2+And the concentration is 5 mu M, and the obtained product is placed under a microscope to carry out laser confocal fluorescence imaging. When the probe is taken every 5min, the result is shown in FIG. 5, and the brightness of the fluorescence is obviously enhanced along with the increase of the time, which indicates that the probe can detect Pd in the cells2+. The single photon excitation light is 514nm, and the red channel collects 530nm-600 nm.
EXAMPLE 2 Synthesis of fluorescent Probe
Raw materials of rhodamine B (0.8g) and hydrazine hydrate (0.8mL) are dissolved in 15mL of absolute ethyl alcohol and refluxed for 10 hours at 85 ℃. After the reaction was completed, the solvent was removed by rotary evaporation. Then, the mixture is mixed with ethyl acetate: and (3) using petroleum ether as an eluent, namely 1:1, and purifying the compound by column chromatography to obtain a white solid intermediate rhodamine hydrazide (60%).
The intermediate product rhodamine lactam (0.653g) and 8-hydroxyquinoline-2-formaldehyde (0.478g) are dissolved in 10ml ethanol, acetic acid (0.1ml) is added, and the mixture is heated under reflux at 70 ℃ for 4 hours. After the reaction was completed, the solvent was removed by rotary evaporation. Then, the mixture is mixed with ethyl acetate: and (3) purifying the compound by column chromatography to obtain light yellow powder, namely the final probe (40%).
EXAMPLE 3 Synthesis of fluorescent Probe
Raw materials of rhodamine B (1.2g) and hydrazine hydrate (0.4mL) are dissolved in 35mL of absolute ethyl alcohol and refluxed for 8 hours at 70 ℃. After the reaction was completed, the solvent was removed by rotary evaporation. Then, the mixture is mixed with ethyl acetate: and (3) using petroleum ether as an eluent, namely 1:1, and purifying the compound by column chromatography to obtain a white solid intermediate rhodamine hydrazide (76%).
The intermediate product rhodamine hydrazide (0.944g) and 8-hydroxyquinoline-2-formaldehyde (0.2g) are taken and dissolved in 5ml ethanol, acetic acid (0.001ml) is added, and the mixture is heated under reflux at 80 ℃ for 6 h. After the reaction was completed, the solvent was removed by rotary evaporation. Then, the mixture is mixed with ethyl acetate: and (3) purifying the compound by column chromatography to obtain light yellow powder, namely the final probe (55%) with petroleum ether as 1: 1.
It should be noted that the above examples are only used to illustrate the technical solutions of the present invention and not to limit them. Although the present invention has been described in detail with reference to the examples given, those skilled in the art can modify the technical solution of the present invention as needed or equivalent substitutions without departing from the spirit and scope of the technical solution of the present invention.
Claims (14)
1. The application of the fluorescent probe in detecting palladium ions is characterized in that the structural formula of the fluorescent probe is as follows:
2. use according to claim 1, characterized in that: the preparation method of the fluorescent probe comprises the following steps: the rhodamine B, hydrazine hydrate and 8-hydroxyquinoline-2-formaldehyde are taken as raw materials and are prepared by the following reaction route:
3. use according to claim 2, characterized in that: the solvent of the reaction system of rhodamine B and hydrazine hydrate is ethanol.
4. Use according to claim 3, characterized in that: the ethanol is absolute ethanol.
5. Use according to claim 2, characterized in that: the molar ratio of rhodamine B to hydrazine hydrate is 1: 5-10.
6. Use according to claim 2, characterized in that: the reaction temperature of rhodamine B and hydrazine hydrate is 75-85 ℃, and the reaction time is 8-12 h.
7. Use according to claim 2, characterized in that: the reaction temperature of the compound of the formula (II) and 8-hydroxyquinoline-2-formaldehyde is 75-85 ℃, and the reaction time is 3-8 h.
8. Use according to claim 7, characterized in that: the temperature for the reaction of the compound of the formula (II) and 8-hydroxyquinoline-2-carbaldehyde is 80 ℃, and the reaction time is 6 hours.
9. Use according to claim 2, characterized in that: the solvent for the reaction of the compound of formula (II) with 8-hydroxyquinoline-2-carbaldehyde is ethanol.
10. Use according to claim 9, characterized in that: the ethanol is absolute ethanol.
11. Use according to claim 2, characterized in that: the mass ratio of the compound of formula (II) to 8-hydroxyquinoline-2-carbaldehyde was 1: 1.
12. Use according to claim 2, characterized in that: the catalyst for the reaction of the compound of formula (II) with 8-hydroxyquinoline-2-carbaldehyde is acetic acid.
13. An optical sensor, characterized by: the optical sensor comprises a fluorescent probe for use according to claim 1.
14. The optical sensor of claim 13, wherein: the optical sensor is an optical sensor for detecting palladium ions.
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