CN108949159A - A kind of fluorescence probe detecting palladium ion and its synthetic method and application - Google Patents
A kind of fluorescence probe detecting palladium ion and its synthetic method and application Download PDFInfo
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract
The present invention provides a kind of fluorescence probes for detecting palladium ion:.Above-mentioned fluorescence probe can be applied to the quantitative detection of palladium ion concentration in solution or biological cell system.The fluorescence probe high sensitivity of detection palladium ion of the present invention, interference are small；When detection, can with the naked eye observe the variation of solution colour, along under ultraviolet lamp it has also been observed that fluorescence color change, be a kind of fluorescence probe with the sensing function that adds lustre to.The synthesis step of fluorescence probe of the present invention is few, and last handling process is relatively easy, has broad application prospects in biomolecule detection field.
Description
Technical field
The invention belongs to small organic molecule fluorescence probe fields, and in particular to one kind detects palladium ion based on rhodamine
Ratiometric fluorescent probe and its synthetic method.
Background technique
Heavy metal plays an important role in the science such as physics, chemistry and environment, wherein palladium metal is special due to its
Physicochemical properties be widely used in various industries.However, a large amount of of palladium use the residual that will cause its in the environment,
Cause Heavy-Metal-Contaminated Environments problem and people's health problem.Therefore, the detection of palladium ion is particularly important.It is confirmed through research,
It has an effect after in conjunction with the large biological molecules such as internal palladium ion and amino acid, protein, DNA and vitamin B6, upset cell is just
The processes such as normal signal transduction and physiological activity.Macroscopical Symptoms are to increase asthma, alopecia, miscarriage, nausea and other serious
Body illness probability.For the crowd of susceptible, can cause even if under by very low palladium ion invasion serious
Allergic reaction.Therefore constructing efficient, highly selective, high sensitivity and the method for short response time quantitative detection palladium is people's mesh
Preceding urgent problem to be solved.
Fluorescence probe has the advantages that good selectivity, high sensitivity, and detection limit small, easy to operate to equipment dependence are low,
Online lossless detection in situ in living body level may be implemented.Since early 1980s Tsien reports calcium ion fluorescence
After the work of probe, fluorescence probe is rapidly progressed, and is had become modern life science, disease early diagnosis and clinic and is controlled
The indispensable research tools in fields such as treatment.
Summary of the invention
Aiming at the problems existing in the prior art, the present invention provides a kind of ratio based on rhodamine detection palladium ion
Type fluorescence probe, the selective good and high sensitivity of the probe, fast response time.
It is a further object of the present invention to provide a kind of synthetic method of above-mentioned fluorescence probe, raw material is easy to get, synthesis step is simple
It is single.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of fluorescence probe detecting palladium ion, structural formula are as shown in the formula (I):
Formula (I).
A kind of synthetic method of above-mentioned fluorescence probe, comprising the following steps:
(1) under nitrogen protection, compound 1 and compound 2 are heated to reflux for 90 DEG C in methane sulfonic acid, isolate and purify to obtain compound
1-1:
；
(2) compound 1-1 and hydrazine hydrate are heated to reflux in ethanol to fully reacting, isolate and purify to obtain compound 1-2:
；
(3) in the presence of triethylamine, compound 1-2 and compound 3 are in DCM(methylene chloride) in normal-temperature reaction, isolate and purify
Compound 1-3:
；
(4) under nitrogen protection, in dehydrated alcohol, 80 DEG C of heating reflux reactions are isolated and purified for compound 1-3 and compound 4
To fluorescence probe:
。
In step (1), the reaction time is 16-24 hours.
In step (1), purification procedures are that reaction solution pours into ice water, filter, is dry, solid is with methanol: dichloromethane
Alkane=1:20(v/v) it is that leacheate crosses silica gel column chromatography.
In step (2), the reaction time is 3-5h.
In step (2), the standard of fully reacting is reaction solution redfree fluorescence under 365nm ultraviolet lamp.
In step (3), reaction time 20-60min.
In step (2) and (3), purification procedures are to remove the crude product of solvent with methanol: methylene chloride=1:30(v/
V) silica gel column chromatography is crossed for leacheate.
In step (4), the reaction time is 16-24 hours.
In step (4), purification procedures are to remove the crude product of solvent with methanol: methylene chloride=1:40(v/v) it is leaching
Washing lotion crosses silica gel column chromatography.
A kind of application of above-mentioned fluorescence probe palladium ion in detection organism.The fluorescence probe can be applied to solution or
The quantitative detection of palladium ion concentration in biological cell system.
Probe is broadly divided into two classes to the response mechanism of metal ion, and one kind is corrdination type, and one kind is response type.The present invention
Probe in carbonyl O be conjugated with palladium ion, lead to the chelation evoked open loop of rhodamine spirolactams, generate fluorescence hair
Penetrate red shift.Compound after the capable of emitting blue-fluorescence of script probe, probe and palladium ion coordination issues red fluorescence enhancing, performance
Blue-fluorescence for system after addition palladium ion weakens, red fluorescence enhancing:
。
The invention has the benefit that
The fluorescence probe high sensitivity of detection palladium ion of the present invention, interference are small；When detection, can with the naked eye it observe
To the variation of solution colour, along with it has also been observed that fluorescence color changes, being a kind of there is sensing of adding lustre under ultraviolet lamp
The fluorescence probe of function.The synthesis step of fluorescence probe of the present invention is few, and last handling process is relatively easy.It is visited based on the fluorescence
The specific and significant color change of needle, the probe can carry out real-time qualitative and quantitative detection, lead in biomolecule detection
Domain has broad application prospects.
Detailed description of the invention
Fig. 1 is fluorescence probe1H NMR spectra；
Fig. 2 is fluorescence spectrum of the fluorescence probe before and after palladium ion is added；
Fig. 3 is I of the fluorescence probe to various concentration palladium ion594/I472Fluorescence ratio；
Fig. 4 is selective histogram of the fluorescence probe to different ions and molecule；
Fig. 5 is the image of palladium ion in fluorescence probe detection cell.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not by the limit of following embodiments
System.
The synthesis of 1 fluorescence probe of embodiment
(1) synthesis of compound 1-1: Weigh Compound 1(500 mg, 1.59 mmol, 1 eq respectively), compound 2(282
Mg, 1.59 mmol, 1eq) it is dissolved in 3mL methane sulfonic acid, it stirs, is heated to reflux.90 DEG C of temperature, nitrogen protection is reacted 24 hours,
It is cooled to room temperature, reaction solution is poured into ice water, filter, vacuum drying, with methanol: methylene chloride=1:20(v/v) it is leacheate
It crosses column chromatography to be isolated and purified to obtain compound 1-1, weigh, yield 70%:
；
(2) synthesis of compound 1-2: compound 1-1(900 mg, 1.97 mmol, 1 eq) be dissolved in 10 mL ethyl alcohol, then by
2 mL of hydrazine hydrate is added dropwise in drop, is heated to reflux, and after detecting fully reacting with TCL plate, decompression is spin-dried for solvent and obtains crude product, and with first
Alcohol: methylene chloride=1:30(v/v) it is that leacheate is crossed silicagel column and separated, obtain compound 1-2.Weighing, yield 87%:
；
(3) compound 1-2(200 mg, 0.426 mg, 1 eq) synthesis of compound 1-3: is dissolved in 8 mL DCM(dichloromethanes
Alkane) in, then compound 3(194 mg, 0.638 mmol, 1.5 eq is added in stirring), 2 drop triethylamines are added dropwise in reaction, and room temperature is anti-
Answer half an hour, decompression is spin-dried for solvent, crude product is obtained, with methanol: methylene chloride=1:30(v/v) it is that leacheate crosses pillar layer separation
Compound 1-3 is obtained, yield 69%:
；
(4) synthesis of fluorescence probe: by compound 1-3(70 mg, 0.1 mmol, 1 eq) and compound 4(21 mg, 0.1
Mmol, 1 eq) it is dissolved in 3 mL dehydrated alcohols, nitrogen protection, 24 h of heating reflux reaction, after fully reacting, decompression is spin-dried for molten
Agent obtains crude product with methanol: methylene chloride=1:40(v/v) be that leacheate crosses pillar layer separation and obtains fluorescence probe:
。
2 fluorescence probe of embodiment with palladium ion concentration increase fluorogram variation
Palladium ion fluorescence probe prepared by Example 1 is dissolved in n,N-Dimethylformamide (DMF), and 1 mmol/L storage is made
Standby liquid.It is added in the centrifuge tube of 4 mL from 20 μ L are taken out in stock solution, the palladium ion of different equivalents (0-15 eq) is added
Standard solution is diluted to 2 mL with the solution that PBS buffer solution (0.1 mol/L, pH=7.5) and ethyl alcohol volume ratio are 1:1, into
Row fluorescent scanning (excitation wavelength is 400 nm).Fluorescence spectrum is as shown in Figure 2.From Figure 2 it can be seen that since palladium ion is added, fluorescence
Intensity fluorescence at 472 nm gradually weakens, and certain ratio is presented in the fluorescence enhancement at 594 nm, fluorescence intensity.With I594/
I472For ordinate, abscissa mapping is made with the palladium ion of 1-15 equivalent, as shown in Figure 3.As seen from Figure 3, dense with palladium ion
Degree increases, I594/I472It is linear related.Therefore, which is Ratio-type probe.
Selectivity of 3 fluorescence probe of embodiment to different molecular or ion
It is added in the centrifuge tube of 4 mL from 20 μ L are taken out in embodiment 2 in fluorescence probe stock solution, is separately added into equimolar
The competition molecular criteria solution of amount, one of them is added the palladium ion standard solution of equimolar amounts, detects solution after 10 min
Fluorescent emission intensity at 594 nm, as shown in figure 4, wherein 1-15 is respectively as follows: 1.Mg2+; 2.Fe3+; 3.Mn2+; 4.Cr2+;
5.S2O3 2-; 6.Ag2+; 7.Cd2+; 8.Cu2+; 9.Ni2+; 10.NH4 +; 11.Al3+; 12.Cys; 13.Co2+;
14.HSO3 -;15. blank.It can be found that the fluorescence of other ion-pair compounds has little effect, and palladium ion solution plus
Enter to make the fluorescence significant changes of compound.The probe can resist the interference of many kinds of substance, high specificity.
Visual retrieval of 4 fluorescence probe of embodiment to palladium ion
From taking 20 μ L to be added in the sample cell of 24 mL in embodiment 2 in fluorescence probe stock solution respectively, then respectively plus
Enter the palladium ion standard solution of 10 moles, palladium ion can make the buffering of the PBS:EtOH volume ratio 1:1 of fluorescence probe molten
Apparent color change occurs for liquor, and solution colour becomes orange red from faint yellow.Above-mentioned sample cell is seen in the UV lamp
Survey: palladium ion can make probe issue bright fluorescent red-orange, and explanation is that this probe is a kind of with the glimmering of the sensing function that adds lustre to
Light probe.
5 fluorescence probe of embodiment is to intracellular palladium ion fluorescence imaging
Fluorescence imaging will be carried out to intracellular palladium ion in probe application of the present invention and HeLa cell specific steps are as follows: point
10 μM of probes are not added to after cultivating 30 min in carbon dioxide incubator in the culture solution that 2 parts are given birth to HeLa cell, are used
Culture solution rinses 3 times, and then a palladium ion aqueous solution for being added 10 μM, another addition equivalent amount of water after being incubated for 10min, are used
Culture solution rinses 3 times, is imaged that (blue channel is excited using 405nm, and red channel obtains image point with Laser Scanning Confocal Microscope
Not Shi Yong 561nm excite):
(1) light field is imaged, as shown in Fig. 5 a and e: it can be seen that the rough profile of cell；
(2) fluorescent emission is detected in blue channel, as shown in Fig. 5 b and f: blue-fluorescence weakens after palladium ion is added；
(3) in red Air conduct measurement fluorescent emission, as shown in Fig. 5 c and g: the system redfree fluorescence of palladium ion not being added, works as addition
Feux rouges enhances after palladium ion；
Illustrate that this fluorescence probe can carry out fluorescence imaging to intracellular palladium ion.
Claims (6)
1. a kind of fluorescence probe for detecting palladium ion, structural formula are as shown in the formula (I):
Formula (I).
2. a kind of synthetic method of fluorescence probe as described in claim 1, which comprises the following steps:
(1) under nitrogen protection, compound 1 and compound 2 are heated to reflux for 90 DEG C in methane sulfonic acid, isolate and purify to obtain compound
1-1:
；
(2) compound 1-1 and hydrazine hydrate are heated to reflux in ethanol to fully reacting, isolate and purify to obtain compound 1-2:
；
(3) in the presence of triethylamine, compound 1-2 and compound 3 are in DCM(methylene chloride) in normal-temperature reaction, isolate and purify
Compound 1-3:
；
(4) under nitrogen protection, in dehydrated alcohol, 80 DEG C of heating reflux reactions are isolated and purified for compound 1-3 and compound 4
To fluorescence probe:
。
3. synthetic method according to claim 2, which is characterized in that in step (1), the reaction time is 16-24 hours；Step
Suddenly in (2), the reaction time is 3-5h；In step (3), reaction time 20-60min；In step (4), the reaction time is
16-24 hours.
4. synthetic method according to claim 2, which is characterized in that in step (2), the standard of fully reacting is reaction solution
The redfree fluorescence under 365nm ultraviolet lamp.
5. synthetic method according to claim 2, which is characterized in that in step (1), purification procedures are fallen for reaction solution
Enter in ice water, filter, is dry, solid is with methanol: methylene chloride=1:20(v/v) it is that leacheate crosses silica gel column chromatography；
In step (2) and (3), purification procedures are to remove the crude product of solvent with methanol: methylene chloride=1:30(v/v) be
Leacheate crosses silica gel column chromatography；
In step (4), purification procedures are to remove the crude product of solvent with methanol: methylene chloride=1:40(v/v) it is leacheate
Cross silica gel column chromatography.
6. a kind of application of fluorescence probe as described in claim 1 palladium ion in detection organism.
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|---|---|---|---|
| CN201811075069.5A CN108949159B (en) | 2018-09-14 | 2018-09-14 | Fluorescent probe for detecting palladium ions and synthetic method and application thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394977A (en) * | 2021-11-24 | 2022-04-26 | 徐州医科大学 | Fluorescent probe for respectively and simultaneously detecting hydrogen sulfide and carbon monoxide and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777768A (en) * | 2016-04-26 | 2016-07-20 | 济南大学 | Fluorescent probe for detecting hydrogen sulfide and hypochlorous acid in cell lysosomes simultaneously or respectively as well as preparation method and application of fluorescent probe |
| CN106632363A (en) * | 2016-11-07 | 2017-05-10 | 山东大学 | Mitochondrial targeted ratio type hypochlorous acid fluorescence probe and application thereof |
-
2018
- 2018-09-14 CN CN201811075069.5A patent/CN108949159B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777768A (en) * | 2016-04-26 | 2016-07-20 | 济南大学 | Fluorescent probe for detecting hydrogen sulfide and hypochlorous acid in cell lysosomes simultaneously or respectively as well as preparation method and application of fluorescent probe |
| CN106632363A (en) * | 2016-11-07 | 2017-05-10 | 山东大学 | Mitochondrial targeted ratio type hypochlorous acid fluorescence probe and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| JUNLI ZHANG 等: "A highly selective fluorescent probe for the detection of palladium(II) ion in cells and aqueous media", 《MICROCHIM ACTA》 * |
| XIANG HAN 等: "Two ratiometric fluorescent probes for hypochlorous acid detection and imaging in living cells", 《TALANTA》 * |
| YAN-RU ZHANG 等: "A ratiometric fluorescent probe for sensing HOCl based on a coumarin–rhodamine dyad", 《CHEM. COMMUN.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394977A (en) * | 2021-11-24 | 2022-04-26 | 徐州医科大学 | Fluorescent probe for respectively and simultaneously detecting hydrogen sulfide and carbon monoxide and preparation method and application thereof |
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