CN105223176A - One utilizes Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound to detect the method for copper ion as fluorescence probe - Google Patents
One utilizes Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound to detect the method for copper ion as fluorescence probe Download PDFInfo
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- CN105223176A CN105223176A CN201510641160.9A CN201510641160A CN105223176A CN 105223176 A CN105223176 A CN 105223176A CN 201510641160 A CN201510641160 A CN 201510641160A CN 105223176 A CN105223176 A CN 105223176A
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- copper ion
- anthraquinone
- dihydroxy
- nitrae
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Abstract
The invention discloses one utilizes Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound to detect the method for copper ion as fluorescence probe, belongs to light technical field of analysis and detection.The present invention has investigated 1 by experiment, 4-dihydroxy-9, the recognition reaction of 10-anthraquinone contracting salicylyl hydrazine and 15 metal ion species, find that probe molecule EXZ has good Selective recognition effect to copper ion, and the fluorescence identifying that the dissolubility of hydroxyl and water makes probe molecule can realize copper ion in aqueous, and be issued to good result in physiological pH condition, the method is green, single-minded to copper ion selectivity, sensitivity is also higher, and fluorescent quenching effect is played within the shorter reaction time, the copper ion that this probe molecule can be successfully applied in living biological cell detects.
Description
Technical field
The invention belongs to light technical field of analysis and detection, be specifically related to one and utilize Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound to detect the method for copper ion as fluorescence probe.
Background technology
Copper is the trace element of needed by human, is distributed widely in biological tissue, and major part exists with organic double compound, and be much metalloprotein, play function with the form of enzyme, these enzymes are vital for life process.Research shows, copper lacks can cause various disease, but also can cause the impact of unfavorable health during copper excessive concentration, as the infringement of cytotoxicity, liver and kidney and nerve degenerative diseases etc.In addition, copper is also one of heavy metal contaminants common in environment.Therefore, the detection method tool setting up accurate and sensitive copper ion is of great significance.The mensuration of current copper ion adopts electrochemical process, extraction spectrophotometric method, Resonance scattering, fluorescence method, atomic absorption spectrography (AAS) and inductively coupled plasma mass spectrometry etc. more.
Anthraquinone analog compound is the compounds that in various natural quinones, quantity is maximum.Long ago, anthraquinone is used as natural dye, finds that they have many medical values and come into one's own afterwards.Such as, they have the effect of anti-inflammation, antiviral, anticancer, hepatic cholagogic, improving eyesight, short intelligence, anti-ageing, anti-mutagenesis and antiultraviolet.In addition, the effects such as anthraquinone analog compound also has that hemostasis is invigorated blood circulation, short sleep effect, effect for reducing blood fat and increase immunologic function, but not about anthraquinone analog compound as fluorescence probe for detecting the relevant report of copper ion.In recent years along with the appearance of laser confocal microscope scanning technique, the research for ion fluorescence chemical sensor provided more favourable means.
Summary of the invention
The technical matters that the present invention solves there is provided that a kind of selectivity is single-minded, sensitivity is higher and Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound that utilizes that the response time is shorter detects the method for copper ion as fluorescence probe.
The present invention adopts following technical scheme for solving the problems of the technologies described above, and one utilizes Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound to detect the method for copper ion as fluorescence probe, it is characterized in that concrete steps are:
(1) in the color comparison tube of multiple 10mL, add 1mL phosphate buffered solution respectively, then to add 0.01mL volumetric molar concentration be respectively 1.0 × 10
-3the DMF-H of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone contracting salicylyl hydrazine of mol/L
2o solution, then adds the copper ion solution of variable concentrations respectively, is settled to 10mL with deionized water, shakes up the fluorescence intensity of each solution of rear mensuration, determines the quantitative relationship of fluorescence intensity and copper ion concentration and production standard curve;
(2) in the color comparison tube of 10mL, add 1mL phosphate buffered solution, then to add 0.01mL volumetric molar concentration be 1.0 × 10
-3the DMF-H of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone contracting salicylyl hydrazine of mol/L
2o solution, then adds solution to be measured, is settled to 10mL with deionized water, shakes up the fluorescence intensity of rear mensuration solution to be measured, determines the concentration of copper ion in solution to be measured according to the quantitative relationship of fluorescence intensity and copper ion concentration.
Further restriction, described phosphate buffered solution is the Na of pH=7.2
2hPO
4-NaH
2pO
4system.
Further restriction, described DMF-H
2dMF and H in O solvent
2the volume ratio of O is 1:99.
Further restriction, shakes up the fluorescence intensity that immixture at least measures solution after 25min.
Further restriction, described fluorescent strength determining condition, for exciting slit 10nm, launches slit 10nm, excitation wavelength 498nm, emission wavelength 575nm.
The structural formula of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound of the present invention is:
。
The present invention has investigated 1 by experiment, 4-dihydroxy-9, the recognition reaction of 10-anthraquinone contracting salicylyl hydrazine and 15 metal ion species, find that probe molecule EXZ has good Selective recognition effect to copper ion, and the fluorescence identifying that the dissolubility of hydroxyl and water makes probe molecule can realize copper ion in aqueous, and be issued to good result in physiological pH condition, the method is green, single-minded to copper ion selectivity, sensitivity is also higher, and fluorescent quenching effect is played within the shorter reaction time, the copper ion that this probe molecule can be successfully applied in living biological cell detects.
Accompanying drawing explanation
Fig. 1 is the change curve of fluorescence intensity △ F with mixed system pH that the embodiment of the present invention 1 blank sample adds mixed system after copper ion;
Fig. 2 is the change curve of fluorescence intensity △ F with the immixture time that the embodiment of the present invention 1 blank sample adds mixed system after copper ion;
Fig. 3 is the fluorescent absorption spectrogram of the copper ion solution of variable concentrations in the embodiment of the present invention 2;
Fig. 4 is the linear regression curves of the fluorescent absorption intensity of the copper ion solution of variable concentrations in the embodiment of the present invention 2;
Fig. 5 is the fluorescent absorption spectrogram that in the embodiment of the present invention 3, different metal ion adds probe molecule standard configuration solution;
Fig. 6 is the impact on mixed system fluorescence intensity when different metal ion and copper ion coexist in the embodiment of the present invention 4;
Fig. 7 is the change curve of changing value with copper ion and EXZ proportioning of fluorescent quenching in the embodiment of the present invention 5;
Fig. 8 is the laser confocal microscope photo of mdck cell in the embodiment of the present invention 6;
Fig. 9 is that in the embodiment of the present invention 6, mdck cell adds the laser confocal microscope photo after probe molecule EXZ and copper ion.
Embodiment
Be described in further details foregoing of the present invention by the following examples, but this should be interpreted as that the scope of the above-mentioned theme of the present invention is only limitted to following embodiment, all technology realized based on foregoing of the present invention all belong to scope of the present invention.
Embodiment 1
The optimization of experiment condition
1, the selection of probe molecule concentration
The concentration increasing probe molecule can increase absorbance and fluorescence intensity, is beneficial to improve to measure the selectivity of metallic ion and the range of linearity of typical curve.But when concentration is too high, blank fluorescence intensity also can increase along with the increase of probe molecule concentration, and concentration is too low, and be difficult to after adding ion cancellation detect fluorescent absorption peak, consider the sensitivity and linear measurement range of method, the concentration of probe is chosen as 1.0 × 10
-5mol/L.
2, the selection of buffer solution
In the color comparison tube of 10mL, add 1mL phosphate buffered solution, then to add 0.01mL volumetric molar concentration be 1.0 × 10
-3the DMF-H of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone contracting salicylyl hydrazine of mol/L
2o solution, is then settled to 10mL with deionized water and is mixed with blank sample.
In different buffer systems as HAc-NaAc, Na
2hPO
4-NaH
2pO
4, NaHCO
3-Na
2cO
3the pH value that lower adjustment is different, investigate the fluorescence spectrum of blank sample, fluorescent strength determining condition is for exciting slit 10nm, launch slit 10nm, excitation wavelength 498nm, find the increase along with pH value, the intensity of the fluorescence emission peak of probe molecule EXZ increased before this gradually, then declined gradually after 7.6.After adding copper ion respectively in the buffer solution of different pH value, after pH to 8.0, fluorescence intensity drops to 50 rapidly, continues to increase alkalescence and then can't detect fluorescence intensity.The value △ F=F that fluorescence intensity reduces
0-F(F
0the fluorescence intensity of mixed system during for not adding copper ion, F is the fluorescence intensity adding mixed system after copper ion) with the situation of change of mixed system pH as Fig. 1, as seen from the figure, the fluorescence intensity of mixed system is more stable within the scope of 5.0-7.6, consider and will investigate the application of probe molecule in biological cell, so the Na of pH and pH=7.2 of experimental selection physiological condition
2hPO
4-NaH
2pO
4system is as the buffer solution measuring medium.
3, the selection of solvent
This experiment is wished to realize at the recognition reaction of intracellular Fluorescence probe to ion, does not select pure organic solvent when therefore investigating, but have selected water solution system contrast, as DMF-H
2o, THF-H
2o and ethanol-H
2o, experimental result finds at DMF-H
2o(DMF and H
2the volume ratio of O is 1:99) in can the fluorescence intensity of effective detector probe molecule, and the easy stripping of compd E XZ in other water solution system, so experimental selection DMF-H
2o system.
4, the selection of immixture time
Experimental result shows, the fluorescence of blank sample slowly reduces in time, but after adding copper ion, its fluorescence intensity cancellation is rapid, namely tend towards stability after 15min, fluorescence intensity change very little (as Fig. 2) after 25min, therefore select test to measure after adding reagent immixture 25min.
Embodiment 2
In the color comparison tube of multiple 10mL, add 1mL phosphate buffered solution respectively, then to add 0.01mL volumetric molar concentration be respectively 1.0 × 10
-3the DMF-H of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone contracting salicylyl hydrazine of mol/L
2o(DMF and H
2the volume ratio of O is 1:99) solution, then add the copper ion solution ([Cu of variable concentrations respectively
2+] (× 10
-6mol/L): 2, 2.5, 3.0, 3.5, 4, 4.5, 5, 5.5, 6, 8, 10), 10mL is settled to deionized water, the fluorescence intensity of each solution is measured after shaking up immixture 25min, fluorescent strength determining condition is for exciting slit 10nm, launch slit 10nm, excitation wavelength 498nm, emission wavelength 575nm, in mensuration process, solution becomes blue purple by pale red, Fig. 3 is the fluorescent absorption spectrogram of the copper ion solution of variable concentrations, as can be seen from the figure the fluorescent absorption peak red shift at 498nm place is at the new fluorescent absorption peak of 508nm place appearance one, in fluorescent absorption spectrum, fluorescent absorption peak, 575nm place reduces gradually with the increase of copper ion concentration simultaneously, determine the quantitative relationship of fluorescence intensity and copper ion concentration and production standard curve (as Fig. 4), wherein detectability (LOD) is by equation LOD=KS
o/ S provides, K=3, S
ofor the standard deviation (n=6) of blank determination, S is the sensitivity of working curve, and Relevant Analysis parameter lists in table 1.Have good linear relationship and higher sensitivity for analysis by table 1 and Fig. 4 this detection method known, the lowest detection lower limit of this detection method is 5 × 10
-7mol/L.
The analytical parameters of table 1 variable concentrations copper ion
Embodiment 3
In the color comparison tube of multiple 10mL, add 1mL phosphate buffered solution respectively, then to add 0.01mL volumetric molar concentration be respectively 1.0 × 10
-3the DMF-H of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone contracting salicylyl hydrazine of mol/L
2o solution, then adds volumetric molar concentration respectively and is 1.0 × 10
-3mol/L metallic ion standard configuration solution, is settled to 10mL with deionized water, shakes up the fluorescence intensity (as Fig. 5) of each solution of rear mensuration, and result shows, when each metal ion species of same concentration is respectively with probe molecule EXZ effect, to only have Cu
2+add and mixed system reduced in 575nm place fluorescence intensity fluorescent quenching occurs, and when other metallic ion and probe molecule effect, be compared to blank sample, its fluorescence intensity does not have significant change.Show that the identification of probe molecule EXZ to copper ion has good selectivity.
Embodiment 4
The present embodiment investigates probe molecule EXZ to the selectivity of copper ion identification, the impact (as Fig. 6) on mixed system fluorescence intensity when coexisting on each metal ion species of existence common in other 14 kinds of water samples and copper ion.In figure 6, the component of Cu is labeled as only containing 1.0 × 10
-5the fluorescence intensity of mixed system during mol/L copper ion, all the other are the fluorescence intensity of other metallic ion of 10 μMs of copper ions and various variable concentrations multiple mixed system when coexisting, and concentration of metal ions is that the multiple of copper ion concentration is as follows respectively: Na from left to right
+(100 times), K
+(100 times), Mg
2+(100 times), Ni
2+(100 times), Hg
2+(100 times), Co
2+(50 times), Ca
2+(50 times), Ba
2+(20 times), Mn
2+(20 times), Zn
2+(20 times), Pb
2+(10 times), Cd
2+(10 times), Fe
2+(10 times) and Ag
+(5 times).As seen from the figure, EXZ is subject to Ag to the response of copper ion except omiting
+impact outside, substantially not by the interference of other coexistent metallic ion, there is good selectivity.
Embodiment 5
Acylhydrazone group easily and heavy metal ion generation mating reaction, make the fluorescence generation cancellation of probe molecule EXZ, nitrogen-atoms easily and copper ion coordination, C=N and C=O double bond is had in acylhydrazone group, and hydroxy-anthraquione and acylhydrazone group form reasonable conjugated system, proton on hydroxyl can at intramolecular transfer, and probe molecule is generation fluorescence emission peak under the exciting of light.And after mixed system adds copper ion, with the nitrogen-atoms complex coordination on C=N key, oxygen atom and nitrogen-atoms and copper ion have certain complexing, have blocked the transmission of proton in conjugated system, the fluorescence intensity of anthraquinone analog compound is weakened, fluorescent quenching occurs.
Cu
2+with the complexing of EXZ
As can be seen from experimental data we, when adding copper ion concentration and probe molecule EXZ concentration reaches 1:1 gradually, the changing value of fluorescent quenching reaches stable (as Fig. 7).
Embodiment 6
Probe molecule EXZ is used for animal renal epithelial cell MDCK(normal cell by the present embodiment) in the detection of copper ion, Fig. 8 is the laser confocal microscope photo of mdck cell, wherein A is details in a play not acted out on stage, but told through dialogues mdck cell fluorogram, B is bright field mdck cell fluorogram, self fluorescence is not had from the known mdck cell of laser confocal microscope photo, after probe molecule EXZ enters cell, instrument can detect the fluorescence of cell, and the fluorescence of cell is weakened by the rapid cancellation of copper ion after adding bivalent cupric ion, confocal laser microscope clearly can capture this process (as Fig. 9, wherein A is the laser confocal microscope photo adding probe molecule EXZ, B is the laser confocal microscope photo continued after adding copper ion).
Embodiment 7
The synthesis of probe molecule EXZ
The synthesis of 1, Isosorbide-5-Nitrae-dihydroxy-2-formoxyl-9,10-anthraquinone
；
2, the synthesis of fragrant hydrazides is replaced
；
3, the green syt of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound
。
Embodiment above describes ultimate principle of the present invention, principal character and advantage; the technician of the industry should understand; the present invention is not restricted to the described embodiments; what describe in above-described embodiment and instructions just illustrates principle of the present invention; under the scope not departing from the principle of the invention; the present invention also has various changes and modifications, and these changes and improvements all fall in the scope of protection of the invention.
Claims (6)
1. one kind utilizes Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound to detect the method for copper ion as fluorescence probe, it is characterized in that concrete steps are:
(1) in the color comparison tube of multiple 10mL, add 1mL phosphate buffered solution respectively, then to add 0.01mL volumetric molar concentration be respectively 1.0 × 10
-3the DMF-H of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone contracting salicylyl hydrazine of mol/L
2o solution, then adds the copper ion solution of variable concentrations respectively, is settled to 10mL with deionized water, shakes up the fluorescence intensity of each solution of rear mensuration, determines the quantitative relationship of fluorescence intensity and copper ion concentration and production standard curve;
(2) in the color comparison tube of 10mL, add 1mL phosphate buffered solution, then to add 0.01mL volumetric molar concentration be 1.0 × 10
-3the DMF-H of Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone contracting salicylyl hydrazine of mol/L
2o solution, then adds solution to be measured, is settled to 10mL with deionized water, shakes up the fluorescence intensity of rear mensuration solution to be measured, determines the concentration of copper ion in solution to be measured according to the quantitative relationship of fluorescence intensity and copper ion concentration.
2. Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound that utilizes according to claim 1 detects the method for copper ion as fluorescence probe, it is characterized in that: described phosphate buffered solution is the Na of pH=7.2
2hPO
4-NaH
2pO
4system.
3. Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound that utilizes according to claim 1 detects the method for copper ion as fluorescence probe, it is characterized in that: described DMF-H
2dMF and H in O solvent
2the volume ratio of O is 1:99.
4. Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound that utilizes according to claim 1 detects the method for copper ion as fluorescence probe, it is characterized in that: shake up the fluorescence intensity that immixture at least measures solution after 25min.
5. according to claim 1ly utilize 1,4-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound detects the method for copper ion as fluorescence probe, it is characterized in that: described fluorescent strength determining condition is for exciting slit 10nm, launch slit 10nm, excitation wavelength 498nm, emission wavelength 575nm.
6. Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound that utilizes according to claim 1 detects the method for copper ion as fluorescence probe, it is characterized in that: the structural formula of described Isosorbide-5-Nitrae-dihydroxy-9,10-anthraquinone shrink poplar hydrazide compound is:
。
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| CN106220531A (en) * | 2016-07-27 | 2016-12-14 | 黄淮学院 | For identifying the fluorescent probe of copper ion, membrane material, preparation method and application |
| CN106525782A (en) * | 2016-10-10 | 2017-03-22 | 河南师范大学 | Application of 3, 4-bis(3-indole)-3-pyrroline-2, 5-dione-1-(2-hydroxyphenyl)hydrazone as fluorescent probe in copper ion detection |
| CN106645047A (en) * | 2016-09-20 | 2017-05-10 | 西安交通大学 | Method for detecting copper ion complex in organic solvent by polymer with fluorescence characteristic |
| CN107655868A (en) * | 2017-08-30 | 2018-02-02 | 河南师范大学 | A kind of preparation method of water-soluble gold nano cluster and its application that copper trace in Chinese medicine is determined as fluorescence probe |
| CN109900664A (en) * | 2019-02-19 | 2019-06-18 | 济南大学 | A method of copper ion is detected using non-traditional fluorescent small molecule malonyl hydrazine |
| CN111579542A (en) * | 2019-12-20 | 2020-08-25 | 南京晓庄学院 | Application of derivative |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106220531A (en) * | 2016-07-27 | 2016-12-14 | 黄淮学院 | For identifying the fluorescent probe of copper ion, membrane material, preparation method and application |
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| CN106645047A (en) * | 2016-09-20 | 2017-05-10 | 西安交通大学 | Method for detecting copper ion complex in organic solvent by polymer with fluorescence characteristic |
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| CN106525782A (en) * | 2016-10-10 | 2017-03-22 | 河南师范大学 | Application of 3, 4-bis(3-indole)-3-pyrroline-2, 5-dione-1-(2-hydroxyphenyl)hydrazone as fluorescent probe in copper ion detection |
| CN106525782B (en) * | 2016-10-10 | 2019-02-12 | 河南师范大学 | 3,4- bis- (3- indoles) -3- pyrrolin -2,5- diketone -1-(2- hydroxy phenyl) application of the hydrazone as fluorescence probe in detection copper ion |
| CN107655868A (en) * | 2017-08-30 | 2018-02-02 | 河南师范大学 | A kind of preparation method of water-soluble gold nano cluster and its application that copper trace in Chinese medicine is determined as fluorescence probe |
| CN109900664A (en) * | 2019-02-19 | 2019-06-18 | 济南大学 | A method of copper ion is detected using non-traditional fluorescent small molecule malonyl hydrazine |
| CN111579542A (en) * | 2019-12-20 | 2020-08-25 | 南京晓庄学院 | Application of derivative |
| CN111704557A (en) * | 2019-12-20 | 2020-09-25 | 南京晓庄学院 | Derivative |
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| CN111718276B (en) * | 2019-12-20 | 2021-03-30 | 南京晓庄学院 | Synthesis method of derivative |
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Application publication date: 20160106 |