CN115925784B - Dansyl copper ion fluorescent probe, preparation method and application thereof - Google Patents
Dansyl copper ion fluorescent probe, preparation method and application thereof Download PDFInfo
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- CN115925784B CN115925784B CN202211486567.5A CN202211486567A CN115925784B CN 115925784 B CN115925784 B CN 115925784B CN 202211486567 A CN202211486567 A CN 202211486567A CN 115925784 B CN115925784 B CN 115925784B
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Abstract
The invention provides a dansyl copper ion fluorescent probe, a preparation method and application thereof, and belongs to the technical field of cationic fluorescent probe detection. The chemical structural formula of the dansyl copper ion fluorescent probe provided by the invention is shown as formula I, and the dansyl copper ion fluorescent probe can coordinate with copper ions to cause fluorescence quenching, and can be completely used for detecting the concentration of copper ions; the combination ratio of the probe and copper ions is 1:1, and the applicable pH range is 6-12; the probe in the invention detects copper ions in the linear range of 0-25 mu M, the detection limit is 1.52 mu M, and the probe has higher sensitivity; the probe has higher selectivity and higher response speed to copper ions; the concentration of copper ions detected by the probe is very close to the concentration of copper ions actually added, the relative average deviation is about 5% or less, and the concentration of copper ions in an actual water sample can be effectively detected.
Description
Technical Field
The invention belongs to the technical field of detection of cationic fluorescent probes, and particularly relates to a dansyl copper ion fluorescent probe, a preparation method and application thereof.
Background
Copper ion (Cu) 2+ ) Is the third abundant transition metal of human body, and plays an important role in various biological processes such as cell growth, ion transport, enzyme activity and the like. In addition, copper ions play an important role in plant growth and are widely present in soil and water environments. Abnormal copper ion concentrations, including too high or too low, can be detrimental to human health or environmental safety. The national standard of China (GB 5749-2006) sets the threshold for copper ions in drinking water to 1.0mg/mL, i.e., 15.7. Mu.M, and the U.S. Environmental Protection Agency (EPA) sets the threshold to 20. Mu.M. The accurate determination of copper ion concentration is of great importance to human health and environmental protection.
Compared with other methods, the fluorescence method for detecting copper ions has great advantages. The interaction occurs after the fluorescent probe encounters copper ions, the luminescence color or the luminescence intensity of the fluorescent probe is obviously changed, and the concentration of the copper ions can be quantitatively detected. The fluorescent probe is used for detection, and has the advantages of high sensitivity, quick response, simple process, low cost and the like. At present, a few fluorescent probes for detecting copper ions are reported, but most of the fluorescent probes have the problems of poor water solubility, organic solvent requirement, complex synthesis and the like. Therefore, the development of the copper ion fluorescent probe with good water solubility, simple synthesis, good selectivity and high sensitivity has important significance.
Disclosure of Invention
In order to solve the technical problems, the invention provides a dansyl copper ion fluorescent probe, a preparation method and application thereof. The chemical structural formula of the dansyl copper ion fluorescent probe provided by the invention is shown as formula I, and the dansyl copper ion fluorescent probe can coordinate with copper ions to cause fluorescence quenching, and can be completely used for detecting the concentration of copper ions; the combination ratio of the probe and copper ions is 1:1, and the applicable pH range is 6-12; the probe in the invention detects copper ions in the linear range of 0-25 mu M, the detection limit is 1.52 mu M, and the probe has higher sensitivity; the probe has higher selectivity and higher response speed to copper ions; the concentration of copper ions detected by the probe is very close to the concentration of copper ions actually added, the relative average deviation is about 5% or less, and the concentration of copper ions in an actual water sample can be effectively detected.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the invention provides a dansyl copper ion fluorescent probe, the chemical structural formula of which is shown as formula I:
the invention also provides a preparation method of the dansyl copper ion fluorescent probe, which comprises the following steps:
step one: adding the compound 1 into ethanol, cooling, adding thionyl chloride, stirring, steaming to obtain concentrated solution, adding diethyl ether, and recrystallizing to obtain white solid compound 2;
step two: dissolving a compound 2, triethylamine (TDA) and 4-Dimethylaminopyridine (DMAP) in N, N-Dimethylformamide (DMF) and cooling, then adding a Dimethylformamide (DMF) solution of dansyl chloride into the mixture, stirring the mixture, pouring the reaction solution into ethyl acetate and extracting the mixture by water, and finally taking an upper organic phase for rotary evaporation to obtain a green solid compound 3;
step three: dissolving the compound 3 in ethanol, adding a sodium hydroxide aqueous solution, stirring, rotationally evaporating and concentrating, adding dilute hydrochloric acid to separate out a precipitate, and finally recrystallizing with ethanol/diethyl ether to obtain a yellow solid compound 4, namely the dansyl copper ion fluorescent probe;
the chemical structural formula of the compound 1 is shown as a formula II:
the chemical structural formula of the compound 2 is shown as a formula III:
the chemical structural formula of the compound 3 is shown as a formula IV:
preferably, the cooling temperature in the first step is-8 to-12 ℃; SOCl 2 The adding mode is slow dripping; the stirring mode is that stirring is firstly carried out for 1-3 h at room temperature, then reflux stirring is carried out for 7-9 h, and then stirring is continued for 9-11 h at room temperature.
Preferably, the cooling temperature in the first step is-10 ℃; the stirring mode is that stirring is carried out for 2 hours at room temperature, then reflux stirring is carried out for 8 hours, and stirring is continued for 10 hours at room temperature.
Preferably, the cooling temperature in the second step is-8 to-12 ℃; the stirring mode is that stirring is carried out at low temperature firstly and then at high temperature, wherein the temperature of the stirring at low temperature is between-8 ℃ and-12 ℃ for 1.5 to 2.5 hours, the temperature of the stirring at high temperature is between 50 and 70 ℃ for 35 to 45 hours; the number of times of water extraction is 1-4.
Preferably, the cooling temperature in the second step is-10 ℃; stirring at low temperature of-10deg.C for 2 hr; the high-temperature stirring temperature is 60 ℃ and the high-temperature stirring time is 40h; the number of water extractions was 3.
Preferably, the stirring mode in the third step is room temperature stirring, and the stirring time is 22-26 hours; the dilute hydrochloric acid is slowly added dropwise, and the pH value is 2-3.
Preferably, the stirring time in the third step is 24 hours.
Preferably, the preparation method further comprises a process of preparing the sodium salt of the compound 4 by mixing an ethanol solution of the compound 4 with an aqueous solution of sodium hydroxide.
The invention also provides an application of the dansyl copper ion fluorescent probe or the preparation method in copper ion detection.
Compared with the prior art, the invention has the following beneficial effects:
(1) The probe in the invention can coordinate with copper ions through nuclear magnetic hydrogen spectrum and mass spectrum characterization, so that fluorescence quenching is caused, and the concentration of the copper ions can be detected by utilizing the change of fluorescence intensity;
(2) The combination ratio of the probe molecules and copper ions is 1:1, and the applicable pH range is 6-12;
(3) The linear range of the probe molecule for detecting copper ions is 0-25 mu M, the detection limit is 1.52 mu M, and the detection limit is lower than the maximum copper ion concentration specified by Chinese national standards and the American environmental protection agency, which shows that the fluorescent probe concentration has higher sensitivity;
(4) The probe molecules in the invention have higher selectivity on the response to copper ions without being interfered by other metal ions;
(5) The fluorescence intensity of the probe molecule at 558nm is rapidly reduced after the probe molecule is combined with copper ions, and the intensity is basically unchanged after 1min, which indicates that the probe has high response speed to the copper ions and has the capability of rapidly responding to the copper ions;
(6) The concentration of copper ions detected by using the probe molecules in the invention is very close to the concentration of copper ions actually added, and the relative average deviation is about 5% or less, which indicates that the fluorescent probe in the invention can effectively detect the concentration of copper ions in an actual water sample.
Drawings
FIG. 1 shows a nuclear magnetic resonance hydrogen spectrum (600M, D) of a probe molecule in heavy water according to example 1 of the present invention 2 O)；
FIG. 2 shows the change in fluorescence intensity (excitation wavelength: 337 nm) of a probe molecule (40. Mu.M) before and after addition of copper ions (40. Mu.M) in HEPES buffer solution (10 mM, pH 7.4) in example 2 of the present invention;
FIG. 3 is a graph showing fluorescence intensity when the ratio is changed in HEPES buffer solution (10 mM, pH 7.4) in example 2 according to the present invention, wherein the total concentration of probe molecules and copper ions is 40. Mu.M: i 0 For the fluorescence intensity at 558nm without copper ion, I is the fluorescence intensity at different ratios, x Cu The molar ratio of copper ions;
FIG. 4 is a graph showing the maximum emission intensity change of a probe molecule (40. Mu.M) solution before and after copper ion (40. Mu.M) addition at different pH values in example 2 of the present invention;
FIG. 5 is a graph showing the change in fluorescence intensity of a probe molecule (40. Mu.M) at 558nm when copper ions were contained in different concentrations in example 3 of the present invention;
FIG. 6 shows the change in fluorescence of a copper ion (100. Mu.M) quenching probe molecule (40. Mu.M) in the presence of other metal ions in example 4 of the present invention;
FIG. 7 shows the trend of fluorescence intensity of probe molecules (40. Mu.M) with time after addition of copper ions (100. Mu.M) in example 5 of the present invention.
Detailed Description
The following examples further illustrate specific steps and features of the invention, which are intended to be illustrative only and not limiting. The methods used in the present invention are conventional in the art unless otherwise specified. The reagents and materials involved in the present invention are commercially available without specific description.
Example 1 preparation of fluorescent probes
The synthetic route is as follows:
the preparation process comprises the following steps:
compound 1 (1 g,4.5 mmol) was added to 100mL of ethanol and cooled to-10deg.C. Slowly drop SOCl 2 (1.1 mL,15.5 mmol). Stirring was carried out at room temperature for 2h, reflux stirring was carried out for 8h, and stirring was continued at room temperature for 10h. Rotary steaming to obtain concentrated solution, adding diethyl ether, and recrystallizing to obtain white solid compound 2.
Compound 2 (0.3 g,1 mmol), triethylamine (58. Mu.L, 4.1mmol, TDA) and 4-dimethylaminopyridine (0.02 g,0.16mmol, DMAP) were dissolved in 30mLN, N-Dimethylformamide (DMF) and cooled to-10 ℃. To this was added a solution of dansyl chloride (0.23 g,0.83 mmol) in DMF (20 mL). After the completion of the dropwise addition, the mixture was stirred at-10℃for 2 hours, and then at 60℃for 40 hours. The reaction solution was poured into 100mL of ethyl acetate, and extracted three times with water (100 mL). The upper organic phase was taken and distilled to give green solid compound 3.
Compound 3 (0.26 g,0.53 mmol) was dissolved in 20mL of ethanol and aqueous sodium hydroxide (0.047 g,1.18 mmol) was added (5 mL). Stirring at room temperature for 24h. The reaction solution was concentrated by rotary evaporation, diluted hydrochloric acid (pH 2-3) was slowly added dropwise, and a precipitate was formed. Ethanol/diethyl ether recrystallization gave a yellow solid, compound 4.
A solution of Compound 4 (0.19 g,0.41 mmol) in ethanol (25 mL) was mixed with an aqueous solution of sodium hydroxide (0.023 g,0.57 mmol) (4 mL). And refluxing for 2 hours. Rotary evaporation gave a yellow solid, the sodium salt of compound 4.
The sodium salt product was characterized by nuclear magnetic hydrogen spectroscopy and mass spectrometry, wherein the nuclear magnetic hydrogen spectroscopy (600M) is shown in fig. 1.
ESI-MS: M/z 436.1[ (M-H) of the Probe molecule of the invention - ]。
Example 2 fluorescence spectral Properties of Probe molecules before and after binding to copper ions
To detect the change in fluorescence spectra of the probe molecules before and after the interaction with copper ions, 5mL of HEPES buffer solution (10 mM, pH 7.4) was prepared at a concentration of 40. Mu.M. The fluorescence spectrum changes (excitation wavelength 337nm, maximum emission wavelength 558 nm) of the probe solution before and after 20. Mu.L of HEPES solution (10 mM, pH 7.4) containing 10mM copper ions was recorded, and the results are shown in FIG. 2. Further, the binding ratio of the probe molecule to copper ion and the applicable pH range were determined using the working curves, and the results are shown in FIG. 3 and FIG. 4, respectively.
As can be seen from fig. 2: after copper ions are added, fluorescence is quenched, and the luminous intensity is reduced to 20% of the original luminous intensity. Indicating that the probe coordinates to the copper ion, resulting in fluorescence quenching. The concentration of copper ions can be detected by using the change in fluorescence intensity.
As can be seen from fig. 3: the binding ratio of the probe molecules to copper ions in the invention is 1:1.
As can be seen from fig. 4: the pH range suitable for detecting copper ions by the probe molecule is 6-12.
EXAMPLE 3 fluorescence intensity Studies of Probe molecules under copper ion conditions at different concentrations
The concentration of the immobilized probe was 40. Mu.M, copper ions were gradually added in several portions, the addition amount of copper ions was 0 to 120. Mu.M, and the change in fluorescence intensity of the probe molecule at the maximum emission wavelength with the copper ion concentration was recorded, and the result is shown in FIG. 5.
From FIG. 5, it can be calculated that the linear range of the probe molecule for detecting copper ions is 0-25. Mu.M, and the detection limit is 1.52. Mu.M, which is lower than the maximum copper ion concentration specified by the national standards of China and the environmental protection agency of the United states. This indicates that the fluorescent probe concentration has a higher sensitivity.
EXAMPLE 4 investigation of the selectivity of Probe molecules for copper ions
To examine the selectivity of the probe molecule for copper ions, the probe molecule was recorded in the presence of other metal ions Li + ，Na + ，K + ，Ag + ，Zn 2+ ，Ca 2+ ，Cd 2+ ，Co 2+ ，Hg 2+ ，Mn 2+ ，Mg 2+ ，Ni 2+ ，Pb 2+ ，Al 3+ ，Fe 3+ Response to copper ions. The method comprises the following steps: in HEPES buffer (10 mM, pH 7.4), the probe concentration was 40. Mu.M, and the concentrations of copper ion and other metal ion were 100. Mu.M, respectively, and the results are shown in FIG. 6.
As can be seen from fig. 6: the probe molecule of the invention has higher selectivity on the response of copper ions without being interfered by other metal ions.
Example 5 response speed of Probe molecule to copper ion
In HEPES buffer (10 mM, pH 7.4), the luminescence of the probe molecule was strong, and after addition of 100. Mu.M copper ions, fluorescence was quenched. The trend of fluorescence intensity with time after copper ion addition was recorded, and the results are shown in fig. 7.
Fig. 7 shows: the fluorescence intensity at 558nm rapidly decreased, and the intensity remained substantially unchanged after 1 min. This demonstrates that the probe has a very high response speed to copper ions, and has the ability to respond quickly to copper ions.
Application example 1 detection of copper ions in an actual Water sample by Probe molecules
To 5mL of tap water and mineral water, 20. Mu.L of a 10mM concentration probe HEPES buffer solution (10 mM, pH 7.4) was added, respectively, to prepare a 40. Mu.M concentration probe solution. To the probe solution was further added a trace (2.5. Mu.L, 5. Mu.L) of copper chloride mother liquor (10 mM) to obtain a final probe solution containing 5. Mu.M and 10. Mu.M copper ions. The fluorescence emission intensity of the solution was measured, and each sample was measured in parallel three times. The experimental results are shown in table 1.
TABLE 1 actual detection Using probes of the present invention
Table 1 shows: the experimentally determined copper ion concentration is close to the actual added copper ion concentration, with a relative average deviation of about 5% or less. This demonstrates that the fluorescent probe can effectively detect the concentration of copper ions in an actual water sample.
The above embodiments are only illustrative of the preferred embodiments of the present invention and are not intended to limit the scope of the present invention, and various modifications and improvements made by those skilled in the art to the technical solutions of the present invention should fall within the protection scope defined by the claims of the present invention without departing from the design spirit of the present invention.
Claims (10)
1. The dansyl copper ion fluorescent probe is characterized in that the chemical structural formula is shown as formula I:
2. The method for preparing the dansyl copper ion fluorescent probe according to claim 1, which is characterized by comprising the following steps:
step one: adding the compound 1 into ethanol, cooling, adding thionyl chloride, stirring, steaming to obtain concentrated solution, adding diethyl ether, and recrystallizing to obtain white solid compound 2;
step two: dissolving a compound 2, triethylamine (TDA) and 4-Dimethylaminopyridine (DMAP) in N, N-Dimethylformamide (DMF) and cooling, then adding a Dimethylformamide (DMF) solution of dansyl chloride into the mixture, stirring the mixture, pouring the reaction solution into ethyl acetate and extracting the mixture by water, and finally taking an upper organic phase for rotary evaporation to obtain a green solid compound 3;
step three: dissolving the compound 3 in ethanol, adding a sodium hydroxide aqueous solution, stirring, rotationally evaporating and concentrating, adding dilute hydrochloric acid to separate out a precipitate, and finally recrystallizing with ethanol/diethyl ether to obtain a yellow solid compound 4, namely the dansyl copper ion fluorescent probe;
the chemical structural formula of the compound 1 is shown as a formula II:
the chemical structural formula of the compound 2 is shown as a formula III:
the chemical structural formula of the compound 3 is shown as a formula IV:
3. The method according to claim 2, wherein the cooling temperature in the first step is-8 to-12 ℃; SOCl 2 The adding mode is slow dripping; the stirring mode is that stirring is firstly carried out for 1-3 hours at room temperature, then reflux stirring is carried out for 7-9 hours, and then stirring is carried out for 9-11 hours at room temperature.
4. The method according to claim 3, wherein the cooling temperature in the first step is-10 ℃; the stirring was carried out by stirring at room temperature for 2h, then stirring at reflux for 8h, and then stirring at room temperature for 10h.
5. The method according to claim 4, wherein the cooling temperature in the second step is-8 to-12 ℃; the stirring mode is that stirring is carried out at low temperature firstly and then at high temperature, wherein the temperature of the low temperature stirring is-8 to-12 ℃, the time is 1.5 to 2.5 hours, the temperature of the high temperature stirring is 50 to 70 ℃, and the time is 35 to 45 hours; the number of times of water extraction is 1-4.
6. The method according to claim 5, wherein the cooling temperature in the second step is-10 ℃; stirring at low temperature of-10deg.C for 2 hr; the temperature of high-temperature stirring is 60 ℃ and the time is 40h; the number of water extractions was 3.
7. The preparation method of claim 6, wherein the stirring mode in the third step is room temperature stirring, and the stirring time is 22-26 hours; the dilute hydrochloric acid is slowly added dropwise, and the pH value is 2-3.
8. The method according to claim 7, wherein the stirring time in the third step is 24h.
9. The preparation method according to any one of claims 2 to 8, further comprising a process of preparing a sodium salt of compound 4 by mixing an ethanol solution of compound 4 with an aqueous solution of sodium hydroxide.
10. The dansyl copper ion fluorescent probe according to claim 1 or the application of the dansyl copper ion fluorescent probe prepared by the preparation method according to any one of claims 2-9 in copper ion detection.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101914376A (en) * | 2010-07-05 | 2010-12-15 | 吉林大学 | Peptidomimetic fluorescent ion probe and application thereof in metal ion detection |
| CN102503875A (en) * | 2011-11-18 | 2012-06-20 | 厦门大学 | Fluorescent probe for detecting copper ions and preparation method thereof |
| CN106232623A (en) * | 2014-04-22 | 2016-12-14 | Txp制药股份有限公司 | There is the peptide analogues of branched-amino acid probe |
| CN110055053A (en) * | 2019-03-07 | 2019-07-26 | 兰州大学 | A kind of polypeptide fluorescent probe of specific recognition copper ion and its preparation and detection method |
| CN110357896A (en) * | 2019-08-22 | 2019-10-22 | 山西大同大学 | A kind of compound and preparation and its application in detection bivalent cupric ion and strong acid pH |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA3063152A1 (en) * | 2019-05-31 | 2020-11-30 | University Of Guelph | Fluorescent merocyanine dyes, associated conjugates and methods |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101914376A (en) * | 2010-07-05 | 2010-12-15 | 吉林大学 | Peptidomimetic fluorescent ion probe and application thereof in metal ion detection |
| CN102503875A (en) * | 2011-11-18 | 2012-06-20 | 厦门大学 | Fluorescent probe for detecting copper ions and preparation method thereof |
| CN106232623A (en) * | 2014-04-22 | 2016-12-14 | Txp制药股份有限公司 | There is the peptide analogues of branched-amino acid probe |
| CN110055053A (en) * | 2019-03-07 | 2019-07-26 | 兰州大学 | A kind of polypeptide fluorescent probe of specific recognition copper ion and its preparation and detection method |
| CN110357896A (en) * | 2019-08-22 | 2019-10-22 | 山西大同大学 | A kind of compound and preparation and its application in detection bivalent cupric ion and strong acid pH |
Non-Patent Citations (4)
| Title |
|---|
| Electrophoresis in Organogels;Shaul Mizrahi et al.;《Anal. Chem》;第76卷;第5399-5404页 * |
| Multifunctional peptide‐based fluorescent chemosensor for detection of Hg2+, Cu2+ and S2− ions;Xuliang Pang et al.;《Luminescence》;第34卷;第585–594页 * |
| 基于丹磺酰基团的高选择性的铜离子荧光离子探针;王玉芬 等;《吉林地质》;第29卷(第3期);第87-89页 * |
| 多肽荧光探针ＨＷＥＨＨ对水中铜离子的高通量检测;许迪雅 等;《食品与机械》;第38卷(第8期);第60-65页 * |
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