CN107118091B - Preparation of copper ion complex type fluorescent molecular probe and application of copper ion complex type fluorescent molecular probe in aspect of detecting salicylic acid - Google Patents
Preparation of copper ion complex type fluorescent molecular probe and application of copper ion complex type fluorescent molecular probe in aspect of detecting salicylic acid Download PDFInfo
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Abstract
The invention relates to a copper ion complex type fluorescent molecular probe for identifying salicylic acid in a fluorescence opening mode, which has the following structure:
the probe has good selectivity on salicylic acid, and is not influenced by salicylic acid analogues such as Catechol (Catechol), o-methylbenzoic acid (2-MeBA), Benzoic Acid (BA), acetylsalicylic acid (AcetylSA), p-hydroxybenzoic acid (4-OHBA), phenol (phenol), m-hydroxybenzoic acid (3-OHBA), o-methoxybenzoic acid (2-MeOBA), methyl salicylate (MeSate) and Salicylaldehyde (Salicylaldehyde) in the process of identifying salicylic acid. The probe has the characteristics of high sensitivity, high response speed, low detection limit and the like in the process of identifying the SA. The fluorescent image of the probe for recognizing the salicylic acid in the mouse kidney cells is obtained through a two-photon confocal fluorescent microscope.
Description
Technical Field
The invention relates to the technical field of chemical analysis and detection, in particular to application of a copper ion complex type fluorescent molecular probe in the aspect of detecting salicylic acid.
Background
Salicylic Acid (SA) is a signal molecule necessary for inducing Systemic Acquired Resistance (SAR) in plants, and plays an important role in mediating signal transduction of SAR in plants. In recent years, as the role of SA in the mechanism of activating SAR in plants has been receiving much attention, the search for a method capable of detecting endogenous SA in plants has become urgent. The existing methods for detecting the concentration of SA mainly comprise an ultraviolet spectrophotometry method, a fluorescence spectrophotometry method, a colorimetric method, an electrochemical analysis method, a gas chromatography method, a high performance liquid chromatography method and the like, but the methods cannot detect in vivo and cannot reflect the acting position and the conduction path of SA. In the aspect of researching the SA action site, Surface Plasmon Resonance (SPR) technology and isotope tracing methods are mainly used, but the surface plasmon resonance technology is mainly limited to in vitro protein experiments and cannot reflect the biological environment of cells, the isotope tracing method needs to use isotope-labeled exogenous SA, the experimental conditions are harsh and cannot reflect the generation and conduction processes of endogenous SA, and the methods cannot detect endogenous salicylic acid in real time.
The fluorescent molecular probe has the good characteristics of good selectivity, high sensitivity, small cell damage, convenience in observation, capability of real-time detection and the like, has great potential in the aspect of real-time detection of endogenous small molecules, and is an ideal method for detecting endogenous SA. Among many fluorescent molecular probes, the complex fluorescent molecular probe containing metal ions has the advantages of good water solubility, multifunctional detection, easy preparation and the like, and is widely applied, wherein the copper ion complex fluorescent molecular probe is particularly interesting, and a large number of documents report that the complex fluorescent molecular probe has good application in small molecule detection [ Roy, B ]; rao, a.s.; ahn, K.H.Mononuclear Zn (II) -and Cu (II) -complexes of a hydroxynaphthalene-derived Dipicolinamine fluorescent sensitive phosphor chem.org.biomol.2011, 9, 7774-; liu, y.; lv, x.; zhao, y.; liu, j.; sun, y.q.; wang, p.; guo, W.A Cu (II) -based chemical sensing aromatic amine B fluorphoron for fluorescence turn-on detection of cyanide.J. Mater.chem.,2012,22, 1747-1750; hou, j.t.; li, K.; yu, k.k.; wu, m.y.; yu, X.Q.Coumarin-DPA-Cu (II) as interacting aromatic kinase determination in urea and sodium Org.biomol.chem.,2013,11, 717-720; yu, m.; wang, w.; zhang, n.conditional and electric "off-on" detection nitride oxide in solution and in film with a quinoline based fluorescence sensor, spectral. acta, 2014,126, 329-; chen, t.; yin, l.; qin, y.; xu, y.; qian, x.; huang, c.; zhu, W.Highlyysective "Off-On" fluorescent probe for stimulating and imaging in livingcells. biosens. bioelectron 2015,66,259-265 ].
Disclosure of Invention
The invention aims to provide a copper ion complex type fluorescent molecular probe (1-Cu) which is simple to prepare, good in selectivity, high in sensitivity, short in response time and wide in detection range and can be used for identifying salicylic acid in a fluorescence opening mode2+) And the detection of salicylic acid in mouse kidney cells by the probe.
The technical scheme adopted by the invention is as follows: copper ion complex type fluorescent molecular probe (1-Cu)2+) The probe has the following structure:
copper ion complex type fluorescent molecular probe (1-Cu)2+) The preparation method comprises the following steps: mixing curcumin with Cu (NO)3)2Dissolving curcumin and Cu (NO) in mixed solution of N, N-dimethylformamide and water respectively3)2Mixing the mixed solution of N, N-dimethylformamide and water according to the mass ratio of 1:1 to obtain the 1-Cu2+. Wherein the volume ratio of the N, N-dimethylformamide to the water is 7: 3.
The probe recognizes salicylic acid by means of fluorescence turning on.
The copper ion complex type fluorescent molecular probe still has good selectivity on salicylic acid under the condition that other salicylic acid analogues such as catechol, o-methyl benzoic acid, acetylsalicylic acid, p-hydroxybenzoic acid, phenol, m-hydroxybenzoic acid, o-methoxybenzoic acid, methyl salicylate and salicylaldehyde exist.
Probe 1-Cu2+In N, N-dimethylformamide: the mixed solution of water (7:3, v/v) has better solubility, the maximum absorption wavelength and the emission wavelength of the mixed solution are 433nm and 530nm respectively, when 20 times of equivalent of SA is added into the probe, the fluorescence intensity is increased by about 34.8 times, and at 365nm of an ultraviolet lamp, the probe can be obviously seen to have stronger fluorescence when identifying salicylic acid.
The invention has the beneficial effects that:
the copper ion complex type fluorescent molecular probe has different recognition effect on salicylic acid with different volume ratios of N, N-dimethylformamide and water (10:0-0:10, v/v), wherein when the volume of water is gradually increased from 0 to 3 parts, the probe 1-Cu2+The recognition effect on salicylic acid is better and better, and when the volume of water is gradually increased from 3 parts to 10 parts, the probe 1-Cu2+The recognition effect on salicylic acid is gradually reduced, so that when the volume ratio of the N, N-dimethylformamide to the water is 7:3, the recognition effect of the copper ion complex type fluorescent molecular probe on the salicylic acid is the best.
Probe 1-Cu of the present invention2+Can detect SA in complex environment, and probe 1-Cu in the presence of other salicylic acid analogues (Catechol (Catechol), o-methylbenzoic acid (2-MeBA), Benzoic Acid (BA), acetylsalicylic acid (AcetylSA), p-hydroxybenzoic acid (4-OHBA), phenol (phenol), m-hydroxybenzoic acid (3-OHBA), o-methoxybenzoic acid (2-MeOBA), methyl salicylate (MeSate), Salicylaldehyde (Salicylaldehyde))2+The detection of salicylic acid is not affected.
Probe 1-Cu of the present invention2+The sensitivity to the salicylic acid is high, the response to the salicylic acid is between 10 mu M and 700 mu M, the detection limit to the salicylic acid is 3 mu M, the response time is fast, and the salicylic acid can be identified in response within 10 s. The probe 1-Cu can be obtained by a two-photon confocal fluorescence microscope2+Fluorescent image of salicylic acid recognized in mouse kidney cells, which is capable of being in mouse kidney cellsSalicylic acid was detected.
Drawings
FIG. 1 shows a probe 1-Cu of the present invention2+(10. mu.M) in N, N-dimethylformamide: adding 20 times equivalent of salicylic acid and salicylic acid analogues into water (7:3, v/v) mixed solution, wherein the abscissa is wavelength and the ordinate is fluorescence intensity (lambda)ex433nm with a slit of 3 nm);
FIG. 2 shows a probe 1-Cu of the present invention2+(10. mu.M) in N, N-dimethylformamide: adding 20 times equivalent of salicylic acid and salicylic acid analogues into a mixed solution of water (7:3, v/v) at 365nm of an ultraviolet lamp, wherein (1)1, (2)1+ Cu2+,(3)1+Cu2++SA,(4)1+Cu2++BA,(5)1+Cu2++3-OHBA,(6)1+Cu2++4-OHBA,(7)1+Cu2++2-MeOBA,(8)1+Cu2++2-MeBA,(9)1+Cu2++Salicylaldehyde,(10)1+Cu2++MeSate,(11)1+Cu2++Catechol,(12)1+Cu2++phenol,(13)1+Cu2++AcetylSA；
FIG. 3 shows probe 1-Cu of the present invention2+(10. mu.M) in N, N-dimethylformamide: adding 20 times equivalent of salicylic acid analogue to the mixed solution of water (7:3, v/v), wherein the abscissa is the kind of the added salicylic acid analogue, and (1)1-Cu2+(10μM)，(2)1-Cu2++SA，(3)1-Cu2++2-CH3BA+SA，(4)1-Cu2++Salicylaldehyde+SA，(5)1-Cu2++Catechol+SA，(6)1-Cu2++BA+SA，(7)1-Cu2++phenol+SA，(8)1-Cu2++2-MeOBA+SA，(9)1-Cu2++3-OHBA+SA，(10)1-Cu2++4-OHBA+SA，(11)1-Cu2++AcetylSA+SA，(12)1-Cu2++ MeSate + SA, fluorescence intensity (λ) on ordinateex/λem433nm/530nm with a slit of 3 nm);
FIG. 4 shows probe 1-Cu of the present invention2+(10. mu.M) in N, N-dimethylformamide: in the mixed solution of water (7:3, v/v), the left graph shows the change of fluorescence intensity with the increase of SA concentration, the abscissa shows the wavelength, and the ordinate shows the fluorescence intensity (. lamda.)ex433nm with a slit of 3 nm). The right diagram is lambdaemFluorescence intensity at 530nm as a function of increasing SA concentration, with abscissa [ SA ]]/[1-Cu2+]The ordinate is the fluorescence intensity (lambda)ex/λem433nm/530nm with a slit of 3 nm);
FIG. 5 shows probe 1-Cu of the present invention2+(10. mu.M) in N, N-dimethylformamide: when salicylic acid was added in an amount of 20 times the equivalent weight to the mixed solution of water (7:3, v/v), the fluorescence emission spectrum showed a change in fluorescence intensity with time on the abscissa and the fluorescence intensity (. lamda.) on the ordinateex/λem433nm/530nm with a slit of 3 nm);
FIG. 6 shows probe 1-Cu of the present invention2+(10. mu.M) fluorescence image of salicylic acid recognition in mouse kidney cells, wherein (a) mouse kidney cells +1 (30. mu.M), (b) mouse kidney cells +1 (30. mu.M) + Cu2+(2.0equiv), (c) mouse Kidney cells +1 (30. mu.M) + Cu2+(2.0equiv) + SA (10.0equiv), (d) mouse Kidney cells +1 (30. mu.M) + Cu2+(2.0equiv)+SA(20.0equiv)(λex＝885nm)；
FIG. 7 shows probe 1-Cu of the present invention2+(10 μ M) N, N-dimethylformamide in different volume ratios: when salicylic acid of 20 times equivalent is added to the water mixed solution, the change of fluorescence emission spectrum is shown by the abscissa as time and the ordinate as fluorescence intensity (lambda)ex/λem433nm/530nm with a slit of 3 nm);
FIG. 8 shows probe 1-Cu of the present invention2+The high resolution mass spectrum of (1), wherein 430.0473 (theoretical value is 430.0467) is the probe 1-Cu2+Target molecule ion peak of (1).
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in further detail with reference to fig. 1 to 8 of the present specification.
Example (b):
1. probe 1-Cu2+Preparation of
0.0037g curcumin was weighed into a 10mL volumetric flask with N, N-dimethylformamide: dissolving the mixed solution of water (7:3, v/v) and fixing the volume to obtain the concentration of 10-3M curcumin stock solution, 0.0013g Cu (NO) is weighed3)2In a 10mL volumetric flask, the mixture was measured with N, N-dimethylformamide: dissolving the mixed solution of water (7:3, v/v) and fixing the volume to obtain the concentration of 10-3Cu (NO) of M3)2Mixing the two solutions at a volume ratio of 1:1 to obtain probe 1-Cu2+。
2. Probe 1-Cu2+Selectivity to salicylic acid
In N, N-dimethylformamide: in the system of water (7:3, v/v), to 1-Cu2+When 20 times of equivalent of Catechol (Catechol), o-methylbenzoic acid (2-MeBA), Benzoic Acid (BA), acetylsalicylic acid (AcetylSA), p-hydroxybenzoic acid (4-OHBA), phenol (phenol), M-hydroxybenzoic acid (3-OHBA), o-methoxybenzoic acid (2-MeOBA), methyl salicylate (MeSate) and Salicylaldehyde (Saliclylaldehyde) are respectively added into the solution (10 mu M), the increase range of the fluorescence intensity of the system is small, and after the 20 times of equivalent of SA is added, the increase range of the fluorescence intensity of the system is large, and the fluorescence intensity is increased by about 34.8 times, which preliminarily shows that 1-Cu2+Shows better fluorescence selectivity for SA (figure 1). Then, the method is further proved under the condition that the excitation wavelength of an ultraviolet instrument is 365nm, and as can be seen from the figure, the method is applied to 1-Cu2+When SA is added, the fluorescence intensity is obviously increased, and further shows that 1-Cu2+Showed significant selectivity for SA (figure 2).
3. Competitive properties of other salicylic acid analogs to salicylic acid
Probe 1-Cu was tested in the presence of 20-fold equivalents of SA analog (Catechol (Catechol), o-methylbenzoic acid (2-MeBA), Benzoic Acid (BA), acetylsalicylic acid (AcetylSA), p-hydroxybenzoic acid (4-OHBA), phenol (phenol), m-hydroxybenzoic acid (3-OHBA), o-methoxybenzoic acid (2-MeOBA), methyl salicylate (MeSate), Salicylaldehyde (Salicylaldehyde))2+Fluorescence selectivity for SA. By comparing the reaction systemsexAs the fluorescence intensity at 530nm, we found that the fluorescence intensity of the reaction system containing the salicylic acid analog was comparable to that of the simple probe 1-Cu2+The fluorescence intensity of the reaction system is substantially equivalent to that of SA. Indicating that other salicylic acid analogs do not show SAApparent competition effect (FIG. 3), further verifying the probe 1-Cu2+The ability to recognize SA in complex environments also opens the possibility for probes to detect SA in biological environments.
4. Probe 1-Cu2+Sensitivity of (2)
The invention is based on the probe 1-Cu2+Titration experiment with SA discusses probe 1-Cu2+Sensitivity to salicylic acid, when directed to Probe 1-Cu2+When different concentrations of SA are added, the fluorescence intensity is increased along with the increase of the concentration of SA when [ SA ]]/[1-Cu2+]At 70, the fluorescence intensity tends to be stable. Explanation 1-Cu2+Has higher sensitivity in identifying SA and can respond to salicylic acid between 10 and 700 mu M (figure 4).
The present invention utilizes a signal-to-noise ratio method (S/N) [ Guo, l.; xu, y.; ferran, a.r.; chen, g.; kim, D.H. organized gold nanoparticles aggregation for colorimetric sensors with high analytical specifications of diameter.J. am. chem.Soc.,2013,135,12338-]Test probe 1-Cu2+The detection limit of SA was determined mainly by the following method: the probe solution to which the analyte was not added was used as a blank sample, the fluorescence intensity at a specific wavelength was measured 20 times and the average value (average) of the data was calculatedblank) And Standard Deviation (SD)blank) The standard deviation is the noise (N) of the test system; adding a lower amount of the substance to be detected to the probe system under the condition of constant concentration of the probe, measuring the fluorescence intensity at 5 times of specific wavelength (consistent with the wavelength) and calculating the average value (average)sample) And finally, calculating the signal-to-noise ratio (S/N) of the system according to the following formula.
S/N＝(|averagesample-averageblank|)/SDblank
And when the value range of S/N is between 3 and 5, the concentration under the condition is the detection limit of the probe. Probe 1-Cu was obtained by the above-mentioned method2+In N, N-dimethylformamide: the detection limit for SA in a solution of water (7:3, v/v) was 3. mu.M.
5. Probe 1-Cu2+Of p-salicylic acidResponse time
The invention tests the probe 1-Cu2+Response time in identifying SA, test probe 1-Cu when different time intervals2+When the fluorescence intensity of SA was recognized, 1-Cu was found to be within 10s2+Can respond to the identification SA, specification 1-Cu2+The SA can be quickly identified (fig. 5).
6. Probe 1-Cu2+Fluorescence image of salicylic acid recognition in mouse kidney cells
The invention utilizes a two-photon confocal fluorescence microscope to discuss the probe 1-Cu2+The possibility of SA in mouse kidney cells was examined. Curcumin (1) at 30 μ M was first added to the cultured mouse kidney cells in ozone (95% air, 5% CO)2) After incubation for 1.0h at 37 ℃ and rinsing three times with PBS (pH 7.4,0.1M) buffer, imaging was performed under a two-photon confocal fluorescence microscope, and it was found that very significant fluorescence could be observed in the cells (fig. 6a), indicating that probe 1 could enter the cells. Next, 2-fold equivalent of Cu was added to the cells2+After incubation for 2.0h under the same conditions, the cells were rinsed three times with PBS (pH 7.4,0.1M) buffer and imaged under a two-photon confocal fluorescence microscope, and the intracellular fluorescence was quenched (FIG. 6b), indicating that Cu was present2+Enters the cell and interacts with probe 1. Finally, 10-fold and 20-fold equivalent of SA was added to the cells, respectively, and the cells were incubated under the same conditions for 2.5h, then rinsed three times with PBS (pH 7.4,0.1M) buffer solution and imaged under a two-photon confocal fluorescence microscope, and as a result, the fluorescence in the cells was recovered again and gradually increased with increasing concentration (FIGS. 6c-6d), indicating that SA was able to enter the cells and was able to enter the cells together with 1-Cu2+An effect occurs. The above experiments show that the probe 1-Cu2+Detection of SA can be achieved in mouse kidney cells.
Claims (3)
1. A copper ion complex type fluorescent molecular probe is characterized in that: the probe has the following structure:
2. The method for preparing a copper ion-complexed fluorescent molecular probe according to claim 1, wherein: comprises the following steps: mixing curcumin with Cu (NO)3)2Dissolving curcumin and Cu (NO) in mixed solution of N, N-dimethylformamide and water respectively3)2Mixing the materials in a mixed solution of N, N-dimethylformamide and water at a mass ratio of 1:1 to obtain 1-Cu2+。
3. The method for preparing a copper ion-complexed fluorescent molecular probe according to claim 2, wherein: the volume ratio of the N, N-dimethylformamide to the water is 7: 3.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102154004A (en) * | 2011-02-23 | 2011-08-17 | 广东工业大学 | Application of mon-carbonyl curcumin compound-based visual PH fluorescent probe |
| CN102424752A (en) * | 2011-09-21 | 2012-04-25 | 华南师范大学 | Quantum dot-based plant hormone salicylic acid acceptor probe, its preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102154004A (en) * | 2011-02-23 | 2011-08-17 | 广东工业大学 | Application of mon-carbonyl curcumin compound-based visual PH fluorescent probe |
| CN102424752A (en) * | 2011-09-21 | 2012-04-25 | 华南师范大学 | Quantum dot-based plant hormone salicylic acid acceptor probe, its preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| "Curcumin derivatives as metal-chelating agents with potential multifunctional activity for pharmaceutical applications";Erika Ferrari，et al.;《Journal of Inorganic Biochemistry》;20140611;第139卷;38-48 * |
| "荧光探针法研究铜离子-姜黄素体系中1O2的反应机理及在O2-存在下1O2的测定";吕庆銮，等;《高等学校化学学报》;20090331;第30卷;460-464 * |
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