CN107118091A - The preparation and its application in terms of salicylic acid is detected of a kind of copper ion solvay-type fluorescent molecular probe - Google Patents

The preparation and its application in terms of salicylic acid is detected of a kind of copper ion solvay-type fluorescent molecular probe Download PDF

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CN107118091A
CN107118091A CN201710310222.7A CN201710310222A CN107118091A CN 107118091 A CN107118091 A CN 107118091A CN 201710310222 A CN201710310222 A CN 201710310222A CN 107118091 A CN107118091 A CN 107118091A
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probe
acid
salicylic
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salicylic acid
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CN107118091B (en
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杨松
陈冲
王培义
杨林林
吴志兵
李虎
薛伟
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Guizhou University
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    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/77—Preparation of chelates of aldehydes or ketones
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    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • 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"
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • 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
    • G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups

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Abstract

Salicylic acid is recognized by way of fluorescence is opened the present invention relates to a kind of copper ion solvay-type fluorescent molecular probe, the structure of the probe is as follows：The probe has preferable selectivity to salicylic acid, and is not influenceed during identification is salicylic by salicylic acid and its analogs such as catechol (Catechol), o-toluic 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), gaultherolin (MeSate) and salicylides (Salicylaldehyde).The probe has higher sensitivity, fast response time, the low good characteristic of test limit during SA is recognized.By two-photon confocal fluorescent microscope, obtain the probe and salicylic fluoroscopic image is recognized in mouse kidney cell.

Description

A kind of preparation of copper ion solvay-type fluorescent molecular probe and its detection salicylic acid side The application in face
Technical field
The present invention relates to chemical analysis detection technique field, and in particular to a kind of copper ion solvay-type fluorescence molecule is visited Application of the pin in terms of salicylic acid is detected.
Background technology
Salicylic acid (salicylic acid, SA) is induction On Plant Systemica Cquired Resistance (systemic acquired Resistance, SAR) necessary to signaling molecule, played in mediated plant SAR signal transduction it is highly important make With.In recent years, the effect due to SA in plant SAR mechanism is excited receives much concern always, thus seek one kind can be in plant Vivo detection endogenous SA method just becomes very urgent.In the method for existing detection SA concentration, mainly there is ultraviolet spectrometry Photometry, fluorescence spectrophotometry, than chromatmetry, electrochemical methods, gas chromatography and high performance liquid chromatography etc., still This kind of method can not be detected in vivo, it is impossible to reflect SA active position and conducting path.It is main in terms of SA action sites are studied There are Applications of surface plasmon resonance (SPR) and a tracer method, but Applications of surface plasmon resonance primary limitation In external Protein Assav, it is impossible to the biotic environment of reacting cells, and tracer method needs to use the outer of isotope marks Source property SA, experiment condition is harsh and can not reflect endogenous SA generation and conductive process, and above method can not be examined in real time Survey endogenous salicylic acid.
Fluorescent molecular probe have selectivity good, sensitivity it is high, cellular damage is small, be easy to observation, can detect in real time Good characteristic, has huge potentiality in terms of detection endogenous small molecule in real time, is that a kind of ideal detection is endogenous Property SA method.And in numerous fluorescent molecular probes, the solvay-type fluorescent molecular probe of metal ion is due to water Dissolubility is good, multi-functional can detect and easily the advantage such as preparation is widely used, and wherein copper ion solvay-type fluorescent molecular probe is outstanding To be noticeable, existing lot of documents has reported it has preferably application [Roy, B. in small molecule context of detection；Rao, A.S.；Ahn,K.H.Mononuclear Zn(II)-and Cu(II)-complexes of a hydroxynaphthalene- derived dipicolylamine:fluorescent sensing behaviours toward pyrophosphate ions.Org.Biomol.Chem.,2011,9,7774-7779；Liu,Y.；Lv,X.；Zhao,Y.；Liu,J.；Sun,Y.Q.； Wang,P.；Guo,W.A Cu(II)-based chemosensing ensemble bearing rhodamine B fluorophore for fluorescence turn-on detection ofcyanide.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 a chemosensing ensemble towards histidine determination in urine and serum.Org.Biomol.Chem.,2013,11,717-720；Yu,M.；Wang,W.；Zhang,N.Convenient and selective“off–on”detection nitric oxide in solution and thin film with quinoline based fluorescence sensor.Spectrochim.ActaA,2014,126,329-332；Chen, T.；Yin,L.；Qin,Y.；Xu,Y.；Qian,X.；Huang,C.；Zhu,W.Highlyselective“Off–On” fluorescent probe for histidine and its imaging in living cells.Biosens.Bioelectron.,2015,66,259-265]。
The content of the invention
Prepared simply it is an object of the invention to provide one kind, the good, sensitivity of selectivity is high, the response time is short, detection model Enclose wide, salicylic copper ion solvay-type fluorescent molecular probe (1-Cu is recognized by way of fluorescence is opened2+) and the probe To salicylic detection in mouse kidney cell.
The technical solution adopted by the present invention is：A kind of copper ion solvay-type fluorescent molecular probe (1-Cu2+), the probe has Following structure：
A kind of copper ion solvay-type fluorescent molecular probe (1-Cu2+) preparation method, comprise the steps of：By curcumin and Cu(NO3)2In the mixed solution for being dissolved in DMF and water respectively, by curcumin and Cu (NO3)2With the amount of material Ratio be 1:1 ratio can be prepared by 1-Cu in the mixed solution mixing of N,N-dimethylformamide and water2+.Wherein N, N- diformazan The volume ratio of base formamide and water is 7:3.
The probe recognizes salicylic acid by way of fluorescence is opened.
Described copper ion solvay-type fluorescent molecular probe is in other salicylic acid and its analogs catechols, o-methyl-benzene first Acid, benzoic acid, acetylsalicylic acid, P-hydroxybenzoic acid, phenol, m-hydroxybenzoic acid, o-methoxybenzoic acid, salicylic acid first Still there is preferably selectivity in the presence of ester, salicylide to salicylic acid.
Probe 1-Cu2+In N,N-dimethylformamide：Water (7:3, v/v) there is preferable dissolubility in mixed solution, Its maximum absorption wavelength and launch wavelength are respectively 433nm and 530nm, as the SA of 20 times of equivalents of addition into probe, fluorescence About 34.8 times of intensity increase, at uviol lamp 365nm, it can clearly be seen that probe when recognizing salicylic acid with stronger glimmering Light.
Beneficial effects of the present invention：
With different (the 10 of the volume ratio of N,N-dimethylformamide and water:0-0:10, v/v) the copper ion solvay-type Fluorescent molecular probe is different to salicylic recognition effect, wherein when the volume of water is by progressively increasing to 3 parts for 0 part, probe 1-Cu2+Salicylic recognition effect is become better and better, when the volume of water is by progressively increasing to 10 parts for 3 parts, probe 1-Cu2+It is right Salicylic recognition effect is gradually deteriorated again, therefore when the volume ratio of DMF and water is 7:When 3, the copper ion Solvay-type fluorescent molecular probe is best to salicylic recognition effect.
Probe 1-Cu of the present invention2+SA can be detected in complex environment, in other salicylic acid and its analogs (adjacent benzene two Phenol (Catechol), o-toluic acid (2-MeBA), benzoic acid (BA), acetylsalicylic acid (AcetylSA), para hydroxybenzene first Sour (4-OHBA), phenol (phenol), m-hydroxybenzoic acid (3-OHBA), o-methoxybenzoic acid (2-MeOBA), salicylic acid first Ester (MeSate), salicylide (Salicylaldehyde)) in the presence of, probe 1-Cu2+To it is salicylic detection also not by Influence.
Probe 1-Cu of the present invention2+There is higher sensitivity to salicylic acid, to bigcatkin willow between 10 μM -700 μM Acid has response, and it is limited to 3 μM to salicylic detection, and the response time is fast, and identification salicylic acid can be responded within 10s.Pass through Two-photon confocal fluorescent microscope, can also obtain probe 1-Cu2+Salicylic fluoroscopic image is recognized in mouse kidney cell, its Salicylic acid can be detected in mouse kidney cell.
Brief description of the drawings
Fig. 1 is probe 1-Cu of the invention2+(10 μM) are in N,N-dimethylformamide：Water (7:3, v/v) mixed solution In, the situation of change of the salicylic acid of 20 times of equivalents of addition and the fluorescence emission spectrum of salicylic acid and its analogs, abscissa is wavelength, is indulged Coordinate is fluorescence intensity (λex=433nm, slit is 3nm)；
Fig. 2 is probe 1-Cu of the invention2+(10 μM) are in N,N-dimethylformamide：Water (7:3, v/v) mixed solution In, the fluoroscopic image of the salicylic acid of 20 times of equivalents of addition and salicylic acid and its analogs at uviol lamp 365nm, 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 is probe 1-Cu of the invention2+(10 μM) are in N,N-dimethylformamide：Water (7:3, v/v) mixed solution In, situation of change of the salicylic acid and its analogs to the fluorescence emission spectrum of salicylic interference of 20 times of equivalents is added, abscissa is The species of the salicylic acid and its analogs of addition, wherein (1) 1-Cu2+(10 μM), (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, ordinate is fluorescence intensity (λex/λem=433nm/530nm, slit For 3nm)；
Fig. 4 is probe 1-Cu of the invention2+(10 μM) are in N,N-dimethylformamide：Water (7:3, v/v) mixed solution In, left figure be fluorescence intensity with the increased situation of change of SA concentration, abscissa is wavelength, and ordinate is fluorescence intensity (λex= 433nm, slit is 3nm).Right figure is λemFluorescence intensity is with the increased situation of change of SA concentration at=530nm, and abscissa is [SA]/[1-Cu2+] ratio, ordinate be fluorescence intensity (λex/λem=433nm/530nm, slit is 3nm)；
Fig. 5 is probe 1-Cu of the invention2+(10 μM) are in N,N-dimethylformamide：Water (7:3, v/v) mixed solution In, when adding the salicylic acid of 20 times of equivalents, the situation of change for the fluorescence emission spectrum that fluorescence intensity is changed over time, abscissa is Time, ordinate is fluorescence intensity (λex/λem=433nm/530nm, slit is 3nm)；
Fig. 6 is probe 1-Cu of the invention2+The fluoroscopic image that (10 μM) are recognized in mouse kidney cell to salicylic acid, wherein (a) mouse kidney cell+1 (30 μM), (b) mouse kidney cell+1 (30 μM)+Cu2+(2.0equiv), (30 μ of (c) mouse kidney cell+1 M)+Cu2+(2.0equiv)+SA (10.0equiv), (d) mouse kidney cell+1 (30 μM)+Cu2+(2.0equiv)+SA (20.0equiv)(λex=885nm)；
Fig. 7 is probe 1-Cu of the invention2+(10 μM) are in the N,N-dimethylformamide of different volume ratios：Water mixing is molten In liquid, during the salicylic acid of 20 times of equivalents of addition, the situation of change of fluorescence emission spectrum, abscissa is the time, and ordinate is fluorescence Intensity (λex/λem=433nm/530nm, slit is 3nm)；
Fig. 8 is probe 1-Cu of the invention2+High resolution mass spectrum, wherein 430.0473 (theoretical values 430.0467) for visit Pin 1-Cu2+Target molecule quasi-molecular ions.
Embodiment
To make the object, technical solutions and advantages of the present invention clearer, below with reference to this specification accompanying drawing 1-8 to this Invention is described in further detail.
Embodiment：
1st, probe 1-Cu2+Preparation
0.0037g curcumins are weighed in 10mL volumetric flasks, DMF is used：Water (7:3, v/v) mixing Solution dissolving and constant volume, it is 10 to obtain concentration-3M curcumin storing solutions, weigh 0.0013g Cu (NO3)2In 10mL volumetric flasks, Use N,N-dimethylformamide：Water (7:3, v/v) mixed solution dissolving and constant volume, it is 10 to obtain concentration-3M Cu (NO3)2Storage Standby liquid, then by above two solution with 1:1 volume ratio carries out being mixed to get probe 1-Cu2+。
2nd, probe 1-Cu2+To salicylic selectivity
In N,N-dimethylformamide：Water (7:3, v/v) in system, to 1-Cu2+20 times are separately added into (10 μM) to work as The catechol (Catechol) of amount, o-toluic 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), when gaultherolin (MeSate), salicylide (Salicylaldehyde), system fluorescence intensity increasing degree is little, And after the SA of 20 times of equivalents is added, system fluorescence intensity increasing degree is larger, about 34.8 times of fluorescence intensity increase, preliminary explanation 1-Cu2+Preferable fluorescence selectivity (Fig. 1) is shown to SA.Then further carried out under ultraviolet device excitation wavelength 365nm Prove, it can be seen that working as to 1-Cu2+During middle addition SA, fluorescence intensity increase is obvious, illustrates further 1-Cu2+It is right SA shows obvious selectivity (Fig. 2).
3rd, other salicylic acid and its analogs are to salicylic competitiveness
In SA analogs (catechol (Catechol), o-toluic acid (2-MeBA), the benzoic acid of 20 times of equivalents (BA), acetylsalicylic acid (AcetylSA), P-hydroxybenzoic acid (4-OHBA), phenol (phenol), m-hydroxybenzoic acid (3- OHBA), o-methoxybenzoic acid (2-MeOBA), gaultherolin (MeSate), salicylide (Salicylaldehyde)) exist In the case of test probe 1-Cu2+To SA fluorescence selectivity.By relatively more each reaction system in λexFluorescence at=530nm Intensity, it has been found that the fluorescence intensity of the reaction system containing salicylic acid and its analogs and simple probe 1-Cu2+With SA reaction The fluorescence intensity of system is substantially suitable.Illustrate that other salicylic acid and its analogs do not show obvious Competition (Fig. 3) to SA, Further demonstrate probe 1-Cu2+SA ability can be recognized under complex environment, can also be examined for probe in biotic environment SA is surveyed there is provided possible.
4th, probe 1-Cu2+Sensitivity
The present invention passes through probe 1-Cu2+Probe 1-Cu has been inquired into SA titration experiments2+Salicylic sensitivity is recognized, When to probe 1-Cu2+It is middle add various concentrations SA when, with the rise of SA concentration, fluorescence intensity is also increased, when [SA]/ [1-Cu2+During]=70, fluorescence intensity tends towards stability.Illustrate 1-Cu2+When recognizing SA with higher sensitivity, and can be There is response (Fig. 4) to salicylic acid between 10 μM -700 μM.
The present invention utilizes signal to noise ratio method (S/N) [Guo, L.；Xu,Y.；Ferhan,A.R.；Chen,G.；Kim, D.H.Oriented gold nanoparticle aggregation for colorimetric sensors with surprisingly high analytical figures of merit.J.Am.Chem.Soc.,2013,135,12338- 12345] probe 1-Cu is tested2+To SA test limit, mainly it is determined by the following method：It will not add detected The probe solution of thing measures the fluorescence intensity under 20 specific wavelengths and calculates the average value of this group of data as blank sample (averageblank) and standard deviation (SDblank), the standard deviation is the noise (N) of the test system；It is dense in above-mentioned probe The thing to be detected of lower content is added in the case that degree is constant into probe system, 5 specific wavelengths are then measured (with above-mentioned ripple It is long consistent) under fluorescence intensity and calculate its average value (averagesample), finally calculated according to formula below and obtain the system Signal to noise ratio (S/N).
S/N=(| averagesample-averageblank|)/SDblank
Concentration under the conditions of being somebody's turn to do when S/N span is between 3 to 5 is the test limit of probe.Utilize above-mentioned side Method has measured probe 1-Cu2+In N,N-dimethylformamide：Water (7:3, v/v) 3 μM are limited to SA detection in solution.
5th, probe 1-Cu2+To the salicylic response time
The present invention tests probe 1-Cu2+Response time when recognizing SA, as the different time test probe 1- in interval Cu2+When recognizing SA fluorescence intensity, as a result find within 10s, 1-Cu2+Respond to recognize SA, illustrate 1-Cu2+Can be fast Speed identification SA (Fig. 5).
6th, probe 1-Cu2+Salicylic fluoroscopic image is recognized in mouse kidney cell
The present invention has inquired into probe 1-Cu using two-photon confocal fluorescent microscope2+SA's can in detection mouse kidney cell Can property.30 μM of curcumin (1) is added in cultured mouse kidney cell first, in ozone (95% air, 5% CO2) 1.0h is cultivated at 37 DEG C, then eluted three times with PBS (pH=7.4,0.1M) cushioning liquid, in two-photon confocal fluorescent It is imaged under microscope, as a result finds, apparent fluorescence (Fig. 6 a) is able to observe that in cell, illustrate that probe 1 can enter Cell.Then, the Cu of 2 times of equivalents is added into above-mentioned cell2+, 2.0h is cultivated under the same conditions, then with PBS (pH= 7.4,0.1M) cushioning liquid is eluted three times, is imaged, is as a result found, intracellular is glimmering under two-photon confocal fluorescent microscope Light is quenched (Fig. 6 b), illustrates Cu2+Enter cell and interacted with probe 1.Finally, then into above-mentioned cell divide Not Jia Ru 10 times and 20 times equivalents SA, 2.5h is cultivated under the same conditions, then with PBS (pH=7.4,0.1M) cushioning liquid Elution three times, is imaged under two-photon confocal fluorescent microscope, as a result finds, intracellular fluorescence reappears recovery again, and with The rise of concentration, fluorescence gradually strengthens (Fig. 6 c-6d), illustrate that SA can enter cell, and and 1-Cu2+Acted on.With Upper experiment demonstrates probe 1-Cu2+The detection to SA can be realized in mouse kidney cell.

Claims (4)

1. a kind of copper ion solvay-type fluorescent molecular probe, it is characterised in that：The probe has following structure：
The probe recognizes salicylic acid by way of fluorescence is opened.
2. a kind of preparation method of copper ion solvay-type fluorescent molecular probe as claimed in claim 1, it is characterised in that：Comprising Following steps：By curcumin and Cu (NO3)2In the mixed solution for being dissolved in DMF and water respectively, by curcumin with Cu(NO3)2Ratio using the amount of material is 1:1 ratio is mixed in the mixed solution of N,N-dimethylformamide and water and can made Obtain 1-Cu2+。
3. a kind of preparation method of copper ion solvay-type fluorescent molecular probe according to claim 2, it is characterised in that：N, The volume ratio of dinethylformamide and water is 7:3.
4. a kind of copper ion solvay-type fluorescent molecular probe according to claim 1, it is characterised in that：Described copper ion Solvay-type fluorescent molecular probe other salicylic acid and its analogs catechols, o-toluic acid, benzoic acid, acetylsalicylic acid, It is right in the presence of P-hydroxybenzoic acid, phenol, m-hydroxybenzoic acid, o-methoxybenzoic acid, gaultherolin, salicylide Salicylic acid still has preferably selectivity.
CN201710310222.7A 2017-05-05 2017-05-05 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 Active CN107118091B (en)

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CN112759532B (en) * 2021-01-11 2023-06-06 中国人民解放军空军军医大学 Reagent for visual rapid and sensitive detection of bacillus anthracis and detection method thereof
CN113736452A (en) * 2021-09-06 2021-12-03 上海工程技术大学 Method for detecting salicylic acid by using fluorescent micrometer probe and application
CN113736452B (en) * 2021-09-06 2023-05-09 上海工程技术大学 Method for detecting salicylic acid by fluorescent micron probe and application

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