CN102735662B - High sensitivity and high selectivity fluorescence emission spectrum analysis method for zinc ions - Google Patents
High sensitivity and high selectivity fluorescence emission spectrum analysis method for zinc ions Download PDFInfo
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- CN102735662B CN102735662B CN201210202304.7A CN201210202304A CN102735662B CN 102735662 B CN102735662 B CN 102735662B CN 201210202304 A CN201210202304 A CN 201210202304A CN 102735662 B CN102735662 B CN 102735662B
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Abstract
The present invention provides a fluorescence spectrum analysis method for detecting zinc ions by adopting a compound di[(1-hydroxy-2-naphthyl)- methenyl]hydrazone as a probe. According to the method, a Tris-HCl buffer solution is adopted to adjust the pH value to 8 in a DMF/H2O mixing solution with a strictly-controlled H2O content of 10%, the compound di[(1-hydroxy-2-naphthyl)- methenyl]hydrazone is adopted as a fluorescent coloring agent for detecting Zn<2+>, and the fluorescence intensity of the solution can be measured to determine the Zn<2+> content in the solution. According to the present invention, the specific media condition is designed, such that the compound is adopted as the fluorescence enhancing probe for detecting zinc ions so as to perform identification detection on zinc ions in different samples.
Description
Technical field
The fluorescence emission Zymography of a kind of zinc ion of the present invention, belongs to analytical chemistry field.
background technology:
In molecular recognition field, the fluorescence probe with molecular device character by with target substance selectivity bonding, make to change in conjunction with the parameter such as fluorescence enhancing or quencher, fluorescence polarization, wavelength and peak shape, fluorescence lifetime of front and back, the effect of microscopic fields is showed by optical information, thereby the original position realizing on molecular level detects in real time, reaches the effective identification to metallic ion, organic molecule, biomolecule etc.Utilize probe molecule and non-fluorescence or hypofluorescence material to be combined and to form fluorescigenic complex, supermolecule or aggregation and measure with covalency or other forms, be i.e. so-called " fluorescence probe " technology.Due to the highly sensitive and high selectivity of fluorescence analysis, real-time in-situ detects, equipment is simple, and abundant spectral information can be provided, in the fields such as analytical chemistry, biological chemistry, environmental science, medicine and pharmacology, the aspect such as various ion detection, protein molecular marker, DNA and cell detection, immunoassay plays an important role.
Organic fluorescence probe, taking fluorescein, rhodamine, acridine, Coumarins as main representative, has fluorescence quantum yield high, and excitation wavelength is long, and the scope of application is wide.Wherein, can detect Hg
2+, Cu
2+, Pb
2+, Cr
3+, Fe
3+isoionic fluorescence strengthens or the existing a large amount of reports of quencher type rhodamine probe.Aromatics is often used as the fluorescence signal generation group of organic fluorescence probe.There is strong and stable fluorescence taking naphthalene, anthracene, pyrene, quinoline, cyanines class, pyrroles's methine class etc. as the condensed-nuclei aromatics of main representative, Stokes shift is large, in fluorescence probe field, as model fluorophore, constructed fluorescence probe is the sensor of a class function admirable.For example, the calixarenes taking naphthalene as fluorophor, the isostructural fluorescence probe of tripod, show Zn
2+, Hg
2+, Cu
2+isoionic identification, quinazoline are as Co
2+the research of ion fluorescence quencher type probe also has report.
Zinc is one of necessary trace element of human body, is distributed in widely in the cell and body fluid of human body.In transition metal ion, its content is only second to ferric ion, closely related with health.Need to set up trace Zn in fields such as plant, food medicine are clinical
2+detection method.
Trace metal ion is had a wide range of applications to field in the property detection and Identification research in the fields such as living things system, physiology course, environment and food security.Discovery is different from traditional organic fluorescent dye molecule, makes that its sample preparation is simple, assay method is quick, testing cost is cheap, and it is significant to detect respectively the fluorescence probe of many kinds of metal ions, superior performance simultaneously.Trace zinc detection method has the methods such as atomic absorption spectrography (AAS), atomic emission spectrometry, inductively coupled plasma, mass spectroscopy, UV-VIS spectrophotometry, fluorescence method.Fluorescent spectrometry, due to simple to operate, does not need expensive instrument and equipment, has more using value.But due to most developer poorly water-soluble, needing could be for detection of through the complicated pre-service such as extraction, separation, and crucial problem is that sensitivity and the selectivity of detection can not meet more and more higher demand.Fluorescence signal has unrivaled superiority in sensitivity, uses at present fluorescent method to detect the relevant report of zinc ion content also little, finds new for Zn
2+there is the fluorescence probe of sufficiently high selectivity and sensitivity to have challenge and using value.The present inventor finds compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone in research process, at DMF/H
2in the mixed solvent of O (V/V, 9/1), on fluorospectrophotometer, taking 438nm as excitation wavelength, 516nm is fluorescent emission wavelength, is having Zn
2+while existence, can make the fluorescence of probe compound strengthen, at Zn
2+within the scope of finite concentration, Zn
2+concentration is directly proportional to fluorescent emission intensity, and not interference measurement of common coexistent metallic ion, has high sensitivity and high selectivity, for the fluorescence emission Zymography of a kind of zinc ion of the present invention is laid a good foundation.
summary of the invention:
The object of the invention is to use fluorescence spectrophotometry method, quantitatively detect sample zinc ion content, create a kind of new for Zn
2+concentration has the fluorescence emission spectrum quantitative analysis method of sufficiently high selectivity and sensitivity.
The fluorescence emission spectral analysis method of a kind of zinc ion of the present invention, it is characterized in that taking compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone as probe, adopt fluorescence emission spectrum standard measure to measure the concentration of zinc ion, the chemical structural formula of compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone is
Molecular formula C
22h
16n
2o
2english name is Bis (1-hydroxy-2-naphthyl)-methylene hydrazone, fluorescence emission spectrum quantitative analysis method adopts standard calibration curve method: a peek 10.0ml volumetric flask, in each volumetric flask, adding successively concentration is 0.10 mmolL
-1probe compound solution 1ml, Tris-HCl damping fluid 1ml, pH～8.Then in each volumetric flask, add the Zn of variable concentrations
2+standard solution, adds sample liquid in one of them volumetric flask, finally uses DMF and H
2the mixed liquor constant volume of O, to 10.0ml, shakes up, and 25 DEG C of constant temperature are placed half an hour, and on fluorospectrophotometer, taking 438nm as excitation wavelength, 516nm is fluorescent emission wavelength, measures fluorescent emission intensity, draws fluorescence intensity to standard Zn
2+the calibration curve of concentration, the fluorescent emission intensity of solution per sample, utilizes calibration curve to try to achieve Zn in sample solution
2+concentration, calculation sample content, Zn in standard solution
2+concentration is 8.00 × 10
-6～2.00 × 10
-4molL
-1in scope, Zn
2+fluorescence probe emissive porwer is strengthened linear; Other coexisting ion comprises that alkaline metal, earth alkali metal, transition metal, heavy metal, rare earth ion are at concentration and Zn
2+when concentration is identical, the impact of the fluorescence intensity that zinc ion is detected is lower than 5%.DMF chemical name is DMF, and molecular formula is HCON (CH
3)
2, be common organic solvent.DMF and H
2the volume ratio of the mixed solution of O is 9:1, and the probe compound solution of indication is the DMF solution of two [(1-hydroxyl-2-naphthyl)-methine] hydrazone; Indication Tris is trishydroxymethylaminomethane.The present invention is equally applicable to standard addition method: get 6 10.0ml volumetric flasks, in each volumetric flask, adding successively sample solution 1ml, concentration is 0.10 mmolL
-1probe compound solution 1ml, Tris-HCl damping fluid 1ml, pH～8.Then in first volumetric flask, do not add Zn
2+standard solution, adds the Zn of same concentrations different volumes successively in all the other each volumetric flasks
2+standard solution, finally uses DMF and H
2the mixed liquor constant volume of O, to 10.0ml, shakes up, and 25 DEG C of constant temperature are placed half an hour, and on fluorospectrophotometer, taking 438nm as excitation wavelength, 516nm is emission wavelength sequentially determining fluorescence intensity, draws fluorescence intensity to adding Zn
2+the volume calibration curve of standard solution, according to straight-line extrapolation to ordinate be zero with horizontal ordinate intersection, can try to achieve Zn in sample solution
2+concentration, calculation sample content.
Above-mentioned is that the compound method of various reagent is:
(1) compound method of probe compound solution: take two [(1-hydroxyl-2-naphthyl)-methine] hydrazone of 3.4 mg, with DMF dissolving, be mixed with 100mL solution, concentration is 0.100 mmolL
-1;
(2) Zn
2+standard solution: take the pure ZnCl of top grade
227.2 mg, with DMF dissolving, and are mixed with 100mL solution, Zn
2+concentration is 2.00 × 10
-3molL
-1; Arrive suitable concentration with DMF stepwise dilution as required;
(3) Tris-HCl buffer preparation: take 0.242 g Tris DMF and dissolve, being mixed with 500 mL concentration is 0.004 molL
-1solution, pipette certain volume Tris and mix mutually with appropriate HCl, regulate pH value to 8.
(4) preparation of other coexisting ion solution: get nitrate or the hydrochloride of the various metals that top grade is pure, dissolve with DMF, and to be mixed with concentration be 2.00 × 10
-3molL
-1dMF solution.
The above-mentioned analytical approach of the present invention is in the time of got volume change, and various solution additions will be done corresponding variation in proportion.
When the present invention measures zinc ion, coexisting ion Na
+, K
+, Rb
+, Mg
2+, Ca
2+, Sr
2+, Ba
2+, Pb
2+, Bi
2+, Mn
2+, Ni
2+, Cu
2+, Cd
2+, Hg
2+, Al
3+, Fe
3+, Sc
3+, Ti
3+, Cr
3+and Co
2+, at concentration and Zn
2+quite time, to Zn
2+the relative deviation of the fluorescence intensity impact detecting is all in 5%.All interference measurements not.
The inventive method reagent used is analytical reagent, and water used is redistilled water.
Instrument of the present invention is fluorospectrophotometer, and model is Cary Eclipse fluorospectrophotometer, and VARIAN company of the U.S. produces.
The inventive method have large Stokes displacement, high selectivity, detectability extremely low, do not need to separate, the response time is fast, approach the advantages such as neutral test condition.Zn is detected in the field such as (contaminant water), Pharmaceutical Analysis (zinc supplemental treatment medicament), Food Inspection (containing zinc beverage) of can monitoring for Environmental Water
2+content.
Utilize compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone molecule at optimum solvent (DMF/H
2o, V/V, 9/1) in present hypofluorescence, can form the complex of determining coordination ratio with metallic zinc ion under given conditions.Gordian technique in patent of the present invention is to control different DMF/H
2o mixed solvent ratio and certain pH value, just can make compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone become and detect Zn
2+the fluorescence enhancement mode probe of ion.Operation and control method are easy, and unique properties, is the practical application of this organic molecule as fluorescence probe.
brief description of the drawings:
Fig. 1 compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone (10 μ M, DMF/H
2o, V:V=9:1, Tris-HCl, pH～8) detect the fluorescence spectrum of identification zinc ion (200 μ M), other metallic ion (200 μ M): Na
+, K
+, Rb
+, Mg
2+, Ca
2+, Sr
2+, Ba
2+, Pb
2+, Bi
2+, Mn
2+, Ni
2+, Cu
2+, Cd
2+, Hg
2+, Al
3+, Fe
3+, Sc
3+, Ti
3+, Cr
3+and Co
2+interference measurement not in error range, controls pH value of solution as we know from the figure at 8 left and right, DMF/H
2o mixed solvent volume ratio is 9:1, and the fluorescence intensity of probe compound is very weak, with this understanding, adds Zn
2+ion, can make the very hyperfluorescenceZeng Yongminggaoyingguang of probe compound solution in the transmitting of 516nm wavelength place, and other experiment metallic ion comprises Co
2+ion all can not make its fluorescence significantly strengthen.
Fig. 2 compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone is probe in detecting Zn
2+time coexistent metallic ion fluorescence intensity.White: probe; Or probe+metallic ion; Black: probe+Zn
2++ metallic ion.Probe compound is at the DMF/H of pH 8 as we know from the figure
2o(V/V, 9:1) in medium, fluorescent emission very weak (left 1 white bars in figure), adds after other experiment coexisting ion still very weakly to fluorescence probe, to its intensity effect little (in figure from left 3 to 20, the white bars that metallic ion is corresponding), adds Zn
2+after make fluorescence probe significantly strengthen (left 2 white bars in figure), probe and have cobalt ions exist solution in add other metallic ion after on zinc ion make fluorescence probe strengthen impact (black bar in figure) in error range.
Fig. 3 detects Zn
2+calibration curve.Ordinate represents fluorescence intensity, and horizontal ordinate represents the Zn adding
2+concentration of standard solution.
In Fig. 4 lake water sample, detect Zn
2+fluorescence spectrum.In sample liquid, add successively the Zn of different amounts by standard addition method
2+the spectrogram that standard solution records.
Zn in Fig. 5 zinc gluconate sample
2+the fluorescence spectrum of content detection.Press the spectrogram of twice sample of calibration curve replicate determination.
specific implementation method
Embodiment 1: pollute Zn in lake water
2+content detection.
1. lake water sample pre-treatments: get and pollute lake water sample 2.0 L, boil 10 minutes, cooling, leave standstill and place 12 hours, filter, detect water sample pH value.Simmer down to 10ml, cooling for subsequent use.
2. detect: pipette the lake water sample of the treated mistake of 1mL in 10mL volumetric flask, add 1 mL probe compound (10 μ M, DMF), 1 mL Tris-HCl, adds 0,1,2 mL Zn successively
2+(10 μ M), with moisture 10% DMF/H
2o mixed liquor constant volume, 25 DEG C of constant temperature are placed half an hour.Replicate determination 3 times.
3. the spectrogram of measuring is shown in accompanying drawing 4, calculates and the results are shown in Table 1 according to standard addition method.
In table 1 lake water sample, detect Zn
2+
Embodiment 2: zinc-content determination in commercially available zinc gluconate.
Content to zinc in certain brand buccal zinc gluconate tablets detects:
1, pre-treatment: get a slice zinc gluconate 32mg (in zinc 0.32mg) and grind to form powdery, be dissolved in 100mL volumetric flask.Be placed in ultrasound wave and shake 30 minutes, then leave standstill after 2 hours, get supernatant liquor.
2, testing process: add 1 mL probe compound (10 μ M, DMF), add 1 mL Tris-HCl(pH=8), pipette the above-mentioned sample product 1mL of institute in 10mL volumetric flask, with moisture 10% DMF/H
2o mixed liquor constant volume.25 DEG C of constant temperature are placed half an hour, measure its fluorescence intensity at 514nm place.Replicate determination 2 times.
3, the spectrogram of measuring is shown in accompanying drawing 5, calculates following result, in table 2 according to experiment gained calibration curve.
Claims (6)
1. the fluorescence emission Zymography of a zinc ion, it is characterized in that taking compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone as probe, adopt fluorescence emission spectrum standard measure to measure zinc ion concentration, the chemical structural formula of compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone is
Molecular formula C
22h
16n
2o
2english name is Bis (1-hydroxy-2-naphthyl)-methylene hydrazone, fluorescence emission spectrum quantitative analysis method adopts standard calibration curve method: a peek 10.0ml volumetric flask, in each volumetric flask, adding successively concentration is 0.10mmolL
-1probe compound solution 1ml, Tris-HCl damping fluid 1ml, pH～8 then add the Zn of variable concentrations in each volumetric flask
2+standard solution, adds sample solution in one of them volumetric flask, finally uses DMF and H
2the mixed liquor constant volume of O, to 10.0ml, shakes up, and 25 DEG C of constant temperature are placed half an hour, and on fluorospectrophotometer, taking 438nm as excitation wavelength, 516nm is fluorescent emission wavelength, and sequentially determining fluorescent emission intensity is drawn fluorescent emission intensity to standard Zn
2+the calibration curve of concentration, the fluorescent emission intensity of solution per sample, utilizes calibration curve to try to achieve Zn in sample solution
2+concentration, calculation sample content, Zn in standard solution
2+concentration is 8.00 × 10
-6～2.00 × 10
-4molL
-1in scope, Zn
2+fluorescence probe emissive porwer is strengthened in linear relation; Other coexisting ion comprises that alkaline metal, earth alkali metal, transition metal, heavy metal, rare earth ion are at concentration and Zn
2+when concentration is identical, to Zn
2+the relative deviation of the fluorescent emission intensity impact detecting is all in 5%, and DMF chemical name is DMF, and molecular formula is HCON (CH
3)
2, be conventional organic solvent, DMF and H
2the volume ratio of O mixed liquor is 9: 1, and the probe compound solution of indication is the DMF solution of two [(1-hydroxyl-2-naphthyl)-methine] hydrazone; Indication Tris is trishydroxymethylaminomethane.
2. the fluorescence emission Zymography of a zinc ion, it is characterized in that taking compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone as probe, adopt fluorescence emission spectrum standard measure to measure zinc ion concentration, the chemical structural formula of compound two [(1-hydroxyl-2-naphthyl)-methine] hydrazone is
Molecular formula C
22h
16n
2o
2english name is Bis (1-hydroxy-2-naphthyl)-methylene hydrazone, fluorescence emission spectrum quantitative analysis method adopts standard addition method to be: get 6 10.0ml volumetric flasks, in each volumetric flask, adding successively sample solution 1ml, concentration is 0.10mmolL
-1probe compound solution 1ml, Tris-HCl damping fluid 1ml, pH～8 then do not add Zn in first volumetric flask
2+standard solution, adds the Zn of same concentrations different volumes successively in all the other each volumetric flasks
2+standard solution, finally uses DMF and H
2the mixed liquor constant volume of O, to 10.0ml, shakes up, and 25 DEG C of constant temperature are placed half an hour, and on fluorospectrophotometer, taking 438nm as excitation wavelength, 516nm is emission wavelength sequentially determining fluorescent emission intensity, draws fluorescent emission intensity to adding Zn
2+the volume calibration curve of standard solution, according to straight-line extrapolation to ordinate be zero with horizontal ordinate intersection, can try to achieve Zn in sample solution
2+concentration, calculation sample content.
3. the fluorescence emission Zymography of a kind of zinc ion according to claim 1 and 2, is characterized in that the compound method of various reagent is:
(1) compound method of probe compound solution: take two [(1-hydroxyl-2-naphthyl)-methine] hydrazone of 3.4mg, with DMF dissolving, be mixed with 100mL solution, concentration is 0.100mmolL
-1;
(2) Zn
2+standard solution: take the pure ZnCl of top grade
227.2mg, with DMF dissolving, and is mixed with 100mL solution, Zn
2+concentration is 2.00 × 10
-3molL
-1; Arrive suitable concentration with DMF stepwise dilution as required;
(3) Tris-HCl buffer preparation: take 0.242g Tris DMF and dissolve, being mixed with 500mL concentration is 0.004molL
-1solution, pipette certain volume Tris and mix mutually with appropriate HCl, regulate pH value to 8;
(4) preparation of other coexisting ion solution: get nitrate or the hydrochloride of the various metals that top grade is pure, dissolve with DMF, and to be mixed with concentration be 2.00 × 10
-3molL
-1dMF solution.
4. the fluorescence emission Zymography of a kind of zinc ion according to claim 1 and 2, while it is characterized in that measuring zinc ion, other coexisting ion comprises: Na
+, K
+, Rb
+, Mg
2+, Ca
2+, Sr
2+, Ba
2+, pb
2+, Bi
2+, Mn
2+, Ni
2+, Cu
2+, Cd
2+, Hg
2+, Al
3+, Fe
3+, Sc
3+, Ti
3+, Cr
3+and Co
2+, at concentration and Zn
2+quite time, all interference measurements not.
5. the fluorescence emission Zymography of a kind of zinc ion according to claim 1, is characterized in that reagent used is analytical reagent, and institute's water is redistilled water.
6. the fluorescence emission Zymography of a kind of zinc ion according to claim 1, it is characterized in that analyzing instrument used is fluorospectrophotometer.
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| CN103822905B (en) * | 2014-01-17 | 2016-04-27 | 西北师范大学 | 1-naphthalene-3,4,5-tri-(hexadecane oxygen base) benzoyl hydrazone is as the application of sensor in fluorescence identifying silver ion |
| CN104122222B (en) * | 2014-08-07 | 2017-02-08 | 贵州大学 | Absorption spectrum analytical method for detecting ultraviolet ratio of micro-amount Zn＜2+＞or F＜-＞ |
| CN104122243B (en) * | 2014-08-07 | 2017-01-18 | 贵州大学 | Fluorescent spectrum analysis method for detecting trace Zn＜2+＞ and F＜-＞ or AcO＜-＞ |
| CN104198449B (en) * | 2014-08-08 | 2016-08-17 | 贵州大学 | A kind of fluorescent probe method for living cells imaging |
| CN105044061A (en) * | 2015-07-25 | 2015-11-11 | 渤海大学 | High-selectivity method for detecting p-phenylenediamine in aqueous solution |
| CN106770124B (en) * | 2017-01-05 | 2019-06-11 | 昆明理工大学 | It is a kind of for detecting the fluorescent optical sensor and preparation method of zinc ion |
| CN106883846B (en) * | 2017-04-14 | 2019-03-19 | 周口师范学院 | A kind of absolutely water-soluble zinc ion fluorescent, preparation method and applications |
| CN113125365B (en) * | 2021-04-16 | 2022-05-13 | 中国科学院生态环境研究中心 | Device and method for quantitatively identifying nano zinc oxide and zinc ions in solution |
| CN114136943B (en) * | 2021-11-30 | 2024-01-05 | 厦门大学 | Fluorescent analysis method for measuring lithium ions by taking empty phthalocyanine as molecular probe |
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| JPH10232205A (en) * | 1997-02-19 | 1998-09-02 | Shinotesuto:Kk | Method and reagent for measuring zinc ion |
| CN1715919A (en) * | 2005-07-12 | 2006-01-04 | 大连理工大学 | Fluoroboric dye fluorescent probe for cell zinc ion detection |
| KR100954585B1 (en) * | 2008-05-13 | 2010-04-26 | 고려대학교 산학협력단 | Two photon probe for real time monitoring of intracellular free zinc ions, method for preparing the same and method for real time monitoring of intracellular free zinc ions |
| CN101914375B (en) * | 2010-05-25 | 2013-04-24 | 郑州大学 | Molecular fluorescent switch for detecting intracellular zinc ions and application thereof |
| CN102229800B (en) * | 2011-04-26 | 2013-09-04 | 山东大学 | Pyrazoline derivative Zn<2+> fluorescence probe and its application |
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