CN110128394A - A kind of fluorescent chemicals and its application for the detection of underwater gold category ion concentration - Google Patents
A kind of fluorescent chemicals and its application for the detection of underwater gold category ion concentration Download PDFInfo
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- CN110128394A CN110128394A CN201910236421.7A CN201910236421A CN110128394A CN 110128394 A CN110128394 A CN 110128394A CN 201910236421 A CN201910236421 A CN 201910236421A CN 110128394 A CN110128394 A CN 110128394A
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
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- 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"
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- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract
The invention discloses a kind of fluorescence probes for the detection of underwater gold category ion concentration, the compound is fit using N- acetate o-aminoanisole as metal ion network, rhodamine fluorophor is introduced in the molecule thereof, generates the fluorescence indicator of metal ion especially zinc ion.The compound of the present invention can also be applied to cell in-situ and be imaged.It can be suitable for the continuous detection of the concentration of metal ions various environment, especially to the METHOD FOR CONTINUOUS DETERMINATION of zinc ion concentration in water.
Description
Technical field
The invention belongs to organic compound field more particularly to it is a kind of can be used for underwater gold category ion concentration detection it is organic
Compound and its related application.
Background technique
Water is Source of life and the mankind and the material base that all living things are depended on for existence.As China's economic development is fast
Speed, people excessively rely on the investment of water resource, the waste of great lot of water resources and water pollution and domestic water anxiety etc. occur.
The especially diversification of social progress and industrial development, complicated pollutant cause water pollution situation to be aggravated.Face water resource
There is a serious shortage of and pollution, we must establish and practice the theory that blue montains and green waters is exactly Kingsoft Yin Shan, adhere to green harmonious development,
Adhere to sustainable use water resource, more stringent requirements are proposed to water quality detection and control.Zinc is needed by human micro
One of element plays extremely important work in the important physiology courses such as growth in humans's development, reproduction heredity, immune, endocrine
With [1].Zinc is that content is most in brain, maintains microelement necessary to the normal function of brain, and the content of zinc need to remain certain
It is excessive or very few can all cause disease in normal range (NR).Drinking water is after by zinc pollution, it is possible to excessive zinc be caused to enter
Human body.Zinacalism mainly with nausea, have a stomach upset as cardinal symptom, can also cause immunologic hypofunction, reduce high density
Or low density lipoprotein cholesterol, reduce ceruloplasmin ferroxidase activity, eventually lead to atherosclerosis, hypertension,
Coronary heart disease etc..When Zn content is 1mgL in water-1When, there is slight inhibiting effect to aqueous bio oxidation process；Zinc content exists
3mg·L-1~5mgL-1When, milky can be presented in water after boiling, and one layer of grease-like film occur after placing a period of time；
Zinc content is more than 5mgL-1When, there is bitter taste in water.
Therefore, detecting heavy metal research in water becomes an important scientific research task in field of scientific study.Water at present
In the method for quality detection metal ion, most widely used method has inductive coupling plasma emission spectrum method, flow injection point
Analysis and electrochemical process etc. [2].But instrument needed for above-mentioned test method is valuable, and detects time-consuming, step complexity, it is strongly professional,
The method of fluorescence sense detection metal ion chooses with it, high sensitivity, it is easy to detect quick the advantages that cause people wide
General concern and great interest, and biggish development has been obtained in recent years.Fluorescent optical sensor ion detection possesses numerous advantages,
It is expected to substitute previously described conventional method.For example, test process is efficient and convenient, and cheap, " naked eye " Visual retrieval, choosing
Selecting property is good, high sensitivity, and molecular structure is easy to modify optimization.
Summary of the invention
For the above-mentioned and other defect of the prior art, present inventor passes through a large amount of creative research work,
It has invented that a kind of high-efficient, sensitivity is good and favorable reproducibility contains for heavy metal ion such as metal ion especially zinc in water
The organic compound of detection is measured, which introduces fluorophor, can be made into water and detects the fluorescence probe of metal ion, is applicable in
In the continuous detection of water environment and the intracorporal concentration of metal ions of biology.
To realize that above-mentioned and other purposes, the present invention provide the following technical solutions.
In first aspect present invention, a kind of fluorescence organic compound object for the detection of underwater gold category ion concentration, institute are provided
Stating compound includes substituted or unsubstituted N- acetate o-aminoanisole as metal ion network zoarium, and in N- acetate
The contraposition of o-aminoanisole introduces rhodamine fluorophor.
The compound has the following structure formula:
In a kind of preferred embodiment, the metal ion that can be detected with the compounds of this invention be selected from the metals such as zinc ion from
Son.
In second aspect of the present invention, application of the compounds of this invention in water in metal ion content detection is provided.It is a kind of
In preferred embodiment, the metal ion is selected from zinc ion.It is described to be detected as fluorescence inspection in another preferred embodiment
It surveys, it is continuous to detect.
Organic compound of the invention has following technical advantage outstanding as metal ion probe:
1, the present invention can prepare a system by introducing rhodamine fluorophor in N- acetate o-aminoanisole
Column metal ion (especially zinc ion) fluorescence indicator.When metal ion content changes, fluorescence intensity, can be from change
Its fluorescence intensity calculates the content of metal ion in solution.
2, also using fluorescence imaging, probe application of the invention is detected in zinc ion in cell, is applied to organism
The analysis of interior trace metal ion content, realizes noninvasive in situ detection.
Detailed description of the invention
Fig. 1 is the reaction route that the present invention prepares fluorescent type metal ion probe.
Fig. 2 is the schematic diagram that zinc ion of the present invention detects that zinc ion is complexed in fluorescence probe.
Fig. 3 is fluorescence spectra of the metal ion detection fluorescence probe of the present invention to different ions.
Fig. 4 is fluorescence intensity column diagram of the metal ion detection fluorescence probe of the present invention to different ions.
Fig. 5 is the fluorescence emission spectrogram of compound that zinc ion of the present invention detects that various concentration zinc ion is complexed in fluorescence probe.
Fig. 6 is the fluorescence spectra that zinc ion of the present invention detects that zinc ion is complexed in fluorescence probe.
Fig. 7 is that zinc ion fluorescent of the present invention detects intracellular zinc ion and its in situ imaging.
Specific embodiment
By the present invention in that various metals ion can be complexed, so as to be used for N- acetate o-aminoanisole structure
Realize the analysis of micro ion content.The metal that applicant can be complexed the compounds of this invention structure in long-term R&D process
Ion has carried out extensive detection, finds it to Ca2+、Cd2+、 Co2+、Cr3+、Cu2+、Fe2+、Fe3+、Hg2+、K+、Mg2+、Mn2+、Na+、Ni2+、Pb2+、Zn2+And lanthanide metal ion etc. all has certain binding ability, among this, especially has to zinc ion
There is preferable complexing power, there is the complexing power of significant specific binding to zinc ion, can be used as the effective of zinc ion
Carrier.Fluorophor is introduced by the contraposition in above-mentioned aniline structure, photic photoinduced electron principle of transfer is based on, works as ion concentration
When change, fluorescence intensity is changed correspondingly, and the content of effects of ion thus can be calculated from fluorescence intensity.
It may include substituted or unsubstituted N- acetate o-aminoanisole structure in the compounds of this invention.Art technology
Which personnel's determination of being not difficult can carry out and replace without influencing the compounds of this invention complexation of metal ions and showing the ability of fluorescence.
The continuous detection to ion concentration can be achieved using fluorescence intensity change, especially to the inspection of zinc ion concentration
It surveys.Fluorophor commonly used in the art is used equally for the present invention.
It is introduced after fluorophor in ionophore of the invention, a series of molecules generated can be outstanding to metal ion
It is that zinc ion generates fluorescence response.Such molecule can generate the glimmering of varying strength in the sample of different zinc ion concentrations
Light can be detected with sepectrophotofluorometer.Applicant confirms said effect in an experiment, fluorescence intensity in sample zinc from
The increase of sub- concentration and increase, increasing degree can be up to more than ten times.
Since binding ability of the chelation structure for different metal ions is variant, it is contemplated that actual detection application needs
It wants, the most suitable test object of organic compound of the invention is zinc ion；Also other metal ions be can detect, including but unlimited
In Ca2+、Co2+、Cr3+、Cu2+、Fe2+、Fe3+、 K+、Mg2+、Mn2+、Na+、Ni2+、Zn2+, it is used especially for scientific research purposes.
Attached drawing 1 shows the synthesis road of ion carrier compound and fluorescence indicator of the present invention by taking particular compound as an example
Line.It should be noted that being used herein as particular compound only for the purpose for facilitating understanding, those skilled in the art can basis
The synthetic route of these particular compounds carries out necessary change to prepare other ion carrier compounds for use in the present invention
And indicator.
With reference to shown in attached drawing 1, it is shown that a kind of preferred molecular structure (also referred to as zinc ionophoric) i.e. N- of the invention
The synthetic route of acetate o-aminoanisole and zinc ion fluorescent.
This specification illustrates the present invention above in conjunction with specific embodiment, it should be appreciated that these description and
Explaination is intended merely to more fully understand the present invention, without constituting to any restriction of the invention.Those skilled in the art are reading
Necessary change can be carried out after present specification to a specific embodiment of the invention without departing from spirit of the invention
And range.Protection scope of the present invention is limited by the accompanying claims, and covers the equivalents of claim.
The present invention is further detailed below with reference to embodiment.In the following embodiments, specificization is provided
Object structure is closed to illustrate the structure type of the compounds of this invention, preparation method and its inspection as zinc ion concentration detection probe
Survey performance.Provided embodiment is merely to illustrate how the present invention can be implemented, and does not constitute and is particularly limited to.It is special with this field
The those skilled in the art of industry knowledge can be drawn inferences about other cases from one instance by following lifted specific example, prepare metal ion especially zinc
A series of color developing agents and fluorescence indicator of ion.
Unless separately there is other explanations in the application context, otherwise technical term use herein and abbreviation all have this
Conventional sense known to the technical staff of field；Unless otherwise stated, raw materials used compound is quotient in following embodiments
Purchase obtains.
The various compounds that the present invention is previously mentioned are prepared according to reaction process described in Fig. 1, the reaction of each step
Specific step is as follows:
The synthesis of compound 2: respectively by compound 1 (12.3g, 100mmol), bromoacetate (66.8g, 400mmol),
Potassium carbonate (55.2g, 400mmol), n,N-Dimethylformamide (DMF) 100ml are added in the there-necked flask of 500ml.In control
Temperature is 150 DEG C, after reacting 18h, the detection of TLC (PE: EA=9: 1) contact plate, and raw material fully reacting.Stop reacting, cooling down,
Suitable quantity of water and methylene chloride are added into there-necked flask, is completely dissolved solid, is transferred to separatory funnel, extracts three times, receives repeatedly
Collect organic phase, anhydrous sodium sulfate is dry, was spin-dried for column and obtains product 9.2g.
The synthesis of compound 3: under ice bath, respectively by compound 2 (9.1g, 30.8mmol), n,N-Dimethylformamide
(DMF) 15ml is added in 100mL there-necked flask, and phosphorus oxychloride (10ml, 107.3mmol) is added dropwise dropwise, goes to after being added dropwise
Overnight, TLC (PE: EA=4: 1) detection, raw material reacts completely for room temperature reaction.Reaction solution is slowly poured into 1: 1 ice water mixed liquor
200ml adds sodium bicarbonate to adjust pH 8-9, is extracted water phase three times with ethyl acetate, anhydrous sodium sulfate is dry, is spin-dried for, obtains
Product (Off-white solid) 8.5g.
The synthesis of compound 4: respectively by compound 3 (0.2g, 0.62mmol) and 3- hydroxy-n, N- diethylaniline
(0.31g, 1.86mmol), 10mL propionic acid, 20mg p-methyl benzenesulfonic acid sulfuric monohydrate are added to 50mL single necked round bottom flask
In, 60 DEG C are stirred overnight, TLC (PE: EA=4: 1) detection, raw material fully reacting.10mL I grades of water is added into reaction solution, uses
It is 6-7 that sodium bicarbonate, which adjusts pH value,, above-mentioned aqueous solution is extracted with 10mL methylene chloride, anhydrous sodium sulfate is dry, is spin-dried for, must produce
Product.
The synthesis of compound 5: crude Compound 7 (100mg) is used acetic acid: toluene=1: the mixed liquor of 1 total 2mL dissolves,
Gradually by the acetic acid of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 100mg): toluene=1: the mixing drop of 1, total 2ml
It is added in above-mentioned reaction solution, room temperature reaction 3h, TLC (chloroform: methanol=9: 1) contact plate detection raw material reacts completely, is spin-dried for solvent,
Solids is obtained, solid is dissolved with methylene chloride, plate separation is prepared, obtains target compound.
The synthesis of Sensor Zn: 13mg compound 5 is dissolved in 1mL methanol, and 40 DEG C of NaOH solution 2mL hydrolysis, TLC is added
(DCM: MeOH=5: 1) after detecting fully reacting, it is directly used in the property response experiment test of next step.
The present invention is by N- acetate o-aminoanisole fluorophor, so that the molecule is when with complexing of metal ion
The variation for generating fluorescence intensity, to realize trace metal ion automatic detection.The molecule with it is glimmering after complexing of metal ion
The variation of luminous intensity and the concentration of metal ion in solution are directly related, thus can be calculated according to the fluorescence intensity of the molecule
The content of metal ion in solution realizes the quick and precisely detection to metal ion content.
Fig. 3 and Fig. 4 shows zinc ionophoric to the fluorescence emission spectrum and its histogram of different ions.
Fig. 5 shows the zinc ion solution that various concentration is added, and the concentration titrations fluorescence intensity of Sensor Zn responds variation
Curve is gradually increased with zinc ion concentration is added, and the fluorescence of Sensor Zn gradually increases, and takes at maximum emission wavelength 550nm
It is as shown in Figure 6 that corresponding fluorescence intensity response variation relative value does concentration titrations curve to zinc ion concentration.Fig. 7 be the zinc from
Sub- fluorescence probe is successfully applied to zinc ion in cell in situ imaging.Those skilled in the art can be provided according to this specification
Thinking and synthetic method, prepare the zinc ion indicator with complexing power, it will not go into details herein.
In summary experimental result is it is found that organic compound of the invention has good sound for the increase of zinc ion concentration
It answers, in the very low sample of no zinc ion or zinc ion content, fluorescence is very weak, or almost without fluorescence.
Bibliography:
[1] Hou Zhenjiang, Zhang Zongying, Li Yueqiu, trace elements and health research, 2002,19 (4), 65.
[2] it is old just, Wang Binbin, scientific and technical innovation and application, 2016,5,155.
[3] Huarui He, Kenneth Jenkins, Chao Lin, A fluorescent chemosensor for
Calcium with excellent storage stability in water.Anal.Chim.Acta, 2008,611,
197-204.
Claims (6)
1. a kind of fluorescence probe for the detection of underwater gold category ion concentration, the compound includes substituted or unsubstituted N- second
Acidic group o-aminoanisole introduces rhodamine fluorophor as metal ion network zoarium, and in the contraposition of its molecule.
2. organic compound according to claim 1, it is characterised in that the compound has the following structure formula:
3. fluorescence probe described in any one of claims 1 to 2 in water metal ion content detection in application.
4. application according to claim 3, it is characterised in that the metal ion is selected from heavy metal zinc ion.
5. application according to claim 4, it is characterised in that it is described to be detected as fluorescence detection, it is continuous to detect.
6. application according to claim 4, it is characterised in that the detection can be applied to cell fluorescence image checking.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111533724A (en) * | 2020-05-28 | 2020-08-14 | 浙江昂拓莱司生物技术有限公司 | His-tag fluorescent probe with near-infrared property and preparation and application thereof |
| CN114315784A (en) * | 2021-11-30 | 2022-04-12 | 浙江工业大学 | Histidine-labeled fluorescent probe and preparation method and application thereof |
| CN115215878A (en) * | 2022-07-08 | 2022-10-21 | 中国科学院理化技术研究所 | Fluorescent probe for detecting millimole free calcium ions and synthetic method thereof |
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| CN108314650A (en) * | 2018-03-15 | 2018-07-24 | 天津农学院 | It is a kind of to be used for the organic compound and application that metal ion content detects in urine |
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Patent Citations (1)
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| CN108314650A (en) * | 2018-03-15 | 2018-07-24 | 天津农学院 | It is a kind of to be used for the organic compound and application that metal ion content detects in urine |
Non-Patent Citations (2)
| Title |
|---|
| K. R. GEE ET AL.: "Measuring zinc in living cells. A new generation of sensitive and selective fluorescent probes", 《CELL CALCIUM》 * |
| 苏文崎等: "新型罗丹明类Ca2＋荧光探针的合成及光谱性能研究", 《有机化学》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111533724A (en) * | 2020-05-28 | 2020-08-14 | 浙江昂拓莱司生物技术有限公司 | His-tag fluorescent probe with near-infrared property and preparation and application thereof |
| CN111533724B (en) * | 2020-05-28 | 2021-03-05 | 浙江昂拓莱司生物技术有限公司 | His-tag fluorescent probe with near-infrared property and preparation and application thereof |
| CN114315784A (en) * | 2021-11-30 | 2022-04-12 | 浙江工业大学 | Histidine-labeled fluorescent probe and preparation method and application thereof |
| CN115215878A (en) * | 2022-07-08 | 2022-10-21 | 中国科学院理化技术研究所 | Fluorescent probe for detecting millimole free calcium ions and synthetic method thereof |
| CN115215878B (en) * | 2022-07-08 | 2024-03-01 | 中国科学院理化技术研究所 | Fluorescent probe for detecting millimole free calcium ions and synthesis method thereof |
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