CN108314650A - It is a kind of to be used for the organic compound and application that metal ion content detects in urine - Google Patents
It is a kind of to be used for the organic compound and application that metal ion content detects in urine Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- G01N21/6428—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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- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N2021/775—Indicator and selective membrane
Abstract
The invention discloses a kind of organic compounds detected for metal ion content in urine, the compound is with N, N diacetoxyls 2,5 dialkoxy aniline are as complexing of metal ion body, chromophore or fluorophor are introduced in the molecule thereof, generate the colored indicator or fluorescence indicator of metal ion especially zinc ion.The compound of the present invention can also be fixed on hydrophilic high polymers, being made using the characteristic of chromophore or fluorophor can be with nonexpondable reversible metal ion fluorescence probe, 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.
Description
Technical field
The invention belongs to organic compound field more particularly to a kind of can be used for detecting metal ion content in urine and have
Machine compound and its related application.
Background technology
Zinc is one of the essential trace elements of the human body, important in growth in humans's development, reproduction heredity, immune, endocrine etc.
It plays an important role in physiology course [1].Since Raulin in 1869 find zinc it is related with biological growth and development with
Afterwards, over more than 100 years, especially a large amount of research confirms that zinc has important physiological function, trophism in recent years, measures zinc and contains
Measurer has important clinic diagnosis meaning.Its metabolism is extremely close with the generation of certain diseases, development relationship.Therefore, zinc is being cured
It is gradually taken seriously on.
Data shows that " zinc " in human body has following physiological action：(1) promote the growth and development of human body.In growth
If budding children and adolescents lack, depauperation can be caused.When lacking serious, it will " nanism " and intelligence is caused to be sent out
It educates bad.Zinc is the key that brain cell growth, and zinc-deficiency can influence the function of brain, brain cell is made to reduce.(2) human normal food is maintained
It is intended to.Zinc-deficiency can cause the sense of taste to decline, and apocleisis, partial eclipse even different food occur.(3) it enhances human immunity.Zn-ef ficiency is immune device
Thymus development can be just effectively ensured in the nutrient of official's thymus development, only zinc amount abundance, and normal differentiation T lymphocytes promote thin
Born of the same parents' immune function.(4) promote the healing of wound and wound.Zinc supplementation agent is applied to clinical be exactly to be used for treating skin disease earliest.
(5) metabolism and the normal vision of vitamin A are influenced.Zinc clinically show as it is beneficial to eyes, exactly because zinc have promotion tie up
The effect that raw element A absorbs, the absorption of vitamin A be unable to do without zinc.Vitamin A is usually stored in liver, will when human body needs
Vitamin A is transported in blood, this process completes " to mobilize " work by " zinc ".(6) the normal production of sperm of male is maintained
Function.Zinc is largely present in male testical, participates in the entire generation of sperm, ripe and capacitation process.Once male's zinc-deficiency,
Sperm quantity reduction, vigor decline, Semen non-liquefaction are may result in, male sterility is eventually led to.Zinc-deficiency also results in green few
No secondary sex characters occurred, was unable to normal reproductive development year.(7) adjusting influences the various enzymes and receptor of physiological brain function.Zinc
Very important effect is played in the Physiological effect of various mammal brains, it is indispensable in a variety of enzymes and function of receptors are adjusted
It is few, the structure and function of nervous system is also affected, generation, the development with the spiritual aspect obstacle such as obsessive-compulsive disorder have certain
Contact.In addition the biosynthesis of zinc and DNA and RNA, protein is closely related, when zinc deficiency in human body, may cause various
Harmful effect may lead to emotional lability, suspicious, depressed, emotional stability decline and cognitive impairment.
Therefore, zinc ion detection research becomes an important scientific research task in field of scientific study.Detection zinc at present
In the method for element, most widely used method has atomic absorption spectrography (AAS) [2], colorimetric method [3], potentiometric stripping [4], dissolution
Voltammetry [5], inductive coupling plasma emission spectrum method [6], dithizone spectrophotometry [7] etc..
Due to some disadvantages (instrument is valuable, takes, and step is complicated, strongly professional) of above-mentioned test method, fluorescence sense
The method of device detection metal ion causes people's extensive concern and great interest with its unique advantage, and obtains in recent years
Larger development.Fluorescent optical sensor ion detection possesses numerous advantages, is expected to substitute previously described conventional method.Than
Such as, test process is efficient and convenient, cheap, " bore hole " Visual retrieval, and selectivity is good, and high sensitivity, molecular structure is easy to
Modification optimization.
Currently, although many zinc ion identification carriers of document report, fluorescence is utilized for the zinc ion in urine
Sensor assay has not been reported, and presently used zinc ion identification carrier is only used for unitary determination, Wu Falian
Continuous use also just cannot achieve automatic detection.
Invention content
For the above-mentioned and other defect of the prior art, present inventor by a large amount of creative research work,
It has invented that a kind of efficient, sensitivity is good and favorable reproducibility is detected for the especially zinc ion content of the metal ion in urine
Organic compound, which can be fixed on hydrophilic high polymer, can be made into nonexpondable reversible ion fluorescence and visit
Needle, the continuous detection of the ion concentration suitable for various environment.
To realize that above-mentioned and other purposes, the present invention provide the following technical solutions.
In first aspect present invention, a kind of organic compound detected for metal ion content in urine is provided, it is described
Compound include substituted or unsubstituted N, N- diacetoxyl -2,5- dialkoxy aniline as complexing of metal ion body, and
The contraposition of N, N- diacetoxyl -2,5- dialkoxy aniline introduces chromophore or fluorophor.
In a kind of preferred embodiment, the compound has the following structure formula：
Wherein R1、R2Independently selected from the alkyl of 1 to 4 carbon atom；R3、R4It independently is arbitrary group, as long as these bases
Roll into a ball the ion complexation for not influencing the compound and colour developing or fluorescence property；Y is chromophore or fluorophor.
In preferred embodiment, R1、R2Independently selected from the alkyl of 1 to 4 carbon atom；R3、R4Independently selected from
Hydrogen, 1 to 4 carbon atom alkyl and 1 to 4 carbon atom alkoxy.In a kind of preferred embodiment, R1For ethyl, R2For second
Base, R3、R4For hydrogen.
In another preferred embodiment, the chromophore is selected from following structures：
Still in another preferred embodiment, the fluorophor is selected from following structures：
In a kind of preferred embodiment, the metal ion that can be detected with the compounds of this invention is selected from zinc ion.
In second aspect of the present invention, the product detected for metal ion content in urine is provided, the product includes this
Invent above-mentioned organic compound and the hydrophilic high polymers as carrier.The product can be the form of detection kit.It is common
Hydrophilic high polymers be used equally for the present invention, preferably high polymer is aminocellulose or hydrogel.In a kind of preferred embodiment,
The compounds of this invention addition hydrogel is coated into film as fluorescence probe.
In another preferred embodiment, the metal ion is selected from zinc ion.
In third aspect present invention, application of the compounds of this invention in urine in metal ion content detection is provided.One
In kind 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.
The organic compound of the present invention has following technical advantage outstanding as metal ion probe：
1, the present invention introduces chromophore in N, N- diacetoxyl -2,5- dialkoxy aniline, can prepare a system
Row metal ion (especially zinc ion) colored indicator.Reaction condition is mild, safety, product purity can reach 99.0% with
On.
2, by introducing fluorophor in the aniline, a series of metal ions (especially zinc ion) can be prepared
Fluorescence indicator.When metal ion content changes, fluorescence intensity can calculate GOLD FROM PLATING SOLUTION with change from its fluorescence intensity
Belong to the content of ion.
3, also using the complexing group of the molecule other end, the probe of the present invention is fixed on Polymer Surface, is realized micro-
The analysis for measuring metal ion content greatly improves the efficiency, sensitivity and reproducibility.
Description of the drawings
Fig. 1 is the reaction route that the present invention prepares fluorescent type zinc ion dyestuff.
Fig. 2 is the fluorescence spectra that zinc ion of the present invention detects fluorescence probe to different ions.
Fig. 3 is the fluorescence intensity column diagram that zinc ion of the present invention detects fluorescence probe to different ions.
Fig. 4 is that zinc ion of the present invention detects fluorescence probe to fluorescence intensity column diagram in the presence of interfering ion.
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, and the fluorescence of 550 nanometers is strong
Angle value corresponds to zinc ion concentration by 0 μM to 30 μM respectively from low to high.
Fig. 7 is the fluorescence intensity level that zinc ion of the present invention detects that 550 nanometers of various concentration zinc ion are complexed in fluorescence probe
Normalized from low to high.
Specific implementation mode
By the present invention in that with N, various metals ion can be complexed in N- diacetoxyl -2,5- dialkoxy aniline structures, from
And it can be used for realizing the analysis of micro ion content.Applicant can network to the compounds of this invention structure in long-term R＆D process
The metal ion of conjunction 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 to zinc
Ion has preferable complexing power, and that optimal is the complexing power for having significant specific binding to zinc ion, Ke Yizuo
For the effective carrier of zinc ion.Added lustre to or fluorophor by the contraposition introducing in above-mentioned aniline structure, it is electric based on photic induction
Sub- principle of transfer, when ion concentration changes, colour developing or fluorescence intensity change correspondingly, thus can be from ultraviolet absorption value or fluorescence
Intensitometer calculates the content of effects of ion.
It may include substituted or unsubstituted N, N- diacetoxyl -2,5- dialkoxy aniline structures in the compounds of this invention.
Those skilled in the art be not difficult determination can carry out which substitution without influence the compounds of this invention complexation of metal ions and develop the color or
Show the ability of fluorescence.In preferred embodiment, " substituted " refers to being replaced by substituent group selected from the following：1 to 4 carbon atom
Alkyl；The alkoxy of 1 to 4 carbon atom；Halogen, including fluorine, chlorine, bromine, iodine；Halogenated alkyl；Cyano；Nitro；Amino；And benzene
Base.
In the present context, " alkyl " refers to the linear or branched alkyl group of 1 to 4 carbon atom, for example, methyl, ethyl,
N-propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl or tertiary butyl." alkoxy " refers to the alcoxyl with 1 to 4 carbon atom
Base, such as methoxyl group, ethyoxyl, propoxyl group, butoxy.
The continuous detection to ion concentration can be achieved using colour developing principle or fluorescence, especially to the inspection of zinc ion concentration
It surveys.Chromophore or fluorophor commonly used in the art is used equally for the present invention.
On the one hand, it is introduced after chromophore in ionophore, that is, aniline structure of the present invention, a series of points generated
Son can generate color response to metal ion especially zinc ion.Such molecule can generate not in the sample of different ions concentration
Same color can be detected with photometer or naked eyes.Applicant confirms said effect in an experiment.Data show that the molecule can
Using as zinc ion colored indicator.
On the other hand, it is introduced after fluorophor in the ionophore of the present invention, a series of molecules generated can be right
Metal ion especially zinc ion generates fluorescence response.Such molecule can generate difference in the sample of different zinc ion concentrations
The fluorescence of intensity can be detected with sepectrophotofluorometer.Applicant confirms said effect in an experiment, and fluorescence intensity is with sample
The increase of zinc ion concentration in product and increase, increasing degree can be up to tens times.
Since chelation structure is variant for the binding ability of different metal ions, it is contemplated that actual detection application needs
It wants, the most suitable detection object of organic compound of the invention is zinc ion；Also other ions are can detect, including but not limited to
Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Fe2+、Fe3+、 Hg2+、K+、Mg2+、Mn2+、Na+、Ni2+、Pb2+、Zn2+, it is used especially for section
Learn research purposes.
For ease of commercial Application, also the ion detection compound of the present invention can be incorporated into hydrophilic high polymers carrier and use is made
In the product for detecting metal ion content in urine, the product is, for example, the form of kit.Common hydrophilic high polymers are equal
It can be used for the present invention, preferably high polymer is aminocellulose or hydrogel.In a kind of preferred embodiment, by the compounds of this invention
Hydrogel is added and is coated into film as fluorescence probe.
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.
Shown in refer to the 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 N- diacetoxyl -2,5- dialkoxy aniline and zinc ion fluorescence indicator.
This specification illustrates the present invention above in conjunction with specific implementation mode, it should be appreciated that these description and
Explaination is intended merely to more fully understand the present invention, without constituting any restriction to the present invention.Those skilled in the art are reading
Spirit of the necessary change without departing from the present invention can be carried out after present specification to the specific implementation mode of the present 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 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.The embodiment provided 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 has this
Conventional sense known to field technology personnel；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
It is as follows：
The synthesis of compound 1
4- chloro- 1,8 naphthalic anhydrides (10g, 42.99mmol), ethyl glutamate hydrochloride (20.68g, 85.98mmol)
And DIEA (28mL, 171.95mmol) is slowly added in 100mL DMF, 90 DEG C of heating stirring 18h.TLC detections have been reacted
Quan Hou, it is cooling, solvent is screwed out, column chromatography (PE: EA=30: 1) obtains yellow powder product 16g, yield 89.1%.1H NMR
(300MHz, CDCl3)：δ 8.65 (2H, d, J=24 Hz), 8.49 (1H, d, J=17Hz), 7.83 (2H, d), 5.71 (1H, m),
4.18 (2H, m), 4.00 (2H, m), 2.71 (1H, m), 2.37 (3H, m), 1.60 (3H, s), 1.13 (6H, m)13C NMR
(300MHz, CDCl3)：δ 173.076,169.889,163.897,163.637,140.011,132.998,132.208,
132.100,131.555,129.852,129.730,128.451,127.980,123.145,121.633,62.053,
61.025,53.392,31.702,24.632,14.635.
The preparation of compound 2,3 is with reference to known references [8]
The synthesis of compound 4
Weigh 2,5- dimethoxy p-aminophenyl ethamine (4) (1g, 5.10mmol), chloro- 1,8 naphthalimide glutamates of 4-
(1) (2.13g, 5.10mmol), n,N-diisopropylethylamine (DIEA) (0.85ml, 5.10mmol) and N- methylpyrroline ketone
(NMP) 1mL is put into 50mL single port eggplant-shape bottles, and overnight, the reaction was complete for TLC (PE: EA=1: 1) detections, after cooling for 95 DEG C of reactions
It is poured into water, solid is precipitated, filter, be spin-dried for after DCM dissolvings, crude product purifies to obtain 1.2g through column chromatography.1H NMR(CDCl3)δ
8.46 (d, J=7.2Hz), 8.37 (d, J=8.5Hz), 8.00 (d, J=8.3Hz), 7.51 (t, J=7.9Hz), 6.63 (t, J
=4.2Hz), 6.42 (s), 6.31 (s), 5.73 (dd, J=8.8,5.2Hz), 4.25-4.15 (m), 4.01 (ddd, J=
14.2,7.1,2.7Hz), 3.90 (s), 3.78 (s), 3.56-3.48 (m), 3.00 (t, J=6.2Hz), 2.71 (dq, J=
10.3,6.5Hz), 2.55-2.27 (m), 1.17 (dt, J=14.0,7.1Hz)13C NMR(CDCl3) δ 173.299,
170.704,164.850,164.091,152.188,150.851,142.170,136.499,135.625,131.874,
130.531,127.086,124.845,122.924,120.636,116.530,114.045,109.271,104.544,
100.526,78.013,77.589,77.166,61.787,60.904,56.991,56.756,52.921,45.815,
31.798,29.523,24.808,14.648.
The synthesis of compound 5
Weigh compound (4) (173.12 μm of ol of 100mg), bromoacetate (153 μ L, 1.38mmol), N, N- diisopropyls
Base ethamine (DIEA) (458 μ L, 2.77mmol) and potassium iodide (115mg, 692.49 μm of ol) are put into 1mL N, N- dimethyl formyls
In amine (DMF), overnight, the reaction was complete for TLC detections for 110 DEG C of reactions, during cooling is fallen back, oily dope is precipitated, incline water
Phase, dichloromethane re-dissolve, and anhydrous sodium sulfate drying is spin-dried for, crude product purifies to obtain 105mg compounds 5 through column chromatography.1H
NMR(CDCl3) δ 8.47 (d, J=6.8Hz), 8.37 (d, J=8.5Hz), 8.00 (d, J=8.0Hz), 7.52 (t, J=
7.9Hz), 6.72-6.62 (m), 6.56 (s), 6.28-6.21 (m), 5.72 (dd, J=8.9,5.2Hz), 4.21-4.11 (m),
4.00 (dt, J=7.1,4.5Hz), 3.90 (s), 3.74 (s), 3.52 (dd, J=10.4,5.7Hz), 3.02 (t, J=6.2
Hz), 2.77-2.63 (m), 2.40 (dddd, J=18.6,15.5,11.7,7.4Hz), 1.23-1.11 (m)13C NMR
(CDCl3) δ 172.997,171.543,170.391,164.535,163.788,151.670,150.396,146.113,
138.675,135.309,131.611,130.216,126.742,124.643,122.658,120.627,120.333,
115.619,109.147,104.400,104.275,77.707,77.283,76.859,61.499,60.961,60.610,
56.801,56.702,54.312,52.623,45.211,31.491,29.328,24.487,14.509,14.354.
The synthesis of Sensor Zn
It takes 26mg above compounds 5 (34.68 μm of ol) to be dissolved in 2mL methanol, NaOH solution (0.14g, 3.47mmol is added
NaOH is dissolved in 3mL level-ones water), 40 DEG C of reactions to complete hydrolysis, TLC (the reaction was complete for DCM: MeOH=10: 1 detection).
The present invention is by the way that N, N- diacetoxyl -2,5- dialkoxy aniline introduces chromophore or fluorophor so that
The molecule generates the variation of color change or fluorescence intensity when with complexing of metal ion, can to realize trace metal ion
Depending on changing detection or automatic detection.Color change after the molecule and complexing of metal ion or in the variation and solution of fluorescence intensity
The concentration of metal ion is directly related, thus can calculate GOLD FROM PLATING SOLUTION category according to the color change or fluorescence intensity of the molecule
The content of ion realizes the quick and precisely detection to metal ion content.
Fig. 2 and Fig. 3 shows that fluorescence emission spectrum and its block diagram of the zinc ionophoric to different ions, Fig. 4 are shown
Fluorescence response block diagram of zinc ionophoric in the presence of disturbance ion, illustrates ion carrier compound of the present invention as zinc
Ion probe has good selectivity zinc ion.
Fig. 5 shows the zinc ion solution that various concentration is added, the concentration titrations fluorescence intensity response variation of Sensor Zn
Curve is gradually increased with zinc ion concentration is added, and the fluorescence of Sensor Zn gradually increases, until zinc ion concentration increases to
Fluorescence intensity reaches maximum value and no longer changes at 30 μM, and the corresponding fluorescence intensity response in the places maximum emission wavelength 550nm is taken to become
It is as shown in Figure 6 that change relative value does concentration titrations curve to zinc ion concentration.
Those skilled in the art can prepare according to the thinking and synthetic method that this specification is provided with complexing energy
The zinc ion indicator of power, it will not go into details herein.
In summary experimental result is it is found that the organic compound of the present 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] the big feelings of Hao, Xiang Pingping, Zhang Yimin, Pei Xiuying, Ren Bing, Chinese labour health occupational disease magazine, 1993,11
(5), 308.
[3] Li Qing, Wang Keling, medical test, 2011,8 (7), 81.
[4] Liu Hanfang, Lv Xiang, Liang Geqing, modern combination of Chinese tradiational and Western medicine magazine, 2005,14 (10), 1358.
[5] Zhuo Xiaoyun, analytical chemistry, 1985,13 (7), 556.
[6] Zhang Yu, Chang An University's master thesis, 2014.
[7] Liang Qunzhen, Chinese Journal of Health Laboratory Technology, 2008,18 (12), 2789.
[8] 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 (10)
1. a kind of organic compound detected for metal ion content in urine, the compound includes substituted or unsubstituted
N, N- diacetoxyl -2,5- dialkoxy aniline are as complexing of metal ion body, and in N, N- diacetoxyl -2,5- dialkoxies
The contraposition of aniline introduces chromophore or fluorophor.
2. organic compound according to claim 1, it is characterised in that the compound has the following structure formula：
Wherein R1、R2Independently selected from the alkyl of 1 to 4 carbon atom；R3、R4It independently is arbitrary group, as long as these groups are not
Influence the ion complexation and colour developing or fluorescence property of the compound；Y is chromophore or fluorophor.
3. organic compound according to claim 2, it is characterised in that R3、R4Independently selected from hydrogen, 1 to 4 carbon atom
The alkoxy of alkyl and 1 to 4 carbon atom.
4. organic compound according to any one of claim 1 to 3, it is characterised in that the chromophore is selected from：
The fluorophor is selected from：
5. a kind of product detected for metal ion content in urine, which includes described in any one of claims 1 to 4
Organic compound and hydrophilic high polymers as carrier.
6. product according to claim 5, it is characterised in that the hydrophilic high polymers are selected from aminocellulose or hydrogel.
7. product according to claim 5, it is characterised in that the product is kit.
8. application of the organic compound any one of Claims 1-4 in urine in metal ion content detection.
9. application according to claim 8, it is characterised in that the metal ion is selected from zinc ion.
10. application according to claim 8, it is characterised in that it is described to be detected as fluoroscopic examination, it is continuous to detect.
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| CN110003175A (en) * | 2019-03-25 | 2019-07-12 | 天津农学院 | A kind of compound and its application for detecting underwater gold category ion concentration |
| CN110117269A (en) * | 2019-03-25 | 2019-08-13 | 天津农学院 | A kind of fluorescent chemicals and its application for detecting underwater gold category ion concentration |
| CN110128394A (en) * | 2019-03-25 | 2019-08-16 | 天津农学院 | A kind of fluorescent chemicals and its application for the detection of underwater gold category ion concentration |
| CN110128395A (en) * | 2019-03-25 | 2019-08-16 | 天津农学院 | A kind of fluorescence probe and its application for the detection of underwater gold category ion concentration |
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| CN110003175A (en) * | 2019-03-25 | 2019-07-12 | 天津农学院 | A kind of compound and its application for detecting underwater gold category ion concentration |
| CN110117269A (en) * | 2019-03-25 | 2019-08-13 | 天津农学院 | A kind of fluorescent chemicals and its application for detecting underwater gold category ion concentration |
| CN110128394A (en) * | 2019-03-25 | 2019-08-16 | 天津农学院 | A kind of fluorescent chemicals and its application for the detection of underwater gold category ion concentration |
| CN110128395A (en) * | 2019-03-25 | 2019-08-16 | 天津农学院 | A kind of fluorescence probe and its application for the detection of underwater gold category ion concentration |
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