CN100387608C - Glycosyl quinoline and its mercury ion detecting method - Google Patents
Glycosyl quinoline and its mercury ion detecting method Download PDFInfo
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- CN100387608C CN100387608C CNB2006100399394A CN200610039939A CN100387608C CN 100387608 C CN100387608 C CN 100387608C CN B2006100399394 A CNB2006100399394 A CN B2006100399394A CN 200610039939 A CN200610039939 A CN 200610039939A CN 100387608 C CN100387608 C CN 100387608C
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- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 title claims description 33
- 238000000034 method Methods 0.000 title abstract description 18
- -1 Glycosyl quinoline Chemical compound 0.000 title abstract description 13
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 150000002500 ions Chemical class 0.000 claims abstract description 20
- 229910052753 mercury Inorganic materials 0.000 claims abstract description 18
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000003556 assay Methods 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 238000001514 detection method Methods 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 238000011161 development Methods 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 238000001917 fluorescence detection Methods 0.000 abstract 2
- 238000012360 testing method Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 230000002452 interceptive effect Effects 0.000 description 7
- 108010021119 Trichosanthin Proteins 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001506 fluorescence spectroscopy Methods 0.000 description 2
- 125000003147 glycosyl group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JJWSNOOGIUMOEE-UHFFFAOYSA-N Monomethylmercury Chemical compound [Hg]C JJWSNOOGIUMOEE-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The present invention discloses a high selective color development compound for the fluorescence detection of mercury positive ions on the basis of recognition and combination and a method for the fluorescence detection of mercury ions by a compound. The compound is synthesized by the reaction of 2-chinoline aldehyde and D-aminoglucose. The compound has a high selective fluorescent detection to mercury ions and can obviously detect the concentration of the mercury ions, wherein the concentration of the mercury ions reaches 100 ppb. No disturbance is generated from other ions, such as Ag<+>, Fe<2+>, Cd<2+>, Mn<2+>, Co<2+>, Ni<2+>, Cu<2+>, etc. The present invention provides a method for detecting the mercury ions in water by high selectivity and high sensitivity.
Description
Technical field
The invention belongs to identification combination and be used for the cationic ion detection technical field of optical detection mercury, be specifically related to utilize have the glycosyl quinoline compound and use that compound is the mercury ion fluorescent detection method that identification develops the color in this.
Background technology
Because industrial needs, mercury (II) ion ubiquity in environment, and become the environmental problem of a sternness, mercury can enter the methyl mercury of organism generation to the toxic property of nerve, transmits (Science in food chain, 2003,301,1203) to detect mercury ion very important for the simple and efficient sensitive analytical procedure of development.It is reported, carry out context of detection with small molecules identification mercury ion and obtained bigger progress, for example adopt oxidation reduction process (J.Am.Chem.Soc., 2005,127,15666-15667; Inorg.Chem.2001,40,641-644.), chemistry add lustre to method (J.Am.Soc.Chem.2005,127,12351-12356; Org.Lett., 2005,7,5869-5872.), fluorescent method (Organ.Lett., 2005,7,4943-4946.; 2006,8,371-374; Chem.Commun., 2005,3156-3158; 2005,2161-2163.J.Am.Chem.Soc.2005,127,10124-10125.) etc. the identification mercury ion reaches testing goal.Wherein, the highly sensitive test of fluorophotometric method is easy.But, because be used for discerning that the small molecules of mercury ion is low in the water solvability mostly in these methods, poor selectivity and corresponding slower development.Rurack et.a1 (J.Am.Chem.Soc.2003,125,3418-3419). and Lippard et.al (J.Am.Chem.Soc.2003,125,14270-14271.) etc. people's small molecules of having obtained two good water solubility be used for discerning the mercury ion of water, in alcohol and the blending agent of water, detect mercury ion sensitivity in the 20ppb degree, but these compounds is synthetic comparatively complicated.
In order to overcome the defective of above method, special problem aspect water-soluble and selectivity, the inventor is through research with keen determination, discovery is incorporated into the fluorescence chromophoric group with glycosyl, for example glucosamine is incorporated on the quinoline particularly, obtained water-solublely to strengthen greatly, the glycosyl quinoline class fluorescent color-developing agent high to the mercury ion selectivity, its synthetic method is simple, mild condition, product are easy to get, and this compound is used for mercury ion detecting of the present invention obtains good result and finish the present invention.
Summary of the invention
Purpose of the present invention provides a kind of selectivity to detect the fluorescence developing compound of mercury ion, and a kind of method of utilizing this kind compound test mercury ion further is provided, and is directly used in the detection of water sample.
The objective of the invention is to be achieved through the following technical solutions.
Found at first that following formula represents to the fluorescence developing compound that mercury ion has highly selective and solvability is good in water,
This compound is designated hereinafter simply as QG.
This compound is characterised in that: the glycosyl of good water solubility is by carbon-to-nitrogen double bon link to each other with fluorophor formation, the wherein cis of carbon-to-nitrogen double bon and the trans balance of reaching in solution.
This compound interacts with mercury ion when interacting colour developing with mercury ion, and the variation of this part can be represented with accompanying drawing 1.
Because mercury ion and this compound formation coordination compound, cause the variation of electron distributions and molecular configuration in the molecule and the variation of fluorescence intensity takes place, reach the purpose of detection mercury ion.And Ag
+, Fe
2+, Cd
2+, Mn
2+, Co
2+, Ni
2+With Cu
2+Plasma can not produce the variation of fluorescence intensity with its effect.Show the have highly selective of this compound Q G to mercury ion.
Compound of the present invention can be by 2-quinoline aldehyde and D-glucosamine in appropriate solvent, for example synthetic acquisition of reaction in the methyl alcohol equal solvent.Reactant concn can determine that be generally 0.2～2M, 0.5～1M is better according to reactants dissolved degree and speed of response etc.Usually Ammonia is a reaction promotor, for example can use triethylamine.Temperature of reaction is generally 20～70 ℃ as long as keep reaction normally, and 40～50 ℃ better.Follow-up purifying can with various usual methods for example method such as chromatographic separation, recrystallization carry out purifying.The structure of this compound can be by ultimate analysis, infrared spectra, and visible UV spectrum, analysis means such as nuclear magnetic resonance spectrum characterize.
The structure of the coordination compound that forms with metal ion usually can be by ultimate analysis, mass spectrum, nucleus magnetic resonance, and ultraviolet-visible absorption spectroscopy characterizes.
The second, compound of the present invention can be made into the aqueous solution, is used for the fluoroscopic examination of mercury ion selectivity.Generally with compound Q G of the present invention, the water-soluble or pure property aqueous solution, the aqueous solution is more practical and easy to use, is made into finite concentration.Concentration can determine that for compound of the present invention, can be made into volumetric molar concentration is 10 according to test condition and fluorescence intensity intensity of variation
-4-10
-7M, the concentration of conventional testing method can be made into 10
-5-10
-6M.Test concentrations after the to be measured mercurous ionic sample of test adds is 10
-6-10
-4M is better, and 10
-5-10
-4The M scope is better.Concrete test adopts the fluorophotometric method to test, and utilizes the standard working curve method to carry out content and calculates.
Use method test mercury ion of the present invention, be not subjected to other conventional coexisting ion, for example Ag
+, Fe
2+, Cd
2+, Mn
2+, Co
2+, Ni
2+With Cu
2+Isoionic influence has highly selective.Since in water, test, easy to use.The fluorescence intensity height is low to moderate 5.0 * 10 at ion concentration of mercury
-7M (being 100ppb) can have obviously and detects.In sum, technique effect of the present invention is significantly, and the method for mercury ion in a kind of highly selective high sensitivity testing water sample is provided.
Description of drawings
Fig. 1: fluorescence chromophoric mechanism synoptic diagram
The compound of Fig. 2: embodiment 1 is to the selectivity of mercury ion: the fluorescence intensity of different ions.
The compound of Fig. 3: embodiment 1 is to the fluorescence intensity response of ion concentration of mercury.
The compound of Fig. 4: embodiment 1 in the presence of 5 times of interfering ions to the fluorescence response of mercury ion.In every group, what bar-shaped mark was low is the response of interfering ion among the figure, high for adding the response behind the mercury ion.
Embodiment
In order to be illustrated more clearly in content of the present invention, be described as follows with specific embodiment, specific embodiment does not limit context of the present invention.
Embodiment 1 (compound Q G's is synthetic)
With 0.314 gram α-quinoline aldehyde (2 mmole), 0.43g restrains D-glucosamine hydrochloride (2 mmole), and the 0.3ml triethylamine adds in the 20ml methyl alcohol, refluxed 90 minutes, and be chilled to room temperature, filter and collect light-yellow precipitate, the difference water, methyl alcohol, the anhydrous diethyl ether washing precipitation is repeatedly.Vacuum-drying.Productive rate: 66%.Ultimate analysis: C
16H
18N
2O
5Calculated value C 60.35, H 5.70, N 8.80% test value: C 60.56H 5.82N 8.58%.
Embodiment 2 (selectivity experiment)
Compound Q G is made into 1 * 10 in the fluorescence experiments
-5M aqueous solution storing solution, metal cation salt are selected Li (I) for use, Na (I), K (I), Ag (I), Mg (II), Ca (II), Cu (II), Ba (II), Pb (II), Mn (II), Co (II), Ni (II), Cd (II), Zn (II), the nitrate of Hg (II), Fe (II) then adopts vitriol, and the solution of all experiment usefulness all is new preparation, and experiment immediately.Excite at 315nm.In the ion difference test experiments, get storing solution 2ml, add 10 times ion respectively, survey its fluorogram.The results are shown in accompanying drawing 2.
Embodiment 3 (fluorescence intensity working curve)
Take by weighing compound 0.0065 gram of embodiment 1, water-soluble, be mixed with 1 * 10 with the 500ML volumetric flask
-5M standard inventory solution (L).Take by weighing high mercury 0.0144 gram of two water nitric acid, water-soluble, be mixed with 4.0 * 10 with the 10ML volumetric flask
-3The standard inventory solution (F) of M.Measure 2.0 milliliters of stock solution L, add the stock solution F of calculated amount, be mixed with standard testing solution, excite, in its fluorescence intensity of 415nm place test at the 315nm place.Test result is seen accompanying drawing 3.Calculate the compound of embodiment 1 and the binding constant of mercury ion is logK=4.85 ± 0.05 with nonlinear least square method.
Embodiment 4 (test)
With working curve at embodiment 3, add the replacement stock solution with sample to be tested (the our unit laboratory is water sample from the beginning), measure fluorescence intensity at the 415nm place, calculate mercury content from working curve, 2.5 * 10
-6Below the M (0.05 mg/litre).
The coexistence of embodiment 5 interfering ions detects the mercury ion experiment
Compound Q G is made into 1 * 10 in the fluorescence experiments
-5The M aqueous solution.Hg (II) nitrate is made into 4.0 * 10
-3The standard inventory solution of M.Select Li (I) for use as the metal cation salt of interfering ion, Na (I), K (I), Ag (I), Mg (II), Ca (II), Cu (II), Ba (II), Pb (II), Mn (II), Co (II), Ni (II), Cd (II), Zn (II) nitrate, Fe (II) then adopts vitriol, the solution of all experiment usefulness all is new preparation, and experiment immediately.In the interfering ion experiment, earlier 1 * 10
-5The interfering ion that adds 10 times in the aqueous solution of M compound Q G is surveyed its fluorescence, adds 2 times of Hg (II) ion again, surveys its change in fluorescence.Add above-mentioned interfering ion (each ion adds 10 times) simultaneously, add 2 times of Hg (II) ion again, survey its change in fluorescence.Excite at 315nm, in 415nm place fluorescence intensity.
Claims (6)
1. following formula: compound,
The Schiff key connects in the formula is configured as cis and trans, is in balance in solution.
2. mercury ion fluorescent chromogenic assay method, the compound that it is characterized in that claim 1 is a fluorescent agent.
3. the mercury ion fluorescent chromogenic assay method of claim 2, may further comprise the steps: as the fluorescent color-developing agent wiring solution-forming, its concentration is 1 * 10 with the compound described in the claim 1
-7To 1 * 10
-4M gets a certain amount ofly, and the mercury solution that contains to be measured is got a certain amount of adding, measures fluorescence intensity, extrapolates mercury content.
4. the mercury ion fluorescent chromogenic assay method of claim 3, the concentration that it is characterized by wherein said fluorescent color-developing agent wiring solution-forming is 10
-5To 10
-6M.
5. the mercury ion fluorescent chromogenic assay method of claim 3 is characterized in that when measuring ion concentration of mercury, the final concentration that adding contains the described fluorescent color-developing agent behind the mercury solution is 10
-6To 10
-4M.
6. the mercury ion fluorescent chromogenic assay method of claim 3 is characterized in that when measuring ion concentration of mercury, the final concentration that adding contains the described fluorescent color-developing agent behind the mercury solution is 10
-5To 10
-4M.
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|---|---|---|---|
| CNB2006100399394A CN100387608C (en) | 2006-04-27 | 2006-04-27 | Glycosyl quinoline and its mercury ion detecting method |
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|---|---|---|---|
| CNB2006100399394A CN100387608C (en) | 2006-04-27 | 2006-04-27 | Glycosyl quinoline and its mercury ion detecting method |
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| CN100387608C true CN100387608C (en) | 2008-05-14 |
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| CN101726604A (en) * | 2008-10-21 | 2010-06-09 | 成都市华森电子信息产业有限责任公司 | A method for detecting mercuric ions based on MOS electronic gene chip |
-
2006
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Non-Patent Citations (6)
| Title |
|---|
| a "turn-on" fluorescent sensor for the selective detection ofmercuric ion in aqueous media. lippard et al.J.Am.Chem.Soc.,Vol.125 . 2003 |
| a "turn-on" fluorescent sensor for the selective detection ofmercuric ion in aqueous media. lippard et al.J.Am.Chem.Soc.,Vol.125 . 2003 * |
| coupling selectivity with sensitivity in an integratedchemosensor framework :design of a Hg2+-responsive probe,operating above 500nm. rurack et al.J.Am.Chem.Soc.,Vol.125 . 2003 |
| coupling selectivity with sensitivity in an integratedchemosensor framework :design of a Hg2+-responsive probe,operating above 500nm. rurack et al.J.Am.Chem.Soc.,Vol.125 . 2003 * |
| 喹啉基重氮氨基偶氮苯的合成及其与汞显色反应的研究. 赵书林等.分析科学学报，第15卷第3期. 1999 |
| 喹啉基重氮氨基偶氮苯的合成及其与汞显色反应的研究. 赵书林等.分析科学学报，第15卷第3期. 1999 * |
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