CN102183480B - Method for detecting aluminum ions and tin ions in water phase by using water-soluble porphyrin probe - Google Patents
Method for detecting aluminum ions and tin ions in water phase by using water-soluble porphyrin probe Download PDFInfo
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- CN102183480B CN102183480B CN2011100792257A CN201110079225A CN102183480B CN 102183480 B CN102183480 B CN 102183480B CN 2011100792257 A CN2011100792257 A CN 2011100792257A CN 201110079225 A CN201110079225 A CN 201110079225A CN 102183480 B CN102183480 B CN 102183480B
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Abstract
The invention relates to a method for high selective identification of aluminum ions and tin ions in water phase by using a water-soluble porphyrin probe. According to the method, an ultraviolet-visible spectrophotometer and a fluorescence spectrophotometer are used for detecting the characteristic absorption peak and emission peak of water-soluble porphyrin solution to red shift to certain wavelength respectively to identify the existence of aluminum ions or tin ions in water phase; and fluorescence intensity of human lung carcinoma A549 cells are observed under an upright fluorescent microscope to judge the existence of aluminum ions. In the invention, the sensitivity is high, and rapid detection can be realized; the porphyrin probe has a simple structure and is easy to prepare, and both excitation wavelength and emission wavelength are within visible region; the operation is simple, the fabrication cost is low, and the reagent used and the operation process have no toxic and side effects; and the probe has good selectivity to aluminum ions or tin ions, metal ions such as natrium ions, kalium ions, magnesium ions, copper ions, lead ions and the like have no interference on detection, and the invention can realize detection of aluminum ions in cells.
Description
Technical field
The present invention relates to the high selectivity identification that a kind of water-soluble porphyrin probe is applied to aqueous phase aluminium ion and tin ion, belong to the fluorescence analysis technical field of measurement and test.
Background technology
Porphyrin (Porphyrin) compounds is widespread in nature, and it is the macrocyclic compound that contains 4 pyrroles's molecules.Porphyrins is that precursor structure porphines (Porphin) is gone up by other substituting groups replacements; Or the center is by the general name of the substituted a series of derivants of metallic ion; Its parent porphines is that to have rigidity be that the main big ring conjugated structure that has the flexible big π key of 18 electronics concurrently is [referring to (a) Smith K.M., Ed. Porphyrin s and Metalloporphyrins; Elsevier:Amsterdam, 1975. Press:New York, 1966; (b) Dolphin D., Ed. The Porphyrins; Academic Press:New York, 1978-1979.].
Porphyrins has the photoelectric properties of many uniquenesses, good light and thermally stable property; Bigger molar absorptivity is arranged in visible-range, thereby obtained paying close attention to widely and using in fields such as biological chemistry, medicine and pharmacology, analytical chemistry, photocatalysis and material science.In recent years, utilize porphyrin molecule unique electronic structure and photoelectric properties, the aspects such as development of design and synthetic photoelectric functional material and photoelectric device; Become domestic and international ten minutes active research field, for example aspect the quantity of photogenerated charge and energy transfer of the biological photosynthetic reaction centre of simulation, the porphyrin molecule is as the light absorption units in the model compound; Can realize that the photoinduction charge separation is [referring to (a) Gust D., Moore T. A. Science, 1989; 244,35; (b) Wasielewski M. R. Chem. Review, 1992,92,435; (c) Moore T. A., Gust D., et al. Nature, 1984,307,630; (d) Liddell P. A.; Kuciauskas D., Sumida J. P., et al. J.Am.Chem.Soc. 1997,119,1400; (e) Kuciauskas D.; Liddell P. A.; Moore A. L., et al J. Am. Chem. Soc. 1998,120,10880.]; In addition, porphyrin compound at organic effect electron tube (OFETs) [referring to Aramaki S., Sakai Y., Ono N. Appl. Phy. Let., 2004; 84,2085.], divide sub antenna [referring to (a) Li J., Ambroise A., Yang S. I., Diers J. R.; Seth J., Wack C. R., Bocian D. F., Holten D.; Lindsey J. S. J. Am. Chem. Soc., 1999,121,8927; (b) Choi M.S., Aida T., Yamazaki T. et al. Angew. Chem. Int. Ed., 2001,40; 3194.], light-ability converter [referring to Gust D., Moore T. A., Moore A. L. Acc. Chem. Res. 2001,34,40.], photoelectric conversion material is [referring to Crossley M. J.; Burn P. L. Chem.Commun., 1991,21,1569.], molecular switch is [referring to Wasielewiski M.R.; Goszrola D. Z. Science, 1992,257,63.], the molecule logic gate is [referring to Wagner R. W.; Lindsey J. S. J. Am. Chem. Soc., 1996,119,3996.], molecular wire is [referring to Richard W.; Wagner R. W., Lindsey J. S. J. Am. Chem. Soc. 1994,116,9759.], organic solar batteries is [referring to (a) Antohe S.; Tugulea L. Phys. Stat. Sol (A), 1996,1153,581; (b) Takahashi K., Kuraya N., et al. Solar Enegy Materials&Solar Cell, 2000; 61,403.], organic electroluminescent is [referring to Baldo M. A., O ' Bren D. F. et al. Nature, 1998; 395,151.], nonlinear optical material is [referring to Lidzey D. G., Bradley D.C., et al. Nature; 1998,395,53.], optical storage [referring to: (a) Tyler B. N., Neil R. B. Adv. Mater; 2001,13 (5), 347; (b) Liu Z. M., Amir A., Yasseri J., Lindsey J. S.; Et al Science 2003,302 (28), 1543.], molecular recognition and medicine is [referring to Yang Jizhang, Chinese Journal of New Drugs; 1995,4 (3), 59.] etc. the aspect has a wide range of applications.
Porphyrin compound is a kind of desirable fluorescent material; Have high fluorescence quantum yield, big Stokes displacement, long relatively (> 400 nm that excite) with launch (> 600 nm) wavelength; Long relatively exciting the interference that can reduce background fluorescence with emission wavelength, is a kind of ion fluorescence probe of worth further investigation.In addition, porphyrin compound can form stable complex with most metal ions, and the molar absorptivity of its system can reach 1～9 * 10
5L mol
-1Cm
-1[referring to: (a) Kadish K. M., Smith K. M., Guilard R. The Porphyrin Handbook, ed.; Academic Press:New York, 2000; (b) Shi Z. H., Fu C. G. Talanta 1997,44,593-604.].With tetraphenylporphyrin trisulfonic acid photometering copper trace, molar absorptivity is up to 4.76 * 10 1974 young villages and husband
5L mol
-1Cm
-1[referring to: Itoh, J.; Yotsuyanagi, T.; Aomura, K. Japan Anal. 1974,23,1243-1244.] afterwards, the porphyrin analog derivative is just paid attention to by people.Porphyrins has special construction, and very high absorption and emission ratio are arranged in visible-range, is one type of very rising highly sensitive developer.But the porphyrin compound majority as developer is water-insoluble at present, often needs to add some surfactants; Could detect metallic ion at aqueous phase, this feasible mensuration program is loaded down with trivial details, has limited range of application [referring to (a) Hui K. S.; Davis B. A. and Boulton A. A., J. Chromatogr., 1975; 115,581; (b) Kobayashi M., Saitoh K. and Suzuki N., Chromatographia, 1984,18,441; (c) Kobayashi, M.; Saitoh, K. and Suzuki, N., Chromatographia, 1985,20,49.].
Aluminium is a kind of important metal of occurring in nature, with the mankind confidential relation is arranged.The aluminium of low concentration has certain spread effect to soil amonifying bacteria, nitrobacteria, denitrifying bacteria; Then show as inhibiting effect during high concentration, the activity of anaerobion in the water and aerobic bacteria is had adverse influence.Simultaneously, the aluminium poison has become one of principal element that suppresses the plant growth in the acid ground, its main harm plant roots, thus influence crop to nutrition and absorption of water; Aluminium ion concentration is higher than 0.5 mg L
-1The time, can make some fish kills.Aluminium is useful to human body to a certain extent, and it can be alleviated plumbous some to human body and poisons, but the aluminium of excessive absorption can be distributed in organs such as the liver, stomach, spleen, brain, thyroid gland of human body, forms early ageing, dementia, anaemia and some osteopathy.Tin is one of indispensable trace element of human body, and its main physiological function shows anti-tumor aspect, and the absorption of excess amounts of tin can cause the infringement of central nervous system in the human body.The tin of occurring in nature is many to be existed with tetravalent state, and under the condition of anoxic, tin methylates under bacterial action, and the methyl tin of generation is more volatile, often from water, escapes into atmosphere and moves, and environment is polluted.Therefore, selectivity detect in the water body aluminium ion and tin ion the purification of metallic pollution water body, soil, air with repair in have potential significance, for handling waste water, protect environment; Prevent to pollute and have certain directive function [referring to: (a) Kim S. H., Choi H. S., Kim J.; Lee S. J., Quang D. T., Kim J. S.; Org. Lett. 2010,12 (3), 560-563; (b) Wang Y. W., Yu M. X., Yu Y. H., Bai Z. H., Shen Z., Li F. Y., You X. Z., Tetrahedron Lett 2009,50,6169-6172.].
This patent selection water-soluble porphyrin molecule---meta-four (4-sulfonic group phenyl) porphyrin is the ion detection probe; Utilize and measure uv-visible absorption spectra and fluorescence spectrum; Realized aluminium ion and tin ion high selectivity being discerned, and in people's lung cancer A549 cell, successfully detected aluminium ion at aqueous phase.
Summary of the invention
The purpose of this invention is to provide a kind of water-soluble porphyrin molecule that utilizes---meta-four (4-sulfonic group phenyl) porphyrin is in the high selectivity recognition methods of aqueous phase aluminium ion and tin ion, and reported that it detects the application of aluminium ion aspect existing in people's lung cancer A549 cell.
Technical scheme of the present invention is following:
Meta-four (4-sulfonic group phenyl) porphyrin (
1 ), its structural formula is following:
This water-soluble porphyrin solution is in the presence of aluminium ion; Its uv-visible absorption spectra (accompanying drawing 1) has significant change; Characteristic absorption peak (Soret peak) red shift 20 nm, and new absorption peak appears in 497 nm and 713 nm places, its fluorescence emission spectrum (accompanying drawing 3) has significant change; Emission spectrum red shift to 671 nm, fluorescence intensity obviously strengthens.And other kations such as barium, cadmium, iron (II), lithium, magnesium, manganese, sodium, strontium, zinc, copper, nickel, lead can only make the absorption and the fluorescence spectrum generation subtle change of compound.Explain with the said method of this patent, can be at the identification aluminium ion of aqueous phase high selectivity.
This water-soluble porphyrin solution is in the presence of tin ion; Its uv-visible absorption spectra (accompanying drawing 2) has significant change; Characteristic absorption peak (Soret peak) red shift 20 nm; And new absorption peak appears in 494 nm and 644 nm places, and its fluorescence emission spectrum (accompanying drawing 4) has significant change, emission spectrum red shift to 673 nm; Fluorescence intensity obviously strengthens, and other kations such as barium, cadmium, iron (II), lithium, magnesium, manganese, sodium, strontium, zinc, copper, nickel, lead can only make the absorption and the fluorescence spectrum generation subtle change of compound.Explain with the said method of this patent, can be at the identification tin ion of aqueous phase high selectivity.
This water-soluble porphyrin solution is in people's lung cancer A549 cell that aluminium ion exists, and fluorescence intensity obviously strengthens (accompanying drawing 5).Explain with the said method of this patent, can in people's lung cancer A549 cell, show aluminum ions existence.
Detect used instrument: go up the UV-765 of Nereid section type ultraviolet-visible spectrophotometer (sweep limit 380～800 nm; Light path slit 2 nm); The F-4500 of Hitachi type fluorescent emission is sent out spectrometer (excitation wavelength range 414～440 nm, sweep limit 500～800 nm, slit width are 5 nm).Just putting fluorescent microscope AX10.
Beneficial effect of the present invention
The present invention compared with prior art; Its remarkable advantage is: employing water-soluble porphyrin molecule---meta-four (4-sulfonic group phenyl) porphyrin is the ion detection probe; Utilize and measure uv-visible absorption spectra and fluorescence spectrum, realized at aqueous phase identification aluminium ion and tin ion.This method detects fast, and cost simple to operate is low, and agents useful for same and operating process have no side effect.The porphyrin probe structure is simple, be easy to the preparation, excite with emission wavelength all at visible region.In addition, probe has good selectivity to aluminium ion or tin ion, and barium, cadmium, iron (II), lithium, magnesium, manganese, sodium, strontium, zinc, copper, nickel, lead ion do not disturb detecting, and can be implemented in and detect aluminum ions existence in people's lung cancer A549 cell.
Description of drawings
Fig. 1 is at Al
3+There is compound down
1 Ultra-violet absorption spectrum changes;
Fig. 2 is at Sn
4+There is compound down
1 Ultra-violet absorption spectrum changes;
Fig. 3 is at Al
3+There is compound down
1 Fluorescence emission spectrum changes;
Fig. 4 is at Sn
4+There is compound down
1 Fluorescence emission spectrum changes;
Fig. 5 is a compound
1 At Al
3+Change in fluorescence situation in the people's lung cancer A549 cell that exists: a) blank; B) compound 1 is at the intracellular fluorescence imaging of A549; C) compound 1 is at Al
3+The intracellular fluorescence imaging of A549 that exists; D) compound 1 is at Al
3+With the intracellular fluorescence imaging of the simultaneous A549 of ethylenediamine tetraacetic acid.
Specific embodiment
Embodiment 1:With compound
1 Be dissolved in the distilled water, be made into 3.0 * 10
-5Mol/L gets 2 milliliters and puts into cuvette; Compound concentration is 3.0 * 10 in addition
-2The Al of mol/L
3+The WS, measure the Al of 2 microlitres successively with micro syringe
3+Solution adds in the cuvette, measures ultra-violet absorption spectrum.Work as Al
3+Concentration be 2.5 * 10
-4During mol/L, ultraviolet spectrum maximum absorption band red shift to 434 nm, and at 497 nm and two new absorption peaks of 713 nm places appearance, and no longer along with Al
3+Concentration raises and continues red shift.
Embodiment 2:Implementation method is with embodiment 1, just Al
3+Solution changes Sn into
4+Solution is measured ultra-violet absorption spectrum.Work as Sn
4+Concentration be 2.0 * 10
-3During mol/L, ultraviolet spectrum maximum absorption band red shift to 434 nm, and at 494 nm and two new absorption peaks of 644 nm places appearance, and no longer along with Sn
4+Concentration raises and continues red shift.
Embodiment 3:Implementation method is with embodiment 1, just Al
3+Solution changes Na into
+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 4:Implementation method is with embodiment 1, just Al
3+Solution changes Ba into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 5:Implementation method is with embodiment 1, just Al
3+Solution changes Cd into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 6: implementation method is with embodiment 1, just Al
3+Solution changes Cu into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 7:Implementation method is with embodiment 1, just Al
3+Solution changes Fe into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 8:Implementation method is with embodiment 1, just Al
3+Solution changes Li into
+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 9:Implementation method is with embodiment 1, just Al
3+Solution changes Mg into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 10:Implementation method is with embodiment 1, just Al
3+Solution changes Mn into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 11:Implementation method is with embodiment 1, just Al
3+Solution changes Ni into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 12:Implementation method is with embodiment 1, just Al
3+Solution changes Pb into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 13:Implementation method is with embodiment 1, just Al
3+Solution changes Sr into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 14:Implementation method is with embodiment 1, just Al
3+Solution changes Zn into
2+Solution is measured ultra-violet absorption spectrum.Significant change does not take place in absorption spectrum.
Embodiment 15:With compound
1 Be dissolved in the distilled water, be made into 3.0 * 10
-5Mol/L gets 2 milliliters and puts into cuvette; Other prepares 3.0 * 10
-2The Al of mol/L
3+Solution is measured the Al of 2 microlitres successively with micro syringe
3+Solution adds in the cuvette, measures fluorescence emission spectrum, and excitation wavelength is 434 nm.Work as Al
3+Concentration be 6.0 * 10
-4During mol/L, emission spectrum maximum absorption band red shift to 671 nm, fluorescence intensity strengthens about ten times, and no longer along with Al
3+Concentration raises and changes.
Embodiment 16:Implementation method is with embodiment 15, just Al
3+Solution changes Sn into
4+Solution is measured fluorescence emission spectrum, and excitation wavelength is 434 nm.Work as Sn
4+Concentration be 1.8 * 10
-3During mol/L, emission spectrum maximum absorption band red shift to 673 nm, fluorescence intensity strengthens about ten times, and no longer along with Sn
4+Concentration raises and changes.
Embodiment 17:With compound
1 , AlCl
3, ethylenediamine tetraacetic acid is dissolved in the distilled water, is made into 5.0 * 10 respectively
-4, 2.5 * 10
-3, 5.0 * 10
-3Mol/L solution filters for use.In being added with serum and two anti-DMEM nutrient culture media, cultivate the A549 cell, treat that cell length to 50%-60% is o'clock for use.Cultured A549 cell is placed the compound for preparing
1 In the solution, soak after one hour with phosphate buffered saline (PBS) and give a baby a bath on the third day after its birth time, take out creep plate, the glycerine mounting is just being put fluorescent microscope AX10 under with blue-light excited, and photograph, and the discovery cell presents faint green fluorescence.
Embodiment 18:Implementation method is cultured A549 cell to be placed prepare with embodiment 17
1 And AlCl
3Mixed solution in soak after two hours, take out with blue-light excited and take a picture, find the green fluorescence enhancing that cell appears.
Embodiment 19:Implementation method is cultured A549 cell to be placed prepare with embodiment 17
1 , AlCl
3After soaking ten minutes in the mixed solution of ethylenediamine tetraacetic acid, take out with blue-light excited and take a picture, the discovery cell presents faint green fluorescence again.
Claims (3)
1. discern aluminum ions method with the water-soluble porphyrin probe in the aqueous phase high selectivity for one kind, it is characterized in that: the water-soluble porphyrin probe is meta-four (4-sulphenyl) porphyrin, has following structural formula; It is characterized in that: in the WS, in the presence of aluminium ion, uv-visible absorption spectra main peak red shift to 434 nm of meta-four (4-sulphenyl) porphyrin, and be that two new absorption peaks appear in 497 nm and 713 nm places at wavelength, and no longer along with Al
3+Concentration raises and continues red shift; And barium, cadmium, iron (II), lithium, magnesium, manganese, sodium, strontium, zinc, copper, nickel, lead ion can only make the spectrum generation subtle change of water-soluble porphyrin; Near fluorescence emission spectrum red shift to 671 nm, and fluorescence intensity obviously strengthens.
2. one kind with the method for water-soluble porphyrin probe at aqueous phase high selectivity identification tin ion, it is characterized in that: identical in water-soluble porphyrin probe and the claim 1; It is characterized in that: in the WS, in the presence of tin ion, uv-visible absorption spectra main peak red shift to 434 nm of meta-four (4-sulphenyl) porphyrin, and at 494 nm and two new absorption peaks of 644 nm places appearance, and no longer along with Sn
4+Concentration raises and continues red shift; And barium, cadmium, iron (II), lithium, magnesium, manganese, sodium, strontium, zinc, copper, nickel, lead ion can only make the spectrum generation subtle change of water-soluble porphyrin; Near fluorescence emission spectrum red shift to 673 nm, and fluorescence intensity obviously strengthens.
3. one kind shows the method that aluminium ion exists with the water-soluble porphyrin probe in people's lung cancer A549 cell; It is characterized in that: identical in water-soluble porphyrin probe and the claim 1; And in the presence of aluminium ion, dye that green fluorescence obviously strengthens in people's lung cancer A549 cell of meta is arranged-four (4-sulphenyl) porphyrin.
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| CN103487416B (en) * | 2013-03-06 | 2016-01-20 | 中北大学 | A kind of based on the fluorescent optical sensor of asymmetrical porphyrin fluorescence than detection zinc ion |
| CN103755928B (en) * | 2013-09-17 | 2016-03-09 | 华南理工大学 | A kind of water-soluble porphyrin conjugated polymers and preparation method thereof and application |
| CN103674920A (en) * | 2013-12-18 | 2014-03-26 | 南京理工大学 | Application of rhodamine B based fluorescence sensor |
| CN104198448B (en) * | 2014-07-23 | 2017-05-24 | 盐城师范学院 | Probe for detecting aluminum ion, preparation method and kit including the probe |
| CN104792756A (en) * | 2015-05-20 | 2015-07-22 | 东南大学 | Application of tetra-p-sulfonic group-phenyl porphyrin derivative as fluorescent probe in aspect of detecting zinc ions |
| CN105510309B (en) * | 2015-12-17 | 2018-10-26 | 西北师范大学 | A kind of water solubility electrochemical luminescence reagent and method that it is quantitatively detected |
| CN106317063B (en) * | 2016-08-22 | 2018-05-01 | 浙江大学城市学院 | A kind of preparation and application of response type mercury ion fluorescence probe |
| CN106317062B (en) * | 2016-08-22 | 2018-04-06 | 浙江大学城市学院 | A kind of preparation and application for the Ratiometric fluorescent probe for determining cadmium ion |
| CN108414489B (en) * | 2018-03-19 | 2021-02-05 | 西北师范大学 | Double-emission silicon dioxide fluorescent probe for detecting Cu2+In (1) |
| CN114295606B (en) * | 2021-11-10 | 2023-06-09 | 扬州大学 | Microfluidic biological logic gate for detecting ocean copper ions |
| CN115925725A (en) * | 2022-11-25 | 2023-04-07 | 杭州珈晟生物数字技术有限公司 | Aluminum ion fluorescent probe, preparation method and application |
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