CN104004378B - A kind of benzindole hemicyanine dye and uses thereof - Google Patents
A kind of benzindole hemicyanine dye and uses thereof Download PDFInfo
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Abstract
The invention belongs to organic chemistry filed, be specifically related to nitrogen-containing heterocycle compound.Its chemical structure of benzindole hemicyanine dye of the present invention is as shown in the formula shown in (I).Benzindole hemicyanine dye of the present invention is obtained quinoline 4-formaldehyde and 1,1,2-trimethylammonium benzo [e] indole reaction.Benzindole hemicyanine dye of the present invention has ferric ion fluorescence identifying performance, can be used for detecting hydrogen peroxide and glucose.
Description
Technical field
The invention belongs to organic chemistry filed, relate to nitrogen-containing heterocycle compound, be specifically related to benzindole half cyanines.
Background technology
Iron is the indispensable element of the every physiological activity of organism, participate in the transhipment of oxygen in blood, the synthesis of prototropy, DNA and RNA, it is the important component part of various enzyme and oxyphorase, once ferro element lacks in organism, various physiological system will be there is disorderly, cause disease, and excessive iron also exist potential harm.Research shows that in body, iron promoter is too much as relevant with hepatic diseases, diabetes and some tumour in heart with various diseases.Therefore the iron ion probe that design and synthesis selectivity is good, highly sensitive has been a great concern in recent years.The Imaging-PAM that development in recent years is got up has quick nondestructive, and intuitively, sensitivity high, has been widely used in and has detected various compound, such as metal ion, negatively charged ion, pH, glucose, DNA, explosive substance etc.Such as Li Junbo design and synthesis Rhodamine Derivatives, is used for detecting iron ion (Li Junbo, Li Nannan, reverb woods, Wang Jun, Zeng Yan, Wuhan Engineering Univ's journal, 2010,32 (5), 11).
Quinoline has sterilization, hypertension, antidepressant, antianaphylaxis, anti-malarial, biological activity and the pharmacologically active such as antitumor, is often used as the lead compound of synthetic drugs; In addition, because it has excellent metal ion affinity, be often used as the recognition group in chemical sensor, play an important role in synthesis fluorescence sense molecule and bio-imaging etc.The pyranoquinoline as (Hao Huijuan, Zhou Xin, Wu Xue, chemical reagent, 2011,33 (6), 551) design and synthesis such as Hao Huijuan, finds that this quinoline has specific recognition effect to mercury ion.(the Li Xiaobo such as Li Xiaobo, Chang Lingling, Chen Mengxia, Wang Enju, chemical research and application, 2014,26 (1), 97) design and synthesis sulfonyl aminoquinoline, finds that this quinoline has specific recognition effect to zine ion, and does not have fluorescence response to ferric ion.
Cyanine dyes is widely used in the fields such as solar cell, photodynamic therapy (PDT), DNA sequencing, pH probe.Benzindole hemicyanine dye is as a class of cyanine dyes, due to advantages such as its stability are high, absorbing wavelength tunable range is large, molar extinction coefficient is large, the extensive concern of people is obtained in synthesis, character Study and appliance. indole cyanine dyes is an important branch of cyanine dyes, because its molar extinction coefficient is large, fluorescence property good, stability advantages of higher, so be widely applied in infrared laser dye, optic disc storage material, bioanalysis, nucleic acid marking etc. in recent years.Such as, the design and synthesis such as Kang Qiong benzindole hemicyanine dye, have studied the absorption spectra property of dyestuff in different solvents, and the benzindole hemicyanine dye finding synthesis in physiological conditions with the interaction of salmon sperm dna, bovine serum albumin, N,O-Diacetylmuramidase, amylase and Chymotrypsin, find that its fluorescence intensity strengthens (Kang Qiong, Fan Fangli along with the increase of DNA concentration, Bi Weibin, Huang Yi, Fu Yile, Wang Lanying, organic chemistry, 2012,32,567 ~ 573).
Summary of the invention
The object of this invention is to provide a kind of benzindole hemicyanine dye, this benzindole hemicyanine dye can detect ferric ion, hydrogen peroxide and glucose.
The technical scheme that the present invention solves the problem is:
A kind of benzindole hemicyanine dye, its structural formula is for shown in (I):
Benzindole hemicyanine dye of the present invention adopts this area common method synthesis, e.g., quinoline 4-formaldehyde and 1,1,2-trimethylammonium benzo [e] indole reaction is obtained.
The method that the present inventor recommends represents by reacting formula II:
The fluorescence spectrum of benzindole hemicyanine dye of the present invention has a hyperfluorescenceZeng Yongminggaoyingguang peak at 540nm place, under 365nm optical excitation, show green fluorescence.After adding ferric ion, fluorescence generation cancellation, and it is less to add its change in fluorescence of ferrous ion.Because oxidation of divalent iron ion can be ferric ion by hydrogen peroxide, therefore the fluorescence of benzindole hemicyanine dye of the present invention and ferrous ion system can by hydrogen peroxide cancellation.
The method that benzindole hemicyanine dye of the present invention detects ferric ion is made up of following steps:
(1) benzindole hemicyanine dye is dissolved in hydrophilic organic solvent, prepares benzindole hemicyanine dye storing solution, obtain containing the benzindole hemicyanine dye aqueous solution after getting benzindole hemicyanine dye storing solution dilute with water; Described contains in the benzindole hemicyanine dye aqueous solution, and hydrophilic organic solvent content is 0.1% (v/v), and the concentration of benzindole hemicyanine dye is 10 ~ 50mM, and described hydrophilic organic solvent is acetonitrile, THF, DMF or DMSO;
(2) drip detected sample, under wavelength is 365nm optical excitation, observes aqueous solution fluorescence and whether change, if the cancellation of aqueous solution fluorescence color, then contain ferric ion in interpret sample.
The fluorescence spectrum of benzindole hemicyanine dye of the present invention demonstrates a fluorescence peak at 540nm place, and fluorescence color is green; After adding ferric ion, its fluorescence generation cancellation.Its principle is, ferric ion can be had an effect with the quinoline on benzindole hemicyanine dye, affects the conjugation effect of benzindole hemicyanine dye, causes fluorescent quenching.Benzindole hemicyanine dye of the present invention has selectivity to ferric ion, and other metal ions are as K
+, Na
+, Ca
2+, Cu
2+, Pb
2+, Zn
2+, Ag
+, Mg
2+, Hg
2+, Co
2+, Fe
2+, Mn
2+can not the fluorescence of cancellation benzindole hemicyanine dye.
Ferric ion and the fluorescence of ferrous ion to benzindole hemicyanine dye of the present invention produce different effects.The fluorescence of ferric ion cancellation benzindole hemicyanine dye of the present invention, and ferrous ion can not.Because oxidation of divalent iron ion can be ferric ion by hydrogen peroxide, therefore the fluorescence of benzindole hemicyanine dye of the present invention and ferrous ion system can by hydrogen peroxide cancellation.
The method that benzindole hemicyanine dye of the present invention detects hydrogen peroxide is made up of following steps:
(1) benzindole hemicyanine dye is dissolved in hydrophilic organic solvent, prepare benzindole hemicyanine dye storing solution, ferrous chloride is dissolved in water and prepares the ferrous ion aqueous solution, get benzindole hemicyanine dye storing solution and ferrous ion aqueous solution respectively even, then after dilute with water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion; Described contains in the aqueous solution of benzindole hemicyanine dye and ferrous ion, hydrophilic organic solvent content is 0.1% (v/v), the concentration of benzindole hemicyanine dye is 10 ~ 50mM, and the mol ratio of ferrous ion and benzindole hemicyanine dye is 5:1; Described hydrophilic organic solvent is acetonitrile, THF, DMF or DMSO;
(2) drip detected sample, under wavelength is 365nm optical excitation, observes aqueous solution fluorescence and whether change, if the cancellation of aqueous solution fluorescence color, then contain hydrogen peroxide in interpret sample.
The method that benzindole hemicyanine dye of the present invention detects glucose is made up of following steps:
(1) benzindole hemicyanine dye is dissolved in hydrophilic organic solvent, prepare benzindole hemicyanine dye storing solution, ferrous chloride is dissolved in water and prepares the ferrous ion aqueous solution, get benzindole hemicyanine dye storing solution, the ferrous ion aqueous solution and glucose oxidase respectively to mix, then after dilute with water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion; Described contains in the aqueous solution of benzindole hemicyanine dye and ferrous ion, hydrophilic organic solvent content is 0.1% (v/v), the concentration of benzindole hemicyanine dye is 10 ~ 50mM, the mol ratio of ferrous ion and benzindole hemicyanine dye is 5:1, and glucose oxidase is 5 ~ 20U/10mL; Described hydrophilic organic solvent is acetonitrile, THF, DMF or DMSO;
(2) drip detected sample, under wavelength is 365nm optical excitation, observes aqueous solution fluorescence and whether change, if the cancellation of aqueous solution fluorescence color, then contain glucose in interpret sample.
Below for the benzindole hemicyanine dye shown in chemical formula (I), illustrate that benzindole hemicyanine dye is applied as detection ferric ion, the fluorescent probe of hydrogen peroxide and glucose, and in the effect of intracellular Fluorescence imaging.
One, fluoroscopic examination ferric ion
1. the selectivity of fluoroscopic examination ferric ion
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 30mM, gets 10ml benzindole hemicyanine dye acetonitrile solution, with distilled water diluting to 10ml, obtains the benzindole hemicyanine dye aqueous solution.
(2) compound concentration is the KCl of 30mM respectively, NaCl, CaCl
2, Cu (NO
3)
22H
2o, Pb (NO
3)
2, Zn (NO
3)
2, HgCl
2, Ni (NO
3)
26H
2o, Cd (NO
3)
24H
2o, MnCl
24H
2o, AgNO
3, CoCl
26H
2o, FeCl
36H
2oFeCl
24H
2the aqueous solution of O.
(3) get the 10ml benzindole hemicyanine dye aqueous solution, drip the KCl of 0.1ml respectively, NaCl, CaCl
2, Cu (NO
3), Pb (NO
3)
2, Zn (NO
3)
2, HgCl
2, Ni (NO
3)
2, Cd (NO
3)
2, MnCl
2, AgNO
3, CoCl
2, FeCl
3, FeCl
2the aqueous solution, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Found that, the fluorescence color of the benzindole hemicyanine dye aqueous solution is green, adds FeCl
3after the aqueous solution, the fluorescent quenching of the benzindole hemicyanine dye aqueous solution; And add KCl, NaCl, CaCl
2, Cu (NO
3), Pb (NO
3)
2, Zn (NO
3)
2, HgCl
2, Ni (NO
3)
2, Cd (NO
3)
2, MnCl
2, AgNO
3, CoCl
2, FeCl
2the aqueous solution after, the fluorescence color of the benzindole hemicyanine dye aqueous solution remains unchanged.Therefore benzindole hemicyanine dye demonstrates selectivity and fluorescence identifying ability to ferric ion.
Detect the fluorescence spectrum figure of above-mentioned solution as shown in Figure 1.Found that, add ferric ion, in the fluorescence spectrum of solution, the fluorescence peak at 540nm place disappears; And adding other ions, the fluorescence spectrum change of solution is less.Benzindole hemicyanine dye demonstrates good selectivity to ferric ion.
2. the working curve of fluorometric titration ferric ion
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 30mM; Compound concentration is the FeCl of 30mM
3the aqueous solution.
(2) get 10ml benzindole hemicyanine dye acetonitrile solution, add in 10mL volumetric flask; Get the FeCl of different volumes
3the aqueous solution, add in above-mentioned volumetric flask, with distilled water diluting to 10ml, be mixed with the standard test solution of ferric ion different concns, excite at 368m place, 540nm place test its fluorescence intensity.Test result is shown in accompanying drawing 2.The binding constant calculating benzindole hemicyanine dye and ferric ion with nonlinear least square method is 1.503 × 10
6m
-1.
3. the Concentration Testing of ferric ion
Adopt the working curve of above-mentioned preparation, add with sample to be tested (our unit's laboratory preparation) and replace stock solution, measure fluorescence intensity at 550nm place, calculate ferric ion content amount, at below 2.34mM from working curve.
4. interfering ion coexists and detects ferric ion experiment
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 30mM, gets 10ml benzindole hemicyanine dye acetonitrile solution, with distilled water diluting to 10ml, obtains the benzindole hemicyanine dye aqueous solution.
(2) compound concentration is the KCl of 30mM respectively, NaCl, CaCl
2, Cu (NO
3)
22H
2o, Pb (NO
3)
2, Zn (NO
3)
2, HgCl
2, Ni (NO
3)
26H
2o, Cd (NO
3)
24H
2o, MnCl
24H
2o, AgNO
3, CoCl
26H
2o, FeCl
36H
2oFeCl
24H
2the aqueous solution of O.
(3) get the 10ml benzindole hemicyanine dye aqueous solution, add the FeCl of 0.1mL
3the aqueous solution, then drips the KCl of 0.1ml, NaCl, CaCl respectively
2, Cu (NO
3), Pb (NO
3)
2, Zn (NO
3)
2, HgCl
2, Ni (NO
3)
2, Cd (NO
3)
2, MnCl
2, AgNO
3, CoCl
2, FeCl
2the aqueous solution, after mixing, excite at 368nm, in 540nm place fluorescence intensity.Test result is as Fig. 3.
Can know that other metal ions affect less on the fluoroscopic examination of ferric ion by Fig. 3.
Two, fluoroscopic examination hydrogen peroxide
1. the working curve of fluorometric titration hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye DMSO solution of 30mM, and configuration concentration is the ferrous chloride aqueous solution of 30mM; Compound concentration is the hydrogen peroxide solution of 30mM.
(2) 10ml benzindole hemicyanine dye DMSO solution is got and the 1mL ferrous chloride aqueous solution adds in 10mL volumetric flask; Get the aqueous solution of the hydrogen peroxide of different volumes, add in above-mentioned volumetric flask, with distilled water diluting to 10ml, be mixed with the standard test solution of hydrogen peroxide different concns, excite at 368m place, in its fluorescence intensity of 540nm place test.Test result is shown in Fig. 4.Detect the fluorescence spectrum of above-mentioned solution.Found that, after adding hydrogen peroxide, in the fluorescence spectrum of solution, the fluorescence peak at 540nm place disappears.Calculating the cancellation constant of hydrogen peroxide to benzindole hemicyanine dye and ferrous ion system with nonlinear least square method is K
a=3.734 × 10
5m
-1.
2. the Concentration Testing of hydrogen peroxide
Adopt the working curve of above-mentioned preparation, add with sample to be tested and replace stock solution, measure fluorescence intensity at 550nm place, calculate hydrogen peroxide content from working curve, concentration is 41.2mM.Adopting volumetry to detect and obtaining hydrogen peroxide concentration is 44.6mM.
Three, fluoroscopic examination glucose
1. the working curve of fluorometric titration hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye THF solution of 30mM, and configuration concentration is the ferrous chloride aqueous solution of 30mM; Compound concentration is the glucose solution of 30mM.
(2) get 10ml benzindole hemicyanine dye DMSO solution, the glucose oxidase of the 1mL ferrous chloride aqueous solution and 10U adds in 10mL volumetric flask; Get the aqueous solution of the glucose of different volumes, add in above-mentioned volumetric flask, with distilled water diluting to 10ml, be mixed with the standard test solution of glucose different concns, excite at 368m place, in its fluorescence intensity of 540nm place test.Test result is shown in Fig. 5.Detect the fluorescence spectrum of above-mentioned solution.Found that, after adding glucose, in the fluorescence spectrum of solution, the fluorescence peak at 540nm place disappears.
Four, the application of benzindole hemicyanine dye fluorescent imaging in vivo and in vitro
1.MTT method detects cells growth activity
By PC3 cell with every hole 6X10
3individual cell is inoculated in 96 orifice plates, overnight incubation, uses instead and is respectively 5 containing benzindole hemicyanine dye concentration, the nutrient solution of 10,15,20mmol/ml, after continuing to cultivate 24h, inhale and abandon supernatant liquor, every hole adds 200mlMTT reagent (5mg/ml, prepare with PBS), continue to cultivate 4h, discard nutrient solution, every hole adds 150 μ lDMSO, be placed in cell shaking table 10min, dissolve completely to blue particle.By microplate reader (the full-automatic microplate reader of ELX800, Bao Te Instrument Ltd. of the U.S.) under excitation wavelength is 490nm condition, measure each hole absorbance, with the nutrient solution containing cell and MTT for control group, only to add the nutrient solution of equivalent and MTT for blank well.Calculate cell survival rate according to the following equation: cell survival rate (%)=(experimental port absorbance-blank well absorbance)/(control wells absorbance-blank well absorbance) × 100%.Each concentration arranges 5 parallel holes, experiment repetition 3 times.Result as shown in Figure 6.The cytotoxicity that Fig. 6 shows benzindole hemicyanine dye is low.
2. cell cultures and imaging
The PC3 cell of taking the logarithm vegetative period is inoculated in and is equipped with in 6 orifice plates, overnight incubation, the RPMI-1640 used instead containing 10mmol/ml benzindole hemicyanine dye cleans 6 orifice plate 3 times with phosphate buffered saline buffer, removes excessive benzindole hemicyanine dye after continuing to cultivate 30min.After the RPMI-1640 that cell continues to add propidium iodide (10mg/ml) continues to cultivate 30min, clean 6 orifice plate 3 times with phosphate buffered saline buffer, remove excessive propidium iodide.Observe under cell being placed in laser confocal microscope.Green fluorescence is there is in the cell after the process of benzindole hemicyanine dye in tenuigenin.Result shows that benzindole hemicyanine dye has good Cell permeable, can be applied as intracellular fluorescent probe.
Accompanying drawing explanation
The fluorescence spectrum figure of Fig. 1 benzindole hemicyanine dye, wherein benzindole hemicyanine dye concentration is 20 μMs, and ionic concn is 200 μMs.
Fig. 2 adds the fluorescence spectrum figure of benzindole hemicyanine dye after different concns ferric ion, and wherein benzindole hemicyanine dye concentration is 20 μMs.
Fig. 3 adds the fluorescence intensity at the 540nm place of benzindole hemicyanine dye after ferric ion and other metal ions, and wherein benzindole hemicyanine dye concentration is 20 μMs, and ferric ion concentration is 200 μMs, and other concentration of metal ions are 200 μMs.
Fig. 4 adds the fluorescence spectrum figure of benzindole hemicyanine dye and ferrous ion mixed system after different concns hydrogen peroxide, and wherein benzindole hemicyanine dye concentration is 20 μMs, and ferrous ion concentration is 200 μMs.
Fig. 5 adds benzindole hemicyanine dye after different glucose, and the fluorescence spectrum figure of ferrous ion and glucose oxidase mixed system, wherein benzindole hemicyanine dye concentration is 20 μMs, and ferrous ion concentration is 200 μMs, and glucose oxidase is 10U.
The cytotoxicity of Fig. 6 benzindole hemicyanine dye.
Embodiment
With specific embodiment, preparation method of the present invention and effect thereof are described in further detail below.
Embodiment 1
1. the preparation of benzindole hemicyanine dye
In 100ml flask, add 2.09g (10.00mmol) 1,1,2-trimethylammonium-1H-benzo [e] indoles, 1.57g (10.00mmol) 4-quinoline aldehyde and 0.05g ammonium acetate, then add 50ml dehydrated alcohol.React under room temperature after 12 hours, underpressure distillation is except desolventizing, and residual solids silicagel column consists of ethyl acetate at elutriant: under normal hexane=1:1 (v/v), purifying obtains yellow solid 2.05g.Productive rate 59%.
2. the sign of compound
1HNMR(400MHz,DMSO-d
6)δ(ppm)＝8.99(d,J＝4.5Hz,1H),8.61(d,J＝15.9Hz,1H),8.40(d,J＝8.4Hz,1H),8.21(d,J＝8.4Hz,1H),8.12(s,1H),8.10(s,1H),8.06(d,J＝8.2Hz,1H),8.00(d,J＝8.5Hz,1H),7.89(d,J＝8.5Hz,1H),7.84(t,J＝7.5Hz,1H),7.76(s,1H),7.72(d,J＝5.9Hz,1H),7.65(t,J＝7.5Hz,1H),7.54(t,J＝7.5Hz,1H),1.70(s,6H).
13CNMR(100MHz,DMSO-d
6)δ＝184.33,150.73,150.29,148.28,140.55,139.90,132.26,130.44,129.68,129.62,129.49,129.11,128.06,127.21,126.80,125.58,125.38,124.97,123.51,123.09,120.27,117.87,54.28,21.85.
IR(v
-1,LiBr):3452,2961,2915,2851,2024,1639,1568,1498,1458,1386,1115,961,818,756,608.
MS(MALDI-Cl):C
25H
20N
2m/z348.1626for[M+H
+]349.1699.
ElementalAnalysis:CalcdC,86.17；H,5.79；N,8.04.FoundC,86.11；H,5.82；N,8.07.
mp:246.5-247.0℃.
Above-mentioned detected result confirms that the compound of preparation is the benzindole hemicyanine dye shown in chemical formula (I).
Embodiment 2
Benzindole hemicyanine dye detects ferric ion
(1) compound concentration is the benzindole hemicyanine dye DMSO solution of 30mM, gets 10 μ l benzindole hemicyanine dye DMSO solution respectively, and it is rare to 10ml to add distilled water, obtains the benzindole hemicyanine dye aqueous solution;
(2) compound concentration is the iron nitrate aqueous solution of 30mM, and concentration is the ferrous sulfate aqueous solution of 100mM, and concentration is the copper sulfate solution of 30mM;
(3) in the 10ml benzindole hemicyanine dye aqueous solution, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding iron nitrate aqueous solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of ferrous sulfate and copper sulfate, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye demonstrates selectivity and fluorescence identifying ability to ferric ion.
Embodiment 3
Benzindole hemicyanine dye detects ferric ion
(1) compound concentration is the benzindole hemicyanine dye THF solution of 20mM, gets 10 μ l benzindole hemicyanine dye THF solution respectively, and it is rare to 10ml to add distilled water, obtains the benzindole hemicyanine dye aqueous solution;
(2) compound concentration is the ferric chloride in aqueous solution of 15mM, and concentration is the ferrous sulfate aqueous solution of 100mM, and concentration is the magnesium sulfate solution of 30mM;
(3) in the 10ml benzindole hemicyanine dye aqueous solution, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding iron nitrate aqueous solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of ferrous sulfate and magnesium sulfate, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye demonstrates selectivity and fluorescence identifying ability to ferric ion.
Embodiment 4
Benzindole hemicyanine dye detects ferric ion
(1) compound concentration is the benzindole hemicyanine dye DMF solution of 40mM, gets 10 μ l benzindole hemicyanine dye DMF solution respectively, and it is rare to 10ml to add distilled water, obtains the benzindole hemicyanine dye aqueous solution;
(2) compound concentration is the ferric chloride in aqueous solution of 30mM, and concentration is the ferrous chloride aqueous solution of 150mM, and concentration is the zinc nitrate aqueous solution of 30mM;
(3) in the 10ml benzindole hemicyanine dye aqueous solution, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding iron nitrate aqueous solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of iron protochloride and zinc nitrate, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye demonstrates selectivity and fluorescence identifying ability to ferric ion.
Embodiment 5
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 30mM; Compound concentration is the ferrous chloride aqueous solution of 30mM;
(2) get 10 μ l benzindole hemicyanine dye acetonitrile solutions and the 50 μ l ferrous chloride aqueous solution respectively, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion;
(3) compound concentration is the aqueous hydrogen peroxide solution of 30mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding aqueous hydrogen peroxide solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution.We contain the aqueous solution of benzindole hemicyanine dye and zine ion according to aforesaid method preparation and contain the aqueous solution of benzindole hemicyanine dye and nickel ion, add aqueous hydrogen peroxide solution in the above-mentioned aqueous solution after, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye and ferrous ion system demonstrate selectivity and fluorescence identifying ability to hydrogen peroxide.
Embodiment 6
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye DMSO solution of 50mM; Compound concentration is the sulfation water solution of 25mM, get 10 μ l benzindole hemicyanine dye DMSO solution and the 100 μ l ferrous chloride aqueous solution respectively, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion;
(2) compound concentration is the aqueous hydrogen peroxide solution of 10mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding aqueous hydrogen peroxide solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution.We contain the aqueous solution of benzindole hemicyanine dye and cupric ion according to aforesaid method preparation and contain the aqueous solution of benzindole hemicyanine dye and calcium ion, add aqueous hydrogen peroxide solution in the above-mentioned aqueous solution after, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye and ferrous ion system demonstrate selectivity and fluorescence identifying ability to hydrogen peroxide.
Embodiment 7
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye DMF solution of 10mM; Compound concentration is the ferrous chloride aqueous solution of 50mM, get 10 μ l benzindole hemicyanine dye DMF solution and the 10 μ l ferrous chloride aqueous solution respectively, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion;
(2) compound concentration is the aqueous hydrogen peroxide solution of 100mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding aqueous hydrogen peroxide solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution.We contain the aqueous solution of benzindole hemicyanine dye and silver ions according to aforesaid method preparation and contain the aqueous solution of benzindole hemicyanine dye and sodium ion, add aqueous hydrogen peroxide solution in the above-mentioned aqueous solution after, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye and ferrous ion system demonstrate selectivity and fluorescence identifying ability to hydrogen peroxide.
Embodiment 8
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 40mM; Compound concentration is the ferrous chloride aqueous solution of 40mM, get 10 μ l benzindole hemicyanine dye acetonitrile solutions and the 50 μ l ferrous chloride aqueous solution respectively, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion;
(2) compound concentration is the aqueous hydrogen peroxide solution of 20mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding aqueous hydrogen peroxide solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution.We contain the aqueous solution of benzindole hemicyanine dye and divalent manganesetion according to aforesaid method preparation and contain the aqueous solution of benzindole hemicyanine dye and potassium ion, add aqueous hydrogen peroxide solution in the above-mentioned aqueous solution after, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye and ferrous ion system demonstrate selectivity and fluorescence identifying ability to hydrogen peroxide.
Embodiment 9
Benzindole hemicyanine dye detects glucose
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 30mM; Compound concentration is the ferrous chloride aqueous solution of 30mM, get 10 μ l benzindole hemicyanine dye acetonitrile solutions respectively, the 50 μ l ferrous chloride aqueous solution, the glucose oxidase of 10U, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion;
(2) compound concentration is the D/W of 30mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding D/W, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution.We contain the aqueous solution of benzindole hemicyanine dye and mercury ion according to aforesaid method preparation and contain the aqueous solution of benzindole hemicyanine dye and zine ion, add aqueous hydrogen peroxide solution in the above-mentioned aqueous solution after, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye and ferrous ion system demonstrate selectivity and fluorescence identifying ability to hydrogen peroxide.
Embodiment 10
Benzindole hemicyanine dye detects glucose
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 30mM; Compound concentration is the ferrous chloride aqueous solution of 30mM, get 10 μ l benzindole hemicyanine dye acetonitrile solutions respectively, the glucose oxidase of the 50 μ l ferrous chloride aqueous solution and 20U, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain containing benzindole hemicyanine dye, the aqueous solution of ferrous ion and glucose oxidase;
(2) compound concentration is the aqueous hydrogen peroxide solution of 30mM, and concentration is the fructose water solution of 150mM, and concentration is the semi-lactosi aqueous solution of 30mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding D/W, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of fructose and semi-lactosi, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.Benzindole hemicyanine dye, ferrous ion and glucose oxidase enzyme system demonstrate selectivity and fluorescence identifying ability to glucose.
Embodiment 11
Benzindole hemicyanine dye detects glucose
(1) compound concentration is the benzindole hemicyanine dye DMSO solution of 50mM; Compound concentration is the sulfation water solution of 25mM, get 10 μ l benzindole hemicyanine dye DMSO solution respectively, the glucose oxidase of the 100 μ l ferrous chloride aqueous solution and 5U, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain containing benzindole hemicyanine dye, the aqueous solution of ferrous ion and glucose oxidase;
(2) compound concentration is the D/W of 10mM, and concentration is the semi-lactosi aqueous solution of 150mM, and concentration is the fructose water solution of 30mM;
(3) benzindole hemicyanine dye is contained at 10ml, a kind of aqueous solution 0.1ml that step (2) is prepared is dripped respectively in the aqueous solution of ferrous ion and glucose oxidase, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding D/W, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of fructose and semi-lactosi, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.Benzindole hemicyanine dye, ferrous ion and glucose oxidase enzyme system demonstrate selectivity and fluorescence identifying ability to glucose.
Embodiment 12
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye DMF solution of 10mM; Compound concentration is the ferrous chloride aqueous solution of 50mM, get 10 μ l benzindole hemicyanine dye DMF solution respectively, the glucose oxidase of the 10 μ l ferrous chloride aqueous solution and 15U, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain containing benzindole hemicyanine dye, the aqueous solution of ferrous ion and glucose oxidase;
(2) compound concentration is the D/W of 100mM, and concentration is the fructose water solution of 150mM, and concentration is the semi-lactosi aqueous solution of 150mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding D/W, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of fructose and semi-lactosi, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye, and ferrous ion and glucose oxidase enzyme system demonstrate selectivity and fluorescence identifying ability to glucose.
Embodiment 13
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye DMF solution of 20mM; Compound concentration is the ferrous chloride aqueous solution of 20mM, get 10 μ l benzindole hemicyanine dye DMF solution respectively, the glucose oxidase of the 50 μ l ferrous chloride aqueous solution and 20U, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain containing benzindole hemicyanine dye, the aqueous solution of ferrous ion and glucose oxidase;
(2) compound concentration is the D/W of 80mM, and concentration is the fructose water solution of 200mM, and concentration is the semi-lactosi aqueous solution of 200mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding D/W, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of fructose and semi-lactosi, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye, and ferrous ion and glucose oxidase enzyme system demonstrate selectivity and fluorescence identifying ability to glucose.
Embodiment 14
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye DMF solution of 40mM; Compound concentration is the ferrous chloride aqueous solution of 40mM, get 10 μ l benzindole hemicyanine dye DMF solution respectively, the glucose oxidase of the 50 μ l ferrous chloride aqueous solution and 10U, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain containing benzindole hemicyanine dye, the aqueous solution of ferrous ion and glucose oxidase;
(2) compound concentration is the D/W of 60mM, and concentration is the fructose water solution of 200mM, and concentration is the semi-lactosi aqueous solution of 200mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding D/W, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of fructose and semi-lactosi, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye, and ferrous ion and glucose oxidase enzyme system demonstrate selectivity and fluorescence identifying ability to glucose.
Embodiment 15
Benzindole hemicyanine dye detects hydrogen peroxide
(1) compound concentration is the benzindole hemicyanine dye acetonitrile solution of 20mM; Compound concentration is the ferrous chloride aqueous solution of 20mM, get 10 μ l benzindole hemicyanine dye acetonitrile solutions and the 50 μ l ferrous chloride aqueous solution respectively, add in 10mL volumetric flask, rare to 10ml with distilled water, obtain the aqueous solution containing benzindole hemicyanine dye and ferrous ion;
(2) compound concentration is the aqueous hydrogen peroxide solution of 20mM, and concentration is the ferrous chloride aqueous solution of 150mM, and concentration is the sodium chloride aqueous solution of 30mM;
(3) in the aqueous solution of 10ml containing benzindole hemicyanine dye and ferrous ion, drip a kind of aqueous solution 0.1ml that step (2) is prepared respectively, after mixing, under 365nm optical excitation, observe the change in fluorescence of the benzindole hemicyanine dye aqueous solution.
Result shows, after adding aqueous hydrogen peroxide solution, and the fluorescent quenching of the benzindole hemicyanine dye aqueous solution, and after adding the aqueous solution of iron protochloride and sodium-chlor, the fluorescence of the benzindole hemicyanine dye aqueous solution remains unchanged.This result shows, benzindole hemicyanine dye and ferrous ion system demonstrate selectivity and fluorescence identifying ability to hydrogen peroxide.
Claims (1)
1. detect a method for ferric ion, the method is made up of following steps:
(1) benzindole hemicyanine dye is dissolved in hydrophilic organic solvent, prepares benzindole hemicyanine dye storing solution, obtain containing the benzindole hemicyanine dye aqueous solution after getting benzindole hemicyanine dye storing solution dilute with water; Described contains in the benzindole hemicyanine dye aqueous solution, and hydrophilic organic solvent content is 0.1% (v/v), and the concentration of benzindole hemicyanine dye is 10 ~ 50 μMs, and described hydrophilic organic solvent is acetonitrile, THF, DMF or DMSO;
(2) toward step (1) obtain containing dripping the aqueous solution in the benzindole hemicyanine dye aqueous solution detected sample, under wavelength is 365nm optical excitation, observe aqueous solution fluorescence whether to change, if the cancellation of benzindole hemicyanine dye aqueous solution fluorescence color, then contain ferric ion in interpret sample;
The chemical structural formula of above-mentioned benzindole hemicyanine dye is as shown in the formula shown in (I):
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| CN201410258440.7A CN104004378B (en) | 2014-06-11 | 2014-06-11 | A kind of benzindole hemicyanine dye and uses thereof |
| CN201510313799.4A CN104833668B (en) | 2014-06-11 | 2014-06-11 | Application of benzoindohemicyanine dye in detection of hydrogen peroxide |
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| CN101805526A (en) * | 2010-04-10 | 2010-08-18 | 大连理工大学 | Synthesis and application of indole hemicyanine dye |
| CN102618060A (en) * | 2012-03-17 | 2012-08-01 | 江南大学 | Method for preparing asymmetrical cyanine dye and method for detecting bovine serum albumin by asymmetrical cyanine dye |
| CN103756669A (en) * | 2014-01-22 | 2014-04-30 | 山西大学 | Indole pH fluorescence probe, and preparation method and application thereof |
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| CN100425612C (en) * | 2006-04-11 | 2008-10-15 | 山东师范大学 | Fluorescent probe for detecting hydrogen peroxide and its synthesis method and use |
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| WO2011022677A1 (en) * | 2009-08-21 | 2011-02-24 | Massachusetts Institute Of Technology | Optical nanosensors comprising photoluminescent nanostructures |
| JP5800816B2 (en) * | 2010-08-18 | 2015-10-28 | 学校法人同志社 | Metal complexes, fluorescent probes |
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| CN101805526A (en) * | 2010-04-10 | 2010-08-18 | 大连理工大学 | Synthesis and application of indole hemicyanine dye |
| CN102618060A (en) * | 2012-03-17 | 2012-08-01 | 江南大学 | Method for preparing asymmetrical cyanine dye and method for detecting bovine serum albumin by asymmetrical cyanine dye |
| CN103756669A (en) * | 2014-01-22 | 2014-04-30 | 山西大学 | Indole pH fluorescence probe, and preparation method and application thereof |
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