CN107266347A - Organic compound and application based on flower cyanines - Google Patents
Organic compound and application based on flower cyanines Download PDFInfo
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- CN107266347A CN107266347A CN201710623156.9A CN201710623156A CN107266347A CN 107266347 A CN107266347 A CN 107266347A CN 201710623156 A CN201710623156 A CN 201710623156A CN 107266347 A CN107266347 A CN 107266347A
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Abstract
The present invention relates to for detecting superoxide anion (O2 ·‑) and dimercurion fluorescence probe, it is specifically a kind of based on flower cyanines organic compound and application.Compound is used as detection O as shown in structural formula I using the compound2 ·‑With the probe of dimercurion.Present invention detection O2 ·‑With the fluorescence probe of dimercurion, in O2 ·‑Significant change occurs for corresponding fluorescence emission wavelengths and fluorescence intensity with the presence of dimercurion, available for O2 ·‑With the detection of dimercurion, and the interference of external detection condition can be substantially reduced, improve accuracy of detection, detection signal-to-noise ratio is high, sensitivity and selectivity are good.The present invention is compared with traditional sensing techniques, and the fluorescence probe detection of Noninvasive is simple, convenient, quick, and sensitivity is high, and selectivity is good, and the response time is short, and in situ, monitoring, and having wide range of applications in real time can be carried out to detection object.
Description
Technical field
The present invention relates to the fluorescence probe for detecting superoxide anion and dimercurion, specifically one kind is based on
Hua Jing organic compound and application.
Background technology
Mercury is generally acknowledged global environmental contaminants, in the 1950s, the mankind understand mercury since " minamata disease "
(Mercury, Hg) and its compound toxicity.As the purposes of mercury metal (Hg) is more and more wider, the case of mercury poisoning is increasingly
Many, the incidence of disease of mercury poisoning is in sustainable growth trend in China, while also obtaining the extensive concern of government and society.In recent years certain
A little diseases are because of inappropriate medication during diagnosis and treatment, and such as oral mercury, inorganic mercury compound and use are containing in mercury and mercuric compounds
Medicine folk prescription treatment asthma, psoriasis, acne, nasosinusitis etc. cause internal mercury accumulation, are made up using mercurous exceeded whitening spot-removing
Product cause Nonoccupational mercury poisoning case also not rare.Research shows that the pathogenesis of mercury poisoning is intricate, as mercury can be with people
Body metallothionein is combined, and can be replaced the metallic molecule in some enzymes and be changed its vigor；Mercury can be with the sulfydryl on cell membrane
With reference to causing the change of membrane permeability；Mercury poisoning can also cause oxidative stress, the exchange of interference neurotransmitter and ion etc..Especially
It is mercury poisoning rear oxidation stress caused by free radical generation increase and eliminate reduce quite paid attention in recent years.Research shows, mercury
On the one hand is combined in vivo with the polyphenoils such as glutathione, the ability of reduction elimination free radical in vivo；On the other hand it can produce again
Raw free radical, causes body lipid peroxide to improve, causes Oxidation-antioxidation system unbalance.It is glimmering involved by this patent
Light probe will be helpful to explore under mercury ion stimulation, the physiology course of active oxidative burst.
It is presently used for detecting O2·-Method have:Electron paramagnetic resonance method, SOD enzyme activity determination method, high performance liquid chromatography
Method (HPLC) and electrochemical method.To mercury compound detection method, including AAS, atomic emission spectrometry, atom
Absorption spectrometry, Hydride Generation-atomic Fluorescence Spectrometry.But these methods need the pretreatment of sample, it is necessary to multiple mostly
Miscellaneous operational means and large-scale instrument.Therefore, a kind of method for finding convenient and swift detection superoxide anion and mercury ion is compeled
The eyebrows and eyelashes.The advantages of fluorescence probe method is detected with its high-spatial and temporal resolution, non-damaging easy to operate and in situ, in biological active matter
Plant detection field, it has also become a kind of powerful research aid.
The content of the invention
It is an object of the invention to provide a kind of organic compound based on flower cyanines and its application.
To achieve the above object, the technical solution adopted by the present invention is：
A kind of organic compound based on flower cyanines, shown in the organic compound structure formula I based on flower cyanines,
Application of the organic compound based on flower cyanines in cooperation detection superoxide anion and dimercurion.
A kind of fluorescence probe, fluorescence probe is the organic compound based on flower cyanines shown in formula I,
The fluorescence probe is used for qualitative/quantitative ground cooperation detection superoxide anion and dimercurion.
A kind of application of fluorescence probe, the fluorescence probe is in qualitative/quantitative ground cooperation detection superoxide anion and divalence
Application in mercury ion.
Beneficial effects of the present invention：The compounds of this invention is used to detect superoxide anion and dimercurion as linkage
Fluorescence probe, it is before and after detection superoxide anion, and fluorescence produces fluorescence by closing to opening；Before and after detection dimercurion, fluorescence
Probe absorbs and fluorescent emission maximum wavelength has change.Available for aqueous systems, simulation physiological environment and intracellular super oxygen it is cloudy from
The linkage of son and dimercurion is detected, and can substantially reduce the interference of external detection condition, improves accuracy of detection.The present inventionization
Compound is used as fluorescence probe, and available for intracellular superoxide anion and dimercurion linkage detection, this is to further investigation super oxygen
The signal transduction process and mechanism of anion and dimercurion in vivo, further appreciate that superoxide anion and bivalent mercury
The physiology and toxicological effect of ion have important biomedical meaning.The present invention is sensitive with simple, convenient, quick
Degree is high, and selectivity is good, and the response time is short, can carry out in situ, monitoring in real time to detection object, and it is excellent to have wide range of applications etc.
Point.
Brief description of the drawings
Fig. 1 is the fluorescence probe of use provided in an embodiment of the present invention to various concentrations superoxide anion (O2 ·-) before detection
Change in fluorescence afterwards.
Fig. 2 is by the fluorescence probe provided in an embodiment of the present invention used to O2 ·-Selective schematic diagram；Wherein, it is horizontal to sit
Mark is followed successively by from left to right：1st, blank；2、O2 ·-(25μM)；3rd, hydroxyl radical free radical (25 μM)；4th, hydrogen peroxide (200 μM)；5th, peroxide
Change linoleic acid (400 μM)；6th, cumene hydroperoxide (300 μM)；7th, tertbutanol peroxide (250 μM)；8th, nitric oxide (300 μ
M)；9th, peroxidating nitrosyl anion (25 μM)；10th, hypochlorous acid (200 μM).
Fig. 3 is the fluorescence probe of use provided in an embodiment of the present invention to various concentrations Hg2+Change in fluorescence before and after detection.
Fig. 4 is by selective schematic diagram of the fluorescence probe provided in an embodiment of the present invention used to mercury ion；Wherein, it is horizontal
Coordinate is followed successively by from left to right：1st, blank；2、KCl(100μM)；3、Zn(CH3COO)2(100μM)；4、CaCl2(100μM)；5、
MgCl2(100μM)；6、CoCl2(100μM)；7、MnCl2(100μM)；8、FeCl3(100μM)；9、CdCl2(100μM)；10、
CuCl2(100μM)；11、NaCl(100μM)；12、Pb(NO3)2(100μM)；13、NiCl2(100μM)；14、HgCl2(10μM)。
Fig. 5 be the cell of Human Embryonic Kidney HEK -293 provided in an embodiment of the present invention as biological model, cell compound I
15 minutes triple channel fluorograms as a control group of (2 μM) incubations.Wherein, passage 1：750-850nm, passage 2：540-585nm,
Passage 3：585-725nm.
Fig. 6 is that (2 μM) of HEK-293 cell compounds I is incubated 15 minutes, adds (2 μM) of superoxide anion and is incubated 15
Minute, the triple channel fluorogram rinsed with MEM culture mediums after cell three times.Passage 1：750-850nm, passage 2：540-585nm,
Passage 3：585-725nm.
Fig. 7 is that (2 μM) of HEK-293 cell compounds I is incubated 15 minutes, adds superoxide anion (2 μM) and HgCl2
Triple channel fluorogram after (2 μM).Passage 1：750-850nm, passage 2：540-585nm, passage 3：585-725nm.
Embodiment
The present invention is further explained with reference to the accompanying drawings and examples.
Based on flower cyanines organic compound structure formula be：
By chemical compounds I with the superoxide anion reaction inside and outside water body to be determined, simulation physiological environment or organism so as to lead
Fluorescence is caused by closing to opening, gained compound II structure；
Dimercurion inside and outside compound II and water body to be determined, simulation physiological environment or organism is reacted, fluorescence
The absorption of probe and fluorescent emission maximum wavelength have change, gained compound III structure；
Present invention detection O2 ·-With the fluorescence probe of dimercurion, in O2 ·-It is corresponding glimmering with the presence of dimercurion
Significant change occurs for light launch wavelength and fluorescence intensity, available for O2 ·-With the detection of dimercurion, and outside can be substantially reduced
The interference of testing conditions, improves accuracy of detection, and detection signal-to-noise ratio is high, and sensitivity and selectivity are good.In addition, invention O2 ·-With two
This kind of compound of valency mercury ion fluorescence probe, in O2 ·-Also occur significant change with UV absorption in the presence of dimercurion, can
Detected with ultraviolet specrophotometer.This kind of compound can be used for O in complex biological sample as fluorescence probe2 ·-And divalence
The linkage detection of mercury ion, under this is stimulated further investigation mercury ion, O2 ·-With the cell signalling of mercury ion in vivo
With important biomedical meaning.The present invention is compared with traditional sensing techniques, the fluorescence probe detection operation letter of Noninvasive
Single, easily and fast, sensitivity is high, and selectivity is good, and the response time is short, and in situ, monitoring in real time can be carried out to detection object, and
Have wide range of applications.
The preparation of organic compound of the embodiment 1. based on flower cyanines：
Flower cyanines fluorogen shown in chemical compounds I come from commercial goods, then different in the corresponding position modification of fluorogen
Detection moiety, obtained corresponding cyanine compound.Specific embodiment is as follows：
(1) compound II preparation
Flower cyanines fluorogen (0.209g, 0.327mmol) is dissolved in 20ml methanol, by Na2Se (0.05g, 0.4mmol)
It is dissolved in 1ml water, under room temperature condition, by 1ml Na2Se solution is added drop-wise in round-bottomed flask, is flowed back under argon gas protection
30min.Washed with saturated solution of potassium iodide, and neutrality is adjusted to glacial acetic acid, extracted through dichloromethane, rotated.Crude product post
Thin layer chromatography is purified, eluant, eluent selection ethyl acetate and methanol (6:1/v/v), 0.128g (0.187mmol) greens are obtained
Solid chemical compound II, yield 57.2%.
Compound II:1H NMR(500MHz,CDCl3-D1)δ(ppm):1.525-1.762(m,12H),1.925(s,1H),
1.964-2.027(m,1H),2.154-2.321(m,7H),2.470(s,1H),2.515(s,1H),2.530-2.562(d,
1H),2.570-2.612(m,1H),2.613-2.685(q,3H),2.700(s,1H),2.871-2.931(q,1H),3.614-
3.678 (q, 1H), 3.868-3.936 (q, 1H), 4.742-4.812 (q, 1H), 7.295-7.340 (m, 2H), 7.422-7.455
(d,1H),7.460-7.490(m,1H),7.497-7.567(m,2H),7.631-7.686(t,1H),7.828-7.882(m,
1H).13C NMR(125MHz,CDCl3-D1)δ(ppm):141.753,141.150,140.443,129.623,128.329,
127.884,127.223,125.866,125.820,124.944,122.758,122.250,122.143,121.638,
113.436,108.207,91.995,52.990,47.823,45.414,43.083,39.115,36.679,28.582,
28.449,27.099,25.488,25.368,22.149,13.417.LC-MS (API-ES):m/z C34H41N2Se+Calcd
557.24, found [M+H]+557.19.
(2) compound I preparation
Compound II (0.12g, 0.1755mmol) is dissolved in 10ml ethanol, by NaBH4(0.0122g,
0.3225mmol) it is dissolved in 2ml ethanol, under condition of ice bath, by 2ml NaBH4Solution is added drop-wise in round-bottomed flask, in argon gas
The lower reaction 10min of protection.Washed, then extracted through dichloromethane with the saturated solution of potassium iodide of deoxygenation, rotated.Crude product post layer
Analysis chromatogram is purified, eluant, eluent selection dichloromethane and petroleum ether (1:1/v/v), 0.049g (0.08786mmol) is obtained yellow
Color solid chemical compound I, yield 50%.
Compound I:1H NMR(500MHz,CDCl3-D1)δ(ppm):1.027(s,4H),1.053-1.110(t,4H),
1.112-1.153(t,1H),1.182-1.291(m,8H),1.334-1.439(t,6H),1.530-1.623(d,7H),
2.180-2.250(m,1H),2.647-2.680(d,1H),3.206-3.294(m,1H),3.364-3.444(m,1H),6.610
(d, 2H), 6.767 (t, 2H), 7.027 (d, 2H), 7.119 (t, 2H)13C NMR(125MHz,CDCl3-D1)δ(ppm):
162.726,149.414,139.000,130.180,127.451,125.718,124.955,124.114,122.155,
118.673,108.388,104.759,102.424,87.948,85.063,53.430,40.661,33.512,32.697,
31.951,29.723,26.499,25.470,24.332,22.714,14.140,9.967.LC-MS (API-ES):m/z
C34H42N2Se Calcd 558.25,found[M+H]+558.15.
Embodiment 2
Chemical compounds I obtained by preparing is as probe application in aqueous systems, simulation physiological environment and intracellular progress to super oxygen
The detection of anion and mercury ion, simulates physiological condition, and the following experiment carries out (HEPES bufferings under the conditions of pH=7.4
Solution, concentration is 10mM), concentration and probe concentration uses 10 μM.
Responses of the compound I to superoxide anion obtained by above-mentioned preparation：
PH is controlled in pH=7.4 using HEPES cushioning liquid.10 μM of chemical compounds Is are added in each 10ml colorimetric cylinders, so
The superoxide anion (superoxide anion concentration is 0-10 μM) of various concentrations is added afterwards, and pH=7.4 10mM HEPES constant volumes are arrived
10ml, shakes up after solution, balance 10min, working solution in each colorimetric cylinder is poured into fluorescence ware respectively and determines fluorescence spectrum.
Fluorescence intensity is determined at 750-900nm, as shown in Figure 1.The superoxide anion inspection that compound I can be used for realizing in organism
Survey.Meanwhile, product structure is as follows after compound I provided in an embodiment of the present invention reacts with superoxide anion：
Mercury chloride (the HgCl of 0-10 μM of various concentrations is then continuously added into above-mentioned each 10ml colorimetric cylinders again2), shake up
After solution, balance 10min, working solution in each colorimetric cylinder is poured into fluorescence ware respectively and determines fluorescence spectrum.In 540-
Fluorescence intensity is determined at 750nm, as shown in Figure 3.Product can further be used to realize life after detection superoxide anion reaction
HgCl in object2Detection.Meanwhile, further with HgCl2Product structure is as follows after reaction：
Embodiment 3
Selectivity of the chemical compounds I to superoxide anion
PH is controlled in pH=7.4 using HEPES cushioning liquid.Multiple 10ml colorimetric cylinders are taken, and in each 10ml colorimetric cylinders
10 μM of chemical compounds Is of middle addition, add different things to be detected, with the HEPES buffer solution constant volume that 10mM pH are 7.4 to 10ml.Shake up
Solution, at 25 DEG C after balance 10min, working solution in each colorimetric cylinder is poured into fluorescence ware respectively and determines fluorescence spectrum (ginseng
See Fig. 2).Determinand is followed successively by：1st, blank；2nd, superoxide anion (25 μM)；3rd, hydroxyl radical free radical (25 μM)；4th, hydrogen peroxide (200
μM)；5th, peroxidating linoleic acid (400 μM)；6th, cumene hydroperoxide (300 μM)；7th, tertbutanol peroxide (250 μM)；8th, one
Nitrogen oxide (300 μM)；9th, peroxidating nitrosyl anion (25 μM)；10th, hypochlorous acid (200 μM).
Chemical compounds I is to the selectivity of superoxide anion as seen from Figure 2, and chemical compounds I has to superoxide anion to be selected well
Selecting property.
Embodiment 4
After embodiment 2 is operated, pH controls pH=7.4 using HEPES cushioning liquid.10 are added in each 10ml colorimetric cylinders
μM chemical compounds I, then adds concentration from 0-10 μM of superoxide anion, pH=7.4 10mM HEPES constant volumes shake up to 10ml
After solution, balance 10min, working solution in each colorimetric cylinder is poured into fluorescence ware respectively and determines fluorescence spectrum.
Determinand then is sequentially added into above-mentioned each colorimetric cylinder, shakes up and is balanced at solution, 25 DEG C after 10min, by each
Working solution is poured into fluorescence ware respectively in colorimetric cylinder determines fluorescence spectrum (referring to Fig. 4).Determinand is followed successively by：1st, blank；2、
KCl(100μM)；3、Zn(CH3COO)2(100μM)；4、CaCl2(100μM)；5、MgCl2(100μM)；6、CoCl2(100μM)；7、
MnCl2(100μM)；8、FeCl3(100μM)；9、CdCl2(100μM)；10、CuCl2(100μM)；11、NaCl(100μM)；12、
Pb(NO3)2(100μM)；13、NiCl2(100μM)；14、HgCl2(10μM).It can be seen that the proof of a step detects super oxygen by chemical compounds I
The compound II produced after anion has good selectivity to dimercurion, further illustrates that chemical compounds I can be used for assisting
With detection superoxide anion and dimercurion.
Embodiment 6
Compound I selects the cell of Human Embryonic Kidney HEK -293 as biological model in the intracellular imaging of Human Embryonic Kidney HEK -293,
First, at 37 DEG C, cell is incubated 15 minutes as a control group for (2 μM) with compound I, and rinsing three cells of cell with MEM does not have
There is display fluorescence (Fig. 5).
With (2 μM) of compound II 15 minutes are incubated at 37 DEG C, then by cell as a control group, and cell three is rinsed with MEM
Secondary cell shows faint fluorescence (Fig. 5).
Select the cell of Human Embryonic Kidney HEK -293 as biological model, first, at 37 DEG C, cell is incubated with compound I (2 μM)
Educate 15 minutes, then add superoxide anion (2 μM) and be incubated again 15 minutes, rinse cell three times with MEM, there is obvious fluorescence to give birth to
Into (referring to Fig. 6), it is seen that compound I can for directly detection living cells external source addition superoxide anion.
Select the cell of Human Embryonic Kidney HEK -293 as biological model, first, at 37 DEG C, cell is incubated with compound I (2 μM)
Educate 15 minutes, then add HgCl2(2 μM) are incubated 15 minutes, cell are rinsed three times with MEM, in 540-585nm fluoroscopic examinations
(Fig. 7) and 585-740nm fluoroscopic examinations (Fig. 7), there is strong fluorescence generation at two.Therefore, chemical compounds I can be used for collaboration straight
Connect the mercury chloride of detection living cells external source addition.
Above content is to combine specific preferred embodiment further description made for the present invention, it is impossible to assert
The specific implementation of the present invention is confined to these explanations.For general technical staff of the technical field of the invention,
On the premise of not departing from present inventive concept, some simple deduction or replace can also be made, should all be considered as belonging to the present invention's
Protection domain.It is a kind of purposes of noval chemical compound of the present invention as fluorescent dye, it is impossible to assert that the compound of the present invention is only used for
Fluorescent dye, for general technical staff of the technical field of the invention, is being used as fluorescence based on the compounds of this invention
Under the consideration of the identical mechanism of action of dyestuff, some simple inferences can also be made, draw the present invention compound other should
With purposes, protection scope of the present invention should be all considered as belonging to.
Claims (5)
1. a kind of organic compound based on flower cyanines, it is characterised in that：Shown in organic compound structure formula I based on flower cyanines,
2. the application of the organic compound based on flower cyanines as described in claim 1, it is characterised in that：The having based on flower cyanines
Machine compound is in cooperation detection superoxide anion (O2 ·-) and dimercurion in application.
3. a kind of fluorescence probe, it is characterised in that：Fluorescence probe is the organic compound based on flower cyanines shown in formula I,
4. the fluorescence probe as described in claim 3, it is characterised in that：The fluorescence probe is used for qualitative/quantitative ground cooperation detection
Superoxide anion and dimercurion.
5. a kind of application of the fluorescence probe described in claim 3, it is characterised in that：The fluorescence probe is in qualitative/quantitative
Application in cooperation detection superoxide anion and dimercurion.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746416A (en) * | 2017-11-08 | 2018-03-02 | 中国科学院烟台海岸带研究所 | Organic compound and application based on flower cyanines |
| CN112028810A (en) * | 2019-07-23 | 2020-12-04 | 四川大学华西医院 | Preparation method and application of mercury ion probe |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746416A (en) * | 2017-11-08 | 2018-03-02 | 中国科学院烟台海岸带研究所 | Organic compound and application based on flower cyanines |
| CN112028810A (en) * | 2019-07-23 | 2020-12-04 | 四川大学华西医院 | Preparation method and application of mercury ion probe |
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