CN107266347B - Organic compound based on cyanine and application thereof - Google Patents
Organic compound based on cyanine and application thereof Download PDFInfo
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Abstract
The invention relates to a method for detecting superoxide anions (O)2 ·‑) And a fluorescent probe of bivalent mercury ions, in particular to an organic compound based on cyanine and application thereof. The compound is shown as a structural formula I, and the compound is used as detection O2 ·‑And a probe for divalent mercury ions. Detection of O by the invention2 ·‑And a fluorescent probe of divalent mercury ion at O2 ·‑The fluorescence emission wavelength and fluorescence intensity corresponding to the divalent mercury ion are obviously changed, and the fluorescent material can be used for O2 ·‑And the detection of bivalent mercury ions can greatly reduce the interference of external detection conditions, improve the detection precision, and have high detection signal-to-noise ratio and good sensitivity and selectivity. Compared with the traditional detection technology, the non-invasive fluorescent probe has the advantages of simple, convenient and quick detection operation, high sensitivity, good selectivity and short response time, can be used for in-situ and real-time monitoring of a detected target object, and has wide application range.
Description
Technical Field
The invention relates to a fluorescent probe for detecting superoxide anions and divalent mercury ions, in particular to an organic compound based on cyanine and application thereof.
Background
Mercury is a recognized global environmental pollutant, and in the 50 s of the 20 th century, humans began to learn about the toxicity of Mercury (Mercury, Hg) and its compounds from the "water deficiency". With the wider and wider application of metallic mercury (Hg), more and more cases of mercury poisoning exist, the incidence rate of mercury poisoning is in a continuously increasing trend in China, and meanwhile, the mercury poisoning also gets wide attention of governments and society. In recent years, some diseases are treated by improper medicines in the process of diagnosis and treatment, such as oral administration of mercury and inorganic mercury compounds, and the treatment of in vivo mercury accumulation caused by the use of traditional Chinese medicine folk prescription containing mercury and compounds thereof for treating asthma, psoriasis, acne, nasosinusitis and the like, and the non-occupational mercury poisoning cases caused by the application of whitening and freckle-removing cosmetics containing excessive mercury are not rare. Research shows that the pathogenesis of mercury poisoning is complex, for example, mercury can be combined with metallothionein of a human body and can replace metal molecules in certain enzymes to change the activity of the metallothionein; mercury can bind to sulfhydryl groups on cell membranes, causing changes in membrane permeability; mercury poisoning can also cause oxidative stress, interfere with neurotransmitter and ion exchange, and the like. Especially the increased and diminished elimination of free radicals caused by oxidative stress after mercury poisoning has been of great importance in recent years. Research shows that mercury is combined with antioxidants such as glutathione and the like in vivo on one hand, so that the capability of eliminating free radicals in vivo is reduced; on the other hand, free radicals can be generated, so that lipid peroxides in the body are increased, and the imbalance of an oxidation-antioxidation system is caused. The fluorescent probe involved in the patent can help to explore the physiological process of active oxygen explosion under the stimulation of mercury ions.
Currently, for detecting O2·-The methods include electron paramagnetic resonance, SOD enzyme activity assay, High Performance Liquid Chromatography (HPLC) and electrochemical methods. The mercury compound detection method comprises spectrophotometry, atomic emission spectrometry, atomic absorption spectrometry and hydride generation-atomic fluorescence spectrometry. However, most of these methods require pretreatment of the sample, complicated operation means, and large-scale equipment. Therefore, it is urgent to find a method for conveniently and rapidly detecting superoxide anions and mercury ions. The fluorescent probe method has the advantages of high space-time resolution, simple and convenient operation, in-situ non-damage detection and the like, and becomes a powerful research auxiliary tool in the field of bioactive species detection.
Disclosure of Invention
The invention aims to provide an organic compound based on cyanine and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a cyanine-based organic compound having a structural formula I,
the application of the organic compound based on the cyanine in the cooperative detection of superoxide anions and divalent mercury ions.
A fluorescent probe is an organic compound based on cyanine shown in a formula I,
the fluorescent probe is used for qualitatively/quantitatively detecting the superoxide anion and the divalent mercury ion cooperatively.
Use of a fluorescent probe for qualitatively/quantitatively co-detecting superoxide anions and divalent mercury ions.
The invention has the beneficial effects that: the compound is used as a fluorescent probe for linkage detection of superoxide anions and divalent mercury ions, and fluorescence is generated before and after detection of the superoxide anions when the fluorescence is switched off; the maximum wavelengths of the fluorescent probe absorption and the fluorescent emission can be changed before and after the divalent mercury ions are detected. The method can be used for linkage detection of superoxide anions and divalent mercury ions in a water system, a simulated physiological environment and cells, and can greatly reduce the interference of external detection conditions and improve the detection precision. The compound is used as a fluorescent probe, can be used for linkage detection of superoxide anions and divalent mercury ions in cells, and has important biomedical significance for deeply researching the signal transduction process and mechanism of the superoxide anions and the divalent mercury ions in organisms and further understanding the physiological and toxicological effects of the superoxide anions and the divalent mercury ions. The invention has the advantages of simple, convenient and quick operation, high sensitivity, good selectivity, short response time, capability of carrying out in-situ and real-time monitoring on a detection target object, wide application range and the like.
Drawings
FIG. 1 shows different concentrations of superoxide anion (O) using fluorescent probes provided by embodiments of the present invention2 ·-) The change in fluorescence before and after detection.
FIG. 2 shows a fluorescent probe pair O used in the present invention2 ·-A schematic diagram of (a); wherein, the abscissa is sequentially from left to right: 1. blank; 2. o is2 ·-(25. mu.M); 3. hydroxyl radical (25 μ M); 4. hydrogen peroxide (200 μ M); 5. linoleic acid peroxide (400 μ M); 6. cumene hydroperoxide (300 μ M); 7. t-butyl peroxide (250. mu.M); 8. nitric oxide (300 μ M); 9. nitrosyl peroxide anion (25 μ M); 10. hypochlorous acid (200. mu.M).
FIG. 3 shows different Hg concentrations of fluorescent probe used in accordance with an embodiment of the present invention2+The change in fluorescence before and after detection.
FIG. 4 is a schematic diagram of the selectivity of fluorescent probes for mercury ions used in embodiments of the present invention; wherein, the abscissa is sequentially from left to right: 1. blank; 2. KCl (100. mu.M); 3. zn (CH)3COO)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 is a three-channel fluorescence plot of human embryonic kidney HEK-293 cells as a biological model, incubated with Compound I (2 μ M) for 15 min as a control, provided in an example of the present invention. Wherein, the channel 1: 750-850nm, channel 2: 540 — 585nm, channel 3: 585-725 nm.
FIG. 6 is a three-channel fluorescence plot of HEK-293 cells incubated with Compound I (2 μ M) for 15 minutes, followed by addition of superoxide anion (2 μ M) for 15 minutes, and the cells rinsed three times with MEM medium. Channel 1: 750-850nm, channel 2: 540 — 585nm, channel 3: 585-725 nm.
FIG. 7 shows HEK-293 cells incubated with Compound I (2. mu.M) for 15 min, followed by the addition of superoxide anion (2. mu.M) and HgCl2Three channel fluorescence after (2. mu.M). Channel 1: 750-850nm, channel 2: 540 — 585nm, channel 3: 585-725 nm.
Detailed Description
The invention is further explained below with reference to the figures and examples.
The structural formula of the organic compound based on the cyanine is as follows:
reacting the compound I with the water body to be measured, a simulated physiological environment or superoxide anions inside and outside an organism to cause the fluorescence to be switched on from off, and obtaining the structure of a compound II;
reacting the compound II with bivalent mercury ions in a water body to be measured, a simulated physiological environment or inside and outside an organism, wherein the absorption and fluorescence emission maximum wavelengths of a fluorescent probe can be changed, and the structure of the obtained compound III;
detection of O by the invention2 ·-And a fluorescent probe of divalent mercury ion at O2 ·-The fluorescence emission wavelength and fluorescence intensity corresponding to the divalent mercury ion are obviously changed, and the fluorescent material can be used for O2 ·-And the detection of divalent mercury ions, and can greatly reduce the interference of external detection conditions and improve the detectionThe detection precision, the detection signal-to-noise ratio are high, and the sensitivity and the selectivity are good. Further, the invention O2 ·-And a fluorescent probe for divalent mercury ions, in O2 ·-And the ultraviolet absorption is also obviously changed in the presence of divalent mercury ions, and an ultraviolet spectrophotometer can be used for detection. The compound can be used as a fluorescent probe for O in a complex biological sample2 ·-And the linkage detection of bivalent mercury ions, which is used for deeply researching O under the stimulation of mercury ions2 ·-And cell signaling of mercury ions in the body of an organism have important biomedical significance. Compared with the traditional detection technology, the non-invasive fluorescent probe has the advantages of simple, convenient and quick detection operation, high sensitivity, good selectivity and short response time, can be used for in-situ and real-time monitoring of a detected target object, and has wide application range.
Example 1. preparation of cyanine-based organic compounds:
the cyanine fluorophore shown in the compound I is from a commercial product, and then different detection groups are modified on the corresponding positions of the fluorophore to obtain the corresponding cyanine compound. The specific embodiment is as follows:
(1) preparation of Compound II
Cyanine fluorophore (0.209g, 0.327mmol) was dissolved in 20ml methanol and Na was added2Se (0.05g, 0.4mmol) is dissolved in 1ml of water and 1ml of Na is added at room temperature2The Se solution is added into a round-bottom flask dropwise and refluxed for 30min under the protection of argon. Washing with saturated potassium iodide solution, adjusting to neutrality with glacial acetic acid, extracting with dichloromethane, and rotary evaporating. The crude product was purified by column chromatography eluting with ethyl acetate and methanol (6:1/v/v) to give 0.128g (0.187mmol) of compound II as a green solid in 57.2% yield.
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+Calcd557.24，found[M+H]+557.19.
(2) preparation of Compound I
Compound II (0.12g, 0.1755mmol) was dissolved in 10ml ethanol and NaBH was added4(0.0122g, 0.3225mmol) was dissolved in 2ml ethanol and 2ml NaBH was added under ice-bath conditions4The solution was added dropwise to a round bottom flask and reacted for 10min under argon protection. Washing with deoxygenated saturated potassium iodide solution, extracting with dichloromethane, and rotary evaporating. The crude product was purified by column chromatography eluting with dichloromethane and petroleum ether (1:1/v/v) to give 0.049g (0.08786mmol) of compound I as a yellow solid in 50% yield.
A 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/zC34H42N2Se Calcd 558.25,found[M+H]+558.15.
example 2
The prepared compound I is applied to an aqueous system, a simulated physiological environment and a cell as a probe to detect superoxide anions and mercury ions, the following experiments are carried out under the condition of pH 7.4 (HEPES buffer solution, the concentration is 10mM), and the probe concentration is 10 mu M.
Response of compound I prepared above to superoxide anion:
the pH was controlled at 7.4 using HEPES buffer. Adding 10 mu M of compound I into each 10ml colorimetric tube, then adding superoxide anion with different concentrations (the concentration of the superoxide anion is 0-10 mu M), keeping the volume to 10ml with 10mM HEPES with pH 7.4, shaking up the solution, balancing for 10min, and pouring the working solution in each colorimetric tube into a fluorescent dish respectively to measure the fluorescence spectrum. The fluorescence intensity was measured at 750-900nm as shown in FIG. 1. The compound I can be used for realizing the detection of superoxide anions in organisms. Meanwhile, the structure of a product obtained by reacting the compound I provided by the embodiment of the invention with superoxide anion is as follows:
then, 0-10 mu M of mercuric chloride (HgCl) with different concentrations is continuously added into each 10ml colorimetric tube2) Shaking the solution evenly, balancing for 10min, and pouring the working solution in each colorimetric tube into a fluorescent dish respectively to determine the fluorescence spectrum. The fluorescence intensity was measured at 540-750nm, as shown in FIG. 3. The product after detecting the superoxide anion reaction can be further used for realizing HgCl in organisms2Detection of (3). At the same time, further react with HgCl2The structure of the product after reaction is as follows:
example 3
Selectivity of compound I for superoxide anion
The pH was controlled at 7.4 using HEPES buffer. A plurality of 10ml colorimetric tubes were taken, 10. mu.M of Compound I was added to each 10ml colorimetric tube, and the different analytes to be detected were added, and 10ml was made up with 10mM HEPES buffer solution having pH 7.4. After shaking the solution and equilibrating at 25 ℃ for 10min, the working solution in each cuvette was poured into a fluorescent dish for fluorescence spectroscopy (see FIG. 2). The substances to be tested are as follows in sequence: 1. blank; 2. superoxide anion (25 μ M); 3. hydroxyl radical (25 μ M); 4. hydrogen peroxide (200 μ M); 5. linoleic acid peroxide (400 μ M); 6. cumene hydroperoxide (300 μ M); 7. t-butyl peroxide (250. mu.M); 8. nitric oxide (300 μ M); 9. nitrosyl peroxide anion (25 μ M); 10. hypochlorous acid (200. mu.M).
From FIG. 2, it can be seen that compound I has a good selectivity for superoxide anion.
Example 4
After example 2, the pH was controlled to 7.4 using HEPES buffer. Adding 10 mu M of compound I into each 10ml colorimetric tube, adding superoxide anion with the concentration of 0-10 mu M and 10mM HEPES with the pH value of 7.4 to make the volume constant to 10ml, shaking the solution evenly, after balancing for 10min, pouring the working solution in each colorimetric tube into a fluorescent dish respectively to measure the fluorescence spectrum.
Then, the sample to be measured was sequentially added to each cuvette, the solution was shaken up, and after equilibration for 10min at 25 ℃, the working solution in each cuvette was poured into a fluorescent dish to measure the fluorescence spectrum (see fig. 4). The substances to be tested are as follows in sequence: 1. blank; 2. KCl (100. mu.M); 3. zn (CH)3COO)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(10. mu.M). Therefore, one step of proving that the compound II generated after the compound I detects the superoxide anion has good selectivity on the divalent mercury ions, and further, the compound I can be used for cooperatively detecting the superoxide anion and the divalent mercury ions.
Example 6
Imaging of compound I in human embryonic kidney HEK-293 cells were selected as a biological model, first, cells were incubated with compound I (2 μ M) for 15 minutes at 37 ℃ as a control group, and the cells were washed with MEM three times without showing fluorescence (fig. 5).
Cells were incubated with compound II (2 μ M) for a further 15 min at 37 ℃ as a control and washed three times with MEM showing weak fluorescence (fig. 5).
Human embryonic kidney HEK-293 cells were selected as a biological model by first incubating the cells with Compound I (2. mu.M) for 15 minutes at 37 ℃ followed by addition of superoxide anion (2. mu.M) for another 15 minutes, rinsing the cells three times with MEM, with significant fluorescence generation (see FIG. 6), which shows that Compound I can be used to directly detect superoxide anion added exogenously to living cells.
Human embryonic kidney HEK-293 cells were selected as a biological model by first incubating the cells with Compound I (2. mu.M) for 15 min at 37 ℃ and then adding HgCl2(2. mu.M) incubation for 15 min, cells were washed three times with MEM, with intense fluorescence generation at both 540-585nm fluorescence detection (FIG. 7) and 585-740nm fluorescence detection (FIG. 7). Therefore, the compound I can be used for synergistically and directly detecting the mercury chloride exogenously added to living cells.
The foregoing is a more detailed description of the invention in connection with specific preferred embodiments and it is not intended that the invention be limited to these specific details. For those skilled in the art to which the invention pertains, several simple deductions or substitutions can be made without departing from the spirit of the invention, and all shall be considered as belonging to the protection scope of the invention. As the fluorescent dye is one application of the novel compound of the present invention, the compound of the present invention cannot be considered to be used only for the fluorescent dye, and for those skilled in the art to which the present invention pertains, under the consideration of the same action mechanism of the compound of the present invention as the fluorescent dye, several simple reasoning can be made to derive other application applications of the compound of the present invention, which should be considered to be within the protection scope of the present invention.
Claims (2)
1. A cyanine-based organic compound characterized by: the structure of the organic compound based on the cyanine is shown as a formula I,
formula I.
2. Use of a cyanine-based organic compound according to claim 1, in which: the cyanine-based organic compound is used for synergistically detecting superoxide anion (O)2 •-) And divalent mercury ions.
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