CN110437268A - A kind of potassium ion probe and its preparation method and application - Google Patents
A kind of potassium ion probe and its preparation method and application Download PDFInfo
- Publication number
- CN110437268A CN110437268A CN201910832447.8A CN201910832447A CN110437268A CN 110437268 A CN110437268 A CN 110437268A CN 201910832447 A CN201910832447 A CN 201910832447A CN 110437268 A CN110437268 A CN 110437268A
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- Prior art keywords
- probe
- potassium ion
- reaction
- oxygen
- carrier
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- 229910001414 potassium ion Inorganic materials 0.000 title claims abstract description 99
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
The present invention relates to a kind of potassium ion probe and its preparation method and application, potassium ion probe provided by the invention has high selectivity to potassium ion, can emit green fluorescence, detects K+Concentration, and contain hydroxyl in the potassium ion probe, it is easier to it is grafted with carrier, is grafted on carrier jointly with other kinds of probe, realize the multiple response of the same sense film.The present invention also provides a kind of potassium ions and the difunctional sense film of dissolved oxygen, including carrier, and potassium ion probe, oxygen probe and the reference probe provided by the invention of the carrier surface are fixed on by way of chemical bonding, the film has redgreenblue fluorescence, three kinds of fluorescence colors are not interfere with each other, fluorimetry can be used to realize to the accurate of potassium ion and dissolved oxygen while measuring, and the stability of film is high.
Description
Technical field
The present invention relates to technical field of biological materials more particularly to a kind of potassium ion probe and its preparation method and application,
In particular to a kind of potassium ion probe and preparation method thereof, potassium ion and the difunctional sense film of dissolved oxygen and preparation method thereof.
Background technique
Potassium ion (K+) it is one of the most abundant metal ion of content in mammalian cell, account for about human body dry weight
0.35%.It is played in numerous physiological activities and its important role, including heartbeat, contraction of muscle, and nerve signal passes
Lead with kidney excretion etc..K+It is not only involved in and maintains intraor extracellular osmotic pressure and electrolyte balance, adjust blood pressure, also participate in adjusting whole
The transduction of a nervous system biochemical signals.K in mammalian cell cytoplasm+The concentration of ion is about 130-180mM, and extracellular
Concentration be 3.5-5.0mM.Potassium Level maintains between 3.5-5.5mM always in normal serum, when excess intake, leads to
Excessive K is often removed by kidney excretion+.When concentration of blood kalium is higher than 5.5mM, it is referred to as potassemia；In low high concentration
When (5.5-6.0mM) or middle and high concentration (6.1-6.9mM), often cause nausea, fatigue, muscle is powerless, also loses sometimes with the rhythm of the heart
Often；When concentration of blood kalium is higher than 7.0mM, it is even dead to typically result in sudden cardiac arrest.When concentration of blood kalium is lower than 3.5mM, it is referred to as
For hypopotassaemia.Clinically symptom related with hypopotassaemia includes: weakness, paralysis, orthocolosis, intestinal obstruction, Nausea and vomiting
Deng.K+Concentration abnormality is usually the early stage sign of certain diseases, is such as indulged in excessive drinking, apositia, baulimia, heart disease, diabetes, AIDS
Disease and cancer etc..
Therefore, finding can specifically study, measure or the highly sensitive method of real-time monitoring intraor extracellular potassium concentration
It is significant to the exploitation and screening that understand pathologic process and disease related drugs.
Oxygen the fields such as environmental protection, engineering process, marine fishery, industry and agricultural be all very important element or
One of person's parameter, especially in biological field, oxygen is one of important source material of cell metabolism, and even more sustain life work
Dynamic energy source.With the continuous development of scientific research, influence of the oxygen concentration for cell is gradually recognized by us.Although
Oxygen is essential for the metabolism of cell, but the raising of oxygen concentration can also generate certain toxicity.In height
Under concentration oxygen environment, aerobic and microaerophilic cell or tissue will start the protection mechanism of itself to cope with instantly not
Normal environment.Referred to as superoxides (the O of reactive oxygen species2 -) and hydrogen peroxide (H2O2) cell metabolism will be become
By-product constantly accumulates in the cell, because these reactive oxygen species are more more active than normal oxygen molecule, final oxidation is thin
Macromolecular intracellular makes Apoptosis in turn.Similarly, if intracellular oxygen concentration is lower than normal value, it will cause aerobic and micro-
Measure aerobic cell or tissue ischemia damage even cell death.Cell hypoxia, which also results in, there are various diseases
Disease, such as chronic vascular disease, neurological disorder, tuberculosis even cancer etc..
Therefore, intracellular oxygen content can accurately and be accurately measured for understanding the biologic viability of cell, studying
The pathology and diagnosing and treating cancer of various diseases are of great importance.
It is well known that cellular respiration is that a series of metabolism reaction and process in biologic-organ and tissue occurs,
To obtain the energy such as atriphos (ATP) and such as carbon dioxide waste is discharged with this in cell.Although detecting into the cell
Oxygen content has been reported, but cannot still ignore the detection of extracellular oxygen content, and the process of many biological metabolisms is still wanted
It is studied by detecting extracellular oxygen content.In cell metabolism reaction process, mitochondria is support aerobic respiration and obtains
Obtain the critical cellular device of ATP.However, cellular respiration is not to depend on mitochondria, do not needed there are also a kind of type of respiration
Mitochondria, this type of respiration are referred to as non-mitochondria oxygen consumption.And study the feature of non-mitochondria oxygen consumption, then it needs to pass through
Measure extracellular oxygen consumption situation.It therefore, being capable of accurate and oxygen Expenditure Levels of the precise measurement cell in respiratory
Assessment aerobic glycolysis rate, oxidative phosphorylation and drug screening of high throughput etc. are very important.
The opening and closing of potassium-channel and K+Flowing in and out all by internal dissolved oxygen on cell membrane
(DO) influence of concentration.For example, anoxic leads to myocardium K+Forfeiture, lead to myocardial dysfunction.In addition, acute systemic anoxic can
Cause artery K+Concentration increases, so as to cause peripheral circulation vasodilation.Brain disorder and Pulmonary Vascular contraction are also drawn with anoxic
The K risen+It is unbalance related.Therefore, while K is measured+Concentration and DO concentration are extremely important.
CN106929008B discloses a kind of potassium ion fluorescence probe and its preparation method and application, the potassium ion of the invention
Fluorescence probe is using phenyl azepine -18- crown- 6- amine as recognition group, using hemicyanine dye group as fluorophor, has quick to environment
The advantages that sense, good water solubility, accuracy in detection are high, rapid to potassium concentration variation response is a kind of colorimetric, instant ratio
Rate type potassium ion detection probe, can be prepared as Test paper, realize the quick of potassium content height according to test paper color change
Detection, be expected to traditional Chinese medicine injection and red wine and human urine or in terms of detect potassium concentration, have and wide answer
Use prospect.
The preparation and application for the individual particle SPR probe that a kind of real-time monitoring G- tetrad of CN105241845B is formed.It is based on
Good biocompatibility, bigger serface and the SPR high sensitivity of noble metal nano particles, using can specifically be tied with potassium ion
The telomere of conjunction is surface modified noble metal nano particles, and simply and easily constructing can highly sensitive detection potassium ion and real
When monitor G- tetrad forming process individual particle bioprobe.This probe has the function of real-time detection, and detection speed is fast,
The advantages that high sensitivity, detection range is wide.In addition, the dissociation constant K of G- tetrad can be obtained being formed by data Fitting Analysisd
With Gibbs free energy Δ G, and two kinds of binding site forms in forming process.
CN108333162A discloses a kind of fluorescence oxygen probe, and the fluorescence oxygen probe includes that copolymerization has reference probe chemical combination
It the polymer microballoon of object and is dispersed in copolymerization and has fluorescence oxygen probe in the polymer microballoon of reference probe compound
Close object, additionally provide a kind of method for preparing the fluorescence oxygen probe of creativeness, by by reference probe compound with polymerize
Monomer copolymerization, preparation are dispersed with the microballoon of fluorescence oxygen probe compound, and the microballoon can be used as fluorescence oxygen probe, the hair
Bright prepared fluorescence oxygen probe has from reference effect, avoids replacement detection device in conventional fluorescent detection and needs to fluorescence
The problem of probe is recalibrated, moreover, it is not high for detection environmental requirement when in use, it can be used in the water body containing microorganism
The detection of dissolved oxygen concentration in equal dynamic biologicals environment, testing result are missed compared to the testing result of Conventional electrochemical detection device
Difference≤5%.
By the above-mentioned published patent it is found that the sensor of independent measurement potassium concentration or independent measurement oxygen concentration
Good development is obtained.But there is presently no can simultaneously and real-time measurement oxygen and potassium concentration sensor.
Therefore, simultaneously real-time measurement oxygen and potassium concentration are urgently studied in this field how simultaneously.
Summary of the invention
In view of the deficiencies of the prior art, one of the objects of the present invention is to provide potassium ion probes, in particular, in that providing one
Kind is used for the potassium ion probe of potassium ion and the difunctional sense film of dissolved oxygen.The potassium ion probe has height to potassium ion
Selectivity emits green fluorescence, is able to detect K+Concentration.And the potassium ion probe can be connect by hydroxyl with carrier.
For this purpose, the present invention adopts the following technical scheme:
The present invention provides a kind of potassium ion probe, and the potassium ion probe (KS-23) has the following structure:
Potassium ion probe provided by the invention has high selectivity to potassium ion, can emit green fluorescence, detects K+
Concentration, and contain hydroxyl in the potassium ion probe, it is easier to it is grafted with carrier, is connect jointly with other types of probe
Branch realizes the multiple response of the same sense film on carrier.
The Response Mechanism of above-mentioned potassium ion probe is as follows:
The second object of the present invention is to provide a kind of preparation method of potassium ion probe described in the first purpose, the system
Preparation Method includes: to react to obtain the potassium ion probe using compound 3 and compound 3', and reaction equation is as follows:
Preferably, the solvent of the reaction includes any one in ethyl alcohol, toluene and benzene or at least two combinations.
Preferably, catalyst is added in the reaction, the catalyst includes piperidines and/or pyridine.
Preferably, the reaction carries out under reflux.
Preferably, the compound 3 reacts to obtain by compound 2 and 2,4- dimethyl pyrrole, and reaction equation is as follows:
Preferably, the solvent of the reaction includes any one in tetrahydrofuran, dioxane, acetonitrile and methylene chloride
Or at least two combination.
Preferably, catalyst is added in the reaction, the catalyst includes trifluoroacetic acid and/or BF3·Et2O。
Preferably, dehydrogenating agent is added in the reaction, the dehydrogenating agent includes, chloro- 5, the 6- dicyanoquinone of 3- bis- and/or
Spergon.
Preferably, acid binding agent is added in the reaction, the acid binding agent includes triethylamine.
Preferably, the compound 2 reacts to obtain by compound 1 with ethylene bromohyrin, and reaction equation is as shown in formula III:
Preferably, catalyst is added in the reaction, the catalyst includes potassium iodide.
Preferably, acid binding agent is added in the reaction, the acid binding agent includes potassium carbonate.
Preferably, the solvent of the reaction includes CH3In CN, acetone and N,N-dimethylformamide any one or extremely
Few two kinds of combinations.
The third object of the present invention is to provide a kind of potassium ion and the difunctional sense film of dissolved oxygen, the potassium ion and
The difunctional sense film of dissolved oxygen includes carrier, and be fixed on by way of chemical bonding the carrier surface purpose it
Potassium ion probe (KS-23), oxygen probe (OS) described in one and reference probe (RP)；
Preferably, the oxygen probe (OS) has the following structure:
Preferably, the reference probe (RP) has the following structure:
Potassium ion probe, oxygen probe and the reference probe of specific structure are bonded on carrier by the present invention jointly, wherein potassium
Ion probe has response to potassium ion, emits green fluorescence, and oxygen probe has response to dissolved oxygen, emits red fluorescence, and reference is visited
It is all not responding to for potassium ion and dissolved oxygen, emits blue-fluorescence.Therefore the film has redgreenblue fluorescence, and three kinds glimmering
Light color is not interfere with each other, and fluorimetry can be used and realize to the accurate of potassium ion and dissolved oxygen while measuring.
In addition, three kinds of probes are fixed on carrier by way of chemical bonding, keep sense film more stable.
In the present invention, the preparation method of oxygen probe OS is referring to paper: Jiayan Shi, Yifei Zhou, Jiapei
Jiang, Tingting Pan, Zhipeng Mei, Jiaxing Wen, Cheng Yang, Zijin Wang, Yanqing
Tian, European Polymer Journal, 112,214-221 (2019).
Reference probe preparation method referring to described in following paper or patent synthesizes in the present invention:
Patent: CN106947381A
Paper: Q.J.Zhang, J.H.Zhou, H.Li, J.H.He, N.J.Li, Q.F.Xu, D.Y.Chen, H.Li,
J.M.Lu, The Effect of Random and Block Copolymerization with Pendent Carbozole
Donors and Naphthalimide Acceptors on Multilevel Memory Performance, Chem
Asian J.13(2018)853-860.
Preferably, the carrier is the quartzy carrier of TMSPA modification, and the TMSPA has the following structure:
The fourth object of the present invention is to provide potassium ion described in a kind of third purpose and the difunctional sensing of dissolved oxygen is thin
The preparation method of film, the preparation method include the following steps:
(1 ') makes polyethylene glycol methacrylate-styrene polymer (PEGMA), methacrylic acid (MAA), polyethylene glycol dimethyl allene
Acid esters (PEGDMA), oxygen probe and reference probe polymerize in carrier surface, obtain the carrier (F- for being covered with hydrogel layer
OS-RP)；
(2 ') potassium ion probe described in the carrier surface grafting first purpose for being covered with hydrogel layer, obtains institute
State potassium ion and the difunctional sense film of dissolved oxygen.
The present invention obtains stable hydrogel, oxygen probe OS using PEGDMA using PEGMA as hydrogel monomer as crosslinking agent
Contain methacrylic acid ester bond with reference probe RP, while MAA is added, can be with used monomer polymerization, monomer is aggregated
It is integrally formed afterwards with carrier, obtains the film (F-OS-RP) containing oxygen probe, reference probe and pendant carboxylic group, further lead to
It crosses pendant carboxylic group to react with the hydroxyl on KS-23, KS-23 is bonded on carrier, three kinds of probes pass through the side of chemical bonding
Formula improves the stability of film in conjunction with carrier.
Preferably, the carrier surface contains double bond.
Preferably, in step (1 '), the initiator of the polymerization reaction includes azodiisobutyronitrile (AIBN).
Preferably, in step (1 '), the solvent of the polymerization reaction includes n,N-Dimethylformamide (DMF).
Preferably, in step (1 '), the carrier is the quartzy carrier of TMSPA modification.
In a preferred embodiment of the invention, carrier surface is modified with double bond containing and silane-containing key TSMPA, so that gel
Stablize in carrier surface, further promotes the stability of film.
Preferably, in step (1 '), polyethylene glycol methacrylate-styrene polymer, polyethylene glycol dimethacrylate, oxygen probe,
The mass ratio of reference probe, initiator and solvent be 500-1500:20-300:1-15:1-15:5-30:1000, preferably 800:
50:5:5:10:1000。
Preferably, in step (1 '), the mass ratio of the methacrylic acid and the polyethylene glycol methacrylate-styrene polymer is
10-1000:1。
Preferably, in step (1 '), the number-average molecular weight of the polyethylene glycol methacrylate-styrene polymer is 300-2000, preferably
500。
Preferably, in step (1 '), the number-average molecular weight of the polyethylene glycol dimethacrylate is 300-2000, excellent
Select 750.
Preferably, in step (1 '), the polymerization reaction carries out under nitrogen atmosphere.
Preferably, in step (1 '), the temperature of the polymerization reaction is 70-90 DEG C, such as 72 DEG C, 72 DEG C, 73 DEG C, 75
DEG C, 78 DEG C, 80 DEG C, 82 DEG C, 85 DEG C, 88 DEG C etc., preferably 80 DEG C.
Preferably, in step (1 '), time of the polymerization reaction is 0.8-1.5h, for example, 0.9h, 1h, 1.2h, 1.3h,
1.4h etc., preferably 1h.
Preferably, step (1 ') specifically includes: by polyethylene glycol methacrylate-styrene polymer, methacrylic acid, polyethylene glycol two
Methacrylate, oxygen probe, reference probe, initiator and solvent mixing, the quartzy carrier table for taking mixed liquor to modify in TMSPA
Face, polymerase 10 .8-1.5h under the conditions of 70-90 DEG C of temperature, obtains the carrier for being covered with hydrogel layer.
Preferably, in step (2 '), coupling agent and/or catalyst is added.
Preferably, the coupling agent includes 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride.
Preferably, the catalyst includes 4-dimethylaminopyridine.
Preferably, in step (2 '), the mass ratio of the potassium ion probe, coupling agent and catalyst is 2:1000:200.
Preferably, in step (2 '), the reaction dissolvent of the grafting includes n,N-Dimethylformamide.
Preferably, in step (2 '), the reaction time of the grafting is 10-15h, such as 11h, 12h, 13h, 14h etc. is excellent
Select 12h.
Preferably, in step (2 '), the reaction of the grafting carries out at room temperature.
Preferably, step (2 ') specifically comprises the following steps: the carrier for being covered with hydrogel layer being placed in potassium ion
In the mixed solution of probe, coupling agent and catalyst, graft reaction 10-15h is carried out at room temperature, obtains the potassium ion and molten
Solve the difunctional sense film of oxygen.
The fifth object of the present invention is to provide potassium ion described in a kind of third purpose and the difunctional sensing of dissolved oxygen is thin
Application of the film in potassium ion detection and dissolved oxygen detection.
Compared with the prior art, the invention has the following beneficial effects:
(1) potassium ion probe provided by the invention has high selectivity to potassium ion, can emit green fluorescence, detects
K+Concentration, and contain hydroxyl in the potassium ion probe, it is easier to it is grafted with carrier, it is common with other kinds of probe
It is grafted on carrier, realizes the multiple response of the same sense film；
(2) potassium ion probe, oxygen probe and the reference probe of specific structure are bonded on carrier by the present invention jointly, wherein
Potassium ion probe has response to potassium ion, emits green fluorescence, and oxygen probe has response to dissolved oxygen, emits red fluorescence, reference
Probe is all not responding to potassium ion and dissolved oxygen, emits blue-fluorescence.Therefore the film has redgreenblue fluorescence, and three kinds
Fluorescence color is not interfere with each other, and fluorimetry can be used and realize to the accurate of potassium ion and dissolved oxygen while measuring；
(3) present invention obtains stable hydrogel using PEGDMA using PEGMA as hydrogel monomer as crosslinking agent, and oxygen is visited
Needle OS and reference probe RP contain methacrylic acid ester bond, can be with used monomer polymerization, the aggregated rear and carrier of monomer
It is integrally formed, while MAA is added and comes so that accessing the KS-23 of hydroxyl in colloid, three kinds of probes pass through chemical bonding
Mode improves the stability of film in conjunction with carrier.
Detailed description of the invention
Fig. 1 is the preparation method schematic diagram of potassium ion and the difunctional sense film of dissolved oxygen in the embodiment of the present invention 1.
Fig. 2 a is the map that reference probe responds oxygen in test case 1.
Fig. 2 b is the map that reference probe responds potassium ion in test case 1.
Fig. 3 a be in test case 1 film 405 nanometers excitation under film to potassium ion response diagram.
Fig. 3 b be in test case 1 film of the film under 405 nanometers of excitations to the response diagram of oxygen.
Fig. 4 a be in test case 1 oxygen concentration and reference probe to the variation relation figure of oxygen probe fluorescence ratio.
Fig. 4 b be in test case 1 potassium concentration and potassium ion probe to the variation relation figure of reference probe fluorescence ratio.
Fig. 5 a is that film influences comparison diagram to fluorescence intensity to potassium ion and Na ion concentration in test case 2.
Fig. 5 b be in test case 2 film to the fluorescence intensity comparison diagram of potassium ion and different metal ions,
Specific embodiment
Of the invention for ease of understanding, it is as follows that the present invention enumerates embodiment.Those skilled in the art are it will be clearly understood that the implementation
Example is only to aid in the understanding present invention, should not be regarded as a specific limitation of the invention.
Synthesis example 1
This synthesis example provides the synthetic method of potassium ion probe KS-23, specific as follows:
(1) synthesis of compound 2: by 4- hydroxy benzaldehyde (4.8g, 0.04mol), ethylene bromohyrin (4.83g,
0.06mol), KI (3.32g, 0.02mol) and K2CO3(8.29g, 0.06mol) is added in 250ml round-bottomed flask, with 80ml second
Nitrile dissolution, 80 DEG C of reflux 36h.After being cooled to room temperature, vacuum distillation removes acetonitrile, residue CH2Cl2(80mL) is extracted 3 times,
Saturation NaCl solution (80mL) is washed 3 times.Merge organic phase, anhydrous magnesium sulfate dries, filters, and is concentrated, silica gel column chromatography separation, stream
Dynamic property is PE (petroleum ether): EA (ethyl acetate)=1:2 obtains white solid 2.5g, yield 35.3%.
1H NMR (400MHz, Chloroform-d) δ 9.79 (s, 1H), 7.76 (d, J=8.5Hz, 2H), 6.95 (d, J=
8.5Hz, 2H), 4.17-4.04 (m, 2H), 4.04-3.88 (m, 2H), 3.32 (s, 1H).
13C NMR (101MHz, CDCl3) δ 191.55,163.96,132.08,129.89,114.83,69.19,61.01.
(2) synthesis of compound 3: under nitrogen protection, by 2 (2.5g, 15.06mmol) and 2,4- dimethyl pyrrole (3g,
It 31.63mmol) is added in 500ml two-neck bottle, is dissolved with 160mL tetrahydrofuran, after stirring 30min, trifluoroacetic acid 160 is added
μ L, reaction solution color from yellow to red, are stirred overnight.After, it is molten that DDQ (3.74g, 16.57mmol) tetrahydrofuran is slowly added dropwise
Liquid after 3h, is added triethylamine solution (60mL).Continue after stirring 2h, BF is added dropwise3·Et2O(60mL).Continue after stirring 6h, subtracts
It after most of solvent is distilled off in pressure, is dissolved with 150mL methylene chloride, dilute hydrochloric acid is washed 2 times, and saturated sodium bicarbonate solution washes two
Time, saturated sodium chloride solution is washed twice, and anhydrous magnesium sulfate is dry, concentration, silica gel column chromatography separation, mobile phase PE:EA=2:1
Obtain dark red solid 1.25g, yield 22%.
1H NMR (400MHz, Chloroform-d) δ 7.09 (d, J=8.4Hz, 2H), 6.88 (d, J=8.5Hz, 2H),
5.73 (s, 2H), 4.52 (d, J=1.1Hz, 1H), 4.11-4.06 (m, 2H), 4.00-3.94 (m, 2H), 2.18 (s, 6H),
1.85 (s, 6H).
13C NMR (101MHz, CDCl3) δ 157.03,135.05,129.69,126.48,125.54,114.43,
108.65,69.06,61.40,39.43,12.77,11.16.
(3) synthesis of compound K S-23: by compound 3 (102.2mg, 0.2660mmol) and TAC-CHO (160mg,
It 0.2216mmol) is added in 25mL round-bottomed flask, ethyl alcohol 5mL dissolution is added, add 00 μ L of piperidinyl-1, reflux is for 24 hours.It finishes
Afterwards, it being cooled to room temperature, vacuum distillation removes ethyl alcohol, is dissolved with 20mL methylene chloride, and saturated common salt washes three times (3 × 40mL),
Merge organic phase, anhydrous magnesium sulfate is dry, concentration, and silica gel column chromatography separation, mobility DCM:MeOH=75:1 is obtained dark blue
Color solid 55mg, yield 23%.
1H NMR (400MHz, Chloroform-d) δ 7.53 (d, J=15.9Hz, 1H), 7.26-7.01 (m, 8H), 6.89
(d, J=8.0Hz, 2H), 6.67 (d, J=8.3Hz, 2H), 6.61 (s, 2H), 4.34-4.21 (m, 2H), 4.18 (t, J=
4.4Hz, 2H), 4.06 (q, J=4.7Hz, 8H), 3.89-3.83 (m, 2H), 3.70 (dq, J=29.1,8.4,7.2Hz, 16H),
3.56-3.42 (m, 7H), 3.40-3.27 (m, 4H), 2.60 (s, 3H), 2.28 (d, J=21.7Hz, 6H), 1.28 (s, 9H).
Mass spectrum (HRMS): C61H77O10N5BF2, calculated value: 1088.57261, theoretical value: 1088.57690.
Synthesis example 2
This synthesis example provides the synthetic method of reference probe RP, specific as follows:
(1) synthesis of compound 5
Compound 4 (5g, 25.2mmol), 2- ethylaminoethanol (15.4g, 252mmol) and 80 milliliters of ethyl alcohol are at 150 milliliters
It is cooling after being added in round-bottomed flask reflux 10 hours.It filters out and solid is precipitated and with obtaining sterling after ethyl alcohol recrystallization.Yield:
88.5%.
(2) synthesis of RP
Compound 5 (1.50g, 5mmol), Et3N (1.01g, 10mmol) and 80 milliliters of CH2Cl2It is cooled with an ice bath after mixing.
Methacrylic chloride (1.04g, 10mmol) is added later.After room temperature reaction 6 hours, vacuum concentration.Solid silicagel column more than institute
It is purified, is that solvent obtains solid pure product with petrol ether/ethyl acetate (5:1).Yield 89%.
1H NMR (400MHz, Chloroform-d) δ 8.63 (dd, J=7.3,1.1Hz, 2H), 8.25 (dd, J=8.3,
1.1Hz, 2H), 7.78 (dd, J=8.2,7.3Hz, 2H), 6.07 (dt, J=1.8,1.0Hz, 1H), 5.53 (p, J=1.6Hz,
1H), 4.59 (ddd, J=6.0,5.1,1.1Hz, 2H), 4.52 (ddd, J=6.0,5.0,1.1Hz, 2H), 1.89 (t, J=
1.3Hz, 3H).
Nuclear-magnetism instrument model Bruker Avance III, mass spectrograph model used in the characterization of the above synthesis example
Thermo LTQ Orbitrap XL Mass Spectrometer。
Embodiment 1
The present embodiment provides a kind of potassium ion and the difunctional sense film of dissolved oxygen, preparation method is as follows:
(1 ') by polyethylene glycol methacrylate-styrene polymer, methacrylic acid, polyethylene glycol dimethacrylate, oxygen probe,
Reference probe, initiator and solvent mix, wherein polyethylene glycol methacrylate-styrene polymer, polyethylene glycol dimethacrylate, oxygen
Probe, reference probe, initiator and solvent mass ratio be 800:50:5:5:10:1000, take 30 microlitres of mixed liquors to be placed on
On the quartzy carrier of TMSPA modification, top, which is covered to be placed in 80 degree of baking ovens with coverslip, to be polymerize 1 hour.Lid glass after taking-up
Piece removes, and obtains the film for being covered with gel layer；
(2 ') are placed on the film that step (1 ') obtains the 1mL of KS-23 containing 0.2mg, 100mg EDC and 20mg DMAP
The grafting of potassium ion probe is carried out in DMF solution.After reaction carries out 12 hours at room temperature.Film is taken out, with DMF and go from
Sub- water obtains potassium ion and the difunctional sense film of dissolved oxygen after cleaning, and is tested for the property.
The method that potassium ion and the difunctional sense film of dissolved oxygen are prepared in embodiment 1 is as shown in Figure 1.
Test case 1
The difunctional sense film of potassium ion and dissolved oxygen (abbreviation film) of embodiment 1 is placed in quartz surfaces ware, is added
Enter 3 milliliters of water.The concentration of oxygen is regulated and controled by being passed through nitrogen containing different partial and oxygen mixed gas into liquid.Potassium
The concentration of ion is regulated and controled by the way that the KCl of various concentration is added into liquid.It is glimmering that silica dish is placed on PerkinElemer LS55
It is tested in optical tester (PerkinElemer, Waltham, MA, USA).
The map that reference probe responds oxygen and potassium ion in film is set forth in Fig. 2 a and 2b, and excitation wavelength is
350nm.Since the probe does not contain the group responded to potassium ion and oxygen, here it is apparent that reference probe is to potassium ion and oxygen
It does not all respond to, it was demonstrated that the probe is good internal reference.
Fig. 3 a gives the film in film under 405 nanometers of excitations to potassium ion response diagram, the concentration gradient of potassium ion
For 0mM, 20mM, 40mM, 60mM, 80mM, 100mM, 120mM, 150mM, 200mM, 300mM, it can be seen that glimmering at 574 nanometers
Light is increased with the raising of potassium concentration, and the fluorescence intensity from oxygen probe gone out at 670 nanometers is not by potassium ion
The influence of concentration.Fig. 3 b gives the film under 405 nanometers of excitations to the response diagram of oxygen, it can be seen that potassium ion probe is to oxygen
It is not responding to.Only oxygen probe 670 nanometers peak with oxygen concentration reduce and increase.It is achieved that three colors is difunctional
Probe film.
Fig. 4 a gives oxygen concentration and reference probe to oxygen probe fluorescence ratio (F380/F670) variation relation figure, Fig. 4 b gives
Potassium concentration and potassium ion probe are gone out to reference probe fluorescence ratio (F574/F380) variation relation figure, wherein 380nm's
Fluorescence intensity is used for the fluorescence of reference probe, and the fluorescence intensity of 670nm is used for the fluorescence of oxygen probe, 574 nanometers of fluorescence
Intensity is used for the fluorescence of potassium ion probe.
It can be seen that oxygen concentration (passes through the mass flow controller of 21-1-15-0-500-KMG3 model from Fig. 4 a
(Alicat Scientific, Tucson, AZ, USA) is controlled) and fluorescence intensity ratio abide by Stern-Volmer linearly side
Journey illustrates the oxygen concentration that can be very good Ce Liang from anoxic (0mg/L) to saturated oxygen (in 23 DEG C waters, just containing 21% oxygen
Oxygen solubility under normal atmospheric pressure is 8.6mg/L, and saturation oxygen solubility is 40.9mg/L under the conditions of 100% partial pressure of oxygen).Wherein,
Oxygen concentration refers to the concentration of dissolved oxygen.
From in Fig. 4 b it can be seen that probe can more delicately detect from no potassium ion into 100mM potassium solution potassium from
Son, the fluorescence intensity of this segment limit change potassium concentration more sensitive.Sensitivity when although potassium concentration is higher than 100mM
It can decline, still can be detected.Therefore material may be implemented to the solution of no potassium ion solution to the potassium ion containing 250mM into
Row detection.The detection (generally 3.5-5.5mM) that the potassium ion in blood can be applied, also may be implemented to potassium in urine from
The detection (generally 25-125mM) of son has certain application prospect.
Test case 2
By the quartz plate (having a size of 12.7 × 12.7 × 1mm) of the colorimetric sensor films with embodiment 1, by diagonal
It is put into the cuvette of 10 × 10mm.At 45 degree of angles, the buffering that 3mL pH=7.4 is added in cuvette is molten for incident light and quartz plate
Liquid (Tris-HCl) is then gradually added dropwise the KCl solution of 3M, concentration is made to progressively increase to 300mM from 0, titrates each time all etc.
To 1min, data are then collected.
Fig. 5 a, which gives film, influences comparison diagram (F to fluorescence intensity to potassium ion and Na ion concentration0It is that ion is not added
Fluorescence intensity before, F are the fluorescence intensities under different ions concentration), it is relevant to different physiology that Fig. 5 b gives potassium ion
The fluorescence intensity comparison diagram of ion.It can be seen that sodium ion and other ions have little influence on the fluorescence of film.Illustrate to sense thin
Film has the high selectivity to potassium ion.
(2) using 2 films (being obtained by the method for embodiment 1) in the aqueous solution containing about 150mM potassium ion
Oxygen and potassium concentration are measured, measurement data and with electrode measurement obtain value compare, as shown in table 1, hair
Existing error illustrates there is certain application prospect less than 10%.
Table 1
The Applicant declares that the present invention is explained by the above embodiments detailed process equipment and process flow of the invention,
But the present invention is not limited to the above detailed process equipment and process flow, that is, it is above-mentioned detailed not mean that the present invention must rely on
Process equipment and process flow could be implemented.It should be clear to those skilled in the art, any improvement in the present invention,
Addition, selection of concrete mode of equivalence replacement and auxiliary element to each raw material of product of the present invention etc., all fall within of the invention
Within protection scope and the open scope.
Claims (10)
1. a kind of potassium ion probe, which is characterized in that the potassium ion probe has the following structure:
2. a kind of preparation method of potassium ion probe according to claim 1, which is characterized in that the preparation method packet
It includes: reacting to obtain the potassium ion probe using compound 3 and compound 3', reaction equation is as follows:
Preferably, the solvent of the reaction includes any one in ethyl alcohol, toluene and benzene or at least two combinations；
Preferably, catalyst is added in the reaction, the catalyst includes piperidines and/or pyridine；
Preferably, the reaction carries out under reflux.
3. preparation method according to claim 2, which is characterized in that the compound 3 passes through compound 2 and 2,4- diformazan
Base pyrroles reacts to obtain, and reaction equation is as shown in Formula II:
Preferably, the solvent of the reaction include in tetrahydrofuran, dioxane, acetonitrile and methylene chloride any one or extremely
Few two kinds of combinations；
Preferably, catalyst is added in the reaction, the catalyst includes trifluoroacetic acid and/or BF3·Et2O；
Preferably, dehydrogenating agent is added in the reaction, the dehydrogenating agent includes chloro- 5, the 6- dicyanoquinone of 3- bis- and/or tetrachloro
Paraquinones；
Preferably, acid binding agent is added in the reaction, the acid binding agent includes triethylamine.
4. preparation method according to claim 3, which is characterized in that the compound 2 passes through compound 1 and ethylene bromohyrin
Reaction obtains, and reaction equation is as shown in formula III:
Preferably, catalyst is added in the reaction, the catalyst includes potassium iodide；
Preferably, acid binding agent is added in the reaction, the acid binding agent includes potassium carbonate；
Preferably, the solvent of the reaction includes CH3Any one in CN, acetone and N,N-dimethylformamide or at least two
Kind combination.
5. a kind of potassium ion and the difunctional sense film of dissolved oxygen, which is characterized in that the potassium ion and the difunctional biography of dissolved oxygen
Feeling film includes carrier, and be fixed on by way of chemical bonding the potassium described in claim 1 of the carrier surface from
Sub- probe, oxygen probe and reference probe；
The oxygen probe has the following structure:
The reference probe has the following structure:
6. potassium ion according to claim 5 and the difunctional sense film of dissolved oxygen, which is characterized in that the carrier is
The quartzy carrier of TMSPA modification, the TMSPA have the following structure:
7. the preparation method of a kind of potassium ion according to claim 5 or 6 and the difunctional sense film of dissolved oxygen, feature
It is, the preparation method includes the following steps:
(1 ') makes polyethylene glycol methacrylate-styrene polymer, methacrylic acid, polyethylene glycol dimethacrylate, oxygen probe and reference
Probe polymerize in carrier surface, obtains the carrier for being covered with hydrogel layer；
(2 ') are grafted potassium ion probe described in claim 1 in the carrier surface for being covered with hydrogel layer, obtain described
Potassium ion and the difunctional sense film of dissolved oxygen.
8. preparation method according to claim 7, which is characterized in that the carrier surface contains double bond；
Preferably, in step (1 '), the initiator of the polymerization reaction includes azodiisobutyronitrile；
Preferably, in step (1 '), the solvent of the polymerization reaction includes n,N-Dimethylformamide；
Preferably, in step (1 '), the carrier is the quartzy carrier of TMSPA modification；
Preferably, in step (1 '), polyethylene glycol methacrylate-styrene polymer, polyethylene glycol dimethacrylate, oxygen probe, reference
The mass ratio of probe, initiator and solvent is 500-1500:20-300:1-15:1-15:5-30:1000, preferably 800:50:5:
5:10:1000；
Preferably, in step (1 '), the mass ratio of the methacrylic acid and the polyethylene glycol methacrylate-styrene polymer is 10-
1000:1；
Preferably, in step (1 '), the number-average molecular weight of the polyethylene glycol methacrylate-styrene polymer is 300-2000, preferably 500；
Preferably, in step (1 '), the number-average molecular weight of the polyethylene glycol dimethacrylate is 300-2000, preferably
750；
Preferably, in step (1 '), the polymerization reaction carries out under nitrogen atmosphere；
Preferably, in step (1 '), the temperature of the polymerization reaction is 70-90 DEG C, preferably 80 DEG C；
Preferably, in step (1 '), the time of the polymerization reaction is 0.8-1.5h, preferably 1h；
Preferably, step (1 ') specifically includes: by polyethylene glycol methacrylate-styrene polymer, methacrylic acid, polyethylene glycol dimethyl
Acrylate, oxygen probe, reference probe, initiator and solvent mixing, the quartzy carrier surface for taking mixed liquor to modify in TMSPA,
Polymerase 10 .8-1.5h under the conditions of 70-90 DEG C of temperature, obtains the carrier for being covered with hydrogel layer.
9. preparation method according to claim 7 or 8, which is characterized in that in step (2 '), coupling agent is added and/or urges
Agent；
Preferably, the coupling agent includes 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride；
Preferably, the catalyst includes 4-dimethylaminopyridine；
Preferably, in step (2 '), the mass ratio of the potassium ion probe, coupling agent and catalyst is 2:1000:200；
Preferably, in step (2 '), the reaction dissolvent of the grafting includes n,N-Dimethylformamide；
Preferably, in step (2 '), the reaction time of the grafting is 10-15h, preferably 12h；
Preferably, in step (2 '), the reaction of the grafting carries out at room temperature；
Preferably, step (2 ') specifically comprise the following steps: for the carrier for being covered with hydrogel layer to be placed in potassium ion probe,
In the mixed solution of coupling agent and catalyst, graft reaction 10-15h is carried out at room temperature, obtains the potassium ion and dissolved oxygen
Difunctional sense film.
10. a kind of potassium ion according to claim 5 or 6 and the difunctional sense film of dissolved oxygen are in potassium ion detection and molten
Solve the application in oxygen detection.
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| CN115487316A (en) * | 2022-01-26 | 2022-12-20 | 浙江大学 | Potassium ion selective filter membrane/magnetic mesoporous nanocomposite material, fluorescence/magnetic resonance bimodal imaging probe and application |
| CN115487316B (en) * | 2022-01-26 | 2024-06-07 | 浙江大学 | Potassium ion selective filter membrane/magnetic mesoporous nanocomposite, fluorescence/magnetic resonance dual-mode imaging probe and application |
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