CN103588960A - Non-labeled ionic conjugated polyelectrolyte, synthetic method thereof and application to biological detection - Google Patents
Non-labeled ionic conjugated polyelectrolyte, synthetic method thereof and application to biological detection Download PDFInfo
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Abstract
The invention discloses design, detection application of non-labeled ionic conjugated polyelectrolyte. The non-labeled ionic conjugated polyelectrolyte has a structure shown as the general formula (I) shown in the description, and comprises a 9-substituted fluorenes unit and an acceptor unit Ar with electron-withdrawing characteristic, Ar is one substituent groups of benzo[d]thiadiazol, benzo[d]thiazol, thiazole, benzo[d]diazol, boron-dipyrromethene unit, iridium complex containing unit, metalloporphyrin containing unit, perylene bisimide, naphthalimide and the like, the ratio of fluorenes group to Ar (x:y) is 17:3-18:2, the side group comprises m+1 CH2 units, wherein Ion is one water-soluble groups such as quaternary ammonium group, carboxyl or sulfo group. The non-labeled ionic conjugated polyelectrolyte has extremely high solubility and stability, is applicable to multiple non-labeled biological detection, and is a brand-new sensing detection platform.
Description
Technical field
The present invention relates to a class conjugated polyelectrolytes design, be the design of the non-marked conjugated polyelectrolytes that combined by fluorenyl and another kind of luminescent material of a class specifically and apply in the biological detection of tensio-active agent, DNA, protein active substances.
Background technology
The structure of conjugated polymers type material makes it have a large amount of absorptive units.Excitation energy can be moved along polymer backbone, then transfers to chromophore, and this will cause spectral signal to amplify.Therefore, conjugated polymers can serve as luminescent material and the light amplification instrument based on FRET (fluorescence resonance energy transfer) (FRET) of catching.Due to these remarkable performances, conjugated polymers has been used as the optical table of extremely sensitive chemistry and biosensor.
And be applied to biological detection, use is water-soluble conventionally, the conjugated polyelectrolytes of charged (yin, yang ion).The electronegative molecules such as the metal ion in the aqueous solution, organic, biomolecules and biomacromolecule, and conjugated polyelectrolytes by the interaction of static assemble, conformational change or FRET, thereby change fluorescence spectrum.For example, positively charged ion conjugated polythiofuran derivative has been widely used in the quick of DNA, and high-sensitivity detection, because than single stranded DNA (ssDNA), after polymkeric substance and double-stranded DNA (dsDNA) combination, has great conformational change.This conformational change transduction DNA hybridization signal is converted into colorimetric or the convenient detection of fluorescent signal.
In the detection method that tradition is used, thereby often need that DNA or other test substances are carried out to fluorescent mark, realize FRET and detect.Mark in advance so often causes testing process complicated, even in the detection of some unknown materials, is difficult to realize.Markless detection is due to simplicity and low-cost people's the very big interest that causes.Up to the present, the biosensor of great majority based on conjugated polymers still needs to use a fluorescence labeling probe.People brought into use without the embedded dyestuff that shifts to an earlier date mark afterwards, and this embedded dyestuff can well be embedded in dsDNA, but this feature has also limited this detection strategy, can only not be suitable for for detection of DNA other biological molecule.And our polyelectrolyte only needs and detected molecule electrostatical binding just can obtain effective detected result, this makes our range of application of polyelectrolyte more extensive.
Summary of the invention
Technical problem: the object of the invention is to design the conjugated polyelectrolytes that a class has the advantages such as excellent water dissolubility, stability, expand unmarked, the low-cost application that its part biological detects simultaneously.The conjugated polyelectrolytes material of containing in the present invention has good luminescent properties, chemical stability, thermostability, light stability and highly water-soluble, meanwhile, the ionic group that side chain connects, there is suitable electric charge, for extensive, single-minded carrying out non-marked biology, chemical detection provides condition.
Technical scheme: the mentality of designing of a class non-marked conjugated polyelectrolytes of the present invention, its structure can represent by leading to as follows formula I:
Wherein Ar be diazosulfide, benzothiazole, thiazole, benzodiazole, boron fluoride complexing two pyrroles's methine class unit, a kind of containing in the substituting groups such as complex of iridium unit, containing metal porphyrin unit, perylene diimide, naphthalimide; The ratio x:y of fluorenyl and Ar is 17:3～18:2.
Mentality of designing comprises following requirement:
1). in formula I general formula, Ar is diazosulfide, benzothiazole, thiazole, benzodiazole, boron fluoride complexing two pyrroles's methine class unit, a kind of containing in the substituting groups such as complex of iridium unit, containing metal porphyrin unit, perylene diimide, naphthalimide.The selection of this Ar need to have in non-fluorenyl characteristic peak region the feature of good luminous performance.
2). in formula I general formula, the polymerization ratio x:y of fluorenyl and Ar is 17:3～18:2.
3). the selection of above-mentioned requirements and ratio select to be, when this polyelectrolyte disperses when better, system fluorescence only has the characteristic peak of fluorenyl; And when this polyelectrolyte generation is assembled, the characteristic peak of system fluorescence fluorenyl declines and even disappears, and the characteristic peak of Ar occurs and enhancing.
4). in formula I general formula, the side chain of fluorenyl is three to five carbon, and end is charged ionic group form.Such selection is characterised in that, this polyelectrolyte can be extraordinary water-soluble and its aqueous solution preserve at normal temperatures highly stable.
5). above-claimed cpd of the present invention, comparatively typically has several as follows:
M=2, Ion is quaternary amines, Ar is diazosulfide, x:y=17:3; Its structural formula is:
M=2, Ion is quaternary amines, Ar is fragrant complex of iridium, x:y=18:2, its structural formula is:
M=2, Ion is carboxylic acid sodium group, Ar Wei perylene diimide group, x:y=18:2, its structural formula is:
The synthetic method that the present invention proposes compound is as follows:
(1) 2,7-dibromo fluorenes is starting raw material, under alkali effect, and synthetic 9 fluorenes monomer A that two alkyl replace;
(2) fluorenes monomer A, under palladium catalytic condition, heats with Glacial acetic acid potassium, frequency alcohol connection boron ester the fluorenes monomers B that obtains 2,7-hypoboric acid ester in anhydrous dimethyl sulfoxide solvent;
(3) polymkeric substance is synthetic
Fluorenes monomer A, fluorenes monomers B and other are subject to body unit in toluene containing two bromines, use 2M sodium carbonate solution, and triphenylphosphine palladium, as catalyzer, reacts and obtains polymkeric substance, through sedimentation, ionization, obtains ionic conjugated polyelectrolytes.The mean number average molecular weight of polyelectrolyte is more than 15000, and number-average degree of polymerization is greater than 50.
Non-marked ionic conjugated polyelectrolytes material is for biological detecting method, and concrete steps are as follows:
With deionized water, the poly-electrolysis material of conjugation is made into approximately 10
-6m dilute solution;
The solution of test substance is added in the poly-electrolysis material solution of conjugation by micropipette rifle, and add deionized water constant volume, wherein the ultimate density in the poly-electrolysis material test of conjugation is 10
-6m;
Be determined under different test substances existence, ultraviolet-visible absorption spectroscopy, the fluorescence emission spectrum of the poly-electrolysis material of conjugation,, can detect determinand in shortwave and Long wavelength region peak change according to the poly-electrolysis material fluorescence spectrum of conjugation;
The concentration of test substance, electrically charged behavior, the poly-electrolysis material solution microenvironment of conjugation change the mechanism that all can detect as the poly-electrolysis material multi-emitting non-marked of conjugation.
Application aspect, the polyelectrolyte of our design is without being used embedded dyestuff, only needs and detected molecule electrostatical binding just can obtain effective detected result, and this makes our range of application of polyelectrolyte more extensive.
Beneficial effect: compared with prior art, the non-marked conjugated polyelectrolytes material of the present invention's design, has advantages of water-soluble excellence, light/Heat stability is good, with low cost.The present invention has obtained a class non-marked conjugated polyelectrolytes, by methods such as ultraviolet, fluorescence, its optical property is studied.
When it is applied to biomolecule detection, without material and biomolecules are carried out to any mark, and also without any additional dye materials, just can realize well the markless detection to biomolecules.
Accompanying drawing explanation
Fig. 1. the uv-spectrogram of non-marked conjugated polyelectrolytes P1.
Fig. 2. the fluorescence pattern of non-marked conjugated polyelectrolytes P1 in water and in different buffered soln.
Fig. 3. non-marked conjugated polyelectrolytes P1 is for the fluorescence pattern of DNA detection.
Fig. 4. the fluorescence pattern that non-marked conjugated polyelectrolytes P1 detects for range protein.
Embodiment
The general embodiment 1 of non-marked conjugated polyelectrolytes building-up process:
In the Schlenk of 25mL pipe, by 9,9-two (3,3'-dimethyl-1-Propylamino)-fluorenes-2, the two pinacol borates (588.4mg, 1.0mmol) of 7-, two (3, the 3'-dimethyl-1-Propylaminos)-2 of 9,9-, 7-dibromo fluorenes (345.8mg, 0.7mmol), 4, bromo-diazosulfide (the 88mg of 7-bis-, 0.3mmol), 3.5mg tetrakis triphenylphosphine palladium, is dissolved in 12 milliliters of new steamings in tetrahydrofuran (THF) and 6 milliliters of saturated potassium carbonate mixing solutionss.Lucifuge, 85 degree, under argon shield, heated and stirred is 36 hours.The yellow polymer solution sedimentation in ether obtaining, collects solid, is dissolved in ethanol, again uses 350 milliliters of ether sedimentations, obtains yellow thread solid, is neutral polymer.
Get 30 milligrams of neutral polymers, be dissolved in 5 milliliters of methyl-sulphoxides, under 45 degree heated and stirred, add 3 milliliters of monobromethanes, treated that precipitation generates, add 20 milliliters of acetone, under continuing to stir, add 3 milliliters of monobromethanes.Question response 40 as a child, filters solid precipitation, obtains non-marked conjugated polyelectrolytes P1.The structure of P1 is as follows:
According to general embodiment 1 method of non-marked conjugated polyelectrolytes building-up process, by control contain two boric acid ester monomers, containing the ratio of the 3rd monomer shown in two bromine monomers and general formula (1), under similar reaction conditions, can obtain typical structure has several as follows:
M=2, Ion is quaternary amines, Ar is diazosulfide, x:y=18:2; Its structural formula is:
M=2, Ion is quaternary amines, Ar is fragrant complex of iridium, x:y=18:2, its structural formula is:
The general embodiment 2 of non-marked conjugated polyelectrolytes building-up process
In the Schlenk of 25mL pipe, by two (the 1-methyl propionates)-2 of 9,9-, two pinacol borate-the fluorenes (118mg, 0.2mmol) of 7-, 9, two (the 1-methyl propionates)-2 of 9-, 7-dibromo fluorenes (79.4mg, 0.16mmol), 2, bromo-perylene diimide (the 27.7mg of 6-bis-, 0.04mmol), 3mg tetrakis triphenylphosphine palladium, is dissolved in 15 milliliters of new steamings in toluene and 7 milliliters of saturated potassium carbonate mixing solutionss.Lucifuge, 85 degree, under argon shield, heated and stirred is 36 hours.The red polymer solution sedimentation in ethanol obtaining, collects solid, is dissolved in chloroform, again uses 350 milliliters of ethanol sedimentations, obtains the thread solid of scarlet, is neutral polymer.Get 30 milligrams of neutral polymers, be dissolved in 15 milliliters of tetrahydrofuran (THF)s, under 70 degree heated and stirred, add 50% potassium hydroxide solution, treated that precipitation generates, add 20 ml waters, under continuing to stir.Question response 40 as a child, filters solid precipitation, obtains non-marked negatively charged ion conjugated polyelectrolytes.Conjugated polyelectrolytes structure has following characteristics.
M=2, Ion is carboxylic acid sodium group, Ar Wei perylene diimide group, x:y=18:2, its structural formula is:
Following examples are to further illustrate of the present invention, are not limitations of the present invention.
Following examples are that a kind of non-marked conjugated polyelectrolytes P1 has been selected in selection according to the present invention, are applied to biomolecule detection.P1 structural formula is as follows:
Embodiment 1:
In pure aquatic system, add the P1(concentration of 4.5 μ M to calculate with average number of repeat unit), survey its ultra-violet absorption spectrum.Be Fig. 1.
Embodiment 2:
In pure water, Tris buffered soln (pH=7.4) and PBS buffered soln (pH=7.4), add respectively the P1 of 4.5 μ M, survey its fluorescence emission spectrum.Be Fig. 2.Excitation wavelength is 381nm, and slit is (3; 5).
Embodiment 3:
Ordering DNA sequence dna is (5 ' to 3 '): TAA CAA TAA TCC TTT TTT TTT T.In pure aquatic system, add the P1(concentration of 4.5 μ M to calculate with average number of repeat unit), survey its fluorescence.The DNA that adds respectively again 0.25nM, 2.5nM, 25nM, 250nM, 2.5 μ M, surveys respectively its fluorescence, obtains P1 for the fluorescence pattern of DNA detection.Be Fig. 3.Excitation wavelength is 381nm, and slit is (3; 5).
Embodiment 4:
The P1 that adds 4.5 μ M in pure aquatic system, surveys its fluorescence.Add respectively more following albumen: BSA (250nM), AFP (250nM), Hb (250nM), Lys (250nM), Mb (250nM), CEA (250nM), PSA (250nM), NSE (250nM), CA19-9 (250KU), CA125 (250KU), CA153 (5KU), survey respectively its fluorescence, obtain P1 for the fluorescence pattern of Protein Detection.Be Fig. 4.Excitation wavelength is 381nm, and slit is (3; 5).
In the method for traditional polyelectrolyte detection of biological molecule, need to or additionally add in the enterprising row labels of biomolecules and embed other chromophoric grouies.And can find out from above experimental result, apply in the non-marked conjugated polyelectrolytes process of our design, to detected object, needn't use any extra modification or embedded chromophoric group, only need and detected molecule electrostatical binding just can obtain effective detected result, this makes our range of application of polyelectrolyte more extensive.
Claims (9)
1. a non-marked ionic conjugated polyelectrolytes material, is characterized in that having structure shown in following formula I:
Wherein, 9 side chains of fluorenyl are containing m+1 CH
2unit;
Ion is water soluble group;
Ar is that long wave absorbs, the aromatic base of transmitting.
2. non-marked ionic conjugated polyelectrolytes material according to claim 1 and 2, is characterized in that m<5.
3. non-marked ionic conjugated polyelectrolytes material according to claim 1 and 2, is characterized in that, Ion is water soluble group: any in quaternary amines, carboxyl, sulfonic group.
4. non-marked ionic conjugated polyelectrolytes material according to claim 1 and 2, it is characterized in that, Ar is that long wave absorbs, the aromatic base of transmitting: any in diazosulfide, thiazole, benzodiazole, boron fluoride complexing two pyrroles's methine class unit, aryl complex of iridium unit, containing metal porphyrin unit, perylene diimide, naphthalimide substituting group.
5. non-marked ionic conjugated polyelectrolytes material according to claim 1 and 2, is characterized in that in formula I general formula, and the polymerization ratio x:y of fluorenyl and Ar is 17:3～18:2.
6. non-marked ionic conjugated polyelectrolytes material according to claim 1 and 2, it is characterized in that in formula I general formula, Ion group and DNA, PNA, RNA, albumen, polypeptide or the enzyme with electric charge have electrostatic interaction, thereby realize sensing detection function.
7. according to the non-marked ionic conjugated polyelectrolytes material described in claim 1 or 2 or 3, it is characterized in that, the selection of main polymer chain copolymerization units Ar need to have in the 450 above regions of nanometer the feature of good luminous performance; And require, in polyelectrolyte dilute solution, only have the fluorescent emission of poly-fluorenes section, and Ar has faint fluorescent emission or without fluorescent emission; Selection and ratio select to be, when this polyelectrolyte disperses when very good in pure water medium, system fluorescence only has the characteristic peak of fluorenyl; And when this polyelectrolyte generation is assembled, the characteristic peak of system fluorescence fluorenyl declines and even disappears, and the characteristic peak of Ar occurs and enhancing.
8. a non-marked ionic conjugated polyelectrolytes material synthesis method, is characterized in that, the compound of synthetic claim 1 to 7 any one, and its method is as follows:
(1) 2,7-dibromo fluorenes is starting raw material, under alkali effect, and synthetic 9 fluorenes monomer A that two alkyl replace;
(2) fluorenes monomer A, under palladium catalytic condition, heats with Glacial acetic acid potassium, frequency alcohol connection boron ester the fluorenes monomers B that obtains 2,7-hypoboric acid ester in anhydrous dimethyl sulfoxide solvent;
(3) polymkeric substance is synthetic
Fluorenes monomer A, fluorenes monomers B and other are subject to body unit in toluene containing two bromines, use 2M sodium carbonate solution, and triphenylphosphine palladium, as catalyzer, reacts and obtains polymkeric substance, through sedimentation, ionization, obtains ionic conjugated polyelectrolytes.The mean number average molecular weight of polyelectrolyte is more than 15000, and number-average degree of polymerization is greater than 50.
9. a non-marked ionic conjugated polyelectrolytes material biological detecting method, is characterised in that, the compound of claim 1 to 7 any one is for biological detection, and concrete steps are as follows:
With deionized water, the poly-electrolysis material of conjugation is made into approximately 10
-6m dilute solution;
The solution of test substance is added in the poly-electrolysis material solution of conjugation by micropipette rifle, and add deionized water constant volume, wherein the ultimate density in the poly-electrolysis material test of conjugation is 10
-6m;
Be determined under different test substances existence, ultraviolet-visible absorption spectroscopy, the fluorescence emission spectrum of the poly-electrolysis material of conjugation,, can detect determinand in shortwave and Long wavelength region peak change according to the poly-electrolysis material fluorescence spectrum of conjugation;
The concentration of test substance, electrically charged behavior, the poly-electrolysis material solution microenvironment of conjugation change the mechanism that all can detect as the poly-electrolysis material multi-emitting non-marked of conjugation.
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| CN103951813A (en) * | 2014-03-31 | 2014-07-30 | 南京邮电大学 | 9-Aryl substituted flourenyl conjugated polyelectrolyte, and preparation method and application thereof |
| CN104198451A (en) * | 2014-09-02 | 2014-12-10 | 深圳市坤健创新药物研究院 | Sensor array and application of sensor array to aided identification of metal ions |
| CN104610531A (en) * | 2015-02-02 | 2015-05-13 | 华南师范大学 | Amino-modified conjugated polymer as well as preparation method and application thereof |
| CN104788400A (en) * | 2015-04-22 | 2015-07-22 | 中国科学院化学研究所 | Oligofluorene compound and preparation method thereof |
| CN105237745A (en) * | 2015-10-13 | 2016-01-13 | 华南理工大学 | Quaternary phosphonium salt group-containing conjugated polyelectrolyte and its use in organic photoelectric device |
| CN105384917A (en) * | 2015-11-10 | 2016-03-09 | 华南理工大学 | Conjugated polymer with side chain containing sulfonic acid or sulfonate and plane-inverted organic/inorganic hybrid perovskite solar cell prepared from conjugated polymer |
| CN105527433A (en) * | 2015-12-18 | 2016-04-27 | 南京邮电大学 | Fluorescence method for detecting tumor marker |
| CN105859729A (en) * | 2016-04-28 | 2016-08-17 | 华南理工大学 | Porphyrin small organic molecule cathode interface material and preparation method thereof |
| CN106769968A (en) * | 2017-01-06 | 2017-05-31 | 南京邮电大学 | A kind of method that there is π π hyperconjugations in the fragrant hydrocarbon molecule of judgement conjugation |
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| CN104198451A (en) * | 2014-09-02 | 2014-12-10 | 深圳市坤健创新药物研究院 | Sensor array and application of sensor array to aided identification of metal ions |
| CN104610531A (en) * | 2015-02-02 | 2015-05-13 | 华南师范大学 | Amino-modified conjugated polymer as well as preparation method and application thereof |
| CN104788400A (en) * | 2015-04-22 | 2015-07-22 | 中国科学院化学研究所 | Oligofluorene compound and preparation method thereof |
| CN105237745A (en) * | 2015-10-13 | 2016-01-13 | 华南理工大学 | Quaternary phosphonium salt group-containing conjugated polyelectrolyte and its use in organic photoelectric device |
| CN105384917A (en) * | 2015-11-10 | 2016-03-09 | 华南理工大学 | Conjugated polymer with side chain containing sulfonic acid or sulfonate and plane-inverted organic/inorganic hybrid perovskite solar cell prepared from conjugated polymer |
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| CN106905200A (en) * | 2015-12-22 | 2017-06-30 | 安赛伯（天津）生物科技有限公司 | Water-soluble fluorene compound and its application in analysis of protein |
| CN106905200B (en) * | 2015-12-22 | 2018-05-04 | 安赛伯（天津）生物科技有限公司 | Water-soluble fluorene compound and its application in analysis of protein |
| US9896538B2 (en) | 2016-03-28 | 2018-02-20 | Aat Bioquest, Inc. | Polyfluoreno[4,5-cde]oxepine polymers and conjugates thereof |
| US10316136B2 (en) | 2016-03-28 | 2019-06-11 | Aat Bioquest, Inc. | Polyfluoreno[4,5-cde]oxepine conjugates and their use in methods of analyte detection |
| CN105859729A (en) * | 2016-04-28 | 2016-08-17 | 华南理工大学 | Porphyrin small organic molecule cathode interface material and preparation method thereof |
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Application publication date: 20140219 |