CN106147752A - A kind of RNA fluorescent probe and its preparation method and application - Google Patents
A kind of RNA fluorescent probe and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of fluorescent probe and preparation method thereof and the application in detection nucleic acid RNA nucleic acid.Such probe has thiazole orange styryl structures, sees chemical constitution formula (I), and simple in construction, stable, easily prepares.The invention also discloses such probe and can be used for specific detection RNA, can pass through spectrofluorophotometer, or directly observe by the naked eye and under fluorescent lamp, quickly detect the RNA in solution；Can be used for existence and the distribution of RNA in detection, labelling or display living cells.The fluorescent material of the present invention has the most single-minded identification ability for nucleic acid RNA, there is the advantages such as good permeability of cell membrane, relatively low photo-toxic, bio-toxicity and photobleaching simultaneously, overcome other detection methods expensive, equipment requirements is high, the shortcomings such as technical operation is relative complex.
Description
Technical field
The present invention relates to a kind of fluorescent probe and preparation method thereof, and it is in aqueous, detect RNA in gel and in cell
With the purposes of kernel imaging in cell.
Background technology
Small-molecule probe refers to for certain specific objective biomolecule or the detector of the exploitation of biological ion, Small-molecule probe energy
Carry out specificity interaction with specific target molecule, and can be found out by special detection technique.Compared with common detection technique,
Probe technique have highly sensitive, specificity by force, the advantage such as quick and precisely, it is adaptable to molecular image and in real time monitoring.
RNA (ribonucleic acid) organism growth, growth and apoptosis whole during have important regulating and controlling effect；?
In the generating process of numerous disease, RNA plays pivotal role, and the generation such as malignant tumor is in close relations with the abnormal expression of RNA.
But with DNA analysis compared with detection technique, the analysis of RNA is slow with application development with the exploitation of detection technique.
RNA fluorescent probe has high selectivity in complicated solution system or in living cells environment, specifically identifies RNA
Advantage, RNA analyze with detection field there is good application prospect.At present, the most business-like RNA fluorescent probe
The RNASelect that only invitrogen company produces.There are some defects, such as in this fluorescent probe in actual imaging is applied
With RNA response speed compared with the shortcoming such as slow, photo-toxic is big and light stability is poor, its using value of these defective effects.Therefore,
The small-molecule fluorescent probe of exploitation superior performance has the strongest market value.
Summary of the invention
Present invention aims to the deficiencies in the prior art, it is provided that a kind of fluorescent probe.
Further object is that the preparation method that above-mentioned probe is provided.
It is yet a further object of the present invention to provide above-mentioned probe in detection aqueous solution, in gel and the application of RNA in cell.
The present invention is achieved through the following technical solutions above-mentioned purpose:
The invention provides a kind of fluorescent probe, its structural formula is:
X in formula-For anion, can be iodide ion, bromide ion, p-methyl benzenesulfonic acid ion or trifluoromethanesulfonic acid ion etc..Institute
The X stated-For the anion after atom N methylation reaction.
Invention also provides the preparation method of above-mentioned probe, be expressed as follows:
Concretely comprise the following steps: first 4-chloro-2-methyl quinoline is reacted with methylating reagent, obtain compoundAgain by 2-first
Base benzothiazole reacts with methylating reagent, obtainsThen willWithBy mole
Than be 1: 1-1: 1.3 reaction, reaction temperature is 25-100 DEG C, and the response time is 2-5 hour, reaction dissolvent be water, methanol,
One or more in ethanol, reaction is carried out under inorganic base existence condition, obtains intermediateFinally
WillBeing 1: 2-1: 3 reactions in molar ratio with 4-first sulfydryl benzaldehyde, reaction temperature is 130-150 DEG C,
Response time is 2-5 hour, and reaction dissolvent is n-butyl alcohol, with 4-methyl piperidine or piperidines as catalyst, carries out in condensation anti-
Should, obtain final probe compound
Another object of the present invention additionally provides above-mentioned probe in detection aqueous solution, in gel and the application of RNA in cell.
Fluorescent probe of the present invention is at labelling or shows the application that RNA and kernel are distributed in living cells.
Experimental result confirms, utilizes the fluoroscopic image after fluorescent probe labelling of the present invention to show have at Cytoplasm and nucleolar zone
Significantly green light distribution, clearly point out described probe can in living cells the RNA in narrow spectrum imaging kytoplasm and kernel,
And with tradition kernel fluorescent probe or also obtain after carrying out contrast test with the cell after RNase digestion experiment further
Confirmation.
The fluorescent probe that the present invention provides is the RNA Selective recognition fluorescent probe molecule that a class is novel, close with its function
Fluorescent probe ratio, probe of the present invention have low bio-toxicity, membrane permeability is good, colour developing is strong, redye compatible good, light is steady
Qualitative stronger feature, indicates that it has a wide range of applications as RNA and kernel fluorescent probe, be expected to exploitation for RNA and
Physiology that kernel is relevant and pathological research are by simple and direct, biological detection reagent intuitively.
Accompanying drawing explanation
Fig. 1 is probe 6a Yu AT, six kinds of nucleic acid of DA21, LQ1, Oxy28, random, RNA are under 1: 1 concentration
Fluorescence Spectra.
Fig. 2 is the matched curve that probe 6a titrates the fluorescence data of four chain DNAs, double-stranded DNA, RNA.
Fig. 3 is the fluorescence spectrum of probe 6a titration RNA
Fig. 4 be probe 6a titration RNA fluorescence spectrum in C and (F-F0)/F0The curve .. of matching
Fig. 5 is probe 6a Yu DNA and RNA gel electrophoresis figure.
Fig. 6 is the cell imaging figure that probe 6a and dyestuff DAPI redye PC3 cell
Fig. 7 is probe 6a Yu E36 with RNA dyestuff at the after stain PC3 cell of DNase Yu Rnase process
Detailed description of the invention
Technical scheme is further illustrated below by way of specific embodiment.Proved by fluorescence spectrum experiments, the present invention relates to
Compound 6a owing to having bigger electron-conjugated system and plane, occur after specific sedimentation with RNA, fluorescence
Spectrum generation significant change, fluorescence intensity increases Radix Achyranthis Bidentatae, the most only needs under general ultraviolet light irradiation, perusal, simultaneously and its
His nucleic acid effect is more weak, does not has obvious fluorescence signal to respond, and makes such probe have good specific recognition effect.Institute
With, when this probe is mixed by we from different nucleic acid, when this nucleic acid is RNA, the specific effect between itself and probe molecule,
Produce the change of fluorescence spectrum.When nucleic acid is DNA (G-tetra-serobila, double-strand, strand), then will not produce obvious signal and become
Change.As a example by wherein compound 6a, illustrate that the fluorescent probe of the present invention (includes that fluorescence microscope becomes with fluorescence gel in fluorescence method
As instrument) detect in aqueous solution, in gel and the application of RNA in cell
Embodiment one: the synthesis of compound 2
In 25ml round-bottomed flask, weigh 4-chloro-quinaldine 0.2g (1.1236mmol), add the iodomethane of 6 times of moles about
0.96g, sulfolane 1.5ml, heat the mixture to 50 DEG C, after reacting 18 hours, and cooling, shake after adding absolute ether,
Sucking filtration, solid absolute ether washs, and weighs, obtain 0.345g compound 2 after vacuum drying, and productivity is 95.8%:1H NMR
(400MHz, DMSO) δ 8.56 (d, J=8.4Hz, 1H), 8.46 (d, J=8.3Hz, 1H), 8.22 (t, J=8.1Hz, 1H),
8.01 (t, J=7.9Hz, 1H), 7.55 (s, J=7.4Hz, 1H), 4.20 (s, 3H), 3.74 (s, 1H), 2.68 (s, 3H).
Embodiment two: the synthesis of compound 4
In the round-bottomed flask of 25ml, weigh 2-methyl-benzothiazole 0.25g (1.68mmol), add the iodine first of 6 times of moles
Alkane about 1g, dehydrated alcohol 5ml, after reacting 15 hours, be cooled to room temperature by reacted solution, be subsequently adding nothing at 80 DEG C
Water-ethanol and each 5ml of chloroform, sucking filtration after vibration, and wash precipitation with a small amount of ethanol and chloroform, after vacuum drying
Being white powdery solids 0.448g to compound 4, yield is 91.7%:1H NMR (400MHz, DMSO) δ 8.44 (d, J=
8.1Hz, 1H), 8.30 (d, J=8.4Hz, 1H), 7.90 (t, J=7.8Hz, 1H), 7.81 (t, J=7.7Hz, 1H), 4.20 (s, 3H),
3.54 (s, 1H), 3.17 (s, 3H).
Embodiment three: the synthesis of compound 5
The each 0.50g of Weigh Compound 2 and 4, joins in the round-bottomed flask equipped with 10ml methanol, stirs 6 points under room temperature condition
Add 2ml 0.5mol/L sodium bicarbonate aqueous solution after clock, be stirred at room temperature about 1 hour.4ml is added in reacted solution
Saturated KI solution, stir about is sucking filtration after 15 minutes, then washes with 10ml, 4ml washing with acetone, finally gives brick-red solid,
Obtaining 0.98g compound 5 after drying, productivity is 81.7%:1H NMR (400MHz, DMSO) δ 8.77 (d, J=8.3Hz,
1H), 8.18 (d, J=8.7Hz, 1H), 8.02-7.96 (m, 2H), 7.74 (d, J=8.2Hz, 2H), 7.59 (t, J=7.7Hz, 1H),
7.39 (t, J=7.5Hz, 1H), 7.34 (s, 1H), 6.85 (s, 1H), 4.07 (s, 3H), 3.98 (s, 3H), 2.87 (s, 3H).
Embodiment four: the synthesis of compound 6a
Weigh the 5 of 0.0715g (0.160mmol) in the round-bottomed flask of 25ml, add the 4-methylthio phenyl of 2 times of moles
Formaldehyde 0.049g, n-butyl alcohol 1.5ml, 4-methyl piperidine 5, react 3 hours, sucking filtration after cooling at 130～135 DEG C,
Wash solid with n-butyl alcohol, be dried after weighing and obtain 66mg, productivity 71%:1H NMR (400MHz, DMSO) δ 8.73 (d, J=
7.8Hz, 1H), 8.14 (d, J=8.4Hz, 1H), 8.06-8.02 (m, 1H), 8.00-7.95 (m, 1H), 7.87 (d, J=8.5Hz,
2H), 7.76-7.68 (m, 3H), 7.64 (s, 1H), 7.61-7.55 (m, 2H), 7.42-7.35 (m, 3H), 6.87 (s, 1H), 4.13
(s, 3H), 3.97 (d, J=3.7Hz, 3H), 2.56 (s, 3H).
Embodiment five: fluorescent probe 6a is to the different selective fluorescence spectrum experiments of nucleic acid
The compound stock solution of 5mM is diluted to the concentration of 5uM, adds different types of nucleic acid spectrofluorophotometer (narrow
Seam width 10nm, scanning speed 200nm/min, excitation wavelength 475nm) measure its respective fluorescence intensity, find fluorescence
After the combination of probe 6a with RNA, fluorescence intensity is the strongest.
Nucleic acid used in selectivity experiment
Embodiment six: the fluorescent probe 6a fluorescence titration experiment to different nucleic acid
The compound stock solution of 5mM is diluted to the concentration of 5 μMs, is positioned in spectrofluorophotometer, is gradually increased solution
The concentration of middle different nucleic acid, and carry out fluorescent strength determining.Condition determination is: slit width 10nm, scanning speed 200nm/min,
Excitation wavelength 475nm.
Nucleic acid used in fluorescence titration experiment
Embodiment seven: the fluorescent probe 6a mensuration to RNA detection limit
The compound stock solution of 5mM is diluted to the concentration of 5 μMs, then in spectrofluorophotometer (slit width 10nm, scanning
Speed 200nm/min, excitation wavelength 475nm) scanning, then be slowly added into RNA thereto and accomplish to make it saturated. the meter of detection limit
Calculate formula
LOD=K × Sb/m
LOD (binding constant of compound), m are the slopes of concentration C and the done straight line of (F-F0)/F0, SbFor many by instrument blank
The standard deviation of secondary measurement, according to the world, purely and the suggestion of applied chemistry community is usually taken to be 3 to K value, and the LOD that 6a records is
6μg/L。
Embodiment eight: the cell imaging experiment of thiazole orange styrene compound
First cell is inoculated in 6 orifice plates, makes the density of cell be about 2 × 103Individual/mL, then at 37 DEG C, 5%CO2Ring
Border is cultivated 24h.Then discard the cell culture fluid in step 6 orifice plate, wash 3 times with 1 × PBS of pre-cooling, then add pre-
Cold pure methanol 1.5mL room temperature lucifuge places 1min, finally discards pure methanol and washes 3 times with 1 × PBS of pre-cooling, adds 1
Then the compound of 5 μMs of mL places 15min.Discard the compound solution in step 6 orifice plate, wash with 1 × PBS of pre-cooling
3 times, above-mentioned 6 orifice plates add the DAPI solution 1mL 37 DEG C of placement 2min of 1 μM, the most again with 1 × PBS of pre-cooling
Wash 6 times, soak 5min every time.Observation of cell staining conditions under inverted fluorescence microscope.
Embodiment nine: Rnase Yu the DNase cell imaging experiment of thiazole orange styrene compound
First cell is inoculated in 6 orifice plates, makes the density of cell be about 2 × 103Individual/mL, then at 37 DEG C, 5%CO2Ring
Border is cultivated 24h.Then discard the cell culture fluid in step 6 orifice plate, wash 3 times with 1 × PBS of pre-cooling, then add pre-
Cold pure methanol 1.5mL room temperature lucifuge places 1min, finally discards pure methanol and washes 3 times with 1 × PBS of pre-cooling, adds 1mL
The compound of 5uM then place 15min.Discard the compound solution in step 6 orifice plate, wash 3 with 1 × PBS of pre-cooling
Secondary, six orifice plates are separately added into 1mL DNase, the solution of DNase-Free RNase 37 DEG C, 5%CO2Cultivate 3h. to abandon
Remove the enzymatic solution in 6 orifice plates, then wash 3 times with 1 × PBS of pre-cooling, soak 5min every time.Observe thin under inverted fluorescence microscope
Born of the same parents' staining conditions.
Embodiment ten: nucleic acid gel electrophoresis experiment
First by 5 × TBE electrophoretic buffer, Ammonium persulfate. 10%m/V, 6X loading buffer, the double propionic acid amide. (29: 1) of methylene (%,
M/V) prepare, electrophoretic apparatus and configuration gel solution, Casting of gels be then installed, after treating gel cooling, take out comb and dividing plate,
Putting in electrophoresis tank, till buffer flooded glue 1-2mm, DNA sample is made into 5 μMs, and (in mixed liquor, sample-loading buffer is
1X), RNA is made into 5mg/L, takes 10uL respectively and adds in gel loading wells, is connected by whole electrophresis apparatus, and 45V voltage runs 1h, connects
100V voltage and run 3h, take out gel piece, then gel piece is put into bubble dye in stain and compound, contaminated and dry up afterwards, will
It is placed on gel-electrophoretic apparatus observation.
Claims (6)
1. a thiazole orange phenylethylene RNA fluorescent probe, it is characterised in that chemical structural formula is as shown in I:
X in formula-For iodide ion, bromide ion, chloride ion, p-methyl benzenesulfonic acid ion or trifluoromethanesulfonic acid ion.
2. the preparation method of a RNA fluorescent probe as claimed in claim 1, it is characterised in that comprise the steps:
4-chloro-2-methyl quinoline is reacted with methylating reagent, obtains compoundBy 2-methylbenzothiazole with
Methylating reagent reacts, and obtainsThen willReaction, obtainsFinally willReact with 4-first sulfydryl benzaldehyde, obtain final probe compound
3. fluorescent probe as claimed in claim 1 is in the application of detection aqueous solution amplifying nucleic acid RNA.
4. fluorescent probe as claimed in claim 1 RNA application in detection agarose gel or polyacrylamide gel.
5. fluorescent probe as claimed in claim 1 application of RNA in detection cell.
6. fluorescent probe RNA granules stain and application of kernel imaging in eukaryotic cell as claimed in claim 1.
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| CN106188031A (en) * | 2016-06-30 | 2016-12-07 | 广东工业大学 | Thiazole orange styrene derivative and preparation method thereof and the application in preparing drug-resistance bacteria medicine |
| CN108165045A (en) * | 2018-01-15 | 2018-06-15 | 广东工业大学 | Nucleic acid dye compound and its preparation method and application |
| CN108558853A (en) * | 2018-01-15 | 2018-09-21 | 广东工业大学 | A kind of compound and its preparation method and application |
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| CN112410404A (en) * | 2020-05-27 | 2021-02-26 | 江西省肿瘤医院(江西省癌症中心) | Open type two-photon nucleic acid probe and application thereof in FISH |
| CN112679474A (en) * | 2020-12-08 | 2021-04-20 | 南方医科大学顺德医院(佛山市顺德区第一人民医院) | Ratio type fluorescent probe and preparation method and application thereof |
| EP3674381A4 (en) * | 2017-08-25 | 2021-08-18 | Japan Science and Technology Agency | Organic optical material |
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| CN106188031B (en) * | 2016-06-30 | 2019-11-26 | 广东工业大学 | Thiazole orange styrene derivative and preparation method thereof and preparing the application in drug-resistance bacteria medicine |
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| CN111665351A (en) * | 2020-06-20 | 2020-09-15 | 江南大学 | Method for quickly and specifically determining RNA content |
| CN112679474A (en) * | 2020-12-08 | 2021-04-20 | 南方医科大学顺德医院(佛山市顺德区第一人民医院) | Ratio type fluorescent probe and preparation method and application thereof |
| CN115433181A (en) * | 2022-10-12 | 2022-12-06 | 河南省农业科学院农业质量标准与检测技术研究所 | Fluorescent probe based on hemicyanine structure and preparation method and application thereof |
| CN115433181B (en) * | 2022-10-12 | 2024-03-08 | 河南省农业科学院农业质量标准与检测技术研究所 | Fluorescent probe based on hemicyanine structure, and preparation method and application thereof |
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