CN106147753A - Thiazole orange styrene compound is as G-tetra-serobila nucleic acid fluorescent probe - Google Patents
Thiazole orange styrene compound is as G-tetra-serobila nucleic acid fluorescent probe Download PDFInfo
- Publication number
- CN106147753A CN106147753A CN201510213543.6A CN201510213543A CN106147753A CN 106147753 A CN106147753 A CN 106147753A CN 201510213543 A CN201510213543 A CN 201510213543A CN 106147753 A CN106147753 A CN 106147753A
- Authority
- CN
- China
- Prior art keywords
- tetra
- nucleic acid
- probe
- serobila
- stranded structure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
The invention discloses a kind of fluorescent probe and preparation method thereof and the application in detection nucleic acid G-tetra-stranded structure.Such probe has a structure of logical formula (I), and simple in construction, stable, easily prepares.The invention also discloses such probe and can be used for specific nucleic acid detecting G-tetra-serobila secondary structure, spectrofluorophotometer can be passed through, or directly observe by the naked eye the G-tetra-serobila secondary structure quickly detected under fluorescent lamp in solution；Such probe can be used for detecting agarose gel or polyacrylamide gel amplifying nucleic acid G-tetra-stranded structure；Can be used for existence and the distribution of G-tetra-stranded structure in detection, labelling or display living cells.The fluorescent material of the present invention has the most single-minded identification ability for nucleic acid G-tetra-stranded structure, there is good permeability of cell membrane simultaneously, the advantages such as relatively low photo-toxic, bio-toxicity and photobleaching, 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 nucleic acid in gel and in cell
The purposes of G-tetra-serobila secondary structure.
Background technology
The basis of nucleic acid the most still all living things cell, also to the growth of organism, grow, breed, heredity and variation etc.
Great biosis plays dominant force effect.Nucleic acid molecule is divided into two classes: DNA (deoxyribonucleic acid) (DNA) and ribonucleic acid (RNA),
The duplication and synthesis of protein play a part to store and convey hereditary information.
G-tetra-serobila (G-quadruplex) is a kind of special nucleic acid secondary structure.A lot of rich guanine regions tool in human genome
There is the ability forming this structure, including telomerase guanine repetitive sequence, and the promoter region of several genes, as
C-kit, c-myc, c-myb, bcl-2, PDGF, kRAS, VEGF, Rb and insulin gene etc..G-tetra-chain
Body structure has polymorphism, the quantity of chain and the glucosides torsion angle of orientation, the connected mode of loop and guanine and and carbonyl
Many-sided type and conformations determining G-tetra-serobila such as the metal ion of base negative electricity center coordination, these diversityes are also albumen
Multiple recognition site is provided with micromolecular compound.Orientation according to chain is different, and G-tetra-serobila is divided into the most parallel, antiparallel with
Three kinds of conformations of mixed type.
Regulating and controlling effect is all there is in the formation of G-tetra-stranded structure for internal a series of physiological process.Research proves, some starts
The transcription and translation level of the G-tetra-stranded structure meeting appreciable impact gene of subregion, therefore G-tetra-stranded structure has been considered as
To the function of molecular switch, it forms and breaks a series of bodies such as may relate to signal conduction, apoptosis and cell proliferation
Interior important physiological process.So, in vivo or in vitro tests, it is possible to specifically detect G-tetra-stranded structure
Existing or formed, related biological function and exploitation for research G-tetra-stranded structure are with G-tetra-stranded structure as target spot
The aspect such as cancer therapy drug all there is very important effect.
Along with the development of biotechnology, the requirement for nucleic acid marking is more and more higher, carries out DNA by isotope effect in the past
The method of molecule order-checking cannot meet demand, and fluorescent labeling has detection as one, and speed is fast, reproducible, use sample
Amount less, the labelling technique of the advantage such as radiationless in widespread attention, and obtain and develop rapidly.The stain having been found that has porphyrin
Class, cyanines class, phenylethylene etc..And thiazole orange (TO) therein is the non-selective cyanines class nucleic acid fluorescent probe of a kind of classics.
Producing in addition to fluorescence after being combined with other nucleic acid, TO is equally combined on G-tetra-serobila, produces strong fluorescence.But
It is that TO can not efficiently identify G-tetra-serobila secondary structure from the nucleic acid molecules of other forms, thus the poor restriction of selectivity
The application of TO.In order to improve the selectivity of TO, we introduce styrene group in the structure of TO, have obtained a class
Novel structure, and to nucleic acid G-tetra-stranded structure specificity strong fluorescent probe.
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 G-tetra-serobila knot in detection aqueous solution, in gel and in cell
The application of structure.
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 shown in following formula I:
R in formula1It is selected fromOr
R2、R3、R4、R5、R6、R7It is respectively selected from H, F, Cl, Br, OH, OCH3、N(CH3)2、C1-6Alkyl
Or C3-6Cycloalkyl；
X is C or N.
Invention also provides the preparation method of above-mentioned probe, be expressed as follows:
Concretely comprise the following steps:
By 4-chloro-2-methyl quinoline and iodomethane reaction, obtain compoundBy 2-methylbenzothiazole and iodomethane
Reaction, obtainsThen willWithReaction, obtains
Finally willReact with the aromatic aldehyde of different substituents, obtain final probe compound
Present invention also offers above-mentioned probe in detection aqueous solution, in gel and the application of G-tetra-stranded structure in cell.
The present invention provide probe owing to having bigger electron-conjugated system and plane, the charge transfer effect in probe molecule
The strong and weak fluorescent emission intensity that can affect molecule.When occurring after specific effect with G-tetra-stranded structure, intramolecular turn
The flexibility of dynamic double bond is restricted, and makes Intramolecular electron transfer effect strengthen, and fluorescence is also remarkably reinforced.Meanwhile, such is visited
The flexible conjugate planes of the molecular structure of pin, have rotary key so that it is can be easier to be deposited in G quadrantal
In plane, and then with G-tetra-serobila, there is stronger active force, the most weak with the nucleic acid effect of other secondary structures.So,
When this probe is mixed from the nucleic acid of different secondary structures, if this nucleic acid is G-tetra-stranded structure, between itself and probe molecule
Specific effect, produces the change of fluorescence spectrum.When the secondary structure of nucleic acid is other structures, then will not produce significantly letter
Number change.
Compared with prior art, the invention have the advantages that
(1) preparation of such probe is simple, is easy to get, and Stability Analysis of Structures, it is simple to store.
(2) probe that the present invention provides has relatively low bio-toxicity, phototoxicity and photobleaching, and light stability is good.
(3) probe that the present invention provides has good water solublity and good permeability of cell membrane.
(4) spectral region of probe that the present invention provides and the spectral region of biological sample have sufficiently large difference, at non-G-tetra-
Solution that serobila exists and intracellular there is relatively low fluorescence background.
(5) probe that the present invention provides can specifically detect identification G-tetra-stranded structure, it is achieved that G-tetra-stranded structure
With the differentiation of other secondary structures, using simple fluorescence spectrophotometer, the most only need under general ultraviolet light irradiation, perusal just may be used
To identify the secondary structure of nucleic acid samples, fast, easy and simple to handle, with low cost, and can realize detecting on the spot.
Accompanying drawing explanation
Fig. 1 is probe 6a Yu AT, six kinds of nucleic acid of DA21, LQ1, Oxy28, random, RNA are in 1: 1 concentration
Under fluorescence Spectra.
Fig. 2 is the fluorescence spectrum that probe 6a titrates four chain DNAs (Oxy28).
Fig. 3 is that probe 6a titrates C and (F-F in the fluorescence spectrum of four chain DNAs (Oxy28)0)/F0The curve of matching.
Fig. 4 is probe 6a and double-stranded DNA (ds26) and the poly-propionic acid amide. gel electrophoresis figure of G-tetra-serobila (Oxy28)
Fig. 5 is the cell imaging figure of dyestuff DAPI dye PC3 cell.
Fig. 6 is the cell imaging figure of probe 6a dye PC3 cell.
Fig. 7 is the cell imaging figure that probe 6a and dyestuff DAPI redye PC3 cell.
Detailed description of the invention
Technical scheme is further illustrated below by way of specific embodiment.Proved by fluorescence spectrum experiments, the present invention
Owing to having bigger electron-conjugated system and plane, there is specific accumulation with G-tetra-stranded structure in the compound 6a related to
After effect, fluorescence spectrum generation significant change, fluorescence intensity increases Radix Achyranthis Bidentatae, the most only needs under general ultraviolet light irradiation, and naked eyes are seen
Examine, the most weak with the nucleic acid effect of other secondary structures, do not have obvious fluorescence signal to respond, make such probe have very well
Specific recognition effect.So, when this probe is mixed by we from the DNA of different secondary structures, when this DNA is G-tetra-
During stranded structure, the specific effect between itself and probe molecule, produce the change of fluorescence spectrum.When the secondary structure of DNA is
During other structures, then will not produce obvious signal intensity.As a example by wherein compound 6a, illustrate that the fluorescent probe of the present invention exists
G-tetra-serobila nucleic acid in fluorescence method (including fluorescence microscope and fluorescence gel imager) detection aqueous solution, in gel and in cell
The application of secondary structure.
Embodiment one: the synthesis of compound 2
In 25ml round-bottomed flask, weigh 4-chloro-quinaldine 0.2g (1.1236mmol), add iodomethane, solvent sulfolane,
Heat the mixture to 40～60 DEG C, after reacting 18 hours, cooling, shake after adding absolute ether, sucking filtration, solid is washed
Washing several times, weigh after vacuum drying, thin layer chromatography tentatively shows do not have by-product, obtains 0.345g sterling 2, 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
Weighing 2-methyl-benzothiazole 0.25g (1.68mmol) in the round-bottomed flask of 25ml, addition iodomethane, solvent are anhydrous
Ethanol, after reacting 15 hours, is cooled to room temperature by reacted solution, is subsequently adding dehydrated alcohol and chloroform at 80 DEG C
Mixed liquor, sucking filtration after vibration, and precipitate by a small amount of reagent wash, obtain white powdery solids 0.448g, yield after vacuum drying
It 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 3, joins in the round-bottomed flask equipped with 10ml methanol, adds under room temperature condition after stirring
Enter a small amount of 0.5mol/L sodium bicarbonate aqueous solution, open wide stir about 1 hour.The saturated KI of 4ml is added in reacted solution
Solution, stir about is sucking filtration after 5 minutes, is washed with water, and acetone is washed, after finally giving brick-red solid, dry filter concentration
Column chromatography purification, obtains 0.98g compound 4, and 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 M of 0.0756g (0.170mmol)3In the round-bottomed flask of 25ml, add the 4 of 2 times of moles, 4-dimethyl
Amino-benzaldehyde 0.0505g, solvent, n-butanol, 4-methyl piperidine few drops, react 3 hours, after cooling at 120～150 DEG C
Sucking filtration, the mixed solution washing solid configured with n-butyl alcohol and frozen water, vacuum drying obtains 72mg after weighing, productivity 73.4%:1H
NMR (400MHz, DMSO) δ 8.70 (d, J=8.3Hz, 1H), 8.13 (d, J=8.8Hz, 1H), 8.03 (d, J=7.7Hz,
1H), 7.97-7.92 (m, 1H), 7.79 (d, J=8.9Hz, 2H), 7.71 (d, J=7.8Hz, 1H), 7.69-7.64 (m, 2H),
7.63 (s, 1H), 7.56 (t, J=7.8Hz, 1H), 7.43 (d, J=15.7Hz, 1H), 7.36 (t, J=7.6Hz, 1H), 6.79 (d, J=
9.1Hz, 3H), 4.13 (s, 3H), 3.94 (s, 3H), 3.05 (s, 6H).
Embodiment five: the synthesis of compound 6b
The same 6a of synthetic method, obtains 70mg black solid 6b, productivity 76.5%:1H NMR:(400MHz, DMSO-d6)
δ 12.00 (s, 1H), 8.72 (d, J=8.0HZ, 1H), 8.18 (d, J=16.0HZ, 3H), 8.00 (m, 3H), 7.69 (m, 3H),
7.58 (d, J=8.0HZ, 2H), 7.47 (d, J=12.0HZ, 1H), 7.35 (t, J=8.0HZ, 1H), 7.27 (s, 2H), 6.82
(s, 1H), 4.19 (s, 3H), 4.94 (s, 3H).
Embodiment six: the synthesis of compound 6c
The same 6a of synthetic method, obtains 79mg violet solid 6c, productivity 83.5%:1H NMR (400MHz, DMSO) δ 8.70
(d, J=8.5Hz, 1H), 8.12 (d, J=8.9Hz, 1H), 8.07 (d, J=7.9Hz, 1H), 7.95 (t, J=7.8Hz, 1H), 7.73
-7.68 (m, 2H), 7.59 (dd, J=13.5,7.0Hz, 3H), 7.49 (d, J=8.7Hz, 2H), 7.39 (t, J=7.6Hz, 1H),
7.17 (dd, J=24.7,13.8Hz, 3H), 6.83-6.76 (m, 3H), 4.09 (d, J=8.5Hz, 3H), 3.96 (s, 3H), 3.00 (d,
J=11.7Hz, 6H)
Embodiment seven: the synthesis of compound 6d
The same 6a of synthetic method, obtains 76mg red solid 6d, productivity 77.4%:1H NMR (400MHz, DMSO) δ 8.69
(d, J=8.4Hz, 1H), 8.01 (ddd, J=13.8,10.1,7.4Hz, 4H), 7.94-7.89 (m, 1H), 7.69 (t, J=7.4Hz,
1H), 7.64 (d, J=4.5Hz, 1H), 7.60 (d, J=9.5Hz, 1H), 7.58-7.49 (m, 2H), 7.44 (s, 1H), 7.34 (dd, J
=19.2,8.3Hz, 3H), 6.79 (s, 1H), 4.07 (s, 3H), 3.92 (s, 3H).
Embodiment eight: the synthesis of compound 6e
The same 6a of synthetic method, obtains 82mg brown solid 6e, productivity 85.6%:1H NMR (400MHz, DMSO) δ 9.10
(s, 1H), 8.77 (s, 1H), 8.66 (d, J=3.7Hz, 1H), 8.39 (d, J=7.3Hz, 1H), 8.17 (s, 1H), 8.06 (d, J=7.5
Hz, 1H), 7.99 (s, 1H), 7.91 (d, J=15.9Hz, 1H), 7.74 (s, 2H), 7.67 (d, J=18.3Hz, 1H), 7.65-7.52
(m, 3H), 7.41 (s, 1H), 6.91 (s, 1H), 4.16 (s, 3H), 4.00 (s, 3H).
Embodiment nine: the synthesis of compound 6f
The same 6a of synthetic method, obtains 80mg atropurpureus solid 6e, productivity 83.2%:1H NMR (400MHz, DMSO) δ
8.73 (t, J=10.7Hz, 1H), 8.10 (dd, J=18.2,9.6Hz, 2H), 7.97-7.92 (m, 1H), 7.74-7.68 (m, 2H),
7.67-7.61 (m, 2H), 7.60-7.51 (m, 3H), 7.45 (dd, J=13.6,5.9Hz, 2H), 7.42-7.35 (m, 3H), 7.31
(d, J=15.2Hz, 2H), 6.83 (d, J=9.2Hz, 1H), 4.06 (d, J=14.2Hz, 3H), 3.97 (d, J=7.1Hz, 3H).
Embodiment ten: nucleic acid selectivity
DNA configures: DNA sample is purchased from Ying Jun Bioisystech Co., Ltd.DNA is dissolved in right amount Tris-HCl's
In buffer in (PH 7.4,100mM Tris, 60mM KCl) or Tris-acetate buffer (PH 5.5,100mM Tris,
60mM KCl), ultramicron ultraviolet is fixed the denseest, and after heating 5min at 95 DEG C, Slow cooling is annealed to room temperature as storing liquid,
4 DEG C of storages.
The compound stock solution of 5mM is diluted to the concentration of 5uM, adds different types of nucleic acid spectrofluorophotometer
(slit width=10, scanning speed=200, Ex=475nm) measures its respective fluorescence intensity, find this be compounds with
After the combination of G-tetra-serobila DNA, fluorescence intensity is the strongest.
DNA sequence
Embodiment 11: the mensuration of detection limit
The compound stock solution of 5mM is diluted to the concentration of 5uM, then in spectrofluorophotometer (slit width=10, scanning speed
Degree=200, Ex=475nm) scan, then the DNA being slowly added into Oxy28 thereto accomplishes to make it saturated. the calculating of detection limit is public
Formula
LOD=K × Sb/m
LOD (the detection limit of compound), m is concentration C and (F-F0)/F0The slope of done straight line, SbFor by instrument blank repeatedly
The standard deviation measured, 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 0.87
nM.
Embodiment 12: 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 are then installed, take out comb and dividing plate after treating gel cooling, put
Entering in electrophoresis tank, till buffer flooded glue 1-2mm, DNA sample is made into 5 μMs (in mixed liquor, sample-loading buffer is 1 ×),
Taking 10 μ L to add in gel loading wells, connected by whole electrophresis apparatus, 45V voltage runs 1h, and then 100V voltage runs 3h, takes out
Gel piece, then gel piece is put into bubble dye in stain and compound, contaminated and dried up afterwards, be placed on gel-electrophoretic apparatus observation.
Embodiment 13: cell imaging is tested
First cell is inoculated in 6 orifice plates, makes the density of cell be about 2 × 103Individual/mL, then at 37 DEG C, 5%CO2Environment
Middle cultivation 24h.Then discard the cell culture fluid in step 6 orifice plate, wash 3 times with 1 × PBS of pre-cooling, then add pre-cooling
Pure methanol 1.5mL room temperature lucifuge place 1min, finally discard pure methanol and wash 3 times with 1 × PBS of pre-cooling again, addition 1mL
The compound of 5 μMs then place 15min.Discard the compound solution in step 6 orifice plate, wash 3 with 1 × PBS of pre-cooling
Secondary, 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.
Claims (5)
1. a G-tetra-serobila fluorescent probe, it is characterised in that chemical structural formula is as shown in I:
R in formula1It is selected from
R2、R3、R4、R5、R6、R7It is respectively selected from H, F, Cl, Br, OH, OCH3、N(CH3)2、C1-6Alkyl or C3-6
Cycloalkyl；
X is C or N.
2. the preparation method of a G-tetra-serobila fluorescent probe as claimed in claim 1, it is characterised in that comprise the steps:
By 4-chloro-2-methyl quinoline and iodomethane reaction, obtain compoundBy 2-methylbenzothiazole and iodomethane reaction,
ObtainThen willReaction, obtainsFinally
WillReact with the aromatic aldehyde of different substituents, obtain final probe compound
3. the fluorescent probe as claimed in claim 1 application in detection aqueous solution amplifying nucleic acid G-tetra-stranded structure.
4. fluorescent probe as claimed in claim 1 is at detection agarose gel or polyacrylamide gel amplifying nucleic acid G-tetra-stranded structure
In application.
5. the fluorescent probe as claimed in claim 1 application in detection cell amplifying nucleic acid G-tetra-stranded structure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510213543.6A CN106147753B (en) | 2015-04-24 | 2015-04-24 | Thiazole orange styrene compound as G-quadruplex nucleic acid fluorescent probe |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510213543.6A CN106147753B (en) | 2015-04-24 | 2015-04-24 | Thiazole orange styrene compound as G-quadruplex nucleic acid fluorescent probe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106147753A true CN106147753A (en) | 2016-11-23 |
| CN106147753B CN106147753B (en) | 2020-03-10 |
Family
ID=57347509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510213543.6A Active CN106147753B (en) | 2015-04-24 | 2015-04-24 | Thiazole orange styrene compound as G-quadruplex nucleic acid fluorescent probe |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106147753B (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106749208A (en) * | 2016-11-25 | 2017-05-31 | 中山大学 | A kind of polyaryl substituted imidazole fluorescence probe and preparation method thereof and the application in the serobilas of specific detection G tetra- |
| 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 |
| CN110483394A (en) * | 2019-09-02 | 2019-11-22 | 广东工业大学 | A kind of application of compound |
| CN110606862A (en) * | 2019-10-24 | 2019-12-24 | 浙江大学 | Platinum complex fluorescent probe for specifically detecting RNA G-quadruplex, preparation method and application |
| CN111233856A (en) * | 2020-02-17 | 2020-06-05 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting chromium content in soil |
| CN111303143A (en) * | 2020-02-17 | 2020-06-19 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting cadmium content in soil |
| CN111961042A (en) * | 2020-07-23 | 2020-11-20 | 中国科学院化学研究所 | Compound for detecting abnormal amplification of GGCCTG (GGCCTG) repetitive sequence of SCA36 spinal cord gene and detection method |
| CN112079827A (en) * | 2020-08-19 | 2020-12-15 | 广东工业大学 | Thiazole orange derivative, preparation method thereof and application thereof in mitochondria |
| CN114716431A (en) * | 2022-02-17 | 2022-07-08 | 北京富百科生物技术有限公司 | Synthesis and application of phenanthridine and benzothiazole conjugated linked fluorescent dye |
| WO2023019983A1 (en) * | 2021-08-20 | 2023-02-23 | 四川大学 | Nucleic acid fluorescent dye and preparation and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5863753A (en) * | 1994-10-27 | 1999-01-26 | Molecular Probes, Inc. | Chemically reactive unsymmetrical cyanine dyes and their conjugates |
| CN103788940A (en) * | 2012-11-02 | 2014-05-14 | 国家纳米科学中心 | Aggregation-induced emission fluorescent molecule as well as preparation method and fluorescent dye composition, and application of aggregation-induced emission fluorescent molecule and fluorescent dye composition in mitochondria dyeing |
| CN104650609A (en) * | 2013-11-22 | 2015-05-27 | 沈阳药科大学 | Thiazol orange derivative, manufacturing method and application of thiazol orange derivative used as double helix nucleic acid fluorescence molecular probe |
-
2015
- 2015-04-24 CN CN201510213543.6A patent/CN106147753B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5863753A (en) * | 1994-10-27 | 1999-01-26 | Molecular Probes, Inc. | Chemically reactive unsymmetrical cyanine dyes and their conjugates |
| CN103788940A (en) * | 2012-11-02 | 2014-05-14 | 国家纳米科学中心 | Aggregation-induced emission fluorescent molecule as well as preparation method and fluorescent dye composition, and application of aggregation-induced emission fluorescent molecule and fluorescent dye composition in mitochondria dyeing |
| CN104650609A (en) * | 2013-11-22 | 2015-05-27 | 沈阳药科大学 | Thiazol orange derivative, manufacturing method and application of thiazol orange derivative used as double helix nucleic acid fluorescence molecular probe |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| CN106749208A (en) * | 2016-11-25 | 2017-05-31 | 中山大学 | A kind of polyaryl substituted imidazole fluorescence probe and preparation method thereof and the application in the serobilas of specific detection G tetra- |
| CN106749208B (en) * | 2016-11-25 | 2019-10-01 | 中山大学 | A kind of polyaryl substituted imidazole fluorescence probe and preparation method thereof and the application in tetra- serobila of specific detection G- |
| CN108558853B (en) * | 2018-01-15 | 2020-09-11 | 广东工业大学 | Compound and preparation method and application thereof |
| 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 |
| CN110483394A (en) * | 2019-09-02 | 2019-11-22 | 广东工业大学 | A kind of application of compound |
| CN110606862A (en) * | 2019-10-24 | 2019-12-24 | 浙江大学 | Platinum complex fluorescent probe for specifically detecting RNA G-quadruplex, preparation method and application |
| CN111233856A (en) * | 2020-02-17 | 2020-06-05 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting chromium content in soil |
| CN111303143A (en) * | 2020-02-17 | 2020-06-19 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting cadmium content in soil |
| CN111961042A (en) * | 2020-07-23 | 2020-11-20 | 中国科学院化学研究所 | Compound for detecting abnormal amplification of GGCCTG (GGCCTG) repetitive sequence of SCA36 spinal cord gene and detection method |
| CN111961042B (en) * | 2020-07-23 | 2022-08-12 | 中国科学院化学研究所 | Compound for detecting abnormal amplification of GGCCTG (GGCCTG) repetitive sequence of SCA36 spinal cord gene and detection method |
| CN112079827A (en) * | 2020-08-19 | 2020-12-15 | 广东工业大学 | Thiazole orange derivative, preparation method thereof and application thereof in mitochondria |
| WO2023019983A1 (en) * | 2021-08-20 | 2023-02-23 | 四川大学 | Nucleic acid fluorescent dye and preparation and application thereof |
| CN114716431A (en) * | 2022-02-17 | 2022-07-08 | 北京富百科生物技术有限公司 | Synthesis and application of phenanthridine and benzothiazole conjugated linked fluorescent dye |
| CN114716431B (en) * | 2022-02-17 | 2022-11-11 | 北京富百科生物技术有限公司 | Synthesis and application of phenanthridine and benzothiazole conjugated linked fluorescent dye |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106147753B (en) | 2020-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106147753A (en) | Thiazole orange styrene compound is as G-tetra-serobila nucleic acid fluorescent probe | |
| CN106833623B (en) | A kind of fluorescence probe and preparation method thereof | |
| CN107266417B (en) | Indole ethylene substituted quinoline derivative and preparation method and application thereof | |
| CN106147752B (en) | RNA fluorescent probe and preparation method and application thereof | |
| CN102719238B (en) | Dual-functional probe and preparation method and application in detection of G-quadruplex structure thereof | |
| CN104449669B (en) | A kind of polyaryl substituted imidazole fluorescence probe and preparation method thereof and the application in detection G-tetra-stranded structure | |
| KR20240031282A (en) | Compound based cyanine, labeling dye, kit and contrast medium composition for biomolecule comprising the same | |
| CN106459001B (en) | Polymethine compound and its purposes as fluorescent marker | |
| CN106366131B (en) | Physiological pH senses the preparation method and application of binuclear ruthenium | |
| CN108329302A (en) | A kind of half flower cyanines class near infrared fluorescent probe compound of sulfide specificly-response and its preparation method and application | |
| KR102645305B1 (en) | Compound based cyanine, labeling dye, kit and contrast medium composition for biomolecule comprising the same | |
| Lu et al. | Benzothiazole-substituted benzofuroquinolinium dyes as new fluorescent probes for G-quadruplex DNA | |
| CN111217806B (en) | Hemicyanine compound based on benzothiazole-linked heterocycle and preparation method and application thereof | |
| Lou et al. | Detection of adenine-rich ssDNA based on thymine-substituted tetraphenylethene with aggregation-induced emission characteristics | |
| CN113683631A (en) | Organic boric acid glucose probe and preparation method and application thereof | |
| CN104710977B (en) | A kind of double function probe and preparation method thereof and the application in detecting positive parallel conformation G-tetra-serobila | |
| CN107311977B (en) | Indole ethylene compound and preparation method and application thereof | |
| CN114014848B (en) | RNA fluorescent probe and preparation method and application thereof | |
| CN103710021B (en) | Fluorescent dye with nitrobenzimidazole as RNA (ribonucleic acid) recognition group as well as preparation method and application of fluorescent dye | |
| CN111116539A (en) | Fluorescent probe with dual response to viscosity and pH of lysosome in cancer cell, preparation method and application | |
| CN104650610A (en) | Asymmetric near-infrared BODIPY fluorescent dye as well as preparation method and application thereof | |
| CN108148014B (en) | Formaldehyde fluorescent probe and preparation method and application thereof | |
| CN110041248B (en) | 3, 5-bis (2, 4-dimethoxyphenyl) pyridine two-membered ring, preparation method and application thereof | |
| Yu et al. | Selective probes targeting c-MYC Pu22 G-quadruplex and their application in live mice imaging | |
| CN107586292A (en) | Compound, its preparation method, fluorescent dye and fluorescence probe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |