CN106632304B - A kind of two-photon RNA fluorescence probe and its application in living cells imaging - Google Patents
A kind of two-photon RNA fluorescence probe and its application in living cells imaging Download PDFInfo
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Abstract
The present invention relates to a kind of two-photon RNA fluorescence probe and its applications in living cells imaging, and general structure is such as shown in (I), in which: R is alkyl, hydroxyalkyl or ether；X is bromine or iodine.Two-photon RNA fluorescence probe of the present invention is the two-photon fluorescence probe of a kind of novel RNA Selective recognition, it can be applied in being distributed in living cells marking or showing RNA, the probe has the characteristics that membrane permeability is good, cytotoxicity is small, colour developing is strong, can be developed into the relevant physiology of RNA, pathological research biological detection reagent.
Description
Technical field
The present invention relates to a kind of fluorescence probe, in particular to a kind of two-photon fluorescence being imaged for RNA in living cells is visited
Needle.
Background technique
In various living matters in the cell, ribonucleic acid (RNA) is important large biological molecule, in catalysis biological
It is played an extremely important role in the biological processes such as reaction, gene expression regulation.RNA is primarily present in the kernel of nucleus
In area and cytoplasm, positioning, activity, number, form etc. include important life science information, these information are examined with medicine
Break and treats closely bound up.Therefore, the RNA imaging in kernel and cytoplasm has biochemistry, biological medicine, life science etc.
It is of great significance.Current Imaging-PAM, especially two-photon fluorescence imaging technology, in real-time monitoring living cells
The form of middle biomolecule, number etc. are widely applied.Two-photon fluorescence imaging technology have high detection sensitivity,
The advantages such as big penetration depth, image high-fidelity, low phototoxicity and photobleaching, obtain the subjects such as biology, life, medicine
The favor of researchers.To adapt to existing situation, the various two-photon fluorescence probes that different targets in living cells can be imaged are
As research hotspot.
Compared with numerous commercialization probes (such as DNA probe), rna probe is considerably less.There was only Molecular Probe Company at present
(Molecular Probes Co.) provides the probe " SYTO RNA-Select " of an available RNA imaging, but the change of the probe
Structural formula is learned not announce externally yet.Patent CN103265947A, CN103275699A each provide it is a kind of for living cells at
The RNA fluorescence probe of picture, but the probe is not able to achieve two-photon fluorescence imaging.Therefore, in living cells RNA fluorescence imaging detection side
Face still lacks excellent two-photon fluorescence probe, this status is urgently to be resolved.
Summary of the invention
The purpose of the present invention is in view of the above deficiencies, and a kind of two-photon RNA fluorescence probe is provided, the probe is logical with film
The feature that permeability is good, cytotoxicity is small, colour developing is strong.
It is a further object of the present invention to provide two-photon RNA fluorescence probes to mark or show that RNA divides in living cells
The application of cloth.
The technical scheme adopted by the invention is as follows:
A kind of two-photon RNA fluorescence probe, general structure is such as shown in (I):
Wherein: R is alkyl, hydroxyalkyl or ether；X is bromine or iodine.
In above-mentioned two-photon RNA fluorescence probe: the preferred C of the R1-12Alkyl, C1-12Hydroxyalkyl or ether base；Into
The preferred methyl of one step, ethyl, butyl, dodecyl, ethoxy or ether base.
Described two-photon RNA fluorescence probe most preferably 2- [2- (1H- indol-3-yl) the vinyl] -3- (2- ethoxy)
Benzothiazole salt compounded of iodine (referred to as IE).
The preparation method of above-mentioned two-photon RNA fluorescence probe:
First halogenating reaction introduces R base on 2- methylbenzothiazole nitrogen, and obtains benzothiazolium salt, then utilizes benzo thiophene
Azoles salt reacts to obtain final product by knoevenagel with 3- formyl indole.
The two-photon RNA fluorescence probe (IE) to prepare reaction equation as shown in Figure 1.
Above-mentioned two-photon RNA fluorescence probe is in the application for marking or showing that RNA is distributed in living cells.
The cell is HeLa cell.
Two-photon RNA fluorescence probe of the present invention is applied into the dyeing in HeLa cell, the two-photon fluorescence image after label
It has been shown that, has apparent fluorescence distribution in the cytoplasm and nucleolar zone of cell, clearly prompts the probe can be in living cells special secondary school
RNA in one property imaging cells matter and kernel, and reality is compared in the cell after ribalgilase (RNase) digestion experiment
It is further confirmed after testing.It is studied on HeLa cell with cytotoxicity of the mtt assay to the probe, tests HeLa
Cell survival rate of the cell after the probe is incubated for 2,4,8,12,24 hours, within dyeing 12 hours, HeLa cell is deposited
For motility rate also 90% or more, this shows that two-photon fluorescence probe cytotoxicity of the present invention is small, has preferable membrane permeability,
The RNA of cytoplasm and nucleolar zone in living cells can be imaged.
Two-photon RNA fluorescence probe of the present invention is the two-photon fluorescence probe of a kind of novel RNA Selective recognition, the spy
Needle set has the characteristics that membrane permeability is good, cytotoxicity is small, colour developing is strong, can be developed into the relevant physiology of RNA, pathological research life
Quality testing test agent.
Detailed description of the invention
Fig. 1 is that 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine prepares reaction equation；
Fig. 2 is the bis- light of RNA of 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE)
Sub- fluorescence titration figure；A is two-photon fluorescence spectrum；B is variation diagram of the maximum fluorescence intensity with RNA and concentration and probe concentration ratio；
Fig. 3 is 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) to activity
Hela cell is dyed the two-photon fluorescence photo obtained under 800 nm laser irradiations；A is two-photon fluorescence photo；B is
The differential interference microphoto of light field laser scanning；C is the merging figure (common location figure) of two figure of ab；
Fig. 4 be HeLa cell through ribalgilase (RNase) before and after the processing, with 2- [2- (1H- indol-3-yl) ethylene
Base] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) dyeing cell photo comparison figure；A) at ribalgilase (RNase)
Before reason, shone with 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) dyeing HeLa cell
Piece；B) before for ribalgilase (RNase) processing, the differential interference microphoto of light field laser scanning；It c) is ribalgilase
(RNase) it after handling, is dyed with 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE)
HeLa cell photo；D) after for ribalgilase (RNase) processing, the differential interference microphoto of light field laser scanning；
Fig. 5 is that 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) is thin in HeLa
On born of the same parents toxicity (MTT) experiment in cell survival rate with incubation time variation diagram；Incubation time: 2, it 4,8,12,24 hour, incubates
Educate 5 μM of concentration.
Specific embodiment
It further illustrates combined with specific embodiments below.
The synthesis of embodiment 1:2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE)
2- methylbenzothiazole (0.05mol, 7.46g) and ethylene iodohydrin (0.05mol, 7.81g) is dissolved in toluene
It in (50ml), stirs 4 hours, subsequent back flow reaction 30 minutes is cooled to room temperature, filtering, and ether washing obtains N- ethyl alcohol -2-
Methylbenzothiazole salt compounded of iodine.By N- ethyl alcohol -2- methylbenzothiazole salt compounded of iodine (0.01mol, 0.32g) and 3- formyl indole
(0.01mol, 0.145g) is dissolved in methanol (20ml), and a few drop piperidines, back flow reaction 4h are added dropwise, and dehydrated alcohol washing obtains brown
Color powder, yield 77%.
1H NMR (400MHZ): 12.478 (s, 1H), 8.448 (t, J=7.66,2H), 8.342 (d, J=7.96,1H),
8.205 (d, J=4.96,1H), 8.16 (t, J=9.72,1H), 7.798 (t, J=7.76,1H), 7.713 (q, J=9.29,
1H), 7.604 (t, J=5.4,2H), 7.357 (d, J=4.36,2H), 5.261 (t, J=5.68,1H), 4.959 (t, J=
4.34,2H), 3.965 (q, J=4.88,2H)13C NMR(400MHz,DMSO-d6),δ(ppm):173.40,144.44,
142.06,138.38,137.87,129.23,127.81,127.27,,125.17,124.37,124.31,122.89,
121.31,116.72,114.68,113.62,107.11。
The synthesis of embodiment 2:2- [2- (1H- indol-3-yl) vinyl] -3- methylbenzothiazole salt compounded of iodine
(10mmol, 1.49g) 2- methylbenzothiazole and (20mmol, 2.84g) iodomethane are dissolved in 50ml toluene,
Stirring 4 hours, subsequent back flow reaction 30 minutes is cooled to room temperature, filtering, and ether washing obtains N- methyl -2- methyl benzo thiophene
Azoles salt compounded of iodine.(1mmol, 0.291g) N- methyl -2- methylbenzothiazole salt compounded of iodine and 0.145g (1mmol) 3- formyl indole is molten
In 20ml methanol, 3 drop piperidines, back flow reaction 6h are added dropwise, dehydrated alcohol washing obtains brown powder, yield 70%.
IMT-M:1H NMR (400MHZ): 12.497 (s, 1H), 8.466 (t, J=10.6,2H), 8.335 (d, J=8,
1H), 8.275 (t, J=4.42,1H), 8.149 (d, J=8.36,1H), 7.815 (t, J=7.72,1H), 7.712 (t, J=
7.64,1H), 7.595 (t, J=4.5,1H), 7.525 (d, J=15.76,1H), 7.525 (d, J=15.76,1H), 7.370-
7.324(m,2H),4.277(s,3H).13C NMR(400MHz,DMSO-d6),δ(ppm):172.45,144.73,142.41,
138.37,138.04,129.31,127.09,125.20,124.40,124.30,122.90,121.48,116.40,114.70,
113.62,106.22。
The synthesis of embodiment 3:2- [2- (1H- indol-3-yl) vinyl] -3- ethyl diethyldithiocarbamate ether benzothiazole bromide
(10mmol, 1.49g) 2- methylbenzothiazole and (20mmol, 6.75g) 2- bromoethyl ethylether are dissolved in
It in 50ml toluene, stirs 6 hours, subsequent back flow reaction 30 minutes is cooled to room temperature, filtering, and ether washing obtains N- ethyl second
Base ether -2- methylbenzothiazole bromide.By (1mmol, 0.617g) N- ethyl diethyldithiocarbamate ether -2- methylbenzothiazole bromide with
(1mmol, 0.145g) 3- formyl indole is dissolved in 20ml methanol, and 3 drop piperidines, back flow reaction 7h are added dropwise, and dehydrated alcohol is washed
It washs, obtains brown powder, yield 65%.
Measure of merit
(1) the bis- light of RNA of 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE)
Sub- fluorescence titration:
Fixed 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) is in Tris-HCl
Concentration in buffer solution (pH=7.2, Tris and KCl 100mmol/L), is gradually added into RNA, in 800 nm laser irradiation light
Under obtain 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) two-photon fluorescence titration
Spectrogram, as shown in Figure 2.The result shows that being continuously added with RNA, the two-photon fluorescence intensity of probe of the present invention was before this
It increased dramatically, then increase amplitude and slow down.This shows that probe of the invention has apparent fluorescence response to RNA.
(2) HeLa cell culture
HeLa cell strain adhere-wall culture is in the culture solution for including 10% (v/v) fetal calf serum and a small amount of penicillin/streptomycin
In, in 37 DEG C, 5%CO2(v/v) it is cultivated in saturated humidity incubator.Logarithmic phase is grown into cell, contact pin culture: by lid glass
Piece impregnates 30 minutes in chromic acid lotion, and clear water, ultrapure water are cleaned, and drying is put into disposable 35mm sterile petri dish after sterilizing
In；Culture medium in 100mL culture bottle is carefully poured out, cell is washed 2 times with PBS (phosphate buffer, pH=7.4), uses l
(mass fraction) trypsin solution of mL 0.25% digests 2~3 minutes, outwells trypsin solution, a small amount of fresh culture is added and blows
It beats uniformly at cell suspending liquid, after cell count, leaves the cell of proper density, culture medium is added into required volume and is blown and beaten
It is even, it then by cell inoculation into the culture dish for including coverslip, is put into incubator and cultivates, grow cell climbing sheet.24~
After 48h, cell density is grown to up to 50%~70%, it is to be dyed.
(3) 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) is to HeLa cell
Dyeing observation:
2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) is made into 1mM DMSO
Mother liquor is diluted to 5 μM with PBS (phosphate buffer, pH=7.4) when dyeing.Probe molecule by inoculated cell at 5 μM
In solution, it is incubated for 30min under the conditions of 37 DEG C, unbonded extra dye liquor is washed away with PBS, cell growth is covered in glass slide down
On；Then sample is placed in fluorescence imaging on objective table.As a result see that Fig. 3, two-photon fluorescence image are shown in cytoplasm and kernel
There is apparent fluorescence distribution in area, shows that probe of the invention can be in living cells in the imaging cells matter and kernel of specificity
RNA。
(4) 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzothiazole salt compounded of iodine (IE) probe is to HeLa
The dyeing of HeLa cell after cell, RNase digestion process is observed:
Fixed cell preparation: being soaked in 4% (mass fraction) paraformaldehyde solution 30 minutes for the HeLa cell of culture, or
Person fixes 15 minutes with -20 DEG C of methanol, then uses 0.5%Triton X-100 room temperature penetrating 2 minutes, it is thin to obtain fixation to be dyed
Born of the same parents.
Two groups of above-mentioned fixed cells are taken, 2- [2- (1H- indol-3-yl) vinyl] -3- (the 2- hydroxyl second for being 5 μM with concentration
Base) benzothiazole salt compounded of iodine (IE) probe solution is in CO2Hatching dyeing 30 minutes in incubator.2 are rinsed to two groups of cells with PBS
Time, one group of addition 25mg/mL DNase-Free RNase (GE) (ribalgilase) thereto, then two groups of cells 37 DEG C,
5%CO2Under the conditions of be incubated for 2 hours.Then, it is rinsed 2 times with PBS, is observed under wide-field microscope, records fluorescence in two groups of cells
Distribution and brightness change etc..
As a result see Fig. 4, the fluorescence of the HeLa cell without RNase digestion process is concentrated mainly on cytoplasm and nucleolar zone
Domain；And the fluorescence of the HeLa cell after RNase digestion process has focused on nuclear area, cytoplasm and kernel region base
This does not have fluorescence.Since RNase is only capable of hydrolyzing the RNA in cell, which can confirm probe energy of the invention
RNA in enough selective imaging cells.
(5) MTT cytotoxicity experiment
Logarithmic phase HeLa cell is collected, concentration of cell suspension is adjusted, 100ul is added in every hole, and bed board keeps cell tune to be measured close
It spends to the hole 1000-10000 (the sterile PBS of edge hole is filled).5%CO2, 37 DEG C of incubations, until cell monolayer is paved with bottom hole (96 holes
Flat underside) after start respectively 0,12,16,20, time of 22h 5 μM 2- [2- (1H- indol-3-yl) vinyl] -3- is added
(2- ethoxy) benzothiazole salt compounded of iodine (IE) fluorescence probe.To it is adherent for 24 hours when every hole be added 20ul MTT solution (5mg/ml, i.e.,
0.5%MTT), continue to cultivate 4h.If drug can be reacted with MTT, it can first be centrifuged and discard culture solution afterwards, carefully rush 2-3 with PBS
After, the culture solution containing MTT is added.Then, 150ul dimethyl sulfoxide then to every hole is added, sets low-speed oscillation on shaking table
10min dissolves crystal sufficiently.The light absorption value in each hole is measured at enzyme-linked immunosorbent assay instrument OD490nm.
As a result see Fig. 5, HeLa cell is in 5 μM of 2- [2- (1H- indol-3-yl) vinyl] -3- (2- ethoxy) benzo thiophene
Cell survival rate after azoles salt compounded of iodine (IE) incubation 2,4,8,12,24 hours, within dyeing 12 hours, the survival rate of HeLa cell
Also 90% or more, this shows that the RNA of cytoplasm and nucleolar zone in living cells can be imaged in two-photon fluorescence probe of the present invention.
It is that of the invention is discussed in detail in conjunction with specific embodiments above, the scope of protection of the present invention is not limited to this.
Claims (5)
1. a kind of two-photon RNA fluorescence probe, characterized in that it is 2- [2- (1H- indol-3-yl) vinyl] -3- (2- hydroxyl second
Base) benzothiazole salt compounded of iodine.
2. a kind of preparation method of two-photon RNA fluorescence probe described in claim 1, characterized in that by 2- methyl benzo thiophene
Azoles and ethylene iodohydrin are dissolved in toluene, are stirred 3-4 hours, subsequent back flow reaction 30-40 minutes, are cooled to room temperature, and are filtered, second
Ether washing, obtains N- ethyl alcohol -2- methylbenzothiazole salt compounded of iodine；By N- ethyl alcohol -2- methylbenzothiazole salt compounded of iodine and 3- formoxyl Yin
Diindyl is dissolved in methanol, and a few drop piperidines, back flow reaction 3-4h are added dropwise, and dehydrated alcohol washing obtains brown powder.
3. a kind of preparation method of two-photon RNA fluorescence probe according to claim 2, characterized in that 2- methyl benzo
The molar ratio of thiazole and ethylene iodohydrin is 1:1, and N- ethyl alcohol -2- methylbenzothiazole salt compounded of iodine and the molar ratio of 3- formyl indole are
1:1。
4. a kind of two-photon RNA fluorescence probe described in claim 1 is distributed in living cells in preparation label or display RNA
Application in fluorescence probe.
5. application according to claim 4, characterized in that the cell is HeLa cell.
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| CN111995621B (en) * | 2020-08-26 | 2022-09-13 | 广东工业大学 | Benzoindole derivative for G-quadruplex RNA fluorescent probe and preparation method and application thereof |
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| "Selenium Incorporated Cationic Organochalcogen: Live Cell Compatible and Highly Photostable Molecular Stain for Imaging and Localization of Intracellular DNA";Pankaj Gaur，et al.;《ACS Applied Materials & Interfaces》;20160412;第8卷;第10690-10699页以及Supporting Information * |
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