CN103234948A - Application of pyrene and derivative as photosensitive perssad deprotection sensibilization reagent in biological chip production - Google Patents
Application of pyrene and derivative as photosensitive perssad deprotection sensibilization reagent in biological chip production Download PDFInfo
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- CN103234948A CN103234948A CN2013101685923A CN201310168592A CN103234948A CN 103234948 A CN103234948 A CN 103234948A CN 2013101685923 A CN2013101685923 A CN 2013101685923A CN 201310168592 A CN201310168592 A CN 201310168592A CN 103234948 A CN103234948 A CN 103234948A
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Abstract
The invention discloses an application of pyrene and derivative as a photosensitive perssad deprotection sensibilization reagent in biological chip production. The application is characterized in that fluorescence is utilized for strengthening again, three times of deprotection (original ultraviolet light in the first time, energy transfer in the second time, and generated fluorescence in the third time) of a photosensitive perssad is realized, and the deprotection rate of the photosensitive perssad is accelerated. Meanwhile, the fluorescigenic property of a fluorescent compound is also utilized, a destructive effect of a splitting free radical caused by a common photosensitive reagent (as ITX series) is effectively avoided, and the photosensitive perssad deprotection quality is improved.
Description
Technical field
The invention belongs to the biochip technology field, be specifically related to the application as photosensitive group deprotection enhanced sensitivity reagent in the biochip preparation of pyrene and derivant thereof.
Background technology
Due to the application of photosensitive group, the development of biochip original position synthetic technology is quicker.With some specific chemical group of photosensitive radical protection, under the radiation of special wavelength light, when absorbing enough energy, photosensitive group will disconnect with protected reactive group, and this process is called the light deprotection reaction.That is to say, can will expose as the controlled condition of deprotection, some protected group by light area at regular time and quantity carries out deprotection.This technology be widely used in photoconduction to original position synthetic in, by people such as Fodor, adopt photoetching process to synthesize the polypeptide of 5 amino acid lengths the earliest, also be widely used in protein-chip simultaneously, in genetic chip etc. synthetic.The height of the light deprotection efficiency of photosensitive group is to determine one of synthetic whether successful factor of photoetching process.Synthetic with the DNA chip, in the process of the light deprotection repeated and coupling, the time of leaving away of photosensitive group must be moderate, otherwise the DNA probe of synthetic tens base length needs tens hours even several days.How to improve the light receiving efficiency of ultraviolet sensitivity group, particularly in the situation that the raising of the lower light remove-insurance of light intensity efficiency has become a more and more important problem.
In order to improve the efficiency of leaving away of photosensitive group, people have carried out many research work.After photosensitive group and light intensity are determined; select suitable exposure environment to become the determinative of photosensitive group deprotection efficiency; most of lithography experiments are all carried out in solution; in order to improve to greatest extent the photosensitivity of photosensitive group, add photosensitizer and just become one of selection in solvent.Such as Woll, the people such as D propose to adopt triplet state photosensitizer 2-isopropyl thioxanthone (ITX) to serve as the enhanced sensitivity reagent of the synthetic middle photosensitive group deprotection of DNA chip, under oxygen-free environment, have effectively improved the speed of light deprotection.However, current research is not reaching gratifying degree in application widely.
In the process with photoetching process original position synthetic peptide nucleic acid (PNA) chip, find: if add ITX series photosensitizer in the exposure solvent, exposure process will bring a lot of negative effects, even destroy all amino reactive groups, this may be that to have a destructive free radical caused owing to producing after ITX series sensitiser absorption light.Therefore, the negative effect of bringing for overcoming the cracking type photosensitizer, need to find the novel photosensitive agent of a kind of energy for biochip original position synthesis technique.
Some derivant of pyrene and pyrene is the conjugated aromatic compound that a class has fluorescent characteristic, has higher quantum efficiency and can send the fluorescence close with excitation wavelength in lean solution.But such examination material is only used as fluorescent labeling reagent, photopolymerization reagent for a long time, or is applied to the organic optoelectronic field, the report using pyrene and derivant thereof as the application in the biochip preparation of photosensitive group deprotection enhanced sensitivity reagent more not.
Summary of the invention
The present invention is intended to overcome the deficiencies in the prior art and prejudice, and a kind of pyrene and derivant thereof the new purposes as photosensitive group deprotection enhanced sensitivity reagent in the biochip preparation is provided.
In order to achieve the above object, technical scheme provided by the invention is:
Pyrene and derivant thereof are as the application of photosensitive group deprotection enhanced sensitivity reagent in the biochip preparation.
Wherein, the concentration of described pyrene and derivant thereof is 0.08-0.12M, is preferably 0.1M.
Described pyrene derivatives is pyrene methyl alcohol, N-pyrene methylacetamide, Isosorbide-5-Nitrae-bis-pyrene benzene, 1-ethinyl pyrene, 1,3,6 ,-tri-(trimethyl silicane) pyrene etc.
Described biochip is the peptide nucleic acid biochip.
The preparation of described biochip be adopt photoconduction to in-situ synthesis prepare the peptide nucleic acid biochip.
When preparing the peptide nucleic acid biochip, described in-situ synthesis adopts 10-13mW/cm
2, 365nm ultraviolet light, be preferably 12mW/cm
2, 365nm ultraviolet light.
Below in conjunction with principle, the invention will be further described:
The present invention when utilizing in-situ synthesis to prepare the peptide nucleic acid biochip, adopt pyrene and derivant thereof as quick reagent once to accelerate the deprotection speed of photosensitive group.
ITX series photosensitizer is mainly used in the deprotection of the hydroxyl of photosensitive group protection, play reasonable effect in DNA is synthetic, and the synthetic middle ultraviolet light adopted of report polypeptide before is more intense, reaches the 35mW left and right, does not need to use photosensitive reagents.The present inventor is connected on amino at synthetic PNA(photosensitive group) time used weak ultraviolet light (10-13mW/cm
2, 365nm ultraviolet light), therefore, consider and will use photosensitive Contrast agent, found that the subsidiary reaction of ITX series is a lot.The energy meeting cracking ITX do not passed after ITX series photosensitizer is subject to exciting, produce free radical, thereby destroy reaction system; And pyrene and derivant thereof discharge unnecessary energy with the fluorescence form, thereby the negative effect of avoiding, the exciting light and the radiative wavelength that are more unexpectedly this class material differ very little, the wave band that namely both can respond at photosensitive group, like this just be equivalent to light the ultraviolet sensitivity group has been contacted to (being once original ultraviolet light, is exactly once the fluorescence produced in addition) twice.
Photosensitive group is subject to the ultraviolet radiation of certain wavelength, and when photon energy is enough, photosensitive group just will disconnect with protected reactive group, thereby realize deprotection.But in the situation that light intensity is certain or lower, want to accelerate the speed of light deprotection, just must accelerate the absorption efficiency of photosensitive group energy.Under solvent environment, the photosensitizer pyrene, under a certain wave band irradiates, is excited to triplet state, by the collision with photosensitive group, thereby triplet energy state is passed to photosensitive group, accelerates the light deprotection.Electronics in triplet state finally all can consume the ability of oneself due to thermalizing collision usually, thereby not luminous.Yet, fluorescent characteristic due to pyrene, can not only be excited to triplet state, and can be excited to singlet and send fluorescence, this is that after being excited to singlet because of electronics,, through vibration relaxation and interior shifting, electronics arrives the lowermost layer (V=0) of the singlet (S1) be excited, then the form with radiation transits to ground state (S0), sends fluorescence.Wavelength of fluorescence and excitation wavelength are very approaching; can again be absorbed by photosensitive group; that is to say under the acting in conjunction of radiation ultraviolet light and photosensitizer singlet and triplet energy state; increase the absorption of photosensitive group energy; the effect that reaches three deprotections (is original ultraviolet light for the first time; being the energy transmission for the second time, is the fluorescence produced for the third time), and then the deprotection speed of raising photosensitive group.
Not only pyrene has fluorescent characteristic; the derivant of pyrene also has similar character; as N-pyrene methylacetamide; use it for the deprotection of photosensitive group; improve significantly light deprotection speed; simultaneously because the fluorescence that N-pyrene methylacetamide produces is close with the photosensitive group excitation wavelength and fluorescence intensity a little more than pyrene (as shown in Figure 3), more be conducive to the deprotection of photosensitive group.
Disclosed by the invention is the purposes of the derivant of the fluorescigenic compound pyrene of energy and pyrene as the enhanced sensitivity reagent of photosensitive group deprotection; utilize the enhancing again of fluorescence; realized that three deprotections to photosensitive group (are original ultraviolet lights for the first time; the energy transmission for the second time; the fluorescence produced for the third time), accelerated the deprotection speed of photosensitive group.Simultaneously, also because utilize the fluorescigenic performance of fluorescent chemicals, the destruction of the cracking free radical of effectively avoiding general photosensitive reagents (as ITX series) to cause, the quality (as shown in Figure 2) of raising photosensitive group deprotection.
In a word, the present invention proposes to utilize the fluorescence of fluorescence photosensitizer to accelerate the photosensitive group deprotection first, has produced beyond thought effect.Pyrene and derivant thereof are used for to photosensitive group deprotection link, and such reagent can absorb the ultraviolet light of certain wavelength on the one hand, and energy is passed to photosensitive group; Be subject on the other hand certain ultraviolet excitation can produce the fluorescence close with this ultraviolet wavelength; this fluorescence can provide re-expose to photosensitive group; accelerate the speed of photosensitive group deprotection, what overcome that general photosensitive reagents brings produces the negative effect of free radical etc. because of the sensitization cracking simultaneously.
The accompanying drawing explanation
Fig. 1 is that pyrene serves as the synthetic middle photosensitive group exposure efficiency contrast experiment scanning result figure of photosensitizer acceleration peptide nucleic acid chip;
Fig. 2 is that pyrene and ITX serve as the synthetic middle photosensitive group exposure efficiency contrast experiment scanning result figure of photosensitizer acceleration peptide nucleic acid chip;
Fig. 3 is 10
-5the dioxane solution fluorescence spectrum of the pyrene of M concentration and N-pyrene methylacetamide and ITX;
The derivant N-pyrene methylacetamide exposure link contrast experiment scanning result figure of Fig. 4 pyrene and pyrene.
embodiment:
embodiment 1
pyrene serves as photosensitizer and accelerates the experiment of the synthetic middle exposure link of peptide nucleic acid chip
Adopt photoconduction to original position synthetic peptide nucleic acid chip; the process of wherein photosensitive group being carried out to deprotection is synthetic key link; as want synthetic peptide nucleic acid chip probe to be generally 13-17 base length; need to carry out 13-17 exposure; new base in coupling again after each exposure; that is to say, the efficiency of exposure finally directly affects the combined coefficient of whole peptide nucleic acid chain.In this experiment, light intensity is 12mW/cm
2the ultraviolet light of 365nm, the monomer photosensitive group utilized in synthetic is 2-(2-nitrobenzene) the third oxygen carbonyl (NPPOC), sensitization for the proof pyrene, to be modified with the slide of amino of NPPOC protection at different solvents (1, 4-dioxane and pyrene) carry out exposure experiments under the same time gradient in environment (, photosensitive group deprotection process), use the 1-METHYLPYRROLIDONE solution-treated 30 minutes of the rhodamine isothiocyanates of 1mM after exposure, then use respectively 1-METHYLPYRROLIDONE, methyl alcohol, methylene chloride, containing supersound washing in the aqueous solution of 0.3% tween 5 minutes, then use the distilled water rinsing, nitrogen dries up, fluorescence signal is detected and is analyzed by Genepix Pro 4000B scanner.The exposure result that to carry out in organic solvent Isosorbide-5-Nitrae-dioxane (Dixoane) is contrasted with the result in the dixoane solution that adds the 0.1M pyrene, and scanning result as shown in Figure 1.
Under the irradiation of 365nm ultraviolet light; in dioxane, expose; about 10 minutes, saturated phenomenon has appearred; but integral fluorescence low strength; visible in the situation that only use the dioxane solvent, photosensitive group might not realize that leaving away of hundred-percent deprotection or photosensitive group balance occurs to the amino destruction produced too early with exposing in reacting.In the dioxane solution that has added the photosensitizer pyrene, in the time of 17 minutes, occur saturated; but overall signal intensity all is better than in dioxane and exposes; also just say in the situation that light intensity is not strong, add appropriate pyrene and can make the area to be illuminated territory realize deprotection to the full extent.This is the committed step of synthesising biological chip, on the basis of exposure fully, carries out coupling and exposes and can guarantee the accuracy rate that biochip is synthetic again.This embodiment illustrates that the photosensitizer pyrene has really played the effect that improves light deprotection efficiency in the exposure solvent
.
embodiment 2
photosensitizerthe 2-isopropyl thioxanthone
(ITX) with pyrene exposure contrast experiment in peptide nucleic acid (PNA) chip is synthetic
The hydroxyl that photosensitizer ITX accelerates the photosensitive group protection in the synthetic DNA chip plays certain effect, and the spy is exposed photosensitizer ITX and photosensitizer pyrene to experiment in peptide nucleic acid (PNA) is synthetic thus.In this experiment, light intensity is 12mW/cm
2the ultraviolet light of 365nm, the monomer photosensitive group utilized in synthetic is 2-(2-nitrobenzene) the third oxygen carbonyl (NPPOC), (the slide that is modified with the amino of NPPOC protection is carried out to exposure experiments under the same time gradient in different solvents (photosensitizer ITX and pyrene) environment, photosensitive group deprotection process), use the 1-METHYLPYRROLIDONE solution-treated 30 minutes of the rhodamine isothiocyanates of 1mM after exposure, then use respectively 1-METHYLPYRROLIDONE, methyl alcohol, methylene chloride, containing supersound washing in the aqueous solution of 0.3% tween 5 minutes, then use the distilled water rinsing, nitrogen dries up, fluorescence signal is detected and is analyzed by Genepix Pro 4000B scanner.0.1M the experimental result of the DMF solution of photosensitizer ITX exposure and the DMF solution of 0.1M photosensitizer pyrene carry out check analysis, scanning result as shown in Figure 2.
ITX makees photosensitizer, exposure is just not high from starting overall signal intensity, and along with the increase of time shutter, fluorescence intensity continues lower, and the scanning intensity lower than background appears, and this will be attributed to after ITX is subject to ultraviolet lighting in the exposure solvent, and energy is not all transferred on photosensitive group, self cracking produces free radical, and the effects on surface arm molecule has suffered destruction to a certain degree; Pyrene is made enhanced sensitivity reagent, within the time shutter of 20 minutes, exposure signal intensity time gradient rises, and the state that reaches capacity about 15 minutes, after this will give the credit to one side pyrene absorption ultraviolet light, carry out energy and shift sensitization, uv energy is directly passed to photosensitive group, in addition on the one hand, pyrene is after being subject to ultraviolet excitation, send the fluorescence very close with exciting ultraviolet wavelength, and all close with the photosensitive group sensitive wave length, photosensitive group is carried out to re-expose.The derivant of the pyrene shown in Fig. 3 and pyrene and the fluorescence Spectra of ITX can be found out; ITX does not almost have fluorescence; this proof pyrene the short light deprotection of same photosensitizer ITX relatively in have superiority, the destruction of the cracking free radical that its fluorescent characteristic can effectively avoid energy accumulation to cause.
embodiment 3
the derivant N-pyrene methylacetamide of pyrene and pyrene exposure contrast experiment
(a) N-pyrene methylacetamide is synthetic: the synthetic first step is the formylation of pyrene, and in room temperature, pyrene joins in the potpourri of three filter oxygen phosphorus and N-methyl formyl aniline, and solution is heated to 100 ℃, and nitrogen protection obtains the 1-pyrene formaldehyde; Second step is that 1-pyrene formaldehyde and oxammonium hydrochloride effect generate 1-pyrene formaldehyde oxime intermediate; The 3rd step is under the formic acid condition, obtain 1-pyrene methyl amine with zinc powder reduction 1-pyrene first oxime: the 4th step is carried out polycondensation reaction amino and carboxyl, and reactants dissolved is in glacial acetic acid, with acetic anhydride, reflux, obtain final product N-(1-pyrene methyl) acetamide.
(b) derivant of pyrene and pyrene is all the class material with fluorescent characteristic, connects corresponding group on the structure of pyrene, even has the fluorescent characteristic stronger than pyrene.In the present embodiment, contrast NPPOC protects amino exposure experiments to carry out Contrast on effect.In this experiment, light intensity is 12mW/cm
2the ultraviolet light of 365nm, the monomer photosensitive group utilized in synthetic is 2-(2-nitrobenzene) the third oxygen carbonyl (NPPOC), (the slide that is modified with the amino of NPPOC protection is carried out to exposure experiments under the same time gradient in different solvents (pyrene and pyrene methylacetamide) environment, photosensitive group deprotection process), use the 1-METHYLPYRROLIDONE solution-treated 30 minutes of the rhodamine isothiocyanates of 1mM after exposure, then use respectively 1-METHYLPYRROLIDONE, methyl alcohol, methylene chloride, containing supersound washing in the aqueous solution of 0.3% tween 5 minutes, then use the distilled water rinsing, nitrogen dries up, fluorescence signal is detected and is analyzed by Genepix Pro 4000B scanner.Carry out the experiment of light deprotection respectively in the DMF solution of DMF (DMF) solution of 0.1M pyrene and 0.1M N-pyrene methylacetamide, scanning result figure as shown in Figure 4.Can find out, be better than containing the result in the solvent of pyrene containing exposing in the solvent of pyrene acetamide, show as the increase of integral fluorescence intensity and shifting to an earlier date of saturation time.This embodiment can prove, the derivant of pyrene has equally or the effect of enhanced sensitivity that better exposes.
Claims (8)
1. pyrene and derivant thereof are as the application of photosensitive group deprotection enhanced sensitivity reagent in the biochip preparation.
2. application as claimed in claim 1, is characterized in that, the concentration of described pyrene and derivant thereof is 0.08-0.12M.
3. application as claimed in claim 2, is characterized in that, the concentration of described pyrene and derivant thereof is 0.1M.
4. application as claimed in claim 1, is characterized in that, described pyrene derivatives is pyrene methyl alcohol, N-pyrene methylacetamide, Isosorbide-5-Nitrae-bis-pyrene benzene, 1-ethinyl pyrene or 1,3,6 ,-tri-(trimethyl silicane) pyrene.
5. application as described as claim 1 to 4 any one, is characterized in that, described biochip is the peptide nucleic acid biochip.
6. application as claimed in claim 5, is characterized in that, the preparation of described biochip be adopt photoconduction to in-situ synthesis prepare the peptide nucleic acid biochip.
7. application as claimed in claim 6, is characterized in that, adopts 10-13mW/cm when described in-situ synthesis prepares the peptide nucleic acid biochip
2, 365nm ultraviolet light.
8. application as claimed in claim 7, is characterized in that, adopts 12mW/cm when described in-situ synthesis prepares the peptide nucleic acid biochip
2, 365nm ultraviolet light.
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Cited By (2)
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| CN108117587A (en) * | 2017-12-29 | 2018-06-05 | 中南大学 | Photosensitive peptide nucleic acid monomer and its synthetic method |
| JP2021522806A (en) * | 2018-05-09 | 2021-09-02 | ヴィブラント ホールディングス リミテッド ライアビリティ カンパニー | A method of synthesizing a polynucleotide array using a photoactivated agent |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108117587A (en) * | 2017-12-29 | 2018-06-05 | 中南大学 | Photosensitive peptide nucleic acid monomer and its synthetic method |
| CN108117587B (en) * | 2017-12-29 | 2021-08-10 | 中南大学 | Photosensitive peptide nucleic acid monomer and synthesis method thereof |
| JP2021522806A (en) * | 2018-05-09 | 2021-09-02 | ヴィブラント ホールディングス リミテッド ライアビリティ カンパニー | A method of synthesizing a polynucleotide array using a photoactivated agent |
| JP7422087B2 (en) | 2018-05-09 | 2024-01-25 | ヴィブラント ホールディングス リミテッド ライアビリティ カンパニー | Methods for synthesizing polynucleotide arrays using photoactivated agents |
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