CN104792978A - Signal labeled molecule for DNA oxidative damage product 8-hydroxydeoxyguanosine and labeling method - Google Patents
Signal labeled molecule for DNA oxidative damage product 8-hydroxydeoxyguanosine and labeling method Download PDFInfo
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Abstract
The invention discloses a signal labeled molecule for specific detection of a DNA oxidative damage product 8-hydroxydeoxyguanosine and a labeling method. The signal labeled molecule at least contains two functional groups: one functional group can be connected to 8-hydroxydeoxyguanosine through a covalent bond; and the other functional group can generate a detection signal. The signal labeled molecule specifically reacts with 8-hydroxydeoxyguanosine in the presence of a certain concentration of an oxidizing agent so as to form covalent labeling. According to the signal generated by the labeled molecule, a corresponding detection method can be adopted. By measuring a signal such as an optical signal, an electric signal, an electrochemiluminescence signal or a photo-electrochemical signal and the like which is generated by the labeled molecule, quantitative detection of 8-hydroxydeoxyguanosine is detected. The labeled molecule finishes bonding and signal labeling of 8-hydroxydeoxyguanosine through a one-step reaction, and reaction conditions are mild. The signal labeled molecule has good specificity and high labeling rate, and is very suitable for quick and quantitative detection of 8-hydroxydeoxyguanosine.
Description
Technical field
The present invention relates to a kind of the signal labeled molecule and the labeling method that can be used for detecting DNA Oxidation Damage Products 8-OhdG.The method is simple to operate, and specificity is high, can be used for the quantitative test of 8-OhdG.
Background technology
8-OhdG (8-hydroxydeoxguanosine, 8-oxodG) is acknowledged as topmost DNA Oxidation Damage Products label.The generation of 8-OxodG is mainly from a large amount of levels of reactive oxygen species (reactive oxygen species, the ROS) attack to DNA deoxyguanosine C8 position that the processes such as chemical carcinogen metabolism activation or ionising radiation produce.Because 8-OhdG can not only with base A pairing, can also match with base C, therefore in the reproduction process of DNA, this damage usually causes the sudden change of G → T.If this damage fails to be repaired in time, mrna instability will be caused fixed, and then produce gene or genetoxic.At medical diagnostic field, in patient urine, the content of 8-OhdG is often by dangerous as the individual canceration of evaluation or diagnosis and free radical relevant disease biomarker.
The description and report that much detect about 8-OhdG has been had in scientific articles.What Floyd etc. proposed is separated after DNA enzymatic solution through high performance liquid chromatography (HPLC), then utilizing electrochemical detector (ECD) to detect 8-OhdG is that a kind of very effective quantitative detecting method is (see document: Floyd, RA.et al.Free Radic.Res.Commun.1986,1:163-172.).The advantages such as the method has highly sensitive, and sample requirement is little, and selectivity is good.But experimental implementation is loaded down with trivial details, and the result that the incomplete enzymolysis of DNA may cause detected value higher than actual value.When adopting Gc-ms method (GC-MS) to detect 8-OhdG, need to carry out derivatization to 8-OhdG in advance, and derivative reaction is easy to the generation causing accessory substance, cause false-positive result (Ravanat, JL.et al.Chem.Res.Toxicol.1995,8:1039-1045.).Monoclonal antibody and ELISA method are highly sensitive when detecting 8-OhdG, reproducible, but there is cross reaction, and the preparation of antibody is not easy (Osawa T.et al.Oxidative Stress and Aging.Birkhauser Verlag, Basel, Switzerland [C], 1995, pp367-374.).Research in recent years about small-molecule fluorescent probe detection 8-OhdG increases gradually.Fluorescence probe can not only detect the impaired base in complete double-strand, but also can detect in real time in living cells, therefore has larger application prospect.Sasaki etc. have synthesized a series of fluorescence probe that can be used for detecting 8-OhdG, this kind of probe can form multiple hydrogen bond with 8-OhdG, therefore there is very high affinity (Nakagawa, O.et al.Angew.Chem.Int.Ed.2008,47:8983-8983.).The discoveries such as Burrows, 8-OhdG can form a kind of quinones substance under the effect of oxygenant, and this material can be specific with spermine generation addition reaction (Hosford, M.E.et al.J.Am.Chem.Soc.2004,126:9540-9541.).Based on this principle, the Greenberg seminar of Johns Hopkins University has synthesized a kind of spermine-biotin (spermine-biotion, SB) chemical tags.Can be covalently bound with 8-OhdG under the condition that spermine part in this label is deposited at oxygenant, then the effect of enzyme mark Avidin and biotin is utilized, a kind of method establishing similar enzyme linked immunological fluorescence detects DNA Oxidation Damage Products (Xue, L.et al.J.Am.Chem.Soc.2007,129:7010-7011.).The method has very high specificity and sensitivity.Early-stage Study utilizes spermine biotin and ruthenium mark Avidin to carry out two step method specific marker to 8-OhdG, and the PhotoelectrochemicalMethod Method of structure can detect a 8-OhdG from 520 normal bases.In this detection, 8-OhdG on electrode first forms a kind of quinones substance under the effect of oxygenant, add spermine-biotin and biotin labeling is carried out to this quinones substance, add Streptavidin and the biotin specific binding of signaling molecule mark subsequently, completed by this two-step reaction and the signal of 8-OhdG is marked.The method is also used to researching DNA injury repair enzyme Fpg (formamidopyrimidine [the fapy]-DNA glycosylase) repair (Zhang to 8-OhdG, BT.et al.Anal.Chem.2013,84:6048-6053.).
Summary of the invention
The present invention mainly improves for the deficiency of prior art the following aspects:
1) existing chromatographic technique pretreatment process is complicated; 2) existing chromatographic technique requires high to large-scale instrument; 3) existing fluorescence and immunoassay technology specificity not ideal enough; 3) existing sensor technology needs two step method to mark, and operation is comparatively complicated.
For realizing the improvement to above aspect, the invention provides a kind of the signal labeled molecule and the labeling method that can be used for specific detection DNA Oxidation Damage Products 8-OhdG.Be exactly specifically synthesize a kind of signal labeled molecule, utilize its specific covalent marker DNA Oxidation Damage Products 8-OhdG, finally realize the quantitative detection to DNA Oxidation Damage Products 8-OhdG.Compare with fluorescence probe, the signal labeled molecule that this method provides can specific binding 8-OhdG, ensures the accuracy detected.Compare with labelled streptavidin two step method with the spermine-biotin in early stage, the signal labeled molecule that this method provides just can realize the mark to DNA Oxidation Damage Products 8-OhdG by single step reaction, simple to operate.
One aspect of the present invention provides a kind of signal labeled molecule, and this molecule is at least containing two functional groups, and one of them functional group can be connected by covalent bond with 8-OhdG, and another functional group can produce detection signal.
Second aspect of the present invention provides the synthetic method of described signal labeled molecule, and it comprises the following steps:
A () provides the functional group containing primary amine as the part covalently bound with 8-OhdG;
B () provides the organic or inorganic functional group that can produce detection signal;
C () is together covalently bound by chemical reaction by above-mentioned two kinds of functional groups, form signal labeled molecule, for detecting DNA Oxidation Damage Products 8-OhdG;
3rd aspect of the present invention provides a kind of quick, easy, effective electrochemical luminous detection method, except second aspect step of the present invention, also comprises the following steps:
D (), under oxide existent condition, the 8-OhdG in signal labeled molecule and DNA chain is covalently bound;
The electrochemical luminescence signals of (e) measuring-signal labeled molecule, the power according to signal carries out qualitative or quantitative test to sample;
Its representational operation steps is:
The synthesis of (a) signal labeled molecule and purifying;
(b) DNA fixing on surface;
C () signal labeled molecule is covalently bound with 8-OhdG in DNA specifically under oxygenant existent condition;
D signal that () measuring-signal labeled molecule provides, the power according to signal carries out qualitative or quantitative test to sample.
In one aspect of the invention, the signal labeled molecule that can be used for detecting DNA Oxidation Damage Products 8-OhdG provided, there is following feature: this molecule is at least containing two functional groups, one of them functional group can be connected by covalent bond with 8-OhdG, and another functional group can produce detection signal.Compare with other chemical probe, this signal labeled molecule just can be realized the connection of 8-OhdG and signal mark by single step reaction, and reaction conditions is gentle, and specificity is good, mark rate is high, be very applicable to 8-OhdG quick, quantitatively detect.Compare with other probe molecule, the synthesis of this signal labeled molecule is simple, is easy to obtained.
In another aspect of the present invention, the mark mode of described signal labeled molecule to DNA Oxidation Damage Products 8-OhdG is covalent labeling.
In another aspect of the present invention, oxygenant comprises the mineral compound that the potassium ferricyanide, six iridium sodium chlorides and hexabromo iridium acid sodium etc. has oxidation characteristic.
In one embodiment of the invention, DNA comprises the end modified strand or the double stranded polynucleotide that have sulfydryl.
The present invention mainly provides a kind of the signal labeled molecule and the labeling method that can be used for detecting DNA Oxidation Damage Products 8-OhdG, and this molecule just can be obtained by simple chemical reaction.Under oxygenant existent condition, this signal labeled molecule can complete the connection of DNA Oxidation Damage Products 8-OhdG and signal mark by single step reaction, and reaction conditions is gentle, specificity is good, and mark rate is high, be very applicable to 8-OhdG quick, quantitatively detect.The advantage utilizing method of the present invention to detect DNA Oxidation Damage Products 8-OhdG is: reaction one step between (1) signal labeled molecule and DNA Oxidation Damage Products 8-OhdG mark completes, simple to operate, quick; (2) signal labeled molecule and 8-OhdG covalently bound, specificity is very good; (3) low to the requirement of reaction conditions when signal labeled molecule and DNA damage product 8-OhdG react, mark rate is high, is easy to operation; (4) signal labeled molecule not only can 8-OhdG in covalent labeling double-stranded DNA also can 8-OhdG in labeled ssdna; (5) signal labeled molecule preparation method is simple, and experimental cost is low; (6) signal labeled molecule good stability, now joins before using, and can extend the shelf-life of reagent.
More specifically, the invention provides the following:
1. the signal tagged compound detected for DNA Oxidation Damage Products 8-OhdG, it is characterized in that containing two functional group A and B, wherein said functional group A can be connected by covalent bond with the 8-OhdG in DNA, and described functional group B can produce detection signal.
2. the signal tagged compound according to 1, wherein said functional group A is the organo-functional group of band primary amine.
3. the signal tagged compound according to 1, wherein said functional group A is spermine.
4. the signal tagged compound according to 1, wherein said functional group B is the inorganic or organic group that can produce optics, galvanochemistry, electrochemiluminescence, Optical Electro-Chemistry detection signal.
5. the signal tagged compound according to 1, wherein said functional group B is tris (bipyridine) ruthenium or derivatives thereof.
6. the Oxidation Damage Products 8-OhdG in DNA sample is carried out to a method for specific signals mark, signal tagged compound wherein used is the signal tagged compound according to any one of 1-5.
7. the method according to 6, described method comprises the following steps successively:
(1) by described DNA sample and oxidant reaction;
(2) by with described oxidant reaction after described DNA sample and described signal tagged compound react.
8. the method according to 7, wherein said oxygenant is the potassium ferricyanide, six iridium sodium chlorides or hexabromo iridium acid sodium.
9. the method according to 7, the concentration of wherein said oxygenant is 0.5mM-7mM.
Accompanying drawing explanation
Fig. 1 is the schematic diagram of the signal labeled molecule for specific detection DNA Oxidation Damage Products 8-OhdG.
Fig. 2 is the molecular formula of signal labeled molecule according to an embodiment of the invention.
Fig. 3 is the result utilizing signal labeled molecule according to an embodiment of the invention to detect DNA Oxidation Damage Products 8-OhdG.
Embodiment
Describe the present invention below in conjunction with specific embodiment, but should be appreciated that and the invention is not restricted to following examples.
The synthesis of embodiment 1, signal labeled molecule
1, get a 50ml two mouthfuls of round-bottomed flasks, wherein add the protection of nitrogen ball flatly, in two-mouth bottle, add the two pyridine 1.28g of 4-methyl-4'-(3-hydroxypropyl)-2,2'-, DCC1.545g, NHS0.575g, DMF15ml, at room temperature stir 5h.
2, separately get a 50ml two mouthfuls of round-bottomed flasks, wherein add nitrogen protection flatly, another mouth adds 50ml constant pressure funnel, spermine (diaminopropyl tetra-methylenedimine) 10.1g is added in bottle, DMF10ml, step one reaction is terminated rear gained reactant liquor proceed under nitrogen protection in constant pressure funnel, slowly be added drop-wise to vigorous stirring in reaction bulb, dropping terminates rear continuation reaction 1h, decompression removing DMF, 2M hydrochloric acid is added in residue, methylene chloride, separatory, saturated sodium bicarbonate washes twice, saturated sodium-chloride washes twice, namely removal of solvent under reduced pressure obtains crude product, crude product (compound 1) does not need to be further purified and can carry out the next step.
3, successively compound 1 is added at the 50ml two-mouth bottle that condenser pipe is housed, cis-dichloro two (2, 2 '-dipyridine) ruthenium dihydrate, water 10ml, methyl alcohol 15ml, add hot reflux 6h, after reaction terminates, removal of solvent under reduced pressure, then in residue, water 20ml is added, cross and filter excessive cis-dichloro two (2, 2 '-dipyridine) ruthenium dihydrate, obtain glassy yellow aqueous solution, add saturated hexafluorophosphoric acid sodium water solution wherein, obtain yellow mercury oxide and product, add ether sedimentation after dissolving with hot acetone and obtain pure products, this product is required signal labeled molecule, its molecular formula as shown in Figure 2.
Embodiment 2, gold electrode surfaces DNA incubation time are optimized
By in the end modified damping fluid having the DNA of sulfydryl to be dissolved in containing fresh TCEP-Tris, get 4 μ l and be added drop-wise to the gold electrode surfaces handled well, cover electrode cap, hatch 8h, 16h and 40h respectively.Spend deionized water after end, nitrogen dries up, and infiltrate in the sulfydryl hexanol of 200ul and hatch a period of time, deionization is cleaned nitrogen and dried up.First by the electrode modified, the Tris solution be placed in containing 3.5 μMs of RuHex sweeps CV, sweeps speed for 50mV/s.Then clear water is cleaned the Tris solution be placed in containing 50 μMs of RuHex and is swept CV, sweeps speed for 50mV/s.Relatively different time hatches lower CV figure, finds that the DNA of hatching electrode surface through 40h assembles saturated, more stable.
Embodiment 3, gold electrode surfaces DNA concentration optimization
Select that 0.1,0.5,1,2,5 μM of five variable concentrations are end modified has the DNA solution of sulfydryl to be added drop-wise to gold electrode surfaces, incubated at room respectively.Deionized water is cleaned, and nitrogen dries up, and infiltrate in sulfydryl hexanol and hatch a period of time, deionization is cleaned nitrogen and dried up.By the electrode modified, the Tris solution be placed in containing 50 μMs of RuHex sweeps CV, sweeps speed for 50mV/s.Relatively the CV figure of variable concentrations DNA, reaches capacity when the sample concentration of discovery DNA is 2 μMs.
Embodiment 4, build electrochemiluminescence reaction system
By the oligonucleotide of TAKARA company synthesis containing a 8-OhdG, sequence is as follows: 5 '-GGACTG/8-oxodGuo/GAGGAGATGGGGGAGGAG-3 ' (A chain); By following two oligonucleotides of Sangon Biotech's synthesis, sequence is respectively: 5 '-GGACTGGGAGGAGATGGGGGAGGAG-3 ' (B chain), 5 '-CTCCTCCCCCATCTCCTCCCAGTCC-C6-SH-3 ' (C chain).A chain, B chain are hybridized with C chain respectively, forms Duplex1 and Duplex2.According to the condition optimized, get the Duplex that 4ul concentration is 2uM, be added drop-wise to gold electrode surfaces, keep certain humidity, incubated at room 48h.Cleaned by electrode deionized water, nitrogen dries up, and is statically placed in the sulfydryl hexanol aqueous solution of 10mM and closes 2h.Deionized water is cleaned, and nitrogen dries up, and drips the signal labeled molecule of preparation in embodiment 1, and room temperature leaves standstill reaction 30min, and then drip the chlordene iridium acid sodium aqueous solution that 1ul concentration is 0.6mM, mixing, room temperature leaves standstill reaction.After terminating, deionized water is cleaned, and carries out electrochemiluminescence detection.
Embodiment 5, electrochemiluminescence detect
Electrochemiluminescence detects and carries out in tripropyl amine (TPA) solution.Electrochemical appliance adopts three-electrode system: gold electrode is working electrode, and Ag/AgCl electrode is contrast electrode (3M KCl), and platinized platinum is auxiliary electrode.Photomultiplier is just to below gold electrode.Electrochemical luminescence signals is converted into electric signal, exports with voltage system.Can be seen by Fig. 3, the signal labeled molecule of embodiment can react with the DNA Oxidation Damage Products 8-OhdG be assembled in gold electrode surfaces Duplex1 under oxygenant six iridium sodium chloride existent condition, produces the electrochemical luminescence signals risen; Contrast because assembled Duplex2 is not containing 8-OhdG, so oxygenates six iridium sodium chloride group is substantially the same with the signal of the group that adds water.These results show that the signal labeled molecule of the embodiment that we synthesize can by single step reaction specific covalent marker DNA Oxidation Damage Products 8-OhdG under oxide six iridium sodium chloride existent condition.
Claims (9)
1. the signal tagged compound detected for DNA Oxidation Damage Products 8-OhdG, it is characterized in that containing two functional group A and B, wherein said functional group A can be connected by covalent bond with the 8-OhdG in DNA, and described functional group B can produce detection signal.
2. signal tagged compound according to claim 1, wherein said functional group A is the organo-functional group of band primary amine.
3. signal tagged compound according to claim 1, wherein said functional group A is spermine.
4. signal tagged compound according to claim 1, wherein said functional group B is the inorganic or organic group that can produce optics, galvanochemistry, electrochemiluminescence, Optical Electro-Chemistry detection signal.
5. signal tagged compound according to claim 1, wherein said functional group B is tris (bipyridine) ruthenium or derivatives thereof.
6. the Oxidation Damage Products 8-OhdG in DNA sample is carried out to a method for specific signals mark, signal tagged compound wherein used is the signal tagged compound according to any one of claim 1-5.
7. method according to claim 6, described method comprises the following steps successively:
(1) by described DNA sample and oxidant reaction; And
(2) by with described oxidant reaction after described DNA sample and described signal tagged compound react.
8. method according to claim 7, wherein said oxygenant is the potassium ferricyanide, six iridium sodium chlorides or hexabromo iridium acid sodium.
9. method according to claim 7, the concentration of wherein said oxygenant is 0.5mM-7mM.
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| CN106222266A (en) * | 2016-07-29 | 2016-12-14 | 中国科学院生态环境研究中心 | A kind of method detecting nucleic acid base disappearance and dedicated kit thereof |
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| CN106222266A (en) * | 2016-07-29 | 2016-12-14 | 中国科学院生态环境研究中心 | A kind of method detecting nucleic acid base disappearance and dedicated kit thereof |
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Application publication date: 20150722 |