CN105823764B - Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound and its preparation method and application - Google Patents
Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound and its preparation method and application Download PDFInfo
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Abstract
The present invention relates to a kind of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound and its preparation method and application, which is keyed by amide with cup [4] aromatic hydrocarbons adenine derivative by graphene oxide and is formed；Preparation method includes: that graphene oxide is carried out chloride by (1)；(2) excessive cup [4] aromatic hydrocarbons adenine derivative is dissolved with organic solvent, it is added under the graphene oxide powder room temperature of chloride and stirs 6~96h, obtain black particle suspension, centrifuge separation, with saturated common salt water washing, distilled water is then added and is centrifuged, dries, obtain black powder, as cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound；The compound can be applied in terms of the identification of tetra- serobila of oncogene promoter region G-, combination or stabilization.Compared with prior art, preparation is simple by the present invention, can provide the new selection scheme detected by biological macrocycle molecule for tetra- serobila of G-.
Description
Technical field
The present invention relates to a kind of Calixarene Derivatives composite materials, derivative more particularly, to a kind of cup [4] aromatic hydrocarbons adenine
Object-graphene oxide composite material and its preparation method and application.
Background technique
With the development of the society, huge variation, global warming, ozone layer has occurred in the living environment of mankind nowadays
The various pollution problems such as cavity, bio-diversity reduction, acid rain sprawling, sharp reduction of the forests and desertification of land, it is following each
Kind disease increases, and cancer is to seriously endanger one of the principal disease of human health.Various anticancer drugs increase therewith, therefore seek
Low toxicity, the efficient, anticancer drug with anticancer activity are mankind nowadays urgent problems to be solved.
Promoter is that one section of important genetic region is being lost positioned at the section of DNA sequence of gene 5 ' end upstream regulatory region
It passes and refers to one section of DNA sequence dna that gene can be made to be transcribed on learning.Promoter can determine the expression of gene, that is, can determine that
Which proteinoid cell produces.If promoter region gene makes a variation, the expression that gene controls will be seriously affected, it is this
Variation is common in malignant tumour.Therefore inhibiting the research of the expression of oncogene becomes anticancer drug action method.In document
Report various metal complexs largely to detect tetra- serobila of oncogene promoter G-, but with this stereochemical structure of calixarenes
Macrocyclic compound is not reported also to detect the article of tetra- serobila of G-.
Summary of the invention
It is an object of the present invention to overcome the above-mentioned drawbacks of the prior art and provide a kind of oncogene promoters
G- tetra- serobila in area has cup [4] aromatic hydrocarbons adenine derivative-graphene oxide of recognition reaction, combination and stabilization multiple
Condensation material, preparation is simple for the compound, provides the new selection detected by biological macrocycle molecule for tetra- serobila of G-
Scheme.
The purpose of the present invention can be achieved through the following technical solutions:
A kind of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound, the compound is by graphene oxide and cup
[4] aromatic hydrocarbons adenine derivative is keyed to be formed by amide.
Preferably, which passes through amido bond by the graphene oxide and cup [4] aromatic hydrocarbons adenine derivative of chloride
Connection is formed.
The amido bond by aromatic hydrocarbons adenine derivative-NH2- C (O) Cl base of base and the graphene oxide of chloride
Amidation process occurs to be formed.
The chemical formula of described cup [4] the aromatic hydrocarbons adenine derivative is C55H70O4N5Br, structural formula are as follows:
Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound preparation method, comprising the following steps:
(1) graphene oxide is subjected to chloride, obtains the graphene oxide powder of chloride；
(2) excessive cup [4] aromatic hydrocarbons adenine derivative is dissolved with organic solvent, the graphene oxide powder of chloride is added
6~96h is stirred under last room temperature, obtains black particle suspension, is centrifugated, with saturated common salt water washing, is then dried, obtain
Black powder, as cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound.
Organic solvent in step (2) is DMF.
Preferably, the stirring at normal temperature time in step (2) is 36h.
It is added distilled water to pH=7 with saturated common salt water washing in step (2) and is centrifuged, so that chloride
Graphene oxide powder surface it is clean.
Cup [4] the aromatic hydrocarbons adenine derivative being added in step (2) should be excessive, so that cup [4] aromatic hydrocarbons adenine is derivative
Object is connected on graphene oxide as far as possible, because when calixarenes amount is few, cup [4] aromatic hydrocarbons adenine for being connect on graphene oxide
Comparatively derivative will lack, cannot play collaboration of the two in terms of the identification of tetra- serobila of G-, combination or stabilization well
Effect.
Step adds graphene oxide into the mixed solution of chlorinating agent and auxiliary agent in (1), ultrasonic by graphene oxide powder
It is broken and be uniformly dispersed, 12~96h is reacted under the conditions of 60~80 DEG C and carries out chloride, is centrifuged repeatedly washing with tetrahydrofuran, it is cold
Freeze the graphene oxide powder for being dried to obtain chloride.
Preferably, the acyl chloride reaction in step (1) reacts 48h under the conditions of 70 DEG C.
Chlorinating agent described in step (1) is thionyl chloride, and the auxiliary agent is DMF.
DMF in step (1) as auxiliary agent plays the role of catalyst and solubilizer.
Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound tetra- serobila of oncogene promoter region G- identification,
In conjunction with or stablize aspect application.
The oncogene promoter is the oncogene DNA sequence dna of the mankind.
Graphene oxide has good surface-active, and a large amount of π-π binding sites and hydrogen bond that surface can provide, warp
After crossing chloride processing, it can be good at generating with cup [4] aromatic hydrocarbons adenine derivative and react, form compound.Calixarenes is
A kind of good molecular receptor, but itself to DNA or base there is no specific recognition capability, cannot be directly used to DNA
Identification, therefore adenine is connected on calixarenes, so that calixarenes has the recognition capability to DNA, so calixarenes-gland is fast
Purine derivative has the recognition capability to tetra- serobila DNA of G-, but water-soluble bad.Although there is a large amount of π-on graphene oxide surface
π binding site and hydrogen bond, but its surface can not adsorb tetra- serobila of G- well, and since graphene oxide graphene oxide has
There are the specific surface area of super large, a large amount of hydrophilic functional groups in surface, a large amount of hydrophilic functional groups have water solubility well, so will
The selection that cup [4] aromatic hydrocarbons adenine derivative can both play cup [4] aromatic hydrocarbons adenine derivative in conjunction with graphene oxide is known
Other performance can play the good water-soluble and bio-compatibility of graphene oxide again.But carboxyl and cup above graphene oxide
[4] combination of amino contained by aromatic hydrocarbons adenine derivative condensing agent, and reaction condition is difficult to control, so being difficult directly to connect
It to together, first passes through graphene oxide chloride, amidation process then is occurring with amino, reaction condition is mild, work
Skill is simple, and is easy to for the two being connected to together.
Compound of the invention have concurrently Calixarene Derivatives pair specific identification ability and graphene oxide it is excellent
Bio-compatibility achievees the purpose that accurate measurements to improve the sensitivity in tetra- serobila detection process of G-.This patent design
Synthesis combines cup [4] aromatic hydrocarbons adenine derivative-graphene oxide, this composite material shows the detection to tetra- serobila of G-
Performance.During fluorescence sense, introducing this composite material of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide can be incited somebody to action
Its unique excellent properties is integrated into the running of sensor molecules, to improve entire Operation System.This patent is antineoplastic
Object provides some theoretical foundations in the application of anti-tumor aspect.
Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound of the invention is by fluorescence experiments to oncogene G-
Four serobilas have enhancement effect of fluorescence, illustrate that with tetra- serobila of oncogene promoter region G- recognition reaction can occur for the composite material.It is logical
CD spectrum experiment is crossed, finds being continuously increased with derivatives concentration, the maximum positive absorption peak of CD curve and minimal negative absorption peak are simultaneously
There is no obviously deviating, illustrate that the composite material can stablize the structure of tetra- serobila of promoter region G-.Pass through PCR instrument thermostabilization
Property experiment, testing the composite material is improved the melting temperature of tetra- serobila of G- of fluorescent marker, illustrates that the material can
So that the structure of tetra- serobila of G- is more stable.
Compared with prior art, compound of the invention has recognition reaction to tetra- serobila of oncogene promoter region G-, combines
Effect and stabilization, provide it is a kind of detected by the method for bio-sensing with biological macrocycle molecule tetra- serobila of G- newly
Selection scheme.And preparation is simple for the compound, is easy to large-scale industrial production.
Detailed description of the invention
Fig. 1 is the infrared spectrogram for the compound that embodiment 1 is prepared；
Fig. 2 is the XDR figure for the compound that embodiment 1 is prepared；
Fig. 3 is the compound that is prepared of embodiment 1 in potassium ion buffer solution, is acted on tetra- serobila bcl-2DNA of G-
Fluorescence spectra；
The CD that Fig. 4 is the compound that is prepared of embodiment 1 in potassium ion buffer solution, with the interaction of tetra- serobila of G-
Titration figure；
The unwinding temperature that Fig. 5 is the compound that is prepared of embodiment 1 in potassium ion buffer solution, with the effect of tetra- serobila of G-
Spend experimental curve diagram.
Specific embodiment
The present invention is described in detail with specific embodiment below in conjunction with the accompanying drawings.
Embodiment 1
A kind of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound (AC+GO), the compound is by graphite oxide
Alkene is keyed to be formed by amide with cup [4] aromatic hydrocarbons adenine derivative.
The preparation method of the compound the following steps are included:
(1) 100mg graphene oxide is weighed, is added in the mixed solution of 20mL thionyl chloride and the DMF of 1mL, ultrasound makes
It is uniformly dispersed, and is transferred in three-necked bottle after mixing under the conditions of 70 DEG C and reacts 48h, after reaction with tetrahydrofuran repeatedly from
The heart washing, be freeze-dried chloride graphene oxide powder 0.085g.
(2) excessive cup [4] aromatic hydrocarbons adenine derivative is dissolved with the DMF of 50mL, step (1) resulting chloride is added
Graphene oxide powder in, stir 36h at normal temperature, obtain the black particle suspension of good dispersion, be centrifugated, with full
And brine It, distilled water are once centrifugated, and dry to obtain black powder product 0.076g, as cup [4] aromatic hydrocarbons adenine
Derivative-graphene oxide compound (AC+GO).
Infrared figure:
AC:3404 ,-Ar-OH
2952 ,-CH3 ,-CH2
2869 ,-CH2
1643 ,-C=N
1595 ,-NH2
1360 ,-C (CH3) 3
GO:
3410 ,-OH
1714 ,-C=O
1621 ,-C=C
1220 ,-C-H
1044 ,-C-O
AC+GO:
3354 ,-N-H
3133 ,-Ar-OH
1646 ,-C=O
1410 ,-C-OH
By the infared spectrum of Fig. 1 it is found that the graphene oxide after amidation occurs in amido bond in 3354cm-1
N-H key stretching vibration absworption peak, occur the C=O absorption peak in amido bond at 1646cm-1.Thus it can tentatively demonstrate,prove
Bright, calixarenes adenine derivative-graphene oxide successfully connects in surface of graphene oxide.
XRD diagram: 100 be the characteristic peak of graphene oxide；It 16.80, is that cup [4] aromatic hydrocarbons adenine is derivative at 26.80,430
Object-graphene oxide characteristic peak.
By in the XRD diagram of Fig. 2 it is found that after in conjunction with calixarenes adenine derivative, the characteristic peak of graphene oxide GO from
100 are displaced to 16.80, this is that occur near 26.80 and 430 two wide and wide caused by interlayer oxygen-containing functional group is reduced
This peak of diffraction maximum is consistent substantially with the characteristic peak positions of graphene, and the above XRD result illustrates there is partial oxidation in amidation process
Graphene reduction, product remains the structure of graphene oxide, while producing a part of graphene-structured again, stacks shape in a jumble
At diffraction maximum.It can thus be appreciated that calixarenes obtained and graphene oxide are rather than two kinds by covalently bound product
Simple mechanical mixture.
AC+GO is used to detect tetra- serobila of G-.
Tris-HCl-K buffer solution A: 10mM Tris, 100mM KCl, pH=7.0；
Preparation method: accurately weighing 1.212g Tris salt, and 7.46g KCl is completely dissolved simultaneously with 100mL triple distillation water
Mixing, slowly adjusts pH value to 7.0 with the dilute hydrochloric acid diluted by triple distillation water, 1000ml volumetric flask is transferred to, with triple steamings
Distilled water constant volume shakes spare after mixing.
Phosphate buffer solution B:10mM KH2PO4-K2HPO4, 100mM KCl, pH=7.0；
Preparation method: 0.174g K is weighed with electronic balance2HPO4·3H2O and 0.746gKCl, with 100mL volumetric flask and
It is 100mM KCl, 10mM K that triple distillation water, which is configured to concentration,2HPO4Solution；Weigh 0.136g KH2PO4With 0.746g KCl,
It is 100mM KCl, 10mM KH with above-mentioned same preparation method compound concentration2PO4Solution.Taking volume is 61.5mL K2HPO4
With 38.5mL KH2PO4Solution is mutually mixed, and the phosphate buffer solution for the PH=7 that concentration is 100mM KCl can be obtained.
The preparation (concentration 200uM) of complex solution:
The compound of 2mg is weighed with electronic balance, volume is fixed by required concentration, dissolution first is shaken with the DMF of 150uL, then
It is settled to required volume with high purity water, concussion can uniformly obtain the complex solution of 200uM.
The preparation of DNA solution and the measurement of concentration:
(1) tetra- serobila DNA (bcl-2DNA) of G-
Preparation method: taking the bcl-2DNA of about 10OD, adds buffer solution A to dissolve with the volume of corresponding label, water is used after sealing
Bath is heated to 90 DEG C and is kept for 10 minutes, is put into refrigerator and refrigerates 24 hours or more after being slowly cooled to room temperature, spare.
(2) fluorescent marker bcl-2DNA
Preparation method: taking the fluorescent marker bcl-2DNA of about 2OD, adds buffer solution B to dissolve with the volume of corresponding label, sealing
Afterwards with heating water bath to 90 DEG C and keep 10 minutes, be put into refrigerator and refrigerate 24 hours or more after being slowly cooled to room temperature, it is spare.
One, the fluorescence titration experiment of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound
Instrument: 7000 fluophotometer of Hitachi FP；
Instrument parameter: excitation wavelength: 480nm, slit width: 10nm, voltage: 500V；
Scanning range: 500-700nm；
When experiment, taking volume is the cuvette that the compound that 10uL concentration is 200uM is added to 1990uL buffer solution A
In, repeatedly it is uniformly mixed solution with the slow compressing of liquid-transfering gun, it is 100uM's that 10uL concentration is then added every time into cuvette
DNA solution, with liquid-transfering gun, compressing is uniform repeatedly, and detection fluorescence rises situation.It operates, is added dropwise repeatedly until last at least 4 repeatedly
The fluorescence peak of secondary titration will not change.Its result is as shown in Figure 3.
The result shows that: as shown in Figure 3, exist in TrisK buffer solution, with the continuous dropwise addition of DNA, on fluorescence peak is continuous
It rises, finally reaches saturation.Illustrate that the compound and tetra- serobila of G- have recognition capability.
Two, the CD titration experiments of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound
Instrument: JASCO J-815；
Instrument parameter: scanning range: 225-350nm；
CD spectrum can effectively indicate the secondary structure of DNA.Tetra- serobila of parallel type G- occur near 270nm it is positive most
There is negative maximum absorption band near 240nm in big absorption peak；Antiparallel type structure has maximum positive absorption peak in wavelength 290nm,
There is negative maximum absorption band near 260nm；Mixed type has positive absorption peak near 290nm and has shoulder seam near 265nm.
As a result as shown in Figure 4；
The result shows that: under the conditions of potassium ion, tetra- stranded structure of G oncogene promoter region DNA parallel type G-, and with multiple
The increase of object concentration is closed, there is no transformations for the positive and negative absorption peak of CD map, it is known that derivative can stablize tetra- serobila of parallel type G-.
Three, the Study on Thermal Deformation experiment of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound
Instrument: BIORAD icycler (iQ5) PCR instrument
The thermostabilization research of tetra- serobila of G- is to carry out fluorescence resonance energy transfer technology using PCR instrument.Test compound
To the melting temperature T of fluorescent label DNAmThe change of value.To reflect different composite object concentration to tetra- serobila DNA thermodynamics of G-
The difference of stabilization.As a result as shown in Figure 5
The result shows that: in the presence of there is no compound, the T of tetra- serobila of G-mIt is worth smaller；With the addition and concentration of compound
Increase, TmValue gradually increases.Ultimately joining complex concentration is that 7um makes tetra- serobila T of G-mValue increases 5 DEG C.In potassium buffer
Lower compound has concentration dependent to the stabilization of tetra- serobila of G-, and has certain stabilizing power.
Embodiment 2
A kind of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound (AC+GO), the compound is by graphite oxide
Alkene is keyed to be formed by amide with cup [4] aromatic hydrocarbons adenine derivative.
The preparation method of the compound the following steps are included:
(1) 100mg graphene oxide is weighed, is added in the mixed solution of 20mL thionyl chloride and the DMF of 1mL, ultrasound makes
It is uniformly dispersed, and is transferred in three-necked bottle after mixing under the conditions of 60 DEG C and reacts 96h, after reaction with tetrahydrofuran repeatedly from
The heart washing, be freeze-dried chloride graphene oxide powder.
(2) excessive cup [4] aromatic hydrocarbons adenine derivative is dissolved with the DMF of 50mL, step (1) resulting chloride is added
Graphene oxide powder in, stir 96h at normal temperature, obtain the black particle suspension of good dispersion, be centrifugated, with full
And brine It, distilled water are once centrifugated, and dry to obtain black powder product, as cup [4] aromatic hydrocarbons adenine derivative-
Graphene oxide compound (AC+GO).
The compound has identification, combination and stabilization to tetra- serobila of oncogene promoter region G-.
Embodiment 3
The compound of the present embodiment is substantially the same manner as Example 1, the difference is that, the preparation of the compound of the present embodiment
Method the following steps are included:
(1) 100mg graphene oxide is weighed, is added in the mixed solution of 20mL thionyl chloride and the DMF of 1mL, ultrasound makes
It is uniformly dispersed, and is transferred in three-necked bottle after mixing under the conditions of 80 DEG C and reacts 12h, after reaction with tetrahydrofuran repeatedly from
The heart washing, be freeze-dried chloride graphene oxide powder.
(2) excessive cup [4] aromatic hydrocarbons adenine derivative is dissolved with the DMF of 50mL, step (1) resulting chloride is added
Graphene oxide powder in, stir 6h at normal temperature, obtain the black particle suspension of good dispersion, be centrifugated, with full
And brine It, distilled water are once centrifugated, and dry to obtain black powder product, as cup [4] aromatic hydrocarbons adenine derivative-
Graphene oxide compound (AC+GO).
The compound has identification, combination and stabilization to tetra- serobila of oncogene promoter region G-.Cancer described herein
Gene promoter is the oncogene DNA sequence dna of the mankind.
Claims (9)
1. a kind of application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound, which is characterized in that applied
Identification, combination or the stable aspect of tetra- serobila of oncogene promoter region G-, the compound is by graphene oxide and cup [4] aromatic hydrocarbons gland
Purine derivative is keyed to be formed by amide.
2. the application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 1, feature
It is, which is keyed by amide with cup [4] aromatic hydrocarbons adenine derivative by the graphene oxide of chloride and is formed.
3. the application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 2, feature
Be, the amido bond by aromatic hydrocarbons adenine derivative-NH2- C (O) the Cl base of base and the graphene oxide of chloride hair
Raw amidation process is formed.
4. the application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 1, feature
It is, the chemical formula of the cup [4] aromatic hydrocarbons adenine derivative is C55H70O4N5Br, structural formula are as follows:
5. the application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 1, feature
It is, preparation method includes the following steps:
(1) graphene oxide is subjected to chloride, obtains the graphene oxide powder of chloride；
(2) excessive cup [4] aromatic hydrocarbons adenine derivative is dissolved with organic solvent, the graphene oxide powder that chloride is added is normal
Temperature is lower to stir 6~96h, obtains black particle suspension, is centrifugated, with saturated common salt water washing, be then added distilled water into
Row centrifuge separation, drying obtain black powder, as cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound.
6. a kind of application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 5,
It is characterized in that, the organic solvent in step (2) is DMF.
7. the application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 5, feature
It is, step adds graphene oxide into the mixed solution of chlorinating agent and auxiliary agent in (1), and ultrasound crushes graphene oxide simultaneously
It is uniformly dispersed, 12~96h is reacted under the conditions of 60~80 DEG C and carries out chloride, be centrifuged repeatedly washing with tetrahydrofuran, freezing is dry
The dry graphene oxide powder for obtaining chloride.
8. the application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 7, feature
It is, chlorinating agent described in step (1) is thionyl chloride, and the auxiliary agent is DMF.
9. the application of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide compound according to claim 1, feature
It is, the oncogene promoter is the oncogene DNA sequence dna of the mankind.
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