CN105823764A - Calix[4]arene adenine derivative-oxidized graphene compound, preparation method and applications thereof - Google Patents
Calix[4]arene adenine derivative-oxidized graphene compound, preparation method and applications thereof Download PDFInfo
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Abstract
The invention relates to a calix[4]arene adenine derivative-oxidized graphene compound, a preparation method and applications thereof. The compound is formed by connecting oxidized graphene and calix[4]arene adenine derivatives through amido bonds. The preparation method comprises the following steps: (1) subjecting oxidized graphene to chloroformylation; (2) dissolving excess calix[4]arene adenine derivatives by an organic solvent, adding chloroformylated oxidized graphene powder, stirring for 6 to 96 hours at a room temperature to obtain a black particle suspension liquid, carrying out centrifugal separation, carrying out saturated salt water washing, adding distilled water, carrying out centrifugal separation, and drying to obtain black powder namely the calix[4]arene adenine derivative-oxidized graphene compound, which can be used to recognize, combine, and stabilize cancer gene promoter region G-quadrome. Compared with the prior art, the preparation technology is simple and easy to perform, and a novel method is provided to detect G-quadrome through biological macro-cycle molecules.
Description
Technical field
The present invention relates to a kind of Calixarene Derivatives composite, especially relate to a kind of cup [4] aromatic hydrocarbons adenine and spread out
Bio-oxidation graphene composite material and its preparation method and application.
Background technology
Along with the progress of society, the living environment of mankind nowadays there occurs huge change, global warming, smelly
The various pollution problems such as oxygen layer cavity, bio-diversity are reduced, acid rain spreads, sharp reduction of the forests and desertification of land,
The various disease of the thing followed increases, and cancer is one of principal disease of serious harm human health.Various anticarcinogens
Thing increases therewith, therefore seek low toxicity, efficiently, the cancer therapy drug with active anticancer be that mankind nowadays is urgently to be resolved hurrily
Problem.
Promoter is one section of important genetic region, is positioned at the section of DNA sequence of gene 5 ' end upstream regulatory region,
Hereditism referring to, one section can make gene carry out the DNA sequence transcribed.Promoter may determine that the expression of gene,
Namely can determine which proteinoid cell produces.If there is variation in promoter region gene, by Gene Handling
Expression has a strong impact on, and this variation is common in malignant tumor.Therefore the research suppressing the expression of oncogene becomes anti-
Cancer drug action method.Document reports various metal complex the most in a large number to detect oncogene promoter G-
Four serobilas, but detect the article of G-tetra-serobila with the macrocyclic compound of this stereochemical structure of calixarenes and also do not report
Road.
Summary of the invention
Defect that the purpose of the present invention is contemplated to overcome above-mentioned prior art to exist and provide a kind of oncogene to start
Sub-district G-tetra-serobila has cup [4] aromatic hydrocarbons adenine derivative-oxidation of recognition reaction, combination and Stabilization
Graphene composite material, preparation is simple for this complex, provides for G-tetra-serobila and is divided by biological macro ring
The new selection scheme of son detection.
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 complex, this complex is by graphene oxide and cup
[4] aromatic hydrocarbons adenine derivative connects formation by amido link.
Preferably, this complex is passed through amide by the graphene oxide of chloride and cup [4] aromatic hydrocarbons adenine derivative
Bonded formation.
Described amido link is by-the NH of aromatic hydrocarbons adenine derivative2-C (O) Cl of the graphene oxide of base and chloride
Base generation amidation process is formed.
The chemical formula of described cup [4] aromatic hydrocarbons adenine derivative is C55H70O4N5Br, its structural formula is as follows:
The preparation method of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex, comprises the following steps:
(1) graphene oxide is carried out chloride, obtain the graphene oxide powder of chloride；
(2) dissolve cup [4] the aromatic hydrocarbons adenine derivative of excess with organic solvent, add the graphite oxide of chloride
Stir 6～96h under alkene powder room temperature, obtain black particle suspension, centrifugation, wash with saturated aqueous common salt,
Then dry, obtain black powder, be cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex.
Organic solvent in step (2) is DMF.
Preferably, the stirring at normal temperature time in step (2) is 36h.
Step (2) is washed to pH=7 with saturated aqueous common salt, adds distilled water and be centrifuged separating so that acyl
The graphene oxide powder surface of chlorination is clean.
Cup [4] the aromatic hydrocarbons adenine derivative added in step (2) should be excessive so that cup [4] aromatic hydrocarbons adenine spreads out
Biology is received on graphene oxide as far as possible, because when calixarenes amount is few, and the cup [4] that graphene oxide connects
Aromatic hydrocarbons adenine derivative will lack comparatively speaking, it is impossible at identification, the knot of G-tetra-serobila both well playing
Close or stablize the synergism of aspect.
Step (1) add graphene oxide in the mixed solution of chlorinating agent and auxiliary agent, ultrasonic by graphite oxide
Alkene is pulverized and is uniformly dispersed, and reacts 12～96h and carry out chloride, with oxolane repeatedly under the conditions of 60～80 DEG C
Centrifuge washing, lyophilization obtains the graphene oxide powder of 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 described auxiliary agent is DMF.
In step (1), DMF as auxiliary agent plays the effect of catalyst and solubilizing agent.
Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex is in the knowledge of oncogene promoter region G-tetra-serobila
, do not combine or stablize the application of aspect.
The described oncogene DNA sequence that oncogene promoter is the mankind.
Graphene oxide has a good surface activity, and a large amount of π-π binding sites that can provide of surface and hydrogen
Key, after chloride processes, it is possible to well produce react with cup [4] aromatic hydrocarbons adenine derivative, formed multiple
Compound.Calixarenes is a kind of well molecular receptor, but itself identifies DNA or base are the most specific
Ability, it is impossible to be directly used in the identification to DNA, therefore adenine received on calixarenes, so that calixarenes tool
There is the identification ability to DNA, so calixarenes-adenine derivative has the identification energy to G-tetra-serobila DNA
Power, but water solublity is bad.Although there are substantial amounts of π π binding site and a hydrogen bond in graphene oxide surface, but its surface
Can not well adsorb G-tetra-serobila, due to graphene oxide graphene oxide, there is the specific surface area of super large again,
The a large amount of hydrophilic functional group in surface, a large amount of hydrophilic functional groups have good water solublity, so by cup [4] aromatic hydrocarbons
Adenine derivative is combined the selection identity that can both play cup [4] aromatic hydrocarbons adenine derivative with graphene oxide
Can play again the good water solublity of graphene oxide and bio-compatibility.But the carboxyl above graphene oxide with
Cup amino contained by [4] aromatic hydrocarbons adenine derivative combines condensing agent to be used, and reaction condition is difficult to control to, so
Be difficult to be directly connected to together, first pass through graphene oxide chloride, then with amino generation amidation process,
Reaction condition is gentle, and technique is simple, and is easy to receive together the two.
The complex of the present invention has the specific identification ability of Calixarene Derivatives pair and the excellent of graphene oxide concurrently
Bio-compatibility, thus improve G-tetra-serobila detection during sensitivity, reach the purpose of accurate measurements.
Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide is combined by this patent design synthesis, and this composite shows
Detection performance to G-tetra-serobila.During fluorescence sense, introduce cup [4] aromatic hydrocarbons adenine derivative-oxidation stone
The excellent properties of its uniqueness can be incorporated in the running of sensor molecules by ink this composite of alkene, thus improves whole
Individual Operation System.This patent is that antitumor drug provides some theoretical foundations in the application of anti-tumor aspect.
Cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex of the present invention passes through fluorescence experiments to oncogene
G-tetra-serobila has enhancement effect of fluorescence, illustrates that this composite can be known with oncogene promoter region G-tetra-serobila
Do not act on.By CD spectrum experiment, finding being continuously increased along with derivatives concentration, CD curve maximum is just inhaled
Receive peak and minimal negative absworption peak does not occur substantially skew, illustrate that this composite can stablize promoter region G-
The structure of four serobilas.Tested by PCR instrument heat stability, test this composite and make fluorescently-labeled G-tetra-
The melting temperature of serobila is improved, and illustrates that described material can make the structure of G-tetra-serobila more stable.
Compared with prior art, the complex of the present invention oncogene promoter region G-tetra-serobila is had recognition reaction,
Combination and Stabilization, it is provided that a kind of biological macrocycle molecule detects G-by the method for bio-sensing
The new selection scheme of four serobilas.And this complex preparation is simple, it is easy to large-batch industrial is raw
Produce.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of the complex that embodiment 1 prepares；
Fig. 2 is the XDR figure of the complex that embodiment 1 prepares；
Fig. 3 be the complex for preparing of embodiment 1 in potassium ion buffer solution, with G-tetra-serobila bcl-2
The fluorescence spectrum figure of DNA effect；
Fig. 4 be the complex for preparing of embodiment 1 in potassium ion buffer solution, with G-tetra-serobila phase interaction
CD titration figure；
Fig. 5 be the complex for preparing of embodiment 1 in potassium ion buffer solution, with G-tetra-serobila effect
Melting temperature experimental curve diagram.
Detailed description of the invention
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 complex (AC+GO), this complex is by aoxidizing
Graphene is connected formation with cup [4] aromatic hydrocarbons adenine derivative by amido link.
The preparation method of this complex comprises the following steps:
(1) weigh 100mg graphene oxide, add the mixing of 20mL thionyl chloride and the DMF of 1mL
In solution, ultrasonic make it be uniformly dispersed, transfer to three-necked bottle reacts under the conditions of 70 DEG C 48h after mixing, instead
Being centrifuged repeatedly washing with oxolane after should terminating, lyophilization obtains the graphene oxide powder 0.085g of chloride.
(2) dissolve cup [4] the aromatic hydrocarbons adenine derivative of excess with the DMF of 50mL, add step (1) institute
In the graphene oxide powder of the chloride obtained, stirring 36h at normal temperatures, the black particle obtaining good dispersion hangs
Supernatant liquid, centrifugation, wash with saturated aqueous common salt, centrifugation of distilled water, dry to obtain black powder product
0.076g, is cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex (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
From the infared spectrum of Fig. 1, the graphene oxide after amidatioon occurs in that amide at 3354cm-1
The stretching vibration absworption peak of the N-H key in key, occurs in that the C=O absworption peak in amido link at 1646cm-1.
Thus can preliminary proof, calixarenes adenine derivative-graphene oxide has successfully been connected on surface of graphene oxide.
XRD figure: 100 is the characteristic peak of graphene oxide；16.80, it is that cup [4] aromatic hydrocarbons gland is fast at 26.80,430
The characteristic peak of purine derivant-graphene oxide.
From in the XRD figure of Fig. 2, after being combined with calixarenes adenine derivative, graphene oxide GO's
Characteristic peak is displaced to 16.80 from 100, and this is that the minimizing of interlayer oxygen-containing functional group causes, attached in 26.80 and 430
Near occur that two these peaks of wide and wide diffraction maximum are consistent substantially with the characteristic peak positions of Graphene, above XRD result
Illustrating have partial oxidation of graphite alkene to reduce in amidation process, product remains the structure of graphene oxide, the most again
Creating a part of graphene-structured, mixed and disorderly stacking defines diffraction maximum.It can thus be appreciated that the calixarenes obtained and oxygen
Functionalized graphene is by covalently bound product rather than two kinds of simple mechanical mixture.
It is used for AC+GO detecting G-tetra-serobila.
Tris-HCl-K buffer A: 10mM Tris, 100mM KCl, pH=7.0；
Compound method: accurately weigh 1.212g Tris salt, 7.46g KCl is complete with 100mL triple distillation water
Dissolve and mix, slowly regulating pH value to 7.0 with the dilute hydrochloric acid diluted by triple distillation water, proceed to 1000ml
Volumetric flask, with triple distillation water constant volume, standby after concussion mix homogeneously.
Phosphate buffered solution B:10mM KH2PO4-K2HPO4, 100mM KCl, pH=7.0；
Compound method: weigh 0.174g K with electronic balance2HPO4·3H2O and 0.746gKCl, holds with 100mL
It is 100mM KCl that measuring bottle and triple distillation water are configured to concentration, 10mM K2HPO4Solution；Weigh 0.136g
KH2PO4With 0.746g KCl, it is 100mM KCl with above-mentioned same compound method compound concentration, 10mM
KH2PO4Solution.Taking volume is 61.5mL K2HPO4With 38.5mL KH2PO4Solution is mutually mixed,
Obtain the phosphate buffered solution of the PH=7 that concentration is 100mM KCl.
The preparation (concentration is 200uM) of complex solution:
Weigh the complex of 2mg with electronic balance, it is fixed that volume presses desired concn, first with the DMF shake of 150uL
Swing dissolving, then be settled to high purity water volume required, concussion uniformly the complex solution of 200uM.
The preparation of DNA solution and the mensuration of concentration:
(1) G-tetra-serobila DNA (bcl-2DNA)
Compound method: take the bcl-2DNA of about 10OD, adds buffer A with the volume of corresponding label and dissolves,
With heating in water bath to 90 DEG C and keep 10 minutes after sealing, after being slowly cooled to room temperature, put into cold preservation 24 in refrigerator
More than hour, standby.
(2) fluorescent labeling bcl-2DNA
Compound method: take fluorescent labeling bcl-2DNA of about 2OD, adds buffer B with the volume of corresponding label
Dissolve, with heating in water bath to 90 DEG C and keep 10 minutes after sealing, put in refrigerator after being slowly cooled to room temperature
Cold preservation more than 24 hours, standby.
One, the fluorescence titration experiment of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex
Instrument: Hitachi FP 7000 fluorophotometer；
Instrument parameter: excitation wavelength: 480nm, slit width: 10nm, voltage: 500V；
Sweep limits: 500-700nm；
During experiment, take volume be 10uL concentration be that the complex of 200uM joins 1990uL buffer solution A
Cuvette in, repeatedly make solution mix homogeneously by the slow compressing of liquid-transfering gun, then add in cuvette every time
10uL concentration is the DNA solution of 100uM, uniform by liquid-transfering gun compressing repeatedly, and detection fluorescence rises situation.
Repeatable operation, dropping is repeatedly until the fluorescence peak of last at least 4 titration will not change.Its result such as Fig. 3
Shown in.
Result shows: as shown in Figure 3, exists at TrisK buffer solution, along with the continuous dropping of DNA, glimmering
Photopeak constantly rises, and finally reaches saturated.Illustrate that this complex and G-tetra-serobila have identification ability.
Two, the CD titration experiments of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex
Instrument: JASCO J-815；
Instrument parameter: sweep limits: 225-350nm；
CD spectrum can represent the secondary structure of DNA effectively.Parallel type G-tetra-serobila goes out near 270nm
The most positive maximum absorption band, occurs the maximum absorption band born near 240nm；Antiparallel type structure is at wavelength
290nm has maximum positive absworption peak, has negative maximum absorption band near 260nm；Mixed type is near 290nm
There is positive absworption peak and near 265nm, have shoulder seam.Result is as shown in Figure 4；
Result shows: under the conditions of potassium ion, G oncogene promoter region DNA parallel type G-tetra-stranded structure,
And along with the increase of complex concentration, the positive and negative absworption peak of CD collection of illustrative plates does not change, it is known that derivant can be steady
Determine parallel type G-tetra-serobila.
Three, the Study on Thermal Deformation experiment of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex
Instrument: BIORAD icycler (iQ5) PCR instrument
The thermally-stabilised research of G-tetra-serobila is to utilize PCR instrument to carry out FRET (fluorescence resonance energy transfer) technology.Test is multiple
Compound melting temperature T to fluorescent label DNAmThe change of value.Thus reflect that different composite substrate concentration is to G-
The difference of four serobila DNA Thermodynamically stable effects.Result is as shown in Figure 5
Result shows: in the presence of not having complex, the T of G-tetra-serobilamIt is worth less；Addition along with complex
With the increase of concentration, TmValue is gradually increased.Ultimately joining complex concentration is that 7um makes G-tetra-serobila TmValue rises
High 5 DEG C.Under potassium buffer, complex has concentration dependent to the Stabilization of G-tetra-serobila, and
And there is certain stabilizing power.
Embodiment 2
A kind of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex (AC+GO), this complex is by aoxidizing
Graphene is connected formation with cup [4] aromatic hydrocarbons adenine derivative by amido link.
The preparation method of this complex comprises the following steps:
(1) weigh 100mg graphene oxide, add the mixing of 20mL thionyl chloride and the DMF of 1mL
In solution, ultrasonic make it be uniformly dispersed, transfer to three-necked bottle reacts under the conditions of 60 DEG C 96h after mixing, instead
Being centrifuged repeatedly washing with oxolane after should terminating, lyophilization obtains the graphene oxide powder of chloride.
(2) dissolve cup [4] the aromatic hydrocarbons adenine derivative of excess with the DMF of 50mL, add step (1) institute
In the graphene oxide powder of the chloride obtained, stirring 96h at normal temperatures, the black particle obtaining good dispersion hangs
Supernatant liquid, centrifugation, wash with saturated aqueous common salt, centrifugation of distilled water, dry to obtain black powder product,
It is cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex (AC+GO).
This complex has identification, combines and Stabilization oncogene promoter region G-tetra-serobila.
Embodiment 3
The complex of the present embodiment is substantially the same manner as Example 1, and difference is, the complex of the present embodiment
Preparation method comprises the following steps:
(1) weigh 100mg graphene oxide, add the mixing of 20mL thionyl chloride and the DMF of 1mL
In solution, ultrasonic make it be uniformly dispersed, transfer to three-necked bottle reacts under the conditions of 80 DEG C 12h after mixing, instead
Being centrifuged repeatedly washing with oxolane after should terminating, lyophilization obtains the graphene oxide powder of chloride.
(2) dissolve cup [4] the aromatic hydrocarbons adenine derivative of excess with the DMF of 50mL, add step (1) institute
In the graphene oxide powder of the chloride obtained, stirring 6h at normal temperatures, the black particle obtaining good dispersion hangs
Supernatant liquid, centrifugation, wash with saturated aqueous common salt, centrifugation of distilled water, dry to obtain black powder product,
It is cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex (AC+GO).
This complex has identification, combines and Stabilization oncogene promoter region G-tetra-serobila.Described herein
The oncogene DNA sequence that oncogene promoter is the mankind.
Claims (10)
1. cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex, it is characterised in that this complex by
Graphene oxide is connected formation with cup [4] aromatic hydrocarbons adenine derivative by amido link.
Cup the most according to claim 1 [4] aromatic hydrocarbons adenine derivative-graphene oxide complex, its feature
Being, this complex is connected by amido link with cup [4] aromatic hydrocarbons adenine derivative by the graphene oxide of chloride
Formed.
Cup the most according to claim 2 [4] aromatic hydrocarbons adenine derivative-graphene oxide complex, its feature
Being, described amido link is by-the NH of aromatic hydrocarbons adenine derivative2The graphene oxide of base and chloride
-C (O) Cl base generation amidation process is formed.
Cup the most according to claim 1 [4] aromatic hydrocarbons adenine derivative-graphene oxide complex, its feature
Being, the chemical formula of described cup [4] aromatic hydrocarbons adenine derivative is C55H70O4N5Br, its structural formula is as follows:
5. the preparation side of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex as claimed in claim 1
Method, it is characterised in that comprise the following steps:
(1) graphene oxide is carried out chloride, obtain the graphene oxide powder of chloride；
(2) dissolve cup [4] the aromatic hydrocarbons adenine derivative of excess with organic solvent, add the graphite oxide of chloride
Stir 6～96h under alkene powder room temperature, obtain black particle suspension, centrifugation, wash with saturated aqueous common salt,
It is subsequently adding distilled water to be centrifuged separating, dries, obtain black powder, be cup [4] aromatic hydrocarbons adenine and derive
Thing-graphene oxide complex.
The system of a kind of cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex the most according to claim 5
Preparation Method, it is characterised in that the organic solvent in step (2) is DMF.
The preparation side of cup the most according to claim 5 [4] aromatic hydrocarbons adenine derivative-graphene oxide complex
Method, it is characterised in that add graphene oxide in the mixed solution of chlorinating agent and auxiliary agent in step (1) is super
Graphene oxide is pulverized and is uniformly dispersed by sound, reacts 12～96h and carries out chloride, use under the conditions of 60～80 DEG C
Oxolane is centrifuged repeatedly washing, and lyophilization obtains the graphene oxide powder of chloride.
The preparation side of cup the most according to claim 7 [4] aromatic hydrocarbons adenine derivative-graphene oxide complex
Method, it is characterised in that the chlorinating agent described in step (1) is thionyl chloride, described auxiliary agent is DMF.
9. cup [4] aromatic hydrocarbons adenine derivative-graphene oxide complex as described in Claims 1 to 4 is arbitrary is in cancer
The identification of gene promoter area G-tetra-serobila, combine or stablize the application of aspect.
The application of cup the most according to claim 9 [4] aromatic hydrocarbons adenine derivative-graphene oxide complex,
It is characterized in that, the described oncogene DNA sequence that oncogene promoter is the mankind.
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| CN107033176A (en) * | 2017-04-20 | 2017-08-11 | 同济大学 | The preparation method and applications of cup [4] aromatic hydrocarbons phenyl boronic acid derivative/multi-wall carbon nano-tube composite material |
| CN107033176B (en) * | 2017-04-20 | 2019-08-02 | 同济大学 | Cup [4] aromatic hydrocarbons phenyl boronic acid derivative/multi-wall carbon nano-tube composite material preparation method and applications |
| CN107604465A (en) * | 2017-09-19 | 2018-01-19 | 旷达纤维科技有限公司 | Hollow coloured polyester fiber of a kind of anlistatig abnormity of high fire-retardance and preparation method thereof |
| CN107604465B (en) * | 2017-09-19 | 2019-10-29 | 旷达纤维科技有限公司 | A kind of antistatic hollow coloured polyester fiber of abnormity and preparation method thereof of high fire-retardance |
| CN109406470A (en) * | 2018-10-26 | 2019-03-01 | 云南大学 | The construction method of fluorescent optical sensor based on competitiveness identification and application |
| CN109406470B (en) * | 2018-10-26 | 2021-03-26 | 云南大学 | Construction method and application of fluorescent sensor based on competitive identification |
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