CN108042565A - A kind of black phosphorus nano material with antibiotic effect and preparation method thereof - Google Patents
A kind of black phosphorus nano material with antibiotic effect and preparation method thereof Download PDFInfo
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- CN108042565A CN108042565A CN201711061537.9A CN201711061537A CN108042565A CN 108042565 A CN108042565 A CN 108042565A CN 201711061537 A CN201711061537 A CN 201711061537A CN 108042565 A CN108042565 A CN 108042565A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/42—Phosphorus; Compounds thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
Abstract
The invention discloses a kind of black phosphorus nano materials of amino ligands surface modification and preparation method thereof and its application in antibacterial field.The amino in sulfamido group with antibiotic effect is introduced nano-material surface by the present invention, assigns its has a broad antifungal spectrum, sterilization of high efficiency, the anti-microbial property for being not likely to produce drug resistance.And the preparation method of the present invention has the characteristics that production technology operation is simple, yield is high, favorable reproducibility is not, it can be achieved that low cost large-scale production, also secondary pollution is generated using black phosphorus nano material to environment.Two-dimentional black phosphorus nano material after modification can significantly inhibit the growth of the growth of gramnegative bacterium and gram-positive bacterium, have excellent antibiotic effect.Therefore, it is huge in field of medical materials application potential.
Description
Technical field
A kind of modified the present invention relates to modified Nano Material Field more particularly to amino ligands black phosphorus nano material and its
Preparation method and its application in antibacterial field.
Background technology
As a kind of emerging ultrathin nanometer material, two-dimentional (2D) nano material is due to its unique architectural characteristic and reason
Change performance, show higher biocompatibility and extensive biomedical applications potential.Two-dimension nano materials be at present
Know most thin nano material, the nanostructured of low dimensional makes them have the specific surface area of superelevation and biological respinse activity, simultaneously
Also there is broad optic response wave band.Nowadays, two-dimension nano materials have been explored applied to a variety of biomedical sectors.Such as medicine
Diagnosis, photo-thermal therapy for loading delivering, the contrast imaging of internal targeting regions and cancer of object etc..
Two-dimension nano materials such as stone still at an early stage, many is studied to the antibiotic effect of two-dimension nano materials at present
Black alkene, graphene oxide, redox graphene, boron nitride, molybdenum disulfide etc. all show certain bacteriostasis efficacy, but all faces
Face the problems such as not degradable, with potential toxic side effect.Market prepares the New Two Dimensional nano material for researching and developing high anti-microbial property
Technology still has urgent demand.
P elements are widely present in animal vegetable tissue, are one of more elements of body burden.Phosphorus is present in human body institute
In some cells, almost take part in it is all maintenance physiology needed for associated metabolic processes, P elements still form skeleton and
The indispensable element of tooth, content are about the 1% of human body weight.And a member newcomer of the black phosphorus as two-dimensional material family, solely
Special characteristic of elements makes it have degradable, high-biocompatibility feature with biological function.The metabolite of black phosphorus in vivo
It is nontoxic phosphate, phosphate and water, can be discharged by body metabolism that there is excellent biological safety.Therefore black phosphorus material
There is inherent advantage for the research and development of antiseptic.In general, black phosphorus is to be transformed by red phosphorus under very High Voltage and higher temperature,
Reactivity is most weak in the allotrope of phosphorus, will not light in air.The two dimension separated by ultrasonic black phosphorus block
Black phosphorus material has the lamellar structure of similar graphene.Due to this ultra-thin low dimensional structures in use environment easily and oxygen
It reacts and is aoxidized with water, therefore serious influence is caused on the medical application of black phosphorus.At present, by being carried out to black phosphorus surface
Method [the Ryder C.R.et al.Nat.Chem.2016,8 (6) modified using diazobenzene derivatives chemical:597-602] with
And doping tellurium [Yang B.et al.Adv.Mater.2016,28 (42):9408-9415] slow down black phosphorus and aoxidize drop in the environment
The method of solution can greatly improve the stability of black phosphorus.106366121 A of patent CN disclose a kind of through ligand modified black of titanium
Phosphorus and preparation method and application, the black phosphorus ligand modified through titanium is the complex of black phosphorus and titanium ligand, black not changing
In the case of the build-in attribute of phosphorus, it is not easy to be aoxidized, oxidation resistance greatly enhances.But at present not yet in relation to the black of antibiotic effect
Phosphorus preparation method, which is seen in, to be delivered.
The two-dimensional nano lamella marginal texture of black phosphorus makes it possible to possess and two-dimensional graphene nano material is similar " receives
Rice knife " effect [Zou X.et al.J.Am.Chem.Soc.2016,138 (7):2064-2077], the periphery wall of bacterium can be punctured
Film causes bacterial death by the membrane structure for destroying bacterium.Since nanometer two-dimensional slice black phosphorus is in its rejected region and edge part
The adsorbable a certain amount of oxygen in position, these absorption oxygen can be with the glutathione inside bacterium when two-dimensional material is contacted with bacterium
Reductases is waited to react, induction intracellular protein inactivation.These absorption oxygen can also induce lipid peroxy reaction, mitochondria work(simultaneously
The peroxidating stress damages such as energy obstacle, so as to disturb the analytic metabolism of bacterium and destroy its elementary cell function, eventually by oxygen
Change the death that stress damage effect causes bacterium.
Antibacterial black phosphorus material is particularly easy to problems with occur during preparation and use：
1. modification process is complicated, low yield, it is difficult to realize large-scale production；
2. the dressing agent used is of high cost, modification effect is undesirable, poor biocompatibility；
3. modification technique does not possess the antibiotic effect for promoting black phosphorus nano material.
Sulfanilamide (SN) is using earliest a kind of chemical synthesis antimicrobial, is played an important role in infectious diseases is treated, mesh
Before be widely used in prevention and treatment the mankind and other animals bacterium infection, have has a broad antifungal spectrum, curative for effect, property is stable,
The advantages that cheap.The Antibacterial Mechanism of sulfa drugs is in the biosynthesis of bacterium dihydrofoilic acid and p-aminobenzoic acid
(p-aminobenzoic acid, PABA) is competitively combined with enzyme, the synthesis of Nucleic acid precurser object is influenced, so as to inhibit bacteria
Growth and breeding.It is very active for the research of sulfonamides compound at present, modifying for chemical structure usually is carried out to precursor structure,
Mainly include sulfoamido structural modification and phenylamino structural modification.The metal complex and its antibacterial activity of sulfonamides compound
It studies relatively fewer.
The content of the invention
It is an object of the invention to provide a kind of preparation methods of amino ligands modification nano material to promote its antibacterial work(
Effect, and further study the effect of it is applied in antibacterial medical field.
Specifically, the amino that the present invention will have antibiotic effect using the method that amino ligands are modified in sulfamido group
The quantum dot surface of black phosphorus nano material or the material is introduced, its has a broad antifungal spectrum, sterilization of high efficiency is assigned, is not likely to produce drug resistance
The anti-microbial property of property.
Therefore, one of the objects of the present invention is to provide a kind of black phosphorus nano material of amino ligands surface modification, improve
Its stability, and the sulfamido group with antibiotic effect is introduced into nano-material surface.
Here, the described method includes：It designs a kind of new amino ligands and modifies black phosphorus nanometer with this amino ligands
Material forms the complex of amino ligands and black phosphorus nano material.
In the present invention, the amino ligands have structure shown in formula (I)
Wherein, R is selected from phenyl, and the phenyl is optionally further by 0-4 hydroxyl, nitro, amino, aldehyde radical, acyl group, alcoxyl
Base, alkyl, halogen atom substitution；
M represents metal ion；
X represents ligancy；It is preferred that represent the natural number of 1-6；More preferably represent 1,2,4 or 6.
The black phosphorus nano material is selected from the quantum dot of two-dimentional black phosphorus or black phosphorus.
Preferably, the R in the amino ligands is selected from by 1-2 hydroxyl, nitro, amino, C1-6Alkyl, C1-6Alkoxy,
The phenyl of halogen substitution.
Preferably, the M is selected from one kind or more in Ti (IV), Cu (II), Ni (II), Zn (II), Co (II) and Ag (I)
Kind.
Alternatively, the surface of the two-dimension nano materials is modified by the amino ligands shown in a variety of formulas (I).
Complex according to the present invention, wherein, " alkyl " refers to the alkyl containing 1-30 carbon atom；It is preferred that lower alkyl
Base, i.e. C1-6Alkyl, including methyl, ethyl, third class, isopropyl, butyl, isobutyl group, tertiary butyl, amyl, isopentyl, tertiary pentyl,
Neopentyl, hexyl, isohesyl, tertiary hexyl, season hexyl.
" alkoxy " refers to RO- groups, and wherein R represents alkyl, and with definitions as described above.
" acyl group " refers toGroup, wherein R represent alkyl, and with definitions as described above.
Of the present invention through in the black phosphorus nano material of amino ligands modification, it is 10~50nm that the black phosphorus, which includes thickness,
One or more in multilayer black phosphorus nanometer sheet and black phosphorus quantum dot.
Another object of the present invention is to provide a kind of preparation method of the nano material of amino ligands surface modification, including
Following steps：
1) solution of p-aminobenzene sulfonic acid and its corresponding derivative and metal ion is coordinated that ammonia is prepared
Ylidene ligands；
2) nano material is scattered in organic solvent；
3) amino ligands are dissolved in organic solvent, heating reaction, obtained described through the black of amino ligands modification
Phosphorus.
Preferably, the heating reaction is carried out in the dark under inert gas shielding.
Preferably, the reaction temperature is 40-70 DEG C, reaction time 12-24h.
Preferably, the concentration of amino ligands is 50-100 μ g/mL.
Preferably, the molar ratio of amino ligands and black phosphorus is 1：1~20：1；More preferable 4：1~15：1.
Preferably, the organic solvent is selected from N-Methyl pyrrolidone, n,N-Dimethylformamide, N, N- diethyl formyls
Amine, DMAC N,N' dimethyl acetamide, dimethyl sulfoxide (DMSO), tetrahydrofuran, ethyl acetate, acetone, methanol, ethyl alcohol, isopropanol, second two
One or more in alcohol, n-butanol, acetonitrile, ether, toluene.
The black phosphorus nano material that another object of the present invention is related to amino ligands surface modification as described above is led in antibacterial
The application in domain.
Germ experiment the result shows that, the present invention prepared by two-dimentional black phosphorus nanometer formulation antibacterial effect it is apparent, to large intestine bar
The growth of bacterium and staphylococcus aureus all has apparent inhibitory action.
In conclusion the present invention provides a kind of black phosphorus of amino ligands modification with antibiotic effect and preparation method thereof
And application.Its preparation method has simple production technology operation, yield height, favorable reproducibility, easily accomplishes scale production.The present invention
Black phosphorus nano material after used preparation method modification has Gram negative bacterium, Gram positive bacteria excellent resist
Bacterium effect, significant increase application potential of the black phosphorus nano material in medical antibacterial field.
Also, nano material of surface modification of the present invention and preparation method thereof possesses advantages below：
1. method of modifying used in the present invention can promote the antibiotic effect of black phosphorus nano material.
2. compared with most of black phosphorus two-dimension nano materials surface modification technology, the operation letter of the method for the present invention production technology
Easily, yield height, favorable reproducibility, easily accomplish scale production.
3. preparation method used in the present invention can effectively modify amino ligands to nano-material surface, experimental result
Show that prepared nano material sample surfaces detect substantial amounts of amino ligands.
4. the present invention can by amino ligands have antibiotic effect amino introduce nano-material surface, assign nano material its
Has a broad antifungal spectrum that his preparation method does not have, sterilization of high efficiency, the anti-microbial property for being not likely to produce drug resistance.
On the other hand, the method according to the invention can also carry out moditied processing according to different material surface characteristics, meanwhile,
Institute's linkage function group can also be replaced and also further can reach imparting by modifying other functional groups on sulphonic acid ester
The purpose of the different physicochemical property of material and application potential.
The present invention using the technology of preparing of amino ligands modification nano material have production technology operation is simple, yield is high,
Favorable reproducibility is, it can be achieved that low cost large-scale production, and the characteristics of do not generate secondary pollution to environment.And the technology of the present invention makes
Amino ligands also can be synthesized voluntarily, and the cost of synthesis is only 100-150 members/g.Black phosphorus material can significantly inhibit after modification
Escherichia coli (E.coli), the growth of staphylococcus aureus (S.aureus) have excellent antibiotic effect.Therefore, anti-
Bacterium field application potential is huge.
Description of the drawings
Fig. 1 amino ligands surface modification black phosphorus materials nuclear-magnetism detects spectrogram.
The transmission electron microscope picture of Fig. 2 black phosphorus and amino ligands modification black phosphorus.
Fig. 3 amino ligands modification black phosphorus material antibiotic effect detection figure：(a) bacterial colony count is taken pictures figure, (b) antibacterial effect
Rate figure.
Specific embodiment
Embodiment is enumerated further below so that the present invention will be described in detail.It will similarly be understood that following embodiment is served only for this
Invention is further described, it is impossible to be interpreted as limiting the scope of the invention, those skilled in the art is according to this hair
Some nonessential modifications and adaptations that bright the above is made all belong to the scope of protection of the present invention.
Following specific technological parameters of example etc. are also only an examples in OK range, i.e. those skilled in the art can
It is done in suitable scope and selected with the explanation by this paper, and do not really want to be defined in hereafter exemplary concrete numerical value.
Embodiment 1
The preparation of black phosphorus (BP) nanometer sheet
25mg black phosphorus crystals are taken, nmp solution is added in 25mL, Probe Ultrasonic Searching 10h, 400W low temperature water bath sonicator in grinding
Supernatant dispersion liquid is taken after sample 2000rpm is centrifuged 10min after 10h, two dimension black phosphorus nanometer sheet is made.
Embodiment 2
The amino ligands of Formula II structure are used in the present embodiment
12mg amino ligands are dissolved in the dichloromethane of 1mL, under the conditions of argon gas is protected and is protected from light, are added it to
1mL has in the dichloromethane dispersion liquid of 50 μ g black phosphorus nanometer sheets, and heating reflux reaction 15h is protected from light in the case where 50 DEG C of nitrogen are protected,
It is then centrifuged 10~20 minutes with 7000~10000 turns of rotating speed, removes supernatant, solid is scattered in ultra-pure water, obtains again
Amino ligands modify the material of black phosphorus,1H-NMR(D2O) detection is as shown in Figure 1.Following embodiment is modified with this amino ligands
Black phosphorus material.
Embodiment 3
It will be seen from figure 1 that the nuclear magnetic signal of amino ligands has on black phosphorus material, illustrate that sulfamate is successfully matched somebody with somebody
Position to black phosphorus surface.
Embodiment 4
The pattern of the black phosphorus nanometer sheet of black phosphorus nanometer sheet and amino ligands modification is studied with transmission electron microscope, the crystalline substance
Body structural research is that the ethanol solution of 20 μ L samples is dropped in carbon to support on film film, with transmission electron microscopy after its natural air drying
Mirror observes sample topography, and before and after finding amino ligands modification, the laminated structure of black phosphorus still retains.Its transmission electron microscope picture
As shown in Figure 2.
Embodiment 5
The amino ligands modification black phosphorus material technology of the present invention can assign the excellent anti-microbial property of black phosphorus material and specifically resist
Bacterium power test implementation process is：
(1) Mueller-Hinton (MH) meat soup is prepared：Weigh beef extract 10g, peptone 10g, agar 15g, NaCl
5g, distilled water 1000mL, PH：7.4,121 DEG C of sterilizing 20min.
(2) actication of culture：Under aseptic condition, 10 μ L strains are drawn in 10mL MH broth bouillons with pipettor, sealing
And gently shake up, it is placed in 37 DEG C of shaking table 200r/min cultures 12-16h.
(3) dilution of bacteria suspension：10 μ L of bacteria suspension are added in 5mL sterile salines after drawing activation, every 10 times of dilutions
Once, (10 are taken-1、10-2、10-3、10-4) concentration dilution liquid 100 μ L do coating experiment, adjust bacteria suspension concentration：Mycetome number is
105-106cfu/mL。
(4) preparation method of beef extract-peptone solid medium (LB culture mediums)：Weigh beef extract 10g, peptone
10g, agar 15g, NaCl 5g, distilled water 1000mL, PH：7.2-7.5 121 DEG C of sterilizing 20min.
(5) after the beef extract-peptone solid medium after sterilizing being cooled to 50 DEG C, poured into per 20mL culture mediums sterile
In culture dish.After cooled and solidified is cultivated, 100 μ L black phosphorus preparations, amino ligands are modified into bacterium of the black phosphorus respectively with 100 μ L activation
Culture dish surface is spread evenly across after suspension blending, each sample is parallel to be repeated 5 times.And correspondence sets up blank control group, the positive
Control group, negative control group.
(6) after black phosphorus preparation is spread evenly across culture dish with bacterium solution, culture dish is placed in 37 DEG C of constant temperature in bacteriological incubator
Constant humidity culture for 24 hours, counts bacterium colony number, and formula is calculated as follows and counts antibacterial efficiency：
Bacteriostasis rate=(control group clump count-processing group clump count)/control group clump count × 100%
Preferably, Escherichia coli (E.coli), staphylococcus aureus (S.aureus) etc. are selected in bacteriostatic experiment.
Two-dimentional black phosphorus nanometer formulation antibacterial effect prepared by the present invention is apparent, to Escherichia coli and staphylococcus aureus
Growth all have apparent inhibitory action (see Fig. 3).In the effect system of physiological saline, the black phosphorus material of amino ligands modification
The antibacterial effect of material is substantially better than the antibacterial effect of black phosphorus before modification, 99.10% is up to the antibiotic rate of Escherichia coli, to gold
The antibiotic rate of staphylococcus aureus is 95.20%, and the antimicrobial efficiency of the black phosphorus material without amino ligands modification is respectively then
15.93% and 41.09%..
In antibacterial experiment according to the present invention, preferred bacteria suspension mycetome number is 105-106cfu/mL.Too low thalline
Concentration can not observe fungistatic effect, and excessively high cell concentration is unfavorable for bacterium colony counting.
Compared to common inhibiting-bacteria preparation.Since two-dimentional black phosphorus nano-antibacterial preparation is metabolizable, biological safety is high.Therefore more
It is suitably applied the production of the antibacterial daily necessities needed for daily life.It can also be applied to the bacteria-suppressing device needed for hygiene medical treatment simultaneously
The research and development of material, antimicrobial agent preparation.
The present invention is it is experimentally confirmed that the two-dimentional black phosphorus nanometer that the nuclear magnetic signal of amino ligands can be prepared in the method for the present invention
It is detected on material upper surface, illustrates that sulphonic acid ester is successfully coordinated to black phosphorus surface；Anti-microbial property testing result shows the present invention
Prepared two-dimentional black phosphorus nanometer formulation antibacterial effect is apparent, to the growth of gramnegative bacterium and gram-positive bacterium all
With apparent inhibitory action.In the effect system of physiological saline, the antibacterial of the black phosphorus material of 50 μ g/mL amino ligands modification
Antibacterial effect with obvious effects better than black phosphorus before modification is up to 99.10% to the antibiotic rate of Escherichia coli.These experimental datas
Show that the technology of preparing success of amino ligands modification black phosphorus nano material is effective, and this new technology of preparing can be carried effectively
The antibacterial applications performance of black phosphorus nano material is risen, has a wide range of applications potentiality.
Claims (11)
- A kind of 1. black phosphorus nano material of amino ligands surface modification, which is characterized in that the structure of the amino ligands such as formula (I) It is shown：Wherein, R be selected from phenyl, the phenyl optionally further by 0-4 hydroxyl, nitro, amino, aldehyde radical, acyl group, alkoxy, Alkyl, halogen atom substitution；M represents metal ion；X represents ligancy；The nano material is selected from the black phosphorus nano material of two dimension or the quantum dot of black phosphorus.
- 2. black phosphorus nano material according to claim 1, which is characterized in that the R in the amino ligands is selected from by 1-2 Hydroxyl, nitro, amino, C1-6Alkyl, C1-6Alkoxy, the phenyl of halogen substitution.
- 3. nano material according to claim 1 or 2, which is characterized in that the M represents Ti (IV), Cu (II), Ni (II), one kind in Zn (II), Co (II).
- 4. nano material according to claim 1, which is characterized in that the surface of the black phosphorus nano material is by a kind of or more Amino ligands modification shown in kind formula (I).
- 5. the preparation method of amino ligands surface modification black phosphorus nano material according to claim 1, which is characterized in that including Following steps：1) black phosphorus nano material is scattered in organic solvent；2) and then by the amino ligands it is dissolved in organic solvent, heating reaction obtains the receiving through amino ligands modification Rice black phosphorus material.
- 6. preparation method according to claim 5, which is characterized in that the heating reaction is protected from light under inert gas shielding It carries out.
- 7. preparation method according to claim 5, which is characterized in that the reaction temperature is 40-70 DEG C, and the reaction time is 12-24h。
- 8. preparation method according to claim 5, which is characterized in that amino ligands and nano black phosphate material feed intake mole Than for 1：1~15：1.
- 9. preparation method according to claim 5, which is characterized in that the organic solvent be selected from N-Methyl pyrrolidone, N,N-dimethylformamide, N, N- diethylformamides, DMAC N,N' dimethyl acetamide, dimethyl sulfoxide (DMSO), tetrahydrofuran, acetic acid second One or more in ester, acetone, methanol, ethyl alcohol, isopropanol, ethylene glycol, n-butanol, acetonitrile, ether, toluene.
- 10. according to claim 5-9 any one of them preparation methods, which is characterized in that the amino ligands are by will be to ammonia Base benzene sulfonic acid or its corresponding derivative and the solution of metal ion are coordinated to be prepared.
- 11. according to the nano black phosphate material of claim 1-4 any one of them amino ligands surface modifications in antibacterial field Using.
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| CN111482618A (en) * | 2020-04-14 | 2020-08-04 | 西南林业大学 | Method for reducing and loading noble metal by black phosphorus nanosheet |
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