CN103999853A - Application of fluorescence arborization nanometer macromolecule in preparing drug carrier - Google Patents
Application of fluorescence arborization nanometer macromolecule in preparing drug carrier Download PDFInfo
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Abstract
The invention provides application of fluorescence arborization nanometer macromolecule in preparing a drug carrier, application of the fluorescence arborization nanometer macromolecule in preparing a compound drug and the compound drug made of the drug carrier and a hydrophobic drug in a mixing mode, and further provides application of the compound drug in pest control. Pests are fed with the compound drug in a feeding or injecting mode, the arborization compound can serve as the drug carrier to package the drug to enter the cells of the pests quickly, the drug can play a role in the pests, the pesticide effect is enhanced, and non-target pests are effectively killed. The new strategy that the fluorescence arborization nanometer macromolecule serves as the pesticide carrier to be applied in the field of pest control is achieved successfully. The pesticide effect of the pesticide is enhanced through the application, the pest killing range is enlarged, and a new approach for avoiding overusing of chemical pesticide is provided. The fluorescence arborization nanometer macromolecule has very high application value in the fields of agricultural pest control and biology scientific research.
Description
Technical field
The present invention relates to pharmaceutical carrier field, specifically, relate to the application in field of pest control as pharmaceutical carrier of the large molecule of a kind of water soluble fluorescence dendroid nanometer.
Background technology
In recent decades, the excessive use of insecticide causes insect to produce pesticide resistance, and agricultural chemicals residual caused a series of environmental problem, and human and animal healthy and safe formed to very large threat.Therefore, in field of pest control, explore a kind of new method, by pharmaceutical carrier, insecticide is sent in pest body, the cytotoxicity, raising insecticide efficiency, the expansion desinsection scope that strengthen insecticide have caused researchers' concern.In recent years, some nano-carriers, such as polymer/nanoparticle, liposome, dendritic macromole etc. have started to be applied to the research field that medicine transmits.Dendritic macromole has the outstanding characteristics such as the excellent structure such as cavity structure, the modifiable functional group of exhibiting high surface and biocompatibility, immune compatibility, biological degradability due to accurate controlled nanostructured, low dispersiveness, inside, it is being had broad application prospects aspect research of pharmaceutical carrier.
Perylene and derivative thereof have good light, heat, chemical stability, high fluorescence quantum yield, narrow fluorescence emission peak, can separate with cell background fluorescence and excellent dyeability, have been widely used in organic electro-optic device, laser dye and biological fluorescent labeling field.In recent years, this compounds has been applied to biological field, as protein target mark, cell specific marker and genophore etc., yet poorly water-soluble has directly affected it in the application in this field, therefore improves the water-soluble of this compounds and in the aqueous solution, keeps high-fluorescence quantum yield significant.
At present, most insecticides are all hydrophobic, water-soluble very poor in physiological environment, and this has just hindered them and has entered cell, thereby have caused low insecticide efficiency.Conventionally with some organic solvents, (as methyl-sulfoxide, DMSO) dissolve insecticide water-soluble to improve it, but these organic solvents often all has high cell toxicity.In addition, although the dendroid pharmaceutical carrier of former studies all has good water-soluble and biocompatibility, do not have fluorescent characteristic, this has just limited its range of application to a certain extent.Thereby, invent a kind of can fluorescence tracking, dendroid nanometer macromolecule medicament carrier that can wrapping and encapsulating hydrophobic drug, studies this class fluorescence dendroid pharmaceutical carrier in the application of control of insect and biomedicine field, will have very important significance.
Summary of the invention
Not enough for prior art, the object of the present invention is to provide Yi Zhong to using the large molecule of fluorescence dendroid nanometer that perylene diimide derivative and analog thereof be fluorescent core and be applied to field of pest control as pharmaceutical carrier.
For achieving the above object, the invention provides the application of the large molecule of a kind of fluorescence dendroid nanometer in preparing pharmaceutical carrier, the large molecule of described fluorescence dendroid nanometer is the compound shown in formula I:
In formula I, n is the arbitrary natural number between 0-6.
Preferably, the large molecule of described fluorescence dendroid nanometer can also select naphthalene, Bi, perylene, terylene and the derivative thereof of Ppolynuclear aromatic hydrocarbon as fluorescent emission group.
The invention provides a kind of pharmaceutical carrier, its active component is the large molecule of dendroid nanometer, and the large molecule of described dendroid nanometer is the compound shown in formula I:
In formula I, n is the arbitrary natural number between 0-6.
Preferably, the large molecule of described fluorescence dendroid nanometer can also select naphthalene, Bi, perylene, terylene and the derivative thereof of Ppolynuclear aromatic hydrocarbon as fluorescent emission group.
The present invention also provides the application of the large molecule of a kind of fluorescence dendroid nanometer in preparing combination drug, and the large molecule of described fluorescence dendroid nanometer is the compound shown in formula I:
In formula I, n is the arbitrary natural number between 0-6;
Described medicine is hydrophobic drug.
Preferably, the large molecule of described fluorescence dendroid nanometer can also select naphthalene, Bi, perylene, terylene and the derivative thereof of Ppolynuclear aromatic hydrocarbon as fluorescent emission group.
Preferably, described hydrophobic drug is Diacloden.
Preferably, the mol ratio of the large molecule of described fluorescence dendroid nanometer and described medicine is 1:1-80.
The present invention also provides the application of a kind of above-mentioned combination drug aspect control of insect, the large molecule of described fluorescence dendroid nanometer is mixed with described medicine, hatch altogether with the cell of insect again, by the endocytosis of cell, the large molecule of fluorescence dendroid nanometer that carries medicine is entered in live body cultured cell;
Or, the large molecule of described fluorescence dendroid nanometer is mixed with described medicine, by feeding or injecting method, the large molecule of fluorescence dendroid nanometer that carries medicine is entered in pest body.
Along with the increasing of drug concentration, cytotoxicity strengthens; Dendrimer algebraically is higher, stronger to the toxicity of cell.
Compared with prior art, the present invention has the following advantages:
1, the large molecule of such fluorescent functional dendroid nanometer has the characteristics such as good light, heat, chemical stability, structure designability, excellent biocompatibility, cell marking.
2, the large molecule of fluorescent functional dendroid nanometer that the present invention prepares has good biocompatibility and very low cytotoxicity.Molecule periphery carries positively charged amino, can enter living cells, and can wrap up loading hydrophobic drug, form a stable compound, can be used as pharmaceutical carrier transmits medicine to enter living insects cultured cell, significantly improve the cytotoxicity of medicine, can effectively kill insect.This new application has strengthened the drug effect of insecticide, has expanded desinsection scope, for avoiding the excessive use of chemical insecticide that new way is provided.Therefore, such carrier has good using value as a kind of novel fluorescence nano macromolecule medicament carrier at biological scientific research field and agricultural insect pests control field.
3, the large molecule of fluorescent functional dendroid nanometer that the present invention prepares has well water-soluble, can in aqueous environment, wrap up and load hydrophobic drug, form stable compound, reduced the use of organic solvent and the cytotoxicity that application brings thereof.
Accompanying drawing explanation
The chemical structural formula of the large molecule G1 of Fig. 1 fluorescent functional dendroid nanometer;
The chemical structural formula of the large molecule G2 of Fig. 2 fluorescent functional dendroid nanometer;
The chemical structural formula of the large molecule G3 of Fig. 3 fluorescent functional dendroid nanometer;
The structure of the fluorescent core analog of Fig. 4 PDI and alternative PDI;
The chemical structural formula of Fig. 5 Diacloden;
The interactional schematic diagram of Fig. 6 G2 and Diacloden;
The interactional uv absorption spectra of Fig. 7 G2 and Diacloden;
Interactional and the fluorescence spectrum spectrogram of Fig. 8 G2 and Diacloden;
Fig. 9 drips after 400 μ M Diaclodens, the relative intensity of fluorescence of G1-G3 (5.0 μ M);
The test of Figure 10 isothermal titration trace heat, figure A Chinese traditional medicine carrier G1, figure B Chinese traditional medicine carrier G2, figure C Chinese traditional medicine carrier G3;
The interactional thermodynamic parameter of Figure 11 G1-G3 and Diacloden;
Figure 12 G1-G3 is combined rear to Cytotoxic detection with medicine;
The dyeing of Figure 13 G2 insect biological tissue, wherein schemes the brain that A-C is larva, and figure D-F is fat-body, and figure G-I is brain;
Figure 14 G2 enters insect larvae enterocyte micro-imaging figure, wherein, the image of the intestines that figure A, A ' they are the insect larvae after the food that contains G2 of feeding under fluorescence, and figure A ' is G2 image under fluorescence; The feed intestines of insect larvae of normal diet of B;
Figure 15 feeds the insect larvae of G2/ medicine in the lethality of different time sections;
Figure 16 insect larvae of G2/ medicine lethality after 120h of feeding;
The upgrowth situation comparison diagram that Figure 17 feeds larva in G2/ medicine complex and control experiment;
The large molecule of Figure 18 fluorescent functional dendroid nanometer is as the schematic diagram of pharmaceutical carrier.
Embodiment
Following examples are used for illustrating the present invention, but are not used for limiting the scope of the invention.
The preparation of the embodiment 1 large molecule of fluorescent functional dendroid nanometer (G1-G3) pharmaceutical carrier
The large molecule of fluorescent functional dendroid nanometer (G1-G3) pharmaceutical carrier is the document synthesized according to this seminar report.Specific experiment step reference literature:
1、Xu?Z,He?B,Shen?J,et?al.Fluorescent?water-soluble?perylenediimide-cored?cationic?dendrimers:synthesis,optical?properties,and?cell?uptake[J].Chem.Commun.,2013,49(35):3646-3648；
2, the synthetic method of water soluble fluorescence dendritic macromole and application thereof, patent publication No.: 103204999A.
The fluorescent functional dendroid nanometer macromolecular structure formula G1-G3 that adopts said method to make, referring to Fig. 1-3.
The structure of the fluorescent core analog of PDI and alternative PDI has multiple, referring to Fig. 4.
Structure and the sign of embodiment 2 based on the large molecule delivery of particles of fluorescent functional dendroid nanometer
The large molecule of fluorescent functional dendroid nanometer (G1-G3) of the different algebraically of preparing with embodiment 1 is respectively prepared combination drug with Diacloden (chemical structural formula is referring to Fig. 5), and referring to Fig. 6, concrete steps are as follows:
1, the load capacity of the large molecule of fluorescent functional dendroid nanometer (G1-G3) of different algebraically to Diacloden
1) ultra-violet absorption spectrum test: the large molecule of fluorescent functional dendroid nanometer (G1-G3) of the different algebraically of embodiment 1 preparation is formulated as to the solution that concentration is 5 μ M by deionized water respectively, add Diacloden (concentration is 0-400 μ M), sample is carried out to ultra-violet absorption spectrum test.Referring to Fig. 7, ultraviolet absorption peak does not have significant change.
2) fluorescence emission spectrum test: by above-mentioned steps 1) sample solution of preparation carries out fluorescence emission spectrum test.Referring to Fig. 8, in G1-G3 sample solution, add respectively after Diacloden, fluorescence emission spectrum strength obviously strengthens, and is attended by slight blue shift; Referring to Fig. 9, when Diacloden concentration reaches 400 μ M, it is original 225% that the fluorescence intensity of G2, G3 sample solution is all approximately increased to, and it is original 192% that the fluorescence intensity of G1 sample solution is increased to, and experiment shows that G1-G3 has the potential as pharmaceutical carrier.
3) isothermal titration trace heat (ITC) test: the G1-G3 of embodiment 1 preparation is formulated as to the solution that concentration is 65 μ M by deionized water respectively, and Diacloden is formulated as by deionized water the solution that concentration is 138 μ M.Then G1-G3 (250 μ L) is expelled in Diacloden solution (1mL), carries out ITC test.Referring to Figure 10, the binding constant of G1-G3 and Diacloden is respectively 2.07 * 10
5m
-1, 3.98 * 10
5m
-1, 5.45 * 10
5m
-1, show that G1-G3 and Diacloden have moderate affinity, and the ability that G2, G3 are combined with Diacloden is better than G1.Meanwhile, referring to Figure 11, thermodynamic parameter all presents Δ H>0 and Δ G<0, shows between G1-G3 and Diacloden it is mainly non-covalent interaction, as hydrophobic interaction or interaction of hydrogen bond.
2, the sign of the large molecule of fluorescent functional dendroid nanometer (G1-G3)/Diacloden combination drug particle of different algebraically
G1-G3/ Diacloden combination drug particle diameter is measured at 25 ℃ by ZetaSizer Nano-ZS (Malvern Instruments, Southborough, the MA) instrument of Britain Ma Erwen company, all experiment replications 3 times.
The dynamic light scattering data of table 1 G1-G3 in the aqueous solution
The compound water solution size that table 2 G1-G3 and Diacloden form
Referring to table 1, the particle diameter of dendrimer G1-G3 in the aqueous solution is approximately 1-4nm, and they and the Diacloden particle diameter after compound is approximately 100-200nm (referring to table 2), show can be assembled into the nano particle that particle diameter is larger (100-200nm) after dendrimer G1-G3 loads hydrophobic drug Diacloden, and in this particle size range, the large molecule of compound is easy to enter cell by endocytosis, is suitable for cell experiment and experiment made on the living research.
The large molecule of embodiment 3 fluorescent functional dendroid nanometer is as the application of pharmaceutical carrier
The large molecule G1-G3 of fluorescent functional dendroid nanometer is mixed with medicine Diacloden respectively, then hatch altogether with cell, endocytosis by cell makes the dendrimer carrier of packaging medicine enter live body cultured cell, or by the method for the insect of feeding, the dendrimer carrier of packaging medicine is entered in insect bodies inner cell.
Particularly, using the large molecule of fluorescent functional dendroid nanometer as pharmaceutical carrier, be applied to live body cultured cell and living insects:
1, the large molecule of dendroid nanometer is combined the rear toxicity to live body cultured cell with medicine
The large molecule G1-G3 of the fluorescent functional dendroid nanometer compound that medicine Diacloden is made with embodiment 1 respectively with variable concentrations, the mol ratio of the large molecule of fluorescence dendroid nanometer and medicine is 1:1-80, then join in cell culture fluid, hatch (the more long-acting fruit of incubation time is better) after a period of time with cell, such dendrimer performance function vector, parcel drug loading enters cell, is convenient to medicine and plays a role in cell.G1-G3 all shows respectively extremely low cytotoxicity when concentration is 0.5 μ M.The present invention Tali
tMcell viability kit Dead Cell Green measured G1-G3 when 0.5 μ M in conjunction with the toxicity to cell after the medicine Diacloden of variable concentrations.G1-G3 joins in cell culture fluid after mixing with medicine respectively, hatches after 48h with cell, adds the dyestuff Dead Cell Green of mark apoptosis, imaging under fluorescence microscope after 0.5h, and cell nucleus is green expression apoptotic cell rate.Referring to Figure 12, along with the increasing of drug concentration, cytotoxicity strengthens; Dendrimer algebraically is higher, stronger to the toxicity of cell.In the situation that there is no dendrimer carrier, medicine itself significantly reduces the toxicity of cell.Therefore, such dendrimer performance function vector, parcel drug loading enters living insects cultured cell, contributes to medicine to play a role in cell, has strengthened the cytotoxicity of medicine.
2, the large molecule living insects of dendroid nanometer tissue staining
According to above, to the synthesis step of these three kinds of dendrimers, spectral analysis, DLS, ITC and Cytotoxic research, select G2 to study its application study on organs of living beings tissue and insect as pharmaceutical carrier.With G2, carry out the biological tissue dyeing of larva.In culture fluid, dissect insect larva, obtain biological tissue intestines, fat-body, brain.In the culture fluid that contains finite concentration G2, vital staining 1h, then cleans 1h with PBS, washes away the G2 remaining on tissue surface, and film-making is placed on imaging under fluorescence microscope, as shown in figure 13.The tested tissue obtaining can both be by G2 mark, and G2 can enter live body insect tissue effectively.
3, G2 can enter the enterocyte of insect living insects
G2 is admixed to the first-instar young of the insect of feeding in fresh feed, after three days, dissect larva and obtain its intestinal tissue, imaging under fluorescence microscope, as shown in figure 14, can very clearly observe G2 and be present in enterocyte.In addition, grow the not impact of G2 on larva, larva can both normally pupate, sprout wings into adult and produce filial generation.
4, the large molecule bound drug of dendroid nanometer killing insect
Under room temperature, G2 is mixed with medicine, after half an hour, join in insect feedstuff, mix rear second instar larvae of feeding separately cotton bollworm with feed.In 24h, 48h, 72h, 96h, 120h, observe and take pictures, and add up its lethality, two control groups are set altogether, be respectively: water/medicine, water.The insecticidal spectrum of this medicine Diacloden comprises homoptera pest, but does not comprise for example cotton bollworm of lepidoptera pest.As expected results, cotton bollworm larvaes all in control group can be grown by normal growth.Yet referring to Figure 15, after 48h, it is that 66.67%, 96h larval mortality rises to 83.3% that the cotton bollworm larvae lethality of the G2/ medicinal composition of feeding has reached 50%, 72h larval mortality.Referring to Figure 16, when having arrived 120h, larval mortality has surpassed 90%.Now in control group water/medicine, larval mortality is less than 20%.Every larva altogether feed 7.2 μ g medicines and 24 μ g G2.Referring to Figure 17, the larva phenotype that G2/ medicine compound is fed has major defect, and body size is significantly less than control group and polypide blackout, finally dead.Therefore, referring to Figure 18, G2 parcel drug loading enters in pest body inner cell, has significantly improved the toxicity of medicine to cell, has strengthened drug effect, has effectively killed non-target pest, has expanded the control spectrum of agricultural chemicals.
Although, above used general explanation, embodiment and test, the present invention is described in detail, on basis of the present invention, can make some modifications or improvements it, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements, all belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (8)
1. the application of the large molecule of fluorescence dendroid nanometer in preparing pharmaceutical carrier, the large molecule of described fluorescence dendroid nanometer is the compound shown in formula I:
In formula I, n is the arbitrary natural number between 0-6.
2. the application of the large molecule of fluorescence dendroid nanometer in preparing combination drug, the large molecule of described fluorescence dendroid nanometer is the compound shown in formula I:
In formula I, n is the arbitrary natural number between 0-6;
Described medicine is hydrophobic drug.
3. application according to claim 2, is characterized in that, described hydrophobic drug is Diacloden.
4. a pharmaceutical carrier, its active component is the large molecule of dendroid nanometer, the large molecule of described dendroid nanometer is the compound shown in formula I:
In formula I, n is the arbitrary natural number between 0-6.
5. a combination drug, is characterized in that, by pharmaceutical carrier claimed in claim 4 and hydrophobic drug, is mixed.
6. combination drug according to claim 5, is characterized in that, described hydrophobic drug is Diacloden.
7. combination drug according to claim 6, is characterized in that, the mol ratio of the large molecule of described fluorescence dendroid nanometer and described hydrophobic drug is 1:1-80.
8. the combination drug as described in as arbitrary in the claim 5-7 application aspect control of insect, the large molecule of described fluorescence dendroid nanometer is mixed with described hydrophobic drug, hatch altogether with the cell of insect again, by the endocytosis of cell, the large molecule of fluorescence dendroid nanometer that carries medicine is entered in live body cultured cell;
Or, the large molecule of described fluorescence dendroid nanometer is mixed with described medicine, by feeding or injecting method, the large molecule of fluorescence dendroid nanometer that carries medicine is entered in pest body.
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| CN115299445B (en) * | 2022-10-08 | 2023-02-03 | 云南省烟草公司昆明市公司 | Compound solution for improving induced disease resistance of lentinan to plants, preparation method and method thereof, and method for preventing and controlling viruses in plants in field |
| CN115299445A (en) * | 2022-10-08 | 2022-11-08 | 云南省烟草公司昆明市公司 | Compound solution for improving induced disease resistance of lentinan to plants, preparation method and method thereof, and method for preventing and controlling viruses in plants in field |
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