CN105477643A - Organism siRNA drug carrier system marked by quantum dots - Google Patents
Organism siRNA drug carrier system marked by quantum dots Download PDFInfo
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- CN105477643A CN105477643A CN201510961956.2A CN201510961956A CN105477643A CN 105477643 A CN105477643 A CN 105477643A CN 201510961956 A CN201510961956 A CN 201510961956A CN 105477643 A CN105477643 A CN 105477643A
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/713—Double-stranded nucleic acids or oligonucleotides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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Abstract
The invention discloses an organism siRNA drug carrier system marked by quantum dots. The organism siRNA drug carrier system is characterized by comprising a PAMAM molecule, wherein the PAMAM molecule is bonded with an siRNA containing 21 base-pairs, and hyaluronic acid molecules which form a PAMAM/HA/siRNA compound system; the hyaluronic acid molecules of the PAMAM/HA/siRNA compound system are further connected with PEG (NH2)2 molecules, wherein PEG (NH2)2 is connected with the quantum dots to form the organism siRNA drug carrier system marked by the quantum dots. According to the invention, the quantum dots and the PAMAM/HA/siRNA compound system are connected in a pioneering manner, so that a drug-targeted site novel method is increased, a novel method for tracking the acting path of the drug is increased, different quantum dots are marked according to different siRNAs, and due to the different sizes and the spectral characteristics of the quantum dots, areas with different natures can be detected by only selecting one exciting light source, therefore, the practical detection process is greatly simplified, and the requirements on the exciting emission source are reduced.
Description
Technical field
The present invention relates to a kind of pharmaceutical carrier, especially relate to a kind of quantum dot-labeled organism siRNA drug carrier.
Background technology
RNA interference is a kind of gene silencing mechanism of endogenous cellular, RNA interference is a selectively Silencing Mechanisms, but the ability that external source siRNA enters cell is very low, this theory on treatment for it is an obstacle, how designing the approach that effective siRNA enters cell, is a very crucial factor for disease therapy.Enter in the approach of cell at siRNA, transmit carrier must effectively can with nucleic acid compound, and contribute to overcoming the obstacle entering cell, and less cytotoxicity etc.
At present, a series of molecule, comprises liposome, and polypeptide etc. have been proved them at the effectiveness transmitting DNA and RNA.Successful siRNA carrier needs follow nucleic acid compound, needs with positive charge, containing high buffer capacity, shows low cytotoxicity, and contain can adorned chemical group, or modifies other molecular radical.Research shows, cationic-liposome DC-Chol/DOPE has been successfully used to the interior transmission of body of DNA medicine.It is equally efficient with commercial transfection reagent lipofectamine2000 to the transfection of Hela cell that DC-Chol mediates siRNA, although toxicity is little compared with lipofectamine2000, is also larger.Make siRNA enter the method for cell, a kind of is that the template of DNA or RNA transmitting coding siRNA sequence is gone inside cell, then proceeds to into siRNA.These siRNA expression systems based on DNA-and RNA-coded sequence are carried into cell by plasmid or virus.Another kind directly carries the method that siRNA enters cell.Directly carry siRNA to enter in the method for cell and there is poor compatibility, there is the defect of cytotoxicity and targeting difference.
Summary of the invention
The object of this invention is to provide a kind of quantum dot-labeled organism siRNA drug carrier system, initiative connects quantum dot PAMAM/HA/siRNA compound system, add the new method in drug targeting site, follow the tracks of the new method of pathways of drug action, it has simplification tracking and monitoring process, reduces the requirement of label to laser emitting source, follow the tracks of multiple action target point simultaneously, realize the tracking of drug effect target spot, have save time, efficient, highly sensitive advantage.
For solving the problems of the technologies described above, the invention provides a kind of quantum dot-labeled organism siRNA drug carrier system, it comprises the PAMAM molecule of a part, this PAMAM molecule is combined with double-strand siRNA and hyaluronan molecule formation PAMAM/HA/siRNA compound system that one contains 21 base pairs;
Hyaluronan molecule in described PAMAM/HA/siRNA compound system also connects PEG (NH
2)
2molecule, this PEG (NH
2)
2quantum dot-labeled organism siRNA drug carrier system is connected to form with quantum dot.
Described quantum dot is CdSe quantum dot, and with carboxyl in described CdSe quantum dot, described CdSe quantum dot is by this carboxyl and PEG (NH
2)
2on amino connect.
Described hyaluronic acid is combined with described PAMAM molecule by the effect of electrostatic attraction.
Described hyaluronic electric charge and described PAMAM molecule charge are than being 0.4-0.6.
Described PAMAM is dissolved in pH and is connected with double-strand siRNA by the effect between positive and negative charge in the buffer of 7.
In described PAMAM/HA/siRNA compound system, hyaluronic carboxyl is rear and PEG-(NH by DCC and NHS activation
2)
2one amino to combine, obtain (PAMAM/HA/siRNA)-PEG-NH
2.
5 × 10 are diluted in after described quantum dot solution is purified
-2phosphoric acid is received in buffer, gets appropriate (PAMAM/HA/siRNA)-PEG-NH
2add in quantum dot solution, stirred at ambient temperature reaction 0.2h, forms quantum dot-labeled PAMAM/HA/siRNA compound system.
The present invention has following Advantageous Effects:
Initiative of the present invention quantum dot PAMAM/HA/siRNA compound system is connected, add the new method in drug targeting site, follow the tracks of the new method of pathways of drug action, its quantum dot different according to different siRNA labellings, because the size of quantum dot, spectral characteristic are different, only need select a kind of excitation source, just can realize detecting region of different nature, thus enormously simplify the process of actual detection, reduce the requirement to laser emitting source.Same principle, quantum dot can become screening siRNA, find the siRNA target spot powerful at cell position, and provides very valuable information for the research of mechanism of drug action.Usually, during medicine generation drug effect, except same target molecule combines, also can be combined by other some molecules in body, have side effects, utilize the quantum dot of different colours fluorescence (or optical spectrum encoded microgranule), just can high flux ground, concurrently research and drug effect, comprise all molecules of target molecule, save time, efficient, highly sensitive.
Accompanying drawing explanation
Fig. 1 is the electromicroscopic photograph figure of PAMAM/HA/siRNA complex systems of the present invention;
Fig. 2 is quantum dot-labeled organism siRNA drug carrier system electromicroscopic photograph figure of the present invention.
Detailed description of the invention
The preparation of embodiment 1 quantum dot
Adopt TOPO as organic coordination solvent, with Cd (CH
3)
2with TOP-Se as pre-reaction material, be injected in 350 DEG C of TOPO solution of vigorous stirring successively, generate a large amount of CdSe nano-particle nucleus at short notice, then be cooled to rapidly 240 DEG C and continue nucleation to stop nano-particle, be warmed up to 260 DEG C-280 DEG C subsequently and maintain a period of time, according to its absorption spectrum side crystal growth, when crystal growth is to required size, reactant liquor is cooled to 60 DEG C.Adding butanols prevents TOPO from solidifying, and adds excessive methanol subsequently, because CdSe nano-particle is insoluble to methanol, can obtain CdSe nano-particle by centrifugal change, can post size controlling between 2.4-13 nanometer by changing temperature.
The present invention adopts TGA or mercaptoethylmaine as stabilizing agent, directly synthesize CdSe semiconductor-quantum-point (quantum yield is 30%, and quantum yield is tried to achieve by comparing nano-particle solution and the rhodamine 6G aqueous solution transmitting integration between 480 ~ 850nm under excitation wavelength with consistent optical density (OD)) in aqueous.
The present invention not only solves the water solubility problems of semi-conductor nano particles, and due to one deck TGA or mercaptoethylmaine coated in the outside of nanoparticle, by means of the functional group of its outer end, can combine with biomolecule, thus reach the object of direct labelling biomolecule.
The connection of embodiment 2PAMAM molecule and the double-strand siRNA containing 21 base pairs
The PAMAM of the ethylenediamine core that the present invention adopts, namely PAMAM is amide imines surface, with positive charge under the DPBS condition of about PH=7.Make it can be combined by electrostatic interaction with some particles with negative charge, can certainly by chemical bond by the amino of end and other point of sub-connection.
PAMAM molecule is as follows with the concrete steps of the connection of the double-strand siRNA containing 21 base pairs:
Step one: prepare certain density PAMAM
Get 30 μ l and contain 10wt.% methanol solution in the tube pipe of 2ml, dry about 10min in vacuum drying oven, removing methanol.Calculate the quality of PAMAM:
Step 2: compound concentration is the siRNA of 8 μm of ol.
By the centrifugal general 1min of dry siRNA (1OD) new for a pipe, then the DEPC water of 150 μ l is added, be configured to the siRNA that concentration is 20 μ l, get in the tube pipe of siRNA to the 1.5ml of 20 μMs of 10 μ l, being diluted to volume with DEPC water is 25 μ l, and now the concentration of siRNA is 8 μMs.
Step 3: preparation PAMAM/siRNA complex systems
The PAMAM molecular surface of a part (G4) is with 64 positive charges in the DPBS of PH=6.8, and a double-strand siRNA containing 21 base pairs is with 42 negative charges, and due to the electrostatic interaction of positive and negative charge, both meetings combine.
Preparation positive and negative charge ratio is the complex of the PAMAM/siRNA of 5, and the quantitative proportion of positive and negative charge is also the ratio of the quantity of the phosphate group (P) of PAMAM outermost end amino (N) and siRNA: N/P.According to the ratio of this PAMAM outermost end amino (N) with the ratio of the quantity of the phosphate group (P) of siRNA, the amount of the PAMAM added just can be calculated.
The PAMAM molecule of the connection of the double-strand siRNA of embodiment 3 containing 21 base pairs is connected with hyaluronic acid further, forms PAMAM/HA/siRNA complex systems.
In order to reach the object of the targeting of siRNA medicine, hyaluronic acid is designed into pharmaceutical carrier.Hyaluronic acid is a kind of macromolecular mucopolysaccharide.The basic construction unit of hyaluronic acid is made up of two parts, and N-acetyl-D glucosamine and D glucuronic acid are formed, and are the main constituent of extracellular matrix.
Obtain solution, the ratio of the amount of substance of the positive charge of hyaluronic negative charge and PAMAM is made to be respectively 0.5, C/N is utilized to represent the ratio of the negative charge of HA and the positive charge of PAMAM, wherein, hyaluronic acid (HA) dissolves with DPBS, the concentration of preparation is respectively 0.4mg/ml, can carry out the preparation of PAMAM/HA/siRNA complex systems according to the ratio of the positive charge of the negative charge and PAMAM that show HA.
The concrete preparation process of PAMAM/HA/siRNA complex systems is as follows: the preparation process adding the order of sample and sample is as follows:
Step one: get 1 Tube pipe, get in siRNA5 μ l to the Tube pipe of 8 μMs, make its C/N=1.0, wherein C/N represents the ratio of the negative charge of HA and the positive charge of PAMAM;
Step 2: add PAMAM, the volume adding the PAMAM of 1ml/mg is respectively 3.73 μ l.Only 15min is put.
Step 3: add HA, add concentration be 0.1mg/ml HA amount be 6.8 μ l.Only 15min is put.
Step 4: Xiang Guanzhong adds DPBS, makes the volume in pipe be all 40 μ l mutually, final formation PAMAM/HA/siRNA compound system.
Embodiment 4 quantum dot is connected with hyaluronic in PAMAM/HA/siRNA compound system
Carboxyl hyaluronic in PAMAM/HA/siRNA compound system is activated rear and PEG-(NH by DCC and NHS
2)
2one amino to combine, obtain (PAMAM/HA/siRNA)-PEG-NH
2.Concrete grammar is as follows: get a certain amount of PAMAM/HA/siRNA compound system and be dissolved in 1mLDMSO, add a certain amount of DCC and NHS, add 100mgPEG-(NH under stirring
2)
2, room temperature reaction 2h.Add 8mL water, cross and filter insoluble matter, supernatant lyophilization, the dry thing of washed with diethylether, obtains (PAMAM/HA/siRNA)-PEG-NH
2.5 × 10 are diluted in after CdSe quantum dot solution is purified
-2phosphoric acid is received in buffer, gets appropriate (PAMAM/HA/siRNA)-PEG-NH
2add in CdSe solution, stirred at ambient temperature reaction 0.2h, form quantum dot-labeled PAMAM/HA/siRNA compound system, i.e. quantum dot-labeled organism siRNA drug carrier system of the present invention, please refer to the electromicroscopic photograph figure of quantum dot-labeled organism siRNA drug carrier system of the present invention shown in Fig. 1.
The water-soluble quantum dot of band carboxyl of preparation is connected with the hyaluronan molecule in PAMAM/HA/siRNA compound system by the present invention, and hyalomitome molecule is combined with PAMAM molecule and connects, PAMAM molecule and contain the connection of double-strand siRNA of 21 base pairs.Like this, by the labelling of quantum dot, can follow the trail of and the position of the transport path of the double-strand siRNA of show tags and its effect and target spot, better disclose the interference mechanism of double-strand siRNA as drug targets.
The present invention is by the medicament carrier system of fluorescent probe labelling and cell (Hela) Dual culture in the medium under aseptic condition, uses the distribution situation of quantum dot in fluorescence microscope cell at set intervals.
The present invention can be different according to different siRNA labellings quantum dot, because the size of quantum dot, spectral characteristic are different, only need select a kind of excitation source, just can realize detecting region of different nature, thus enormously simplify the process of actual detection, reduce the requirement to laser emitting source.Same principle, quantum dot can become screening siRNA, find the siRNA target spot powerful at cell position, and provides very valuable information for the research of mechanism of drug action.Usually, during medicine generation drug effect, except same target molecule combines, also can be combined by other some molecules in body, have side effects, utilize the quantum dot of different colours fluorescence (or optical spectrum encoded microgranule), just can high flux ground, concurrently research and drug effect, comprise all molecules of target molecule, save time, efficient, highly sensitive.
These are only preferred embodiment of the present invention, limiting technical scope of the invention process when not being able to this, therefore all with reference to description of the present invention do simple equivalence change with modify, all still should belong to protection scope of the present invention.
Claims (7)
1. a quantum dot-labeled organism siRNA drug carrier system, it is characterized in that the PAMAM molecule comprising a part, this PAMAM molecule is combined with double-strand siRNA and hyaluronan molecule formation PAMAM/HA/siRNA compound system that one contains 21 base pairs;
Hyaluronan molecule in described PAMAM/HA/siRNA compound system also connects PEG (NH
2)
2molecule, this PEG (NH
2)
2quantum dot-labeled organism siRNA drug carrier system is connected to form with quantum dot.
2. quantum dot-labeled organism siRNA drug carrier system according to claim 1, is characterized in that,
Described quantum dot is CdSe quantum dot, and with carboxyl in described CdSe quantum dot, described CdSe quantum dot is by this carboxyl and PEG (NH
2)
2on amino connect.
3. quantum dot-labeled organism siRNA drug carrier system according to claim 1, is characterized in that,
Described hyaluronic acid is combined with described PAMAM molecule by the effect of electrostatic attraction.
4. quantum dot-labeled organism siRNA drug carrier system according to claim 3, is characterized in that,
Described hyaluronic electric charge and described PAMAM molecule charge are than being 0.4-0.6.
5. quantum dot-labeled organism siRNA drug carrier system according to claim 1, is characterized in that,
Described PAMAM is dissolved in pH and is connected with double-strand siRNA by the effect between positive and negative charge in the buffer of 7.
6. quantum dot-labeled organism siRNA drug carrier system according to claim 1, is characterized in that,
In described PAMAM/HA/siRNA compound system, hyaluronic carboxyl is rear and PEG-(NH by DCC and NHS activation
2)
2one amino to combine, obtain (PAMAM/HA/siRNA)-PEG-NH
2.
7. quantum dot-labeled organism siRNA drug carrier system according to claim 6, is characterized in that,
5 × 10 are diluted in after described quantum dot solution is purified
-2phosphoric acid is received in buffer, gets appropriate (PAMAM/HA/siRNA)-PEG-NH
2add in quantum dot solution, stirred at ambient temperature reaction 0.2h, forms quantum dot-labeled PAMAM/HA/siRNA compound system.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107115320A (en) * | 2017-04-13 | 2017-09-01 | 徐州医科大学附属医院 | A kind of targeted nano granule for loading Temozolomide and preparation method thereof |
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| CN101241140A (en) * | 2008-03-13 | 2008-08-13 | 上海交通大学 | Quantum dot mark based immune blotting detection method |
| CN102552132A (en) * | 2012-02-07 | 2012-07-11 | 苏州大学 | Folic acid-modified cis-platinum targeted nonionic surfactant vesicle and preparation method thereof |
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Cited By (2)
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| CN107115320A (en) * | 2017-04-13 | 2017-09-01 | 徐州医科大学附属医院 | A kind of targeted nano granule for loading Temozolomide and preparation method thereof |
| CN107115320B (en) * | 2017-04-13 | 2019-11-26 | 徐州医科大学附属医院 | A kind of targeted nano granule and preparation method thereof loading Temozolomide |
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Application publication date: 20160413 |