CN109172543A - A kind of novel quercetin nano preparation and preparation method thereof - Google Patents
A kind of novel quercetin nano preparation and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of novel quercetin nano preparations and preparation method thereof.The novel quercetin nano preparation is made of Sodium Hyaluronate and Quercetin.Quercetin and Hyal powder are mixed and be fully ground first, the nanosuspension for adding distilled water to be mixed initially carries out Probe Ultrasonic Searching with ultrasonic cell disintegration instrument to get novel quercetin nano preparation.Novel quercetin nano preparation of the present invention has good particle size and drugloading rate, significantly enhance the dissolubility and bioavilability of hydrophobic drug Quercetin, not only passive target can be realized by tumor locus EPR effect, moreover it is possible to pass through the active targeting of the receptor-mediated realization tumour cell of hyaluronic acid.The preparation method of the novel quercetin nano preparation is easy to operate, does not use organic solvent and chemical reagent, avoids residual solvent and bring potential toxic side effect, be easy to large-scale industrial production.
Description
Technical field
The present invention relates to medical medicine fields, and in particular to a kind of novel quercetin nano preparation and preparation method thereof.
Background technique
Quercetin (Quercetin, QUT) also known as quercetin, Quercetin are a kind of natural Huangs for being widely present in nature
Ketone compounds are present in the flower, leaf, fruit of many plants, such as sophora flower, the root bark of tree peony, chrysanthemum；Exist mostly in the form of glucoside,
At rutin (rutin), quercitrin, content is higher in the plants such as hyperin.Because its with anti-oxidant, antiviral and antitumor,
Anti-inflammatory, Cardioprotective, neuroprotection, eye protection, Bones and joints protection etc. a variety of pharmacotoxicological effects and biological effect and by
Concern, wherein the most significant with anti-tumor activity.Pharmaceutical research show Quercetin mainly pass through inhibit tumor cell proliferation,
Transfer, control cell cycle promote the mechanism hair such as apoptosis of tumor cells and the signal path and the protein expression that interfere tumour cell
Wave anticancer function.Although Quercetin has shown good potential applicability in clinical practice in medical domain, because of its poorly water-soluble, mouth
Absorption difference is taken, bioavilability is relatively low, limits the possibility of its further clinical development.Therefore, it finds a kind of new effective
Drug delivery system is to improve the project of the bioavilability and target position delivery efficiency of Quercetin as current primary study.
The appearance of new nanometer formulation technology provides new method to solve this problem, and nanometer formulation is made in drug
Afterwards, can have the characteristics that controlled release, sustained release, targeting, curative effect improve and toxic side effect reduces.Common carrier material can be divided into life
Biodegradable material and biological non-degradable material, wherein biodegradable material is obtained due to its good biocompatibility
It is widely applied.
Hyaluronic acid (hyaluronic acid, HA) is a kind of negatively charged biodegradable linear polymeric polysaccharide,
It is widely used in drug delivery system as good targeting material.It is cytoplasm and extracellular matrix it is main at
Point, there is good biocompatibility, hydrophily, stability and degradable in vivo, contain various active group in structure,
Be conducive to further chemical modification.In addition, the Specific marker of hyaluronic acid and tumor cell surface overexpression, such as
CD44 affinity with higher.CD44 is a kind of transmembrane glycoprotein, is the most important hyaluronic acid receptor of cell surface, multinomial
Research shows that it has expression, such as lung carcinoma cell, breast cancer cell in Several Kinds of Malignancy cell surface.The work of CD44 receptor
There is some difference for distribution of the change state in normal and tumor microenvironment, and the CD44 receptor of the state of activation is in tumor microenvironment
Distribution of specific.The native ligand of CD44 is hyaluronic acid, studies have shown that with CD44 receptor specificity can occur for hyaluronic acid
In conjunction with, based on hyaluronic acid be material administration nano-drug administration system have fluorescent dye with tumour-specific targeting effect, tumor locus can be reinforced
Drug accumulation reduces dosage and reduces toxic side effect to improve drug concentration.But many deliverings based on hyaluronic acid
System is directed to the chemical modification of hyaluronic acid, and the chemical modification of hyaluronan molecule will affect the spy of itself and CD44 receptor
The opposite sex combines, and chemical modification process may use the organic solvent and chemical reagent for having genotoxic potential.
The present invention passes through the multiple non-covalent work between Linear Polymer hyaluronan and insoluble drug Quercetin
It exerts oneself to construct safe and effective novel quercetin nano preparation, wherein noncovalent interaction power mainly includes hydrogen bond action, Fan De
Magnificent power and hydrophobic interaction.The novel quercetin nano preparation preparation manipulation is simple, has ideal particle size
And drugloading rate, and without using any organic solvent and surfactant.Hyalomitome in the novel quercetin nano preparation
Acid without chemical modification there is good tumour cell to target ability, is expected to improve the bioavilability of Quercetin, improves Mongolian oak
The tumor locus targeted delivery efficiency of Pi Su, enhances its antitumor curative effect, and reduce toxic side effect.
Summary of the invention
The purpose of the present invention is to provide a kind of novel quercetin nano preparations, on the one hand improve bioavilability, another
Aspect improves its tumor-targeting, heightens the effect of a treatment, and reduces toxic side effect.The novel quercetin nano preparation only by Quercetin and thoroughly
Bright matter acid sodium composition.
It is a further object of the present invention to provide the preparation methods of novel quercetin nano preparation.The preparation manipulation is simple, easily
In large-scale production.Without using any surfactant, organic solvent and chemical reagent, its safety is substantially increased.
Novel quercetin nano preparation of the present invention is by hy-drophilic polysaccharide Sodium Hyaluronate and insoluble drug quercitrin
The preferred mass ratio of element composition, the insoluble drug Quercetin and hy-drophilic polysaccharide Sodium Hyaluronate is 1:2~1:9.
The purpose of the present invention can be achieved through the following technical solutions:
Step 1: weighing Sodium Hyaluronate and Quercetin 1:2~1:9 in mass ratio and be sufficiently mixed, then sufficiently ground
Mill.4~12min of every grinding, 1~8min of pause is re-mixed, after this process operates 2~5 times, in 50~70 DEG C of baking ovens
Dry 3~8min, the process for re-mixing and grinding reciprocal 3~6 times, totally 40~120min.
Step 2: weighing the mixed-powder that a certain amount of step 1 obtains and mixed with distilled water, stirred under the conditions of room temperature is protected from light
20~60min is mixed, the initial nanosuspension that concentration is 0.02~8mg/mL is obtained.
Step 3: the initial nanosuspension that step 2 is acquired, with ultrasonic cell disintegration instrument 5~20min of ultrasound, i.e.,
Obtaining novel quercetin nano preparation, the power of the ultrasonic cell disintegration instrument is 100~300W, the Probe Ultrasonic Searching time is 3~
20min, wherein ultrasonic every 5~20s of work time, 5~20s is to get novel quercetin nano preparation for interval.
Step 4: novel quercetin nano preparation is marked with Green fluorescent dye Coumarin-6, using laser confocal scanning
Micro- sem observation cellular uptake situation.
It is an advantage of the invention that using Sodium Hyaluronate can with Quercetin occur noncovalent interaction formed nanoparticle come
Prepare novel quercetin nano preparation.Sodium Hyaluronate has good biocompatibility, degradable in vivo and without immunogene
Property, the water solubility for containing drug is not only improved, the dispersion stabilization of drug in water is increased, also ensures novel Quercetin
The internal safety of nanometer formulation, while can also be specifically bound with the CD44 receptor on malignant cell surface.In addition,
The novel quercetin nano preparation preparation manipulation simple possible, repeatability is good, and drugloading rate is high, is not involved with any organic
Solvent, surfactant and chemical reagent can avoid the potential toxic side effect of residual solvent bring.
Novel quercetin nano preparation prepared by the present invention increases the dissolution rate and solubility of Quercetin significantly,
And there is good cancer target performance.Mass ratio by changing drug and Sodium Hyaluronate can the novel Quercetin of Effective Regulation
The partial size and drugloading rate of nanometer formulation, the drugloading rate of novel quercetin nano preparation prepared by the present invention is up to 15% or more.
Detailed description of the invention
Fig. 1 is the outside drawing of novel quercetin nano preparation
Fig. 2 is the grain size distribution of novel quercetin nano preparation
Fig. 3 is the external release profile of novel quercetin nano preparation
Fig. 4 is the thermogram of Quercetin bulk pharmaceutical chemicals and novel quercetin nano preparation
Fig. 5 is the results of FT-IR figure of different preparations
Fig. 6 is the cell toxicity test after different preparations are handled for 24 hours
Fig. 7 is cellular uptake fluorescence microscope figure
Fig. 8 is the gross tumor volume size figure of 4T1 tumor-bearing mice
Specific embodiment
The present invention is described in more detail by the following examples:
Embodiment:
1. the preparation of novel quercetin nano preparation
The mixed-powder of quercetin nano preparation is obtained using improvement polishing.By 50mg Hyal powder and 10mg
Quercetin powder is uniformly mixed, after being fully ground 15min, the dry 5min in 70 DEG C of baking ovens.The operating process is repeated four times.Claim
The mixed-powder that 12mg is prepared is taken, 3mL distilled water is added, room temperature is protected from light stirring 30min, and revolving speed 400r/min will be obtained
Initial nanosuspension be transferred in 5mL EP pipe.Probe Ultrasonic Searching, ultrasound condition are as follows: function are carried out using ultrasonic cell disintegration instrument
Rate 150W, ultrasonic time 5min, the every work 10s interval 5s of ultrasound is to get novel quercetin nano preparation.The novel quercitrin of gained
The appearance of plain nanometer formulation is shown in Fig. 1；Droplet measurement result is shown in Fig. 2.As seen from the figure, the average grain diameter of novel quercetin nano preparation
About 200nm.The encapsulation rate of novel quercetin nano preparation is (86.2 ± 6.8) %, and drugloading rate is (13.8 ± 1.4) %.
2. release in vitro behavior is investigated
The vitro drug release of novel quercetin nano preparation is investigated using dialysis, precision measures the novel quercitrin of 1mL
Plain nanometer formulation and each three parts of Quercetin suspension, are placed in activated bag filter that (the molecule interception of bag filter is 8000-
14000Da), it immerses in the conical flask equipped with PBS (pH=7.4) of the 40mL containing 3.0%SDS, in 37 ± 0.5 DEG C, 120r/min
Constant temperature oscillator in carry out release in vitro investigation.According to preset point in time sampling, while supplementing corresponding isothermal equivalent
Fresh dissolution medium, by ultraviolet spectrometry light method measure 374nm place absorbance A value, according to absorbance result calculate its tire out
Product release rate.As a result see that Fig. 3, the drug dissolution of novel quercetin nano preparation are significantly improved.
3. Differential Scanning Calorimetry analyzes (DSC)
Take appropriate Quercetin bulk pharmaceutical chemicals and novel quercetin nano preparation to carry out DSC scanning analysis respectively (see Fig. 4).It is tied
Fruit shows do not occur the characteristic absorption peak of Quercetin in novel quercetin nano preparation, this shows Quercetin in novel Mongolian oak
Exist in skin element nanometer formulation with amorphous forms.
4. IR spectrum scanning
After taking appropriate Quercetin bulk pharmaceutical chemicals, novel quercetin nano preparation and potassium bromide mixed pressuring plate respectively, carry out infrared
Spectroscopic assay (see Fig. 5).
5. cytotoxicity experiment
Novel quercetin nano preparation is detected to the inhibiting effect of mouse mastopathy cell 4T1 using mtt assay.Take logarithm raw
Long-term 4T1 cell, with 7 × 104The cell concentration of a/mL is inoculated in 96 orifice plates, in 37 DEG C, 5%CO2It is cultivated in incubator
Overnight.It is respectively set blank group, control group and experimental group (the Quercetin suspension, new of 5 μ g/mL, 20 μ g/mL, 80 μ g/mL
Type quercetin nano preparation).96 orifice plates are taken out, old culture medium, the novel quercetin nano system of every group of addition various concentration are given up
Agent continues culture for 24 hours, adds the serum free medium containing MTT (5mg/mL) solution, is protected from light in incubator and is incubated for 4h.Then it is added
DMSO solution dissolves first a ceremonial jade-ladle, used in libation, measures its OD value at 490nm wavelength with microplate reader.
In addition, interact to verify the specificity of hyaluronic acid and the highly expressed CD44 receptor of 4T1 cell surface, it will
4T1 cell is inoculated in 96 orifice plates by same concentration, is placed in overnight incubation in incubator.Give up old culture medium, high concentration is added
Free hyaluronic acid solution pretreatment 2h to block CD44 receptor add the novel quercetin nano preparation of various concentration
Continue culture for 24 hours.Remaining operation is consistent with cell toxicity test, calculates its cell inhibitory rate.See Fig. 6 the result shows that, with quercitrin
Plain suspension compares, and the cell inhibitory rate of novel quercetin nano preparation significantly improves and in concentration accordance with tolerance.However in CD44
After receptor is blocked by the hyaluronic acid of high concentration, the cell inhibitory rate of novel quercetin nano preparation has obvious decline to become
Gesture.This demonstrate the CD44 receptors that novel quercetin nano preparation can specifically bind 4T1 cell surface.
6. the fluorescence microscope of cellular uptake nanometer formulation
Novel quercetin nano preparation is marked with fat-soluble fluorescent dye Coumarin-6, it is micro- by laser confocal scanning
The novel quercetin nano preparation of sem observation enters the fluorescence intensity of cell.For Receptor Competition Inhibition test, control group is perfume
The novel quercetin nano preparation that legumin -6 marks, experimental group are free hyaluronic acid+novel quercetin nano system of high concentration
Agent.Firstly, pre-processing 2h with free hyaluronic acid, as receptor blocking pharmacon, the Coumarin-6 label of equivalent is then added
Novel quercetin nano preparation.The 4T1 cell of logarithmic growth phase, with every hole 1 × 105It is burnt that a cell concentration is inoculated in copolymerization
In culture dish, in 37 DEG C, 5%CO2It is incubated overnight in incubator, is then located respectively in the way of experimental group and control group
Reason.30min is cultivated in incubator, gives up old culture medium, is washed 3 times with PBS solution, cell is fixed with 4% paraformaldehyde, most
The fluorescence intensity of two groups of cells is observed under Fluorescence laser confocal scanning microscope afterwards.As a result as shown in fig. 7, control group (A)
Fluorescence intensity to be significantly stronger than experimental group (B), illustrate high concentration dissociate hyaluronic acid competitively press down as receptor blocking pharmacon
The CD44 receptor that 4T1 cell shows has been made, 4T1 cell can have been significantly reduced, novel quercetin nano preparation is marked to Coumarin-6
Intake.As a result further demonstrating novel quercetin nano preparation can be swollen by the receptor-mediated cell endocytic entrance of CD44
Oncocyte is enriched with drug in specific lesions position, to improve oncotherapy effect.
7. the zoopery of novel quercetin nano preparation
By in novel quercetin nano preparation tail vein injection to 4T1 tumor-bearing mice body, treats 16 days, measure lotus knurl daily
The weight and tumor size of mouse are compared with the 4T1 tumor-bearing mice for doing same treatment processing with Quercetin bulk pharmaceutical chemicals, such as scheme
Shown in 8, significantly less than Quercetin bulk pharmaceutical chemicals group, this shows novel the mouse tumor volume of novel quercetin nano preparation for treating group
Quercetin nano preparation has more obvious anti-tumor effect than Quercetin bulk pharmaceutical chemicals.
Claims (4)
1. a kind of novel quercetin nano preparation, it is characterised in that: the drug-loading system is made of Sodium Hyaluronate and Quercetin, institute
The Sodium Hyaluronate molecular weight stated is 20000~500000Da.
2. a kind of novel quercetin nano preparation according to claim 1, it is characterised in that: the Quercetin with it is transparent
The preferred mass ratio of matter acid sodium is 1:2~1:9.
3. a kind of novel quercetin nano preparation according to claim 1, it is characterised in that its average grain diameter be 50nm~
500nm。
4. a kind of preparation method of novel quercetin nano preparation according to claim 1, it is characterised in that including following
Step:
(1) appropriate Quercetin and Sodium Hyaluronate are weighed according to the ratio of 1:2~1:9, be uniformly mixed, obtain Quercetin with it is transparent
The mixture of matter acid sodium；
(2) after mixture obtained by step (1) being fully ground 2~15min, dry 2~10min；
(3) operation of step (2) is repeated into 2~6 times, i.e. acquisition Quercetin and Sodium Hyaluronate mixed-powder；
(4) it weighs the resulting Quercetin of a certain amount of step (3) and Sodium Hyaluronate mixed-powder is mixed with distilled water, in room temperature item
Stirring is protected from light under part, gained suspension carries out Probe Ultrasonic Searching with ultrasonic cell disintegration instrument to get novel quercetin nano preparation.
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Cited By (4)
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| CN112138169A (en) * | 2020-09-14 | 2020-12-29 | 广东药科大学 | Application of natural polysaccharide in increasing solubility of insoluble drug |
| CN113304264A (en) * | 2021-06-13 | 2021-08-27 | 重庆医科大学 | Quercetin tellurium nanoparticles and preparation method thereof |
| CN116966151A (en) * | 2023-09-21 | 2023-10-31 | 河南中医药大学 | Preparation method and application of multiple-response doxorubicin-quercetin co-delivery system |
| GB2624638A (en) * | 2022-11-22 | 2024-05-29 | Landa Labs 2012 Ltd | Nano-Carriers for Drug Delivery and Methods of Preparing the Same |
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| CN116966151A (en) * | 2023-09-21 | 2023-10-31 | 河南中医药大学 | Preparation method and application of multiple-response doxorubicin-quercetin co-delivery system |
| CN116966151B (en) * | 2023-09-21 | 2024-04-05 | 河南中医药大学 | Preparation method and application of multiple-response doxorubicin-quercetin co-delivery system |
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Application publication date: 20190111 |