CN106986951A - A kind of hydrophobic polysaccharide and its preparation method and application - Google Patents
A kind of hydrophobic polysaccharide and its preparation method and application Download PDFInfo
- Publication number
- CN106986951A CN106986951A CN201610038059.9A CN201610038059A CN106986951A CN 106986951 A CN106986951 A CN 106986951A CN 201610038059 A CN201610038059 A CN 201610038059A CN 106986951 A CN106986951 A CN 106986951A
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- Prior art keywords
- polysaccharide
- hydrophobic
- hydrophobic polysaccharide
- vaccine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/02—Bacterial antigens
- A61K39/08—Clostridium, e.g. Clostridium tetani
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5161—Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
- A61K2039/6087—Polysaccharides; Lipopolysaccharides [LPS]
Abstract
The present invention relates to technical field of organic synthesis, more particularly to a kind of hydrophobic polysaccharide and its preparation method and application, the hydrophobic polysaccharide is that the hydroxyl of glucan is reacted with succinic anhydride, first prepare the glucan butyrate with butyric acid group, reacted again with dicyclohexylcarbodiimide (DCC), carboxyl is set to be modified by dicyclohexylurea (DCU) (DCU), end group is modified and be connected using butyric acid as linking arm with glucan with ester bond by DCU.Preparation method is using glucan or other polysaccharide as raw material, prepared with butyric anhydride and dicyclohexylcarbodiimide (DCC) reaction, its molecular weight ranges is between 20K 500K, the hydrophobic polysaccharide has self-emulsifying, suitably as protein medicaments, the especially carrier of amino acid, vaccine type medication.
Description
Technical field
The present invention relates to technical field of organic synthesis, more particularly to a kind of hydrophobic polysaccharide and its preparation method and application.
Background technology
Protein in biological cell keeps its biological activity under glycoprotein, water and certain temperature, when it leaves the environment of human body, is easy for inactivation, occurs cohesion rotten.And as many protein medicaments such as vaccine of medicinal application, though through inactivation treatment, storage request condition is harsh, made troubles for transport, preservation.The present invention is that hydrophobic polysaccharide is substituted to traditional vaccine protectant, proteic drugs is packaged in the center of polysaccharide shell, albumen is with hydrophobic polysaccharide under hydrogen bond and hydrophobicity effect; carry out bridge joint conjunction; when pH conditions change, this bridge joint closes disintegration, discharges protein exhibits drug action.As the hydrophobic polysaccharide for containing thing, into organism after can also be degraded in the presence of acid condition or enzyme and discharge protein and play pharmacological activity.Hydrophobic polysaccharide synthesized by the present invention, yet there are no information.
The content of the invention
First purpose of the present invention is to provide a kind of hydrophobic polysaccharide, and it is that, using succinic acid as linking arm, the succinic acid that end group is modified with dicyclohexylurea (DCU) is connected with ester bond with the hydroxyl of glucan to polysaccharide that the hydrophobic polysaccharide, which is,.The molecular weight of the hydrophobic polysaccharide is between 2K-50K.
The hydrophobic polysaccharide, with self-emulsifying, can individually carry medicine as emulsifying agent.
The step of second object of the present invention is to provide the preparation method of above-mentioned hydrophobic polysaccharide, the preparation method and the reaction mechanism mechanism of reaction are：
(1) glucan succinate is prepared：Glucan and succinic anhydride reaction are obtained into butyric acid glucan by catalyst of pyridine in the solution；
(2) hydrophobic polysaccharide is prepared：In a solvent, the butyric acid glucan is 20 according to weight ratio with dicyclohexylcarbodiimide: (1-10) reacts, and obtains the hydrophobic polysaccharide.
Preferably, the concrete operations of step (2) are：Weight ratio according to polysaccharide and dicyclohexylcarbodiimide is 20: (1-10) meter, the polysaccharide is dissolved in solvent, dicyclohexylcarbodiimide is added into the solvent, reacted under the conditions of 10-80 DEG C, water is added in the completely backward reaction solution of reaction, filtering removes dicyclohexylurea (DCU) solid and impurity, obtains filtrate, alcohols solvent is added into the filtrate and separates out solid, the solid is hydrophobization heparin.
Wherein, the solvent is dimethylformamide, dimethyl sulfoxide (DMSO) or dichloromethane.
The alcohols solvent is ethanol.
Third object of the present invention is to provide application of the above-mentioned hydrophobic polysaccharide as pharmaceutical carrier in medicine preparation.
Preferably, the hydrophobic polysaccharide is applied to the carrier separately as albumen, polypeptide and amino acids drug.
It is further preferred that the hydrophobic polysaccharide is particularly suitable for the carrier separately as vaccine type medication.Infection of the antigenic source of the vaccine in bacterium, virus, fungi and protozoon to animal, such as microorganism Influenza A types, Influenza Type Bs, hepatitis C virus, hepatitis A virus, hepatitis B virus, Rotavirus viruses, Cytomegalovirus：CMV viruses, RS viruses, pharynx conjunctiva heat, HIV, varicellazoster virus, the simple viral types of 1 type 2 of herpes, ATL (adult T cell leukemia) viruses, Coxsackie viruses, entero viruses, sudden dermexanthesis is viral (HHV-6), measles virus, rubella virus, the scorching virus of popular parotid gland, the acute scorching virus of grey white pulp, japanese encephalitis virus, hydrophobin, hepatitis C virus, Norwalk viruses, hydrophobin, RS viruses, Cytomegalovirus viruses, foot and mouth disease virus, infectious gastroenteritis virus, rubella virus, ATL viruses, adeno viruses, Echovirus, Herpes viruses, natural poxvirus, dengue fever fever viruses, yellow fever virus, West Nile virus, SARS (virus), Ebola hemorrhagic fever virus, Marburg hemorrhagic fever, Lassa fever viruses, Hantavirus, pathogenic virus such as Nipah virus infection etc.；The bacterium is the pathogenicity coliforms such as intestinal tube hemorrhagic coliform, staphylococcus aureus, meningitis bacterium, Pseudomonas aeruginosa, the chain coccus of worm tooth, Cholera bacterium, Typhus bacterium, Chlamydophila felis dysentery characterized by blood in the stool bacterium, pneumococcus, bacillus pertussis, Corynebacterium diphtheriae bacterium, tetanolysin, Influenza bacterium, pestis bacterium, botulinum bacterium, Bacillus anthracis charcoal ancient sacrificial utensil bacterium, hare germ, Salmonella bacterium, VRE (enterococcus), tulase, dysentery characterized by blood in the stool bacterium, Salmonella Typhi intestines bacterium, Salmonella Paratyphi A bacterium, Chlamydophila felis bacterium, Ameba dysentery characterized by blood in the stool, Legionella bacterium, Lyme borreliosis bacterium, the pathogenic bacterias such as brucellosis disease (undulant fever) bacterium；The Rickettsia such as Coxiella burnetii Q heat, Chlamydia；The protozoon classes such as malaria protozoon, Cryptosporidium Tyzzer；The proteantigen of the microorganisms such as the fungies such as cryptococcosisaspergillosis.Pathogenic microorganism proteantigen also includes amino acid, enzyme, hormone and immune regulator, and the molecular weight of these materials is not limited, can be between 100-100 ten thousand.
Fourth object of the present invention is to provide more than one and states the method that any hydrophobic polysaccharide prepares load powder for carrier：Camptothecine or camptothecin derivative are subjected to emulsification treatment with the hydrophobic polysaccharide in alkaline aqueous solution and produce load powder.
Preferably, the weight ratio of the vaccine and the hydrophobic polysaccharide is 1: 1-1: 20, preferably 1: 3-1: 10.
The present invention provides a kind of method for being prepared preferably by carrier of any of the above-described hydrophobic polysaccharide and carrying powder：It is 1: 3-1: 10 meters according to the weight ratio of camptothecine or camptothecin derivative and hydrophobic polysaccharide, first vaccine is dissolved in the alkali lye that pH value is 7.2-10, then hydrophobic polysaccharide is added, using mulser emulsification treatment until forming nano-particle under the conditions of 1-10 DEG C, obtain mixed solution, load powder is produced, particle is rounded, between 10-1000 nanometers of particle diameter.
Brief description of the drawings
The electron microscope image for the tetanus vaccine nano-particle particle in aqueous that Fig. 1 loads for hydrophobic polysaccharide described in embodiment 3.
Embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
The preparation method of the polysaccharide of embodiment 1
A kind of preparation method of polysaccharide, the preparation method is specially：Glucan 20g (dalton of molecular weight 2-50 ten thousand) is dissolved in 200ml dimethyl sulfoxide (DMSO)s, plus butanoic anhydride 10g, pyridine 2ml in room temperature reaction 4h, plus deionized water stopped reaction.Plus 2.54L ethanol.Static 3h, separates out precipitation, is refined again with ethanol, be dried under reduced pressure to obtain butyric acid polysaccharide.
The method that embodiment 2 prepares hydrophobic polysaccharide by raw material of polysaccharide
The butyric acid polysaccharide 200mg that embodiment 1 is prepared is dissolved in dimethyl sulfoxide (DMSO), plus dicyclohexylcarbodiimide 50mg, 1h is reacted under the conditions of 10 DEG C, after reaction completely, the 20ml aqueous solution is added into reaction solution, filtering removes DCU solids, dialysis, which is carried out, using 1000ml deionized waters goes the removal of impurity, dialyzate is obtained, 500ml ethanol is then added into the dialyzate, the material of precipitation is the hydrophobic polysaccharide.
Embodiment 3 carries the preparation of powder
The present embodiment provides the hydrophobic polysaccharide prepared using embodiment 2 as carrier, prepares the method for carrying powder, and methods described is：
40mg tetanus vaccines are dissolved in the 18mLpH9 NaOH aqueous solution, 80mg hydrophobic polysaccharides are added, in room temperature, emulsification 10min obtains mixed solution, produces the nano-particle for loading vaccine.This hydrophobic polysaccharide medicine-carried nano particles are rounded in alkaline aqueous solution, in polydispersion state.Fig. 1 loads the photo that tetanus vaccine nano-particle is taken under inverted microscope by hydrophobic polysaccharide.
Although above having used general explanation, embodiment and experiment, the present invention is described in detail, on the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to the scope of protection of present invention.
Claims (10)
1. a kind of hydrophobic polysaccharide, the hydrophobic polysaccharide is using succinic acid as linking arm and terminal carboxyl group is modified with dicyclohexylurea (DCU).
2. hydrophobic polysaccharide according to claim 1, it is characterised in that：The molecular weight of the hydrophobic polysaccharide is between 20K-500K.
3. prepare the method for the hydrophobic polysaccharide described in claim 1 or 2, it is characterised in that methods described comprises the following steps：
(1) butyric acid esterificated polysaccharide is prepared：Glucan is first reacted with succinic anhydride in a solvent, butyric acid esterificated polysaccharide or the reaction carried out with other dicarboxylic anhydrides is obtained；
(2) hydrophobic polysaccharide is prepared：In a solvent, the polysaccharide is 20 according to weight ratio with dicyclohexylcarbodiimide: (1-10) reacts, and obtains the hydrophobic polysaccharide.
4. preparation method according to claim 3, it is characterised in that：Before hydrophobic polysaccharide is prepared, first the polysaccharide is pre-processed, the pretreatment is：Polysaccharide is soluble in water, ion exchange column is crossed, using deionized water as eluent, eluent is collected, and alkali is added into salt into the eluent, it is dried under reduced pressure and produces after freezing；Preferably, the alkali is tri-n-butylamine.
5. the method according to claim 3 or 4, it is characterised in that：The concrete operations of step (2) are：The polysaccharide is dissolved in solvent, dicyclohexylcarbodiimide is added into the solvent, reacted under the conditions of 10-80 DEG C, water is added in the completely backward reaction solution of reaction, filtering removes dicyclohexylurea (DCU) solid and impurity, filtrate is obtained, alcohols solvent is added into the filtrate and separates out solid, the solid is hydrophobic polysaccharide；Preferably, the solvent is dimethylformamide, dimethyl sulfoxide (DMSO) or dichloromethane；Preferably, the alcohols solvent is ethanol.
6. application of the hydrophobic polysaccharide that any described preparation method of hydrophobic polysaccharide or claim 3-5 described in claim 1 or 2 is obtained as pharmaceutical carrier in medicine preparation, it is characterised in that：The medicine is amino acids, peptides, vaccine or protide.
7. a kind of hydrophobic polysaccharide with described in claim 1 or 2, or any described hydrophobic polysaccharides of claim 3-5 prepare the method for carrying powder for carrier, it is characterised in that：Methods described is：Vaccine is emulsified in the basic conditions with the hydrophobic polysaccharide, medicament-carried nano emulsion is obtained, the infection of the antigenic source of the vaccine in bacterium, virus, fungi and protozoon to animal.
8. method according to claim 7, it is characterised in that：The weight ratio of the vaccine type medication and the hydrophobic polysaccharide is 1: 1-1: 20, preferably 1: 4-1: 10.
9. the method according to claim 7 or 8, it is characterised in that：Methods described is：It is 1: 1-1: 10 meters according to the weight ratio of vaccine and hydrophobic polysaccharide, first vaccine is dissolved in the alkaline aqueous solution that pH value is 8-10, then add hydrophobic polysaccharide, use the processing of probe emulsifier until forming nano-particle under the conditions of 2-10 DEG C, mixed solution is obtained, corresponding antioxidant, preservative, antifreezing agent and amino acid etc. can also be added.
10. according to any described methods of claim 7-9, it is characterised in that：Described hydrophobic polysaccharide can also be prepared by raw material with low anticoagulant property heparin, starch, amylopectin, amylose, pulullan polysaccharide, ethoxy dextran, mannosan, levulan, synanthrin, chitin, chitosan, xyloglucan and water-soluble cellulose etc..
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| CN201610038059.9A CN106986951A (en) | 2016-01-21 | 2016-01-21 | A kind of hydrophobic polysaccharide and its preparation method and application |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107674100A (en) * | 2017-09-28 | 2018-02-09 | 中国科学院烟台海岸带研究所 | A kind of preparation method of inulin short-chain aliphatic ester |
| CN107827997A (en) * | 2017-10-25 | 2018-03-23 | 蚌埠医学院 | A kind of hydrophobization glucan and its preparation method and application |
| CN110156911A (en) * | 2019-05-20 | 2019-08-23 | 蚌埠医学院 | Hydrophobic polysaccharide and its preparation method and application |
| CN113563493A (en) * | 2021-07-01 | 2021-10-29 | 蚌埠医学院 | Hydrophobic polysaccharide and preparation method and application thereof |
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Cited By (5)
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| CN107674100A (en) * | 2017-09-28 | 2018-02-09 | 中国科学院烟台海岸带研究所 | A kind of preparation method of inulin short-chain aliphatic ester |
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| CN113563493B (en) * | 2021-07-01 | 2022-06-24 | 蚌埠医学院 | Hydrophobic polysaccharide and preparation method and application thereof |
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Application publication date: 20170728 |