CN108085352A - A kind of method of two enzymes method control cyclodextrin inclusion compound sustained release - Google Patents
A kind of method of two enzymes method control cyclodextrin inclusion compound sustained release Download PDFInfo
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- CN108085352A CN108085352A CN201810066474.4A CN201810066474A CN108085352A CN 108085352 A CN108085352 A CN 108085352A CN 201810066474 A CN201810066474 A CN 201810066474A CN 108085352 A CN108085352 A CN 108085352A
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- cyclodextrin
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
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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
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
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Abstract
A kind of method of two enzymes method control cyclodextrin inclusion compound sustained release, belongs to food, drug and textile garment technical field.The invention enables cyclodextrin inclusion compound under the collective effect of cyclodextrin glycosyl transferases and carbohydrase, under conditions of guest molecule rate of release is controllable, so that it is released in the slave cyclodextrin cavity that guest molecule is progressively stablized in inclusion compound, to utilize inclusion compound guest molecule to greatest extent.The present invention can be continual and steady holding system in inclusion compound guest molecule（Essence, fragrance and pigment）Uniformly, speed it is controllable, thoroughly release, and non-disposable release, and the invention can utilize guest molecule to greatest extent；Can also its rate of release be adjusted according to the release demand of guest molecule in inclusion compound, medicaments uniformity, speed are controllable, thoroughly discharge to reach.
Description
Technical field
The present invention relates to a kind of methods of two enzymes method control cyclodextrin inclusion compound sustained release, and in particular to cyclodextrin inclusion compound exists
Uniform, speed controllably, thoroughly discharges under the collective effect of cyclodextrin glycosyl transferases and carbohydrase, to improve guest molecule most
Big utilization rate belongs to food, drug and textile garment technical field.
Background technology
Cyclodextrin be by D- glucopyranose units by α-（1→4）A kind of cyclic oligomer that-glucosides key connection forms
Maltose.According to the difference of the number of glucose unit（6-13）, cyclodextrin can be divided into α-, β-, γ-,
δ-, θ-cyclodextrin etc..In addition to more than mother body cyclodextrin, at present again occur functional group modification cyclodextrin,
Cyclodextrin dimmer and Cyclodextrin Polymer etc..Cyclodextrin is a kind of ring type oligosaccharide without reproducibility, by cyclodextrin glycosyl
Transferase acts on starch and obtains, and hydrophilic exterior surfaces and a hydrophobicity inside aperture, this cyclic structure to permit containing there are one
Perhaps cyclodextrin embedding guest molecule and formed include compound, here it is cyclodextrin food, pharmacy, textile industry have very greatly should
The reason for potentiality.
Since cyclodextrin surface is dispersed with numerous reactive hydroxyls, while have there are one hydrophobic cavity, make it have very much
Special performance, can be with the extremely extensive all kinds of objects of scope, such as organic molecule, inorganic ions, complex even indifferent gas
Body etc. forms host-gust inclusion complexes by intermolecular interaction, so as to have shielding, control release, active protection to object
Etc. functions, thus use food, medicine and field of textiles extensively.
And current research is only conceived to the preparation of cyclodextrin inclusion compound to improve the water solubility of guest molecule, biology work
Property, and the problems such as often have ignored the utilization rate of guest molecule in cyclodextrin inclusion compound.Cyclodextrin inclusion compound is main in the application
There are the following problems：1）Guest molecule because disposably discharge it is too fast cause its bioactivity reduction；2）Guest molecule is in natural item
Part slowly discharges, so as to which expected effect be not achieved；3）Object in cyclodextrin inclusion compound hollow cavity cannot discharge completely
And the problems such as causing guest molecule that cannot be fully utilized, needs to solve.
The content of the invention
It is that guest molecule in current cyclodextrin inclusion compound cannot be stablized, controllable, complete it is an object of the invention to overcome
The problem of complete utilization, provides a kind of two enzymes method control cyclodextrin inclusion compound release method so that guest molecule be able to it is uniform,
Speed it is controllable, the thoroughly release stablized.
Technical scheme, a kind of method of two enzymes method control cyclodextrin inclusion compound sustained release, step are as follows：
（1）The preparation of mixed solution：Cyclodextrin and guest molecule are proportionally included, cyclodextrin inclusion compound is prepared
Mixed solution；
（2）The preparation of cyclodextrin inclusion compound：By step（1）Obtained mixed solution is freeze-dried under vacuum, so
Cyclodextrin inclusion compound mixture is washed using water or organic reagent afterwards；Acquired solution after washing is filtered, is removed
Filtrate obtains filter residue；Filter residue in vacuum drying chamber is dried, cyclodextrin inclusion compound is made；
（3）The preparation of reaction substrate solution：By step（2）Gained cyclodextrin inclusion compound is dissolved in phosphate buffer solution, is obtained
Cyclodextrin inclusion compound mass concentration is the reaction substrate solution of 0.05%-2%；
（4）Double enzyme reactions：In step（3）Gained reaction substrate solution adds in cyclodextrin glycosyl transferases and carbohydrase carries out instead
Should so that guest molecule is uniform, speed is controllable, thoroughly release.
The cyclodextrin include alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, glucosyl group-alpha-cyclodextrin, glucosyl group-
Beta-cyclodextrin, glucosyl group-gamma-cyclodextrin, malt-base-alpha-cyclodextrin, malt sugar group-beta-cyclodextrin, malt-base-γ-
One kind in cyclodextrin, maltotriose glycosyl-alpha-cyclodextrin, G 3-β-CD or maltotriose glycosyl-gamma-cyclodextrin.
The guest molecule mainly includes water-insoluble guest molecule, unstable guest molecule, volatile guest molecule
The guest molecule of son and biologically active labile.
The guest molecule is specially sodium benzoate, vanillic aldehyde, storax, beta carotene, curcumin, lycopene, cloth
Ibuprofen, clarithromycin, VitAVitE, ethyl propionate, valeric acid, carvacrol, Bilobanoate, caryophyllus oil, Rosa Damascana,
Alpha, beta-lonone, cinnamon oil, cinnamic acid aldehyde, cinnarizine, andrographolide, benzhexol, graphene, Indomethacin, Norfloxacin,
Galic essential oil, salicylic acid, ginsenoside, ferroheme, daunorubicin, brilliant green, ethylparaben, taxol, Paeonol, dimension amine
Ester, Gardenia Yellow, volatile argyi leaf oil, adenosine, Herba Houttuyniae volatile oil, Florfenicol, Tilmicosin, orinase, double chlorine
Fragrant acid sodium, aspirin, silymarin, menthol, peppermint oil, muscone, Puerarin, berberine, Artemisia oil or flavonoids
The substances such as substance.
Step（1）It is specific as follows：According to Host-guest ratio it is 1 by cyclodextrin and guest molecule:1-100 is included, and is specially
10-24h is stirred at ambient temperature, and cyclodextrin inclusion compound mixed solution is prepared by saturated solution method.
Step（2）It is specific as follows：By step（1）Obtained mixed solution is freezed under -50 DEG C, 10-30Pa vacuum
Dry 24-48h, then carries out cyclodextrin inclusion compound mixture washing 1-3 times using water or organic reagent；To gained after washing
Solution is filtered, and obtains filter residue, and filter residue is dried 6-24h in 25-55 DEG C, the vacuum drying chamber of 10-50Pa, is obtained
Cyclodextrin inclusion compound.
Step（2）Middle organic reagent is one kind in absolute ethyl alcohol, n-hexane, methanol or ether.
Step（3）It is specific as follows：By step（2）Gained cyclodextrin inclusion compound is dissolved in that pH is 4.0-8.0, concentration is 10 mM-
In the phosphate buffer of 200 mM, the reaction substrate solution that mass concentration is 0.05%-2% is obtained.
Take step（3）900 μ L of gained reaction substrate solution add in 1-500 μ L cyclodextrin glycosyl transferases in centrifuge tube
CGTase and 1-500 μ L carbohydrase is placed in 30-60 DEG C of reaction 0.5-48h so that two enzymes method control cyclodextrin inclusion compound is delayed
It releases.
Beneficial effects of the present invention：Cyclodextrin inclusion compound of the present invention is in cyclodextrin glycosyl transferases and the common work of carbohydrase
Under, under conditions of guest molecule rate of release is controllable so that the slave cyclodextrin cavity that guest molecule is progressively stablized in inclusion compound
In release, with to greatest extent utilize inclusion compound guest molecule.
The present invention can be applied to food and field of textiles, inclusion compound guest molecule in holding system that can be continual and steady
（Essence, fragrance and pigment）Uniformly, speed it is controllable, thoroughly release, and non-disposable release, and the invention can be with maximum limit
Degree utilizes guest molecule.
The present invention can also be applied to drug field, can adjust it according to the release demand of guest molecule in inclusion compound and release
Rate is put, medicaments uniformity, speed are controllable, thoroughly discharge to reach.
Description of the drawings
Fig. 1 is inclusion compound cyclodextrin host molecule hydrolysis figure in embodiment 1.
Specific embodiment
1 sodium benzoate of embodiment-Benexate Hydrochloride at the uniform velocity, slowly, thoroughly discharges under the action of double enzymes
（1）Take 1.14 g（0.001mol）Beta-cyclodextrin is dissolved in 100mL water, and 0.15g is added in into the aqueous solution of beta-cyclodextrin
（0.001mol）Sodium benzoate stirs 12h under conditions of room temperature；
（2）By step（1）Obtained solution carries out freeze-drying 48h under -50 DEG C, 10Pa vacuum, obtains sodium benzoate-β-ring
The mixture of cyclodextrin inclusion compound, with -4 DEG C of milli-Q water powder 3 times, until existing in cold water without sodium benzoate；
（3）By step（2）Solution dried under conditions of 45 DEG C, be made sodium benzoate-Benexate Hydrochloride；
（4）By step（3）Sodium benzoate-Benexate Hydrochloride be dissolved in the phosphate buffer solution of pH 5.5, be made 1%
Reaction substrate solution；
（5）Take step（4）900 μ L of solution add in 50 μ L CGTase and 50 μ L saccharification enzyme reactions, object in centrifuge tube
Molecule sodium benzoate speed in the duration of 6 h uniformly thoroughly discharges.
Embodiment 2：Vanillic aldehyde-Benexate Hydrochloride at the uniform velocity, slowly, thoroughly discharges under the action of double enzymes
（1）1.14 g beta-cyclodextrins is taken to be dissolved in 100 mL water, 0.15 g vanillic aldehydes are added in into the aqueous solution of beta-cyclodextrin,
12h is stirred under conditions of room temperature；
（2）By step（1）Obtained solution is freeze-dried for 24 hours under -50 DEG C, 30Pa vacuum, obtains vanillic aldehyde-β-ring paste
The mixture of inclusion compounds, with ethyl alcohol washing powder 3 times, until existing in ethyl alcohol without vanillic aldehyde；
（3）By step（2）It is dried under conditions of 25 DEG C, vanillic aldehyde-Benexate Hydrochloride is made；
（4）By step（3）Powder is dissolved in the phosphate buffer solution of pH 5.5, and 1% reaction substrate solution is made；
（5）Take step（4）900 μ L of solution add in 200 μ L CGTase and 200 μ L saccharification enzyme reactions, visitor in centrifuge tube
Body molecule vanillic aldehyde speed in the duration of 2 h uniformly thoroughly discharges.
Embodiment 3：Beta carotene-gamma-cyclodextrin inclusion compound at the uniform velocity, slowly, thoroughly discharges under the action of double enzymes
（1）2.27 g gamma-cyclodextrins is taken to be dissolved in 100 mL water, 0.53 g β-Hu Luo are added in into the aqueous solution of gamma-cyclodextrin
Bu Su hexane solutions, room temperature stir 12h under conditions of being protected from light；
（2）By step（1）Obtained liquid is freeze-dried 36h under -50 DEG C, 20Pa vacuum, obtains beta carotene-γ-ring paste
The mixture of inclusion compounds, with ethyl alcohol washing powder 3 times, until existing in ethyl alcohol without beta carotene；
（3）By step（2）Solution drying is protected from light under conditions of 30 DEG C, be made beta carotene-gamma-cyclodextrin inclusion compound；
（4）By step（3）Powder is dissolved in the phosphate buffer solution of pH 5.5, and 1% reaction substrate solution is made；
（5）Take step（4）900 μ L of solution add in 10 μ L CGTase and 10 μ L saccharification enzyme reactions, guest molecule in centrifuge tube
Beta carotene speed in the duration of 13h uniformly stablizes release.
Embodiment 4：Vanillic aldehyde-malt sugar group-beta-cyclodextrin inclusion compound under the action of double enzymes at the uniform velocity, slowly, thoroughly
Release
（1）1.14 g malt sugar group-beta-cyclodextrins is taken to be dissolved in 100 mL water, to malt sugar group-beta-cyclodextrin it is water-soluble in plus
Enter 0.15 g vanillic aldehydes, 12 h are stirred under conditions of room temperature；
（2）By step（1）Obtained liquid is freeze-dried 48h under -50 DEG C, 15Pa vacuum, obtain vanillic aldehyde-malt-base -
The mixture of Benexate Hydrochloride, with ethyl alcohol washing powder 3 times, until existing in ethyl alcohol without vanillic aldehyde；
（3）By step（2）Solution dried under conditions of 30 DEG C, be made vanillic aldehyde-malt sugar group-beta-cyclodextrin inclusion compound；
（4）By step（3）Powder is dissolved in the phosphate buffer solution of pH 5.5, and 1% reaction substrate solution is made；
（5）Take step（4）900 μ L of solution add in 10 μ L CGTase and 10 μ L saccharification enzyme reactions, guest molecule in centrifuge tube
Vanillic aldehyde speed in the duration of 20h uniformly stablizes release.
Claims (9)
- A kind of 1. method of two enzymes method control cyclodextrin inclusion compound sustained release, it is characterised in that step is as follows：（1）The preparation of mixed solution：Cyclodextrin and guest molecule are proportionally included, cyclodextrin inclusion compound is prepared Mixed solution；（2）The preparation of cyclodextrin inclusion compound：By step（1）Obtained mixed solution is freeze-dried under vacuum, so Cyclodextrin inclusion compound mixture is washed using water or organic reagent afterwards；Acquired solution after washing is filtered, is removed Filtrate obtains filter residue；Filter residue in vacuum drying chamber is dried, cyclodextrin inclusion compound is made；（3）The preparation of reaction substrate solution：By step（2）Gained cyclodextrin inclusion compound is dissolved in phosphate buffer solution, is obtained Cyclodextrin inclusion compound mass concentration is the reaction substrate solution of 0.05%-2%；（4）Double enzyme reactions：In step（3）Gained reaction substrate solution adds in cyclodextrin glycosyl transferases and carbohydrase carries out instead Should so that guest molecule is uniform, speed is controllable, thoroughly release.
- 2. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 1, it is characterised in that：The cyclodextrin Including alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, glucosyl group-alpha-cyclodextrin, glucosyl-ss-cyclodextrin, glucosyl group- Gamma-cyclodextrin, malt-base-alpha-cyclodextrin, malt sugar group-beta-cyclodextrin, malt-base-gamma-cyclodextrin, maltotriose glycosyl- One kind in alpha-cyclodextrin, G 3-β-CD or maltotriose glycosyl-gamma-cyclodextrin.
- 3. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 1, it is characterised in that：The guest molecule Son mainly includes water-insoluble guest molecule, unstable guest molecule, volatile guest molecule and biologically active labile Guest molecule.
- 4. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 3, it is characterised in that：The guest molecule Son is specially sodium benzoate, vanillic aldehyde, storax, beta carotene, curcumin, lycopene, brufen, clarithromycin, dimension life Plain A, vitamin E, ethyl propionate, valeric acid, carvacrol, Bilobanoate, caryophyllus oil, Rosa Damascana, alpha, beta-lonone, cinnamon oil, Cinnamic acid aldehyde, cinnarizine, andrographolide, benzhexol, graphene, Indomethacin, Norfloxacin, galic essential oil, salicylic acid, people Ginseng saponin(e, ferroheme, daunorubicin, brilliant green, ethylparaben, taxol, Paeonol, Viaminate, Gardenia Yellow, folium artemisiae argyi are waved Hair oil, adenosine, Herba Houttuyniae volatile oil, Florfenicol, Tilmicosin, orinase, C14H10Cl2NNaO2, aspirin, fine grinding Silibin, menthol, peppermint oil, muscone, Puerarin, berberine, Artemisia oil or Flavonoid substances.
- 5. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 1, it is characterised in that step（1）Specifically It is as follows：According to Host-guest ratio it is 1 by cyclodextrin and guest molecule:1-100 is included, and specially stirs 10- at ambient temperature For 24 hours, cyclodextrin inclusion compound mixed solution is prepared by saturated solution method.
- 6. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 1, it is characterised in that step（2）Specifically It is as follows：By step（1）Obtained mixed solution carries out freeze-drying 24-48h under -50 DEG C, 10-30Pa vacuum, then utilizes Water or organic reagent carry out cyclodextrin inclusion compound mixture washing 1-3 times；Acquired solution after washing is filtered, is filtered Filter residue is dried 6-24h in 25-55 DEG C, the vacuum drying chamber of 10-50Pa, obtains cyclodextrin inclusion compound by slag.
- 7. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 1, it is characterised in that step（2）Middle institute Organic reagent is stated as one kind in absolute ethyl alcohol, n-hexane, methanol or ether.
- 8. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 1, it is characterised in that step（3）Specifically It is as follows：By step（2）Gained cyclodextrin inclusion compound is dissolved in the phosphate-buffered that pH is 4.0-8.0, concentration is 10 mM-200 mM In liquid, the reaction substrate solution that mass concentration is 0.05%-2% is obtained.
- 9. the method for two enzymes method control cyclodextrin inclusion compound sustained release according to claim 1, it is characterised in that step（4）Specifically It is as follows：Take step（3）900 μ L of gained reaction substrate solution add in 1-500 μ L cyclodextrin glycosyl transferases in centrifuge tube CGTase and 1-500 μ L carbohydrase is placed in 30-60 DEG C of reaction 0.5-48h so that two enzymes method control cyclodextrin inclusion compound is delayed It releases.
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| CN112280617A (en) * | 2020-12-04 | 2021-01-29 | 云南中烟工业有限责任公司 | Clathrate compound of column [5] arene and anethole, preparation method and application thereof |
| CN112675315A (en) * | 2021-01-05 | 2021-04-20 | 佛山科学技术学院 | Gamma-cyclodextrin-tilmicosin clathrate compound and preparation method and application thereof |
| CN116437816A (en) * | 2020-11-17 | 2023-07-14 | 德乐有限公司 | Method for selectively separating at least one organic substance having at least one non-polar group, and use of said substance in food, hedonic, cosmetic or pharmaceutical products |
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