CN113234259A - Carboxymethylated carrageenan-oxidized locust bean gum composite micro-hydrogel - Google Patents
Carboxymethylated carrageenan-oxidized locust bean gum composite micro-hydrogel Download PDFInfo
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- CN113234259A CN113234259A CN202110562638.4A CN202110562638A CN113234259A CN 113234259 A CN113234259 A CN 113234259A CN 202110562638 A CN202110562638 A CN 202110562638A CN 113234259 A CN113234259 A CN 113234259A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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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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- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2405/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2401/00 or C08J2403/00
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Abstract
The invention relates to carboxymethylated carrageenan-locust bean oxide gum composite micro hydrogel, wherein a micro hydrogel carrier is mainly prepared by compounding carboxymethylated kappa-carrageenan and locust bean oxide gum in an alkaline aluminum chloride solution; on one hand, the drug loading rate can reach more than 60 percent, the immediate release degree of the drug can be improved, and the drug concentration can be sufficient after oral administration, on the other hand, the complete release time of the drug in simulated gastric juice is 15.6min, the complete release time of the drug in simulated intestinal juice can reach 76.5min, and the drug loading can be carried out aiming at different targeted drugs, so that the effective time of the drug is prolonged.
Description
Technical Field
The invention belongs to the field of medical materials, and particularly relates to carboxymethylated carrageenan-oxidized locust bean gum composite micro-hydrogel.
Technical Field
The micro hydrogel is an elastomer with a pore structure similar to hydrogel, has good hydrophilicity and certain swelling property, has a particle size smaller than that of the hydrogel, is mainly based on a cross-linked polymer matrix such as polyacrylamide, cross-linked polyvinylpyrrolidone, cellulose and the like at present, but has the problems of in vivo degradation residue and the like due to poor biodegradation, and the natural polysaccharide gel component can effectively solve the problems.
Kappa-carrageenan is a natural biomaterial with excellent gel performance, the skeleton of the kappa-carrageenan is mainly formed by connecting sulfated galactose and 3, 6-lacton-D-galactose alternately through alpha-1, 3-glycosidic bond and beta-1, 4-glycosidic bond, the kappa-carrageenan is a naturally formed linear sulfated galactan, the linear sulfated galactan and potassium ions can form gel which can be used as excipient and can be rapidly degraded in acid solution, therefore, the kappa-carrageenan has the potential possibility of immediate release of embedded drugs and is a drug carrier material which can be rapidly disintegrated in gastric acid and has high biodegradation degree; because the carrageenan is potassium-sensitive gel and has water bleeding property to cause gel instability, the carrageenan is modified, and meanwhile, the stability of the carrageenan in different pH values can be adjusted, and the carrageenan is used as a micro-hydrogel carrier for adjustable drug release.
Disclosure of Invention
In order to solve the technical problems, the invention provides a structure of a carboxymethylated carrageenan-oxidized locust bean gum compound, and also aims to provide a preparation method and drug-loading performance parameters of the carboxymethylated carrageenan-oxidized locust bean gum compound micro-hydrogel;
the structural formula of the carboxymethylated carrageenan is shown as the following formula (I):
wherein R is H or CH2COO-；
The structural formula of the locust bean gum oxide is shown as (II):
the preparation method of the carboxymethylated carrageenan comprises the following steps:
the method comprises the steps of hydrating kappa-carrageenan powder for 15min at 85 ℃ and staying overnight at room temperature to form hydrated kappa-carrageenan with the concentration of 5% (w/v), reacting the kappa-carrageenan with chloroacetic acid at the molar ratio of 1:3 at 10-15 ℃ for 2-4 h, gradually heating to 50-80 ℃, stirring for 1-2 h, stopping the reaction, washing with methanol/water (80/20, v/v), adjusting to be neutral with glacial acetic acid, filtering out a product (I), washing with methanol, and drying at 30-40 ℃;
the preparation method of the oxidized locust bean gum comprises the following steps:
adding 0.1-1.2 g of natural locust bean gum and 0.5-2.0 g of sodium periodate into 10% (w/v) of sodium hydroxide solution, reacting in a 250ml round-bottom flask, wrapping with tinfoil paper to shield light so as to avoid the decomposition of the sodium periodate, magnetically stirring at room temperature for 36-48 h, adding ethylene glycol into the mixed solution, and stirring for 0.5h so as to eliminate unreacted sodium periodate, thereby obtaining the locust bean oxide;
the preparation method of the carboxymethylated carrageenan-oxidized locust bean gum composite micro hydrogel comprises the following steps:
1) adding 0.1-0.5 g of sylvite into 90-150 mL of distilled water for dissolving, gradually heating to 50 ℃ by magnetic stirring, adding 2-10 g of carboxymethylated carrageenan and oxidized locust bean gum with the mass mixing ratio of 6-14: 1, stirring and dispersing uniformly, then continuously heating to 80-90 ℃, preserving heat for 1.0h to fully swell the glue solution, degassing the glue solution at high temperature by adopting a vacuum degassing device for 0.5h, removing bubbles, cooling to 50-60 ℃, sealing, and standing for 24 h;
2) adding 25% (w/v) model drug diclofenac sodium into 10-50 mL (w/v) of the glue solution obtained in the step 1, uniformly mixing, extruding the glue solution from a 21-Ga. needle into 100-150 mL of alkaline aluminum chloride solution with the concentration of 12-20% (w/v) and containing 0.05-0.1% (w/v) of Tween 80, wherein the alkaline aluminum chloride is prepared by using a certain amount of AlCl3·6H2Reacting an O aqueous solution with 5-10% (w/v) ammonia water at 60-70 ℃, incubating obtained liquid drops into a gel medium for 10-60 min, filtering and collecting micro-hydrogel particles, washing excessive surface salt or ions with distilled water for 2-3 times, and air-drying;
preferably, the mass mixing ratio of the carboxymethylated carrageenan and the oxidized locust bean gum in the step 1 is 10: 1.
Preferably, the concentration of basic aluminum chloride in said step is 16% (w/v).
Compared with the prior art, the invention has the following beneficial effects:
according to the invention, by preparing the carboxymethylated carrageenan-oxidized locust bean gum composite micro hydrogel as an IR drug loading system, the drug loading rate can reach 80.4%, the drug can be completely disintegrated within 10min in simulated gastric juice, the drug can be rapidly released, sufficient blood concentration is provided, the carboxymethylated carrageenan-oxidized locust bean gum composite micro hydrogel is suitable for being used as a gastric-soluble drug carrier, the side effect of gastric ulcer can be reduced, and the side effect time of the drug can be reduced.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the description is intended to be exemplary only, and is not intended to limit the scope of the present invention. Moreover, in the following description, descriptions of well-known structures and techniques are omitted so as to not unnecessarily obscure the concepts of the present invention.
Example 1
1) Under magnetic stirring, adding 5.5g of carboxymethylated carrageenan and oxidized locust bean gum (1-1, 1-2, 1-3, 1-4 and 1-5) with the mixing ratio of 6-14: 1 into 100mL of distilled water at 50 ℃, gradually heating, stirring and dispersing uniformly, continuing to heat to 80-90 ℃, preserving heat for 1.0h to fully swell the glue solution, degassing the glue solution at high temperature by adopting a vacuum degassing device, removing bubbles for 0.5h, cooling to 50-60 ℃, sealing, and standing for 24 h;
2) adding 25% (w/v) model drug diclofenac sodium into 30mL (w/v) of the glue solution obtained in the step 1, uniformly mixing, extruding the glue solution from a 21-Ga. needle into 120mL of 16% (w/v) basic aluminum chloride solution containing 0.05% (w/v) Tween 80, wherein the basic aluminum chloride is prepared from a certain amount of AlCl3·6H2Reacting an O aqueous solution with 5-10% (w/v) ammonia water at 60-70 ℃, incubating the obtained liquid drops into a gel medium for 50min, collecting micro-hydrogel particles through filtration, washing excessive surface salt or ions with distilled water for 2-3 times, and air-drying.
The results obtained in example 1 were subjected to the measurement of drug loading rate and time to complete drug release under the following conditions:
1) drug loading rate (%): a known quantity of the micro-hydrogel particles (10mg) was crushed and placed in 100mL of pH6.8 phosphate buffer overnight to completely dissolve the encapsulated drug, the suspension was filtered, the filtrate was analyzed by UV spectrophotometer at 276nm and drug loading was calculated according to equation (1) as the three-fold average:
2) drug complete release time (min): testing the immediate release behavior of the micro-hydrogel carrier in simulated gastric fluid, putting 50mg of sample into 500mL of 0.1N HCl solution (pH 1.5), keeping 50rpm and 37 +/-0.5 ℃, taking 5mL of sample at regular intervals, analyzing the sample at 276nm by using a spectrophotometer, supplementing an equal amount of fresh buffer solution to continue testing, recording the time required by complete disintegration of particles, and taking the average value of three times for each sample;
the results obtained according to the above-mentioned measurement method are shown in Table 1;
table 1: influence of mass ratio of carboxymethylated carrageenan and oxidized locust bean gum on drug loading rate and release time of micro-hydrogel carrier
The micro hydrogel is loaded with model drug diclofenac sodium with the content of 25% (w/v), the micro hydrogel is formed by alkaline aluminum chloride and carboxymethylated carrageenan to fix the drug, the drug release time is investigated in simulated gastric juice (pH is 1.5), and the results in Table 1 show that the mixing ratio of the carboxymethylated carrageenan and the oxidized locust bean gum is within the range of 6-14: 1, the proportion of 10:1 (samples 1-3) with stable drug loading rate exists, which indicates that the loading rate of the carboxymethylated carrageenan and the oxidized locust bean gum to the drug is saturated under the compounding ratio, and the complete release time of the corresponding drug is prolonged to 15.8min compared with other proportions.
Example 2
1) Under magnetic stirring, adding 5.5g of carboxymethylated carrageenan and oxidized locust bean gum with the mass mixing ratio of 10:1 into 100mL of distilled water at 50 ℃, gradually heating to raise the temperature, continuing to raise the temperature to 80-90 ℃ after uniformly stirring and dispersing, preserving the heat for 1.0h to fully swell the gum solution, degassing the gum solution at high temperature by adopting a vacuum degassing device for 0.5h, cooling to 50-60 ℃, sealing, and standing for 24 h;
2) adding 25% (w/v) model drug diclofenac sodium into 30mL (w/v) of the glue solution obtained in the step 1, uniformly mixing, extruding the glue solution from a 21-Ga. needle into 120mL of alkaline aluminum chloride solution (marked as 2-1, 2-2, 2-3, 2-4 and 2-5) with the concentration of 12%, 14%, 16%, 18% and 20% (w/v) respectively and containing 0.05% (w/v) Tween 80, wherein the alkaline aluminum chloride is prepared from a certain amount of AlCl3·6H2Reacting an O aqueous solution with 5-10% (w/v) ammonia water at 60-70 ℃, incubating the obtained liquid drops into a gel medium for 50min, collecting micro-hydrogel particles through filtration, washing excessive surface salt or ions with distilled water for 2-3 times, and air-drying.
The results obtained in example 2 were subjected to the measurement of drug loading rate and time for complete drug release under the same conditions as those described in example 1, and the results obtained are shown in Table 2;
table 2: influence of alkaline aluminum chloride on drug loading rate and release time of micro-hydrogel carrier
From the results in table 2, it is understood that the concentration of the basic aluminum chloride ranges from 12% to 20%, and the greater the loading rate of the drug with the increase of the aluminum ion concentration, the greater the content of the immobilized drug, and the greater the release time of the drug, indicating that the stability of the gel structure is increased by the aluminum ion, and the longer the disintegration time, but the fixed content of the drug is also increased, and therefore, the optimum concentration of the basic aluminum chloride is 16% (w/v).
Blank group
1) Under magnetic stirring, adding 5.5g of carboxymethylated carrageenan and natural locust bean gum with the mixing ratio of 10:1 into 100mL of distilled water at 50 ℃, gradually heating to raise the temperature, stirring and dispersing uniformly, continuing to raise the temperature to 80-90 ℃, preserving the heat for 1.0h to fully swell the gum solution, degassing the gum solution at high temperature by adopting a vacuum degassing device for 0.5h, cooling to 50-60 ℃, sealing, and standing for 24 h.
2) Adding 25% (w/v) model drug diclofenac sodium into 30mL (w/v) of the glue solution obtained in the step 1, uniformly mixing, extruding the glue solution from a 21-Ga. needle into 120mL of 16% (w/v) basic aluminum chloride solution containing 0.05% (w/v) Tween 80, wherein the basic aluminum chloride is prepared from a certain amount of AlCl3·6H2Reacting an O aqueous solution with 5-10% (w/v) ammonia water at 60-70 ℃, incubating the obtained liquid drops into a gel medium for 50min, collecting micro-hydrogel particles through filtration, washing excessive surface salt or ions with distilled water for 2-3 times, and air-drying.
The drug release was measured at different pH for the samples of example 2(2-3) and the blank set by: the drug release of the micro-hydrogel carrier samples in 0.1N HCl solution (pH 1.5) and in phosphate buffer solution (pH 4.0, pH 6.8) was maintained at 50rpm, 37 ± 0.5 ℃, 5mL samples were taken at regular intervals and analyzed at 274nm with a spectrophotometer, the test was continued with the addition of an equal amount of fresh buffer, the time required for complete disintegration of the particles was recorded, and the average value was taken three times for each sample;
the results of the tests on the above examples 2(2-3) and the blank samples are shown in Table 3.
Table 3: drug release profile of micro-hydrogel samples at different pH
On the other hand, the drug release conditions of the micro-hydrogels prepared from carboxymethylated carrageenan-natural locust bean gum in example 2 under different pH conditions are examined, and the results in table 3 show that the blank group under the same pH condition has shorter drug release time than the samples in experimental groups 2-3, the release time of the blank group under the condition of pH 1.5 is less than 10min, and the micro-hydrogels are not acid-resistant and can be rapidly released under the acidic condition; the samples in the experimental groups 2-3 can reach higher drug concentration in 15min, the drug release time is prolonged along with the increase of pH, and when the pH value of the solution is 6.8, the drug release time reaches 76.5min, so that the action time is prolonged compared with that of the drug in the blank group.
Claims (7)
1. The carboxymethylated carrageenan-oxidized locust bean gum composite micro hydrogel is characterized by comprising the following components in parts by weight: the micro hydrogel is obtained by compounding carboxymethylated carrageenan and oxidized locust bean gum;
the structural formula of the carboxymethylated carrageenan is shown as the following formula (I):
wherein R is H or CH2COO-；
The structural formula of the locust bean gum oxide is shown as (II):
2. a preparation method of carboxymethylated carrageenan-oxidized locust bean gum composite micro hydrogel is characterized by comprising the following steps:
1) adding 0.1-0.5 g of sylvite into 90-150 mL of distilled water for dissolving, gradually heating to 50 ℃ by magnetic stirring, adding 2-10 g of carboxymethylated carrageenan and oxidized locust bean gum with the mass mixing ratio of 6-14: 1, stirring and dispersing uniformly, then continuously heating to 80-90 ℃, preserving heat for 1.0h to fully swell the glue solution, degassing the glue solution at high temperature by adopting a vacuum degassing device for 0.5h, removing bubbles, cooling to 50-60 ℃, sealing, and standing for 24 h;
2) adding 25% (w/v) model drug diclofenac sodium into 10-50 mL (w/v) of the glue solution obtained in the step 1, uniformly mixing, extruding the glue solution from a 21-Ga. needle into 100-150 mL of alkaline aluminum chloride solution with the concentration of 12-20% (w/v) and containing 0.05-0.1% (w/v) of Tween 80, wherein the alkaline aluminum chloride is prepared by using a certain amount of AlCl3·6H2Reacting an O aqueous solution with 5-10% (w/v) ammonia water at 60-70 ℃, incubating the obtained liquid drops into a gel medium for 10-60 min, collecting micro-hydrogel particles through filtration, and washing excessive surface with distilled waterAnd (5) performing air drying on the flour salt or ions for 2-3 times.
3. The method for preparing carboxymethylated carrageenan-locust bean gum oxide composite micro-hydrogel according to claim 2, wherein the potassium salt in the step 1 can be one of potassium chloride, potassium sorbate and potassium citrate.
4. The preparation method of the carboxymethylated carrageenan-locust bean oxide gum composite micro-hydrogel according to claim 2, wherein the mass mixing ratio of the carboxymethylated carrageenan and the locust bean oxide gum in the step 1 is 10: 1.
5. The method for preparing carboxymethylated carrageenan-locust bean gum oxide composite micro-hydrogel according to claim 2, wherein the concentration of the basic aluminum chloride in the step 2 is 16% (w/v).
6. The method for preparing carboxymethylated carrageenan-locust bean gum oxide composite micro-hydrogel according to claim 2, wherein the incubation time of the alkaline liquid drop in the step is 50 min.
7. The carboxymethylated carrageenan-oxidized locust bean gum composite micro-hydrogel according to claim 1, wherein the carboxymethylated carrageenan-aluminum composite micro-hydrogel carrier can be completely disintegrated within 15.6min, and the diclofenac sodium drug can be rapidly released in gastric juice to reduce the side effect of gastric ulcer.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130274225A1 (en) * | 2010-07-19 | 2013-10-17 | Actamax Surgical Materials, Llc | Method for making a polysaccharide dialdehyde having high purity |
| CN103709267A (en) * | 2013-11-28 | 2014-04-09 | 江南大学 | Preparation method of dialdehyde carboxymethyl chitosan |
| CN108530670A (en) * | 2018-02-07 | 2018-09-14 | 四川大学 | Based on carragheen from anti-freezing heparan microballoon and the preparation method and application thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130274225A1 (en) * | 2010-07-19 | 2013-10-17 | Actamax Surgical Materials, Llc | Method for making a polysaccharide dialdehyde having high purity |
| CN103709267A (en) * | 2013-11-28 | 2014-04-09 | 江南大学 | Preparation method of dialdehyde carboxymethyl chitosan |
| CN108530670A (en) * | 2018-02-07 | 2018-09-14 | 四川大学 | Based on carragheen from anti-freezing heparan microballoon and the preparation method and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| SABYASACHI MAITI等: ""Novel gastroulcer protective micro(hydro)gels of sulfated locust bean gum-aluminium complex for immediate release of diclofenac sodium"", 《JOURNAL OF DRUG TARGETING》 * |
| 宁正祥主编: "《食品生物化学》", 28 February 2013, 华南理工大学出版社 * |
| 王玉等: "《药品检验》", 31 October 2011, 中国医药科技出版社 * |
| 贲长恩等: "《组织化学》", 30 November 2001, 人民卫生出版社 * |
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Application publication date: 20210810 |