CN109126741B - Phosphorus adsorbent and preparation method and application thereof - Google Patents
Phosphorus adsorbent and preparation method and application thereof Download PDFInfo
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
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- B01J20/26—Synthetic macromolecular compounds
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
- C08F251/02—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof on to cellulose or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F289/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
Abstract
The invention provides a phosphorus adsorbent and a preparation method and application thereof, wherein the phosphorus adsorbent has the following structure:
wherein X is a natural polymer organic matter containing hydroxyl. The phosphorus adsorbent is prepared by grafting polyallylamine on a natural high molecular organic matter under an initiating system; or grafting polyacrylamide on a natural polymer organic matter under an initiating system, and then performing Hofmann degradation to obtain the polyacrylamide. The initiation system is one of redox agent initiation, photoinitiator initiation, microwave initiation, radiation initiation or thermal initiation. The phosphorus adsorbent has high phosphorus adsorption capacity, can obviously reduce the blood phosphorus level, has no side reaction, high safety and good curative effect, is suitable for popularization and application, and has wide market prospect.
Description
Technical Field
The invention relates to the technical field of oral phosphorus adsorbents, and particularly relates to a phosphorus adsorbent and a preparation method and application thereof.
Background
Phosphorus is widely found in nature and is one of the essential elements in animal and plant tissues. Phosphorus is abundant in human body, and its metabolic process is closely related to human health. For example, the failure of kidney function in end-stage renal disease (ESRD) patients leads to difficulty in removing phosphorus, which increases the accumulation of phosphorus in the body and induces hyperphosphatemia. Elevated blood phosphorus levels stimulate increased parathyroid secretion, leading to secondary hyperparathyroidism. Hyperparathyroidism induces renal bone disease, which causes bone tissue to release a large amount of phosphorus, aggravates hyperphosphatemia, and causes vicious circle. Clinical reports show that most of patients suffering from end-stage renal disease have renal osteopathy, and the osteogenesis rate of the patients is smaller than the bone resorption rate, so that bone tissues cannot play the function of a 'phosphorus reservoir' in a normal human body, certain soft tissue organs are forced to replace the bone tissues to play the effect of storing phosphorus, and the increase of serum phosphorus level is aggravated. In addition, hyperphosphatemia-stimulated hyperparathyroidism can lead to hypercalcemia, which in turn can induce fatal cardiovascular diseases.
At present, in literature reports and clinical application, hyperphosphatemia is mainly treated by means of diet control, dialysis treatment and oral phosphorus removal medicines. The phosphorus removing drugs are CN 123011A, CN1169285A, CN102342955A, CN102432055B and CN 103145169B. In reference to related documents and patents, we find that oral phosphorus binders are mainly classified into three categories, the first category is activated carbon, i.e. oral carbon tablets; the second type is a metal ion type phosphorus bonding agent, and the commercialized type is lanthanum carbonate; the third category is the high molecular drugs, commercialized as the imported drug sevelamer. However, the commercially available drugs and the reported oral phosphorus removal drugs have certain toxicity and are easy to cause side effects. Therefore, the development of the bio-based oral phosphorus adsorbent for reducing the side effect of the drug has important research value and commercial prospect.
Disclosure of Invention
The invention aims to provide a phosphorus adsorbent to solve the problems that the existing phosphorus removal medicine has high toxicity and is easy to cause side reaction.
The second purpose of the invention is to provide a preparation method and application of the phosphorus adsorbent.
One of the purposes of the invention is realized by the following technical scheme: a phosphorus sorbent having the structure of formula (i):
in the structure shown in the formula (I), X is a natural macromolecular organic matter containing hydroxyl.
The natural high molecular organic matter is starch, cellulose, protein, lignin, chitin or one of derivatives of the substances.
The gel-type phosphorus adsorbent is obtained by adding a cross-linking agent to enable the phosphorus adsorbent to be cross-linked to generate a gel structure.
The cross-linking agent is hydroxymethyl acrylamide, a compound containing dicarboxyl and diacyl or other compounds capable of generating cross-linking in free radical reaction.
The preparation method of the phosphorus adsorbent comprises the following steps of grafting polyallylamine on a natural high molecular organic substance under an initiating system to prepare the phosphorus adsorbent; or grafting polyacrylamide on a natural polymer organic matter under an initiating system, and then performing Hofmann degradation to obtain the polyacrylamide.
The initiation system is one of redox agent initiation, photoinitiator initiation, microwave initiation, radiation initiation or thermal initiation.
The redox agent is one of copper dipeeriodate, cerium salt, cerium oxide, manganese salt, manganese oxide, iron salt, iron oxide, hydrogen peroxide, hypochlorous acid, hypochlorite, nitric acid or sulfuric acid.
The photoinitiator is a commercial photoinitiator 2959 and the like.
The radiation source in the radiation initiation is gamma-ray, X-ray and the like.
An application of any one of the phosphorus adsorbents in preparation of an oral phosphorus removal medicine.
The phosphorus adsorbent has high phosphorus adsorption capacity, can obviously reduce the blood phosphorus level, has no side reaction, high safety and good curative effect, is suitable for popularization and application, and has wide market prospect.
The preparation method is simple and convenient to operate, can prepare the aminated bio-based phosphorus adsorbent in a short time, can adjust the amination modification degree, and is suitable for industrial production and application.
Drawings
FIG. 1: infrared spectra of the aminated cellulose-based phosphorus sorbent and cellulose.
FIG. 2: and (3) a solid nuclear magnetic spectrum of the aminated cellulose-based phosphorus adsorbent.
FIG. 3: XPS energy spectra of the aminated cellulose-based phosphorus adsorbent and cellulose.
FIG. 4: infrared spectra of starch, starch grafted polyacrylamide and aminated starch-based phosphorus adsorbent.
FIG. 5: and infrared spectrograms of lignin, lignin grafted polyacrylamide and aminated lignin-based phosphorus adsorbent.
FIG. 6: thermogravimetric plots of lignin, lignin-grafted polyacrylamide, and aminated lignin-based phosphorus adsorbents.
FIG. 7: and (3) comparing bond energy of the combination of the amination cellulose base phosphorus adsorbent and phosphorus before and after cellulose degradation.
FIG. 8: photographs of small intestine tissue sections of SD rats (A, B and C from control rats, D, E and F from experimental rats).
FIG. 9: photographs of kidney tissue sections from SD rats (A, B and C from control rats, D, E and F from experimental rats).
Detailed Description
The present invention will be described in detail with reference to specific examples.
Example 1: redox-initiated cellulose-grafted allylamines
A round-bottom flask was charged with 1ml of an aqueous solution of copper diperiodate (0.1mmol), 2g of cellulose (an avadin reagent, particle size 250 μm) was added, 15ml of deionized water was added, 2ml of allylamine was added, the temperature was raised to 35 ℃ and the reaction was stopped for 2 hours. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation and washed 3 times with acetone. The product is dried in vacuum to obtain the phosphorus adsorbent with cellulose as the matrix, and the yield is 75 percent. The reaction process is shown as follows, wherein I represents cellulose. The obtained phosphorus adsorbent is characterized, and the structure is shown in figures 1-3.
Example 2: gamma-ray initiated grafting of cellulose to allylamine
2g of cellulose (an avastin reagent with the particle size of 250 mu m) is added into a round-bottom flask, 10ml of deionized water is added, 2ml of allylamine is added, gamma-ray 70Gy radiation is carried out for 30min, and the reaction is stopped. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation and washed 3 times with acetone. The product is dried in vacuum to obtain the phosphorus adsorbent with cellulose as a matrix, and the yield is 65%. The reaction process is shown as follows, wherein I represents cellulose.
Example 3: photoinitiator initiation of cellulose grafted allylamine
A round-bottomed flask was charged with 2959(50mg) of a commercial photoinitiator, 2g of cellulose (an avastin reagent, particle size 250 μm), 10ml of deionized water, 2ml of allylamine and 1 hour of ultraviolet irradiation to stop the reaction. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation and washed 3 times with acetone. The product is dried in vacuum to obtain the phosphorus adsorbent with the cellulose as the matrix, and the yield is 70 percent. The reaction process is shown as follows, wherein I represents cellulose.
Example 4: redox-initiated starch grafting of allylamines
A round-bottom flask is added with 1ml of copper dipeperiodate (0.1mmol) aqueous solution, 2g of starch (an avadin reagent, medicinal grade) is added, 15ml of deionized water is added, 2ml of allylamine is added, the temperature is raised to 35 ℃, the reaction is carried out for 2h, and the reaction is stopped. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation and washed 3 times with acetone. The product is dried in vacuum to obtain the phosphorus adsorbent taking the starch as the matrix, and the yield is 78%.
Example 5: redox-initiated lignin grafting allylamines
A round-bottom flask was charged with 1ml of an aqueous solution of copper diperiodate (0.1mmol), 2g of lignin (100 μm in carbofuran technology) was added, 15ml of deionized water was added, 2ml of allylamine was added, the temperature was raised to 35 ℃ and the reaction was stopped for 2 hours. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation and washed 3 times with acetone. And (3) drying the product in vacuum to obtain the phosphorus adsorbent taking the lignin as a matrix, wherein the yield is 60%.
Example 6: preparation of aminated bio-based phosphorus adsorbent (cellulose) by Hofman degradation
A round-bottom flask is added with 1ml of copper dipeperiodate (0.1mmol) aqueous solution, 2g of cellulose (an avadin reagent with the particle size of 250 mu m) is added, 15ml of deionized water is added, 500mg of acrylamide is added, the temperature is raised to 35 ℃, the reaction is carried out for 2h, and the reaction is stopped. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation. 5ml of deionized water was added to 1g of the intermediate product, and 0.1ml of an aqueous sodium hydroxide solution (0.01mol/L) and 0.2ml of an aqueous sodium hypochlorite solution (0.01mol/L) were successively added thereto. Heating to 40 ℃ and reacting for 4 h. The reaction mother liquor was dropped into 100ml of acetone, and the precipitate was collected by centrifugation and washed 3 times with acetone. The product is dried in vacuum to obtain the phosphorus adsorbent with the cellulose as the matrix, and the yield is 60 percent. The reaction process is shown as follows, wherein I represents cellulose.
Example 7: preparation of aminated bio-based phosphorus adsorbent (starch) by Hofman degradation
Adding 1ml of copper diperiodate (0.1mmol) aqueous solution into a round-bottom flask, adding 2g of starch (an avadin reagent, medicinal grade), adding 15ml of deionized water, adding 500mg of acrylamide, heating to 35 ℃, reacting for 2 hours, and stopping reaction. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation. 5ml of deionized water was added to 1g of the intermediate product, and 0.1ml of an aqueous sodium hydroxide solution (0.01mol/L) and 0.2ml of an aqueous sodium hypochlorite solution (0.01mol/L) were successively added thereto. Heating to 40 ℃ and reacting for 4 h. The reaction mother liquor was dropped into 100ml of acetone, and the precipitate was collected by centrifugation and washed 3 times with acetone. The product is dried in vacuum to obtain the phosphorus adsorbent taking the starch as the matrix, and the yield is 65 percent. The resulting product was characterized and the results are shown in figure 4.
Example 8: preparation of aminated bio-based phosphorus adsorbent (lignin) by Hofman degradation
A round-bottom flask is added with 1ml of copper dipeperiodate (0.1mmol) aqueous solution, 2g of lignin (100 mu m in carbofuran technology) is added, 15ml of deionized water is added, 500mg of acrylamide is added, the temperature is raised to 35 ℃, the reaction is carried out for 2h, and the reaction is stopped. The reaction mother liquor was dropped into 100ml of acetone, and the precipitated solid was collected by centrifugation. 5ml of deionized water was added to 1g of the intermediate product, and 0.1ml of an aqueous sodium hydroxide solution (0.01mol/L) and 0.2ml of an aqueous sodium hypochlorite solution (0.01mol/L) were successively added thereto. Heating to 40 ℃ and reacting for 4 h. The reaction mother liquor was dropped into 100ml of acetone, and the precipitate was collected by centrifugation and washed 3 times with acetone. And (3) drying the product in vacuum to obtain the phosphorus adsorbent taking the lignin as a matrix, wherein the yield is 50%. The resulting product was characterized and the results are shown in fig. 5 and 6.
Example 9: preparation of gel type phosphorus adsorbent
A round-bottom flask was charged with 1ml of an aqueous solution of copper diperiodate (0.1mmol), 2g of cellulose (an avadin reagent having a particle size of 250 μm) was added, 15ml of deionized water was added, 2ml of allylamine and 50mg of methylolacrylamide were added, the temperature was raised to 35 ℃ and the reaction was stopped for 2 hours. The prepared gel material was dialyzed against deionized water for 5 days. And finally, freeze drying to obtain the aminated bio-based gel phosphorus adsorbent.
Example 9 is applicable to examples 1-8, only 50mg of methylolacrylamide or other crosslinking agent needs to be added in the reaction.
Example 10: measurement of phosphorus adsorption amount
The phosphorus adsorption level of the sample is tested by adopting an ZRS-8G type intelligent dissolution tester of Tianjin Haida science and technology Limited. The second method of dissolution determination was carried out in accordance with the apparatus of the appendix of the second part of the Chinese pharmacopoeia (2015 edition) toPotassium dihydrogen phosphate/sodium hydroxide buffer (pH 6.8) as medium ([ phosphorus ]]1.6mmol/L), temperature 37 ℃, rotation speed 100 rpm. 200mg of the phosphorus adsorbent powder and the gel-type phosphorus adsorbent powder were put into a medium at zero time, and 5mL of liquid was sucked at a specific time. To be provided with
The working solution in the kit is diluted by 100 times to prepare the solution to be detected. Wherein the working solution is prepared by mixing two solutions of R1a and R2a in a volume ratio of 7:3 in Table 1.
Table 1:
the absorbance of the solution to be measured of the reference solution is measured at 340nm by adopting a model ARCHITECT C8000 full-automatic biochemical analyzer of Yapeh corporation, USA, and the phosphorus content in the sample solution is calculated according to Lambert-Beer law by taking the reference prepared in the methodology as reference. The phosphorus adsorption amount (BA) was calculated by the following formula:
wherein M is the molecular weight of phosphate ions and V is KH2PO4Volume of NaOH medium, W is the weight of the sample. When Ct no longer varies with time, the phosphorus adsorption capacity at this point is the equilibrium phosphorus adsorption capacity (BC), in mg/g. The measurement results are shown in Table 2.
Table 2:
example 11: degradation test
500mg of the sample prepared in example 1 was weighed into 0.1M HCl and stirred at 37 ℃ for 2 hours (200 rpm). The suspension is then passed through a high speed stationThe solid residue was collected after centrifugation in a centrifugal motor centrifuge (8000 rpm). Washing the solid residue with water to neutrality, and standing in 10% H2O2The aqueous solution was stirred at 37 ℃ for 12 hours (200 rpm). The suspension was then centrifuged through a high speed bench top electric centrifuge and the solid residue collected at 8000 rpm. The solid residue was washed three times with water, and then freeze-dried using a freeze-dryer. The obtained sample was subjected to measurement of phosphorus adsorption amount, and the result is shown in fig. 7.
Example 12: SD rat test
12 SD male rats were randomly divided into 2 groups of 6 rats, each group being an experimental group and a control group. Wherein, after the laboratory group is weighed at the time of 0, a glass capillary with the inner diameter of 0.9mm (soaked for 1h by using a dilute heparin sodium solution before use) is used for collecting blood at the canthus position of a rat. 1.0mL of plasma was taken, 3.0mL of absolute ethanol was added, vortexed and mixed for 5 minutes, and plasma protein was precipitated. After the precipitation is complete, placing the mixture into a centrifuge, centrifuging the mixture for 15min at 8000r/min, and sucking supernatant fluid
Working solution in the kit is diluted by 25 times to prepare sample solution. Blood phosphorus levels were calculated according to equation 3-1. Thereafter, the aminated cellulose was administered by intragastric administration daily at an amount of 1.0g/kg/day (before administration, the aminated cellulose was formulated into a suspension having a concentration of about 1g/mL using water for injection, and the rats were intragastric administered using a 5mL syringe equipped with an intragastric needle). After 14 days of continuous administration, blood was collected from the canthus of rats using a thin blood vessel of glass with an inner diameter of 0.9mm (soaked in a diluted heparin sodium solution for 1 hour before use). Plasma treatment methods and blood phosphorus level tests were as described above. The test rats were reweighed after blood sampling, and the weight of the rats before and after the test was observed to have any significant change.
After weighing the control rats at time 0, blood was collected at the canthus of the rats using a 0.9mm inner diameter glass capillary (soaked for 1h with a dilute heparin sodium solution before use), and the plasma treatment and blood phosphorus level measurements were as described above. Then, the stomach was perfused with water (the amount of water was the same as that of the suspension given to the rats in the experimental group). After 14 days of continuous administration, blood was collected at the canthus of rats using a 0.9mm inner diameter glass capillary (soaked for 1h in a dilute heparin sodium solution before use), plasma treated and tested for serum phosphorus level as described above, and the test rats were re-weighed after blood withdrawal.
The SD rats in the control group and the experimental group have normal diet, good mental state, no hair color, luster, listlessness and the like in the experimental period. The body mass and the blood phosphorus level change of the rats of the experimental group and the control group are respectively measured, and the pathological section analysis of small intestine tissues and kidney tissues is carried out on the rats of the experimental group and the control group. Table 3 shows the change in body mass and blood phosphorus level of rats before and after administration (water feeding) (wherein SD1-SD6 rats are experimental rats, and SD7-SD12 rats are control rats). FIG. 8 is a photograph of a small intestine tissue section of SD rat. FIG. 9 is a photograph of a kidney tissue section of SD rat.
As can be seen from Table 3, the blood phosphorus levels in the rats in the test group were significantly reduced.
As can be seen from fig. 8 and 9, by visually observing the SD rat small intestine tissue sections, the rat small intestine tissues of the control group and the experimental group were not significantly different, and when the morphology of the rat small intestine tissues stained with hematoxylin-eosin was observed under an OLYMPUS microscope, it was found that the intestinal villi of the rat small intestine tissues of the normal control group and the experimental group were intact, and there were no phenomena such as shedding and shrinkage of villi, and "fish scale" shaped crystals caused by sevelamer hydrochloride reported in the literature were not found. Similarly, by visually observing the SD rat kidney tissue section, the rat kidney tissues of the control group and the experimental group are not obviously different, and the rat kidney tissues after hematoxylin-eosin staining are observed under an OLYMPUS microscope, so that the kidney cortex and medulla structures in the rat kidney tissues of the normal control group and the experimental group are clear, no hyperplasia and deposit exist in a mesentery region, and the basement membrane is diseased. In addition, no decrease in the number of renal bodies, decrease in volume, stenosis of renal capsule, and increase in the degree of lymphocyte infiltration were observed in the kidney tissues of the rats in the control group and the experimental group. The observation of small intestine and kidney tissues of SD rats under a microscope shows that the rat kidney and small intestine tissues of the experimental group have no obvious abnormality after administration, and have no obvious difference from the observation result of a tissue section in a normal control group.
Table 3:
Claims (4)
1. the application of a phosphorus adsorbent in preparing an oral phosphorus removal medicine is characterized in that the phosphorus adsorbent has a structure shown as a formula (I):
（Ⅰ）
in the structure shown in the formula (I), X is a natural macromolecular organic matter containing hydroxyl; the phosphorus adsorbent is prepared by grafting polyallylamine on a natural high molecular organic matter under an initiating system; or grafting polyacrylamide on a natural polymer organic matter under an initiating system, and then performing Hofmann degradation to obtain the polyacrylamide; the initiation system is one of redox agent initiation, photoinitiator initiation, microwave initiation, radiation initiation or thermal initiation; the redox agent is one of copper dipeeriodate, manganese salt, manganese oxide, ferric salt, iron oxide, hydrogen peroxide, hypochlorous acid, hypochlorite, nitric acid or sulfuric acid.
2. The use according to claim 1, wherein the natural high molecular organic substance is one of starch, cellulose, protein, lignin, chitin or derivatives thereof.
3. Use of a gel-type phosphorus adsorbent for the preparation of a medicament for oral phosphorus removal, wherein the gel-type phosphorus adsorbent is obtained by adding a cross-linking agent to cross-link the phosphorus adsorbent used according to claim 1 or 2 to form a gel structure.
4. Use according to claim 3, wherein the cross-linking agent is methylolacrylamide.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1173133A (en) * | 1995-01-12 | 1998-02-11 | 吉尔特药品公司 | Phosphate-binding polymers for oral administration |
| CN1260236A (en) * | 1999-12-31 | 2000-07-19 | 西安交通大学 | Cellulose fibre ion-exchange adsorbent for decolouring and its compounding technology |
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| JPS5995930A (en) * | 1982-11-22 | 1984-06-02 | Agency Of Ind Science & Technol | Cellulose adsorbent graft-polymerized with n-isopropyl acrylamide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1173133A (en) * | 1995-01-12 | 1998-02-11 | 吉尔特药品公司 | Phosphate-binding polymers for oral administration |
| CN1260236A (en) * | 1999-12-31 | 2000-07-19 | 西安交通大学 | Cellulose fibre ion-exchange adsorbent for decolouring and its compounding technology |
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| Title |
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| 烯丙基胺-细菌纤维素的制备及其动力学研究;关晓辉;《材料导报B：研究篇》;20120731;第26卷(第7期);第82-86页 * |
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