CN101259104A - Functionalization mesoporous molecular sieve used in adsorption and sustained-release alkaline drug method - Google Patents
Functionalization mesoporous molecular sieve used in adsorption and sustained-release alkaline drug method Download PDFInfo
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- CN101259104A CN101259104A CNA2008100548896A CN200810054889A CN101259104A CN 101259104 A CN101259104 A CN 101259104A CN A2008100548896 A CNA2008100548896 A CN A2008100548896A CN 200810054889 A CN200810054889 A CN 200810054889A CN 101259104 A CN101259104 A CN 101259104A
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- molecular sieve
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Abstract
The invention relates to a functionalized mesoporous molecular sieve and a method to use the functionalized mesoporous molecular sieve for adsorption and controlled release of alkaline drugs, namely, an alkaline drug is added to water or organic solution to obtain solution A, ensuring that the concentration of the alkaline drug is 1.0-100.0 mg/mL; the functionalized mesoporous molecular sieve is added to the solution A, ensuring that the functionalized mesoporous molecular sieve / solution A is equal to 0.1-0.5g / 10.0-500.0 mL, stirred for 0.5 to 3 days and then filtered, the obtained solid is dried, thus obtaining functionalized mesoporous molecular sieve B capable of absorbing drugs; -CH3 group is grafted on the surface of the unctionalized mesoporous molecular sieve B capable of absorbing drugs by adopting a post-processing method, so as to obtain double-functionalized solid pulvis with absorbed alkaline drug. The functionalized mesoporous molecular sieve of the invention has the advantages of well-distributed drug, large drug loading capacity, availability for convenient adjusting and long time of drug release.
Description
Technical field
The present invention relates to the application of a kind of organic functional mesoporous molecular sieve in alkalescent medicine absorption and slow release.
Technical background
Compare with traditional medicine-feeding technology, the medicament slow release technology have reduce medicine to the toxic and side effects of human body, improve curative effect of medication, advantage such as comfort level when increasing patient's medication, therefore the medicament slow release technical research not only has important therapeutic value, and business potential is arranged very much.Silicon-based mesoporous molecular sieve is because of having very high specific surface area, large pore volume, distribution homogeneous and continuously adjustable within the specific limits pore structure and excellent biological compatibility, make it become a kind of novel carriers [M.Vallet-Reg í in medicament slow release field, A.R á mila, R.P.del Real, J.P é rez-Pariente, Chem.Mater. (chemical material) 2001,13,308-311].Based on these good architectural characteristics of silicon-based mesoporous molecular sieve, people have carried out comparatively deep research to this new drug carrier.Is structure directing agent as U.S. Pat 2002164380 with vitamin E TPGS (Vitamin E d-[alpha]-tocopheryl polyethylene glycol 1000succinate), has synthesized the drug carrier material with mesoporous feature on the basis of adding the Al source.European patent W02006122998 has investigated SiO
2And the Ti-Si composite mesoporous molecular sieve is as the feasibility of slow releasing carrier of medication.
Alkalescent medicine is as a big class in the medicine family, in clinical treatment in occupation of important position very.Up to the present, in research to this new drug carrier of mesopore molecular sieve, people are many to serve as the research subtend with acidic drugs such as ibuprofen, captopril, bovine serum albumin, to the then rare report of the research of alkalescent medicines commonly used such as famotidine, cimetidine.
Summary of the invention
The object of the invention provides the method that a kind of functionalized mesopore molecular sieve carrier is applied to alkalescent medicine absorption and slow release.
Preparation method of the present invention comprises the steps:
(1), alkalescent medicine is joined in water or the organic solvent, making drug concentrations is 1.0-100.0mg/mL, obtains solution A;
(2), functional mesoporous molecular sieve is joined in the solution A, make functional mesoporous molecular sieve: solution A is 0.1-0.5g: 10.0-500.0mL, stir 0.5-3 days after-filtration under the room temperature, place the functional mesoporous molecular sieve B that is drying to obtain the absorption medicine under 40-80 ℃ filtering the gained solid;
(3), the functional mesoporous molecular sieve B that will adsorb medicine adopts the method for post processing at molecular sieve surface graft-CH
3Group can obtain being adsorbed with the Bifunctionalized solid powder of alkalescent medicine.
The solid powder of the present invention's preparation can also carry out tabletting under 1.0-6.0MPa pressure, promptly get tablet.
Aforesaid functional mesoporous molecular sieve is-functionalized SBA-15, SBA-12, MCM-41, MCM-48 or the HMS molecular sieve of COOH-SO
3SBA-15, SBA-12, MCM-41, MCM-48 or HMS molecular sieve that H is functionalized.The synthetic of them can be with reference to following document: Chem.Mater. (chemical material) 1999,11,3285-3295; Phys.Chem.Chem.Phys. (physical chemistry Chemical Physics) 2004,6,2461-2467; Micropor.Mesopor.Mat. (microporous mesoporous material) 2004,72,33-42.The aperture of functional mesoporous molecular sieve in 2.0-8.0nm, specific surface area at 300-1400m
2/ g, functional mesoporous molecular sieve surface-COOH or-SO
3The molar content of H is 5.0-50.0%;
The method of post processing can reference literature [J.Phys.Chem.B (physical chemistry magazine B) 2005,109,16263-16271] in aforesaid (3) step.
Aforesaid alkalescent medicine is meant in the molecular structural formula and contains-NH
2The alkalescent medicine of ,=NH, ≡ N group specifically is meant Penicillin antibiotics, disulfonamide, treatment digestive system and ulcer class medicine and tuberculosis class medicine.Penicillin antibiotics such as amoxicillin, benzathine benzylpenicillin; Disulfonamide such as SIX, sulfadiazine; Treatment digestive system and ulcer class medicine such as famotidine, formonitrile HCN amidine amine; Tuberculosis class medicine such as prothionamide, isoniazid.
Aforesaid organic solvent is ethanol, acetone or chloroform.
Aforesaid-CH
3Be trimethyl, dimethyl or monomethyl.Trimethyl is as-Si (CH
3)
3,-Si (CH
2)
2(CH
3)
3, dimethyl is as=Si (CH
3)
2,=SiCH
2(CH
3)
2, monomethyl such as ≡ SiCH
2CH
3, ≡ SiCH
2CH
2CH
2CH
3
The characteristics that the present invention compared with prior art has are:
By select difference-COOH or-SO
3The mesopore molecular sieve of H content can be regulated the load capacity (200-500mg/g) of alkalescent medicine on mesopore molecular sieve comparatively accurately;
2. by regulating mesopore molecular sieve surface hydrophobicity-CH
3Kind (trimethyl, dimethyl and the monomethyl) rate of release of regulating medicine more efficiently;
3. by increasing molecular sieve surface hydrophobicity-CH
3Can comparatively obviously the slow down rate of release of medicine of amount;
4. in the functionalized carrier acidic-group-COOH or-SO
3H and hydrophobic-CH
3Complement each other, thereby obtained a kind of existing big medicine adsorption capacity, the convenient again adjustable alkalescent medicine carrier of drug releasing rate.
The specific embodiment
Embodiment 1
Synthetic carboxy-functionalized mesopore molecular sieve: according to document Phys.Chem.Chem.Phys. (physical chemistry Chemical Physics) 2004,6, the method described in the 2461-2467.At first 4.0g surfactant P123 is joined HCl among the 2.0M of 120mL, be stirred to P123 and dissolve all that the back adds 6.0mL inorganic silicon source ethyl orthosilicate and 4.0mL contains the organosilan of cyano group as (CH
3CH
2O)
3SiCH
2CH
2CN, 40 ℃ are worn out behind the stirring 24h down.It is 40.0% (mole percent) functional mesoporous molecular sieve down together that filtration back gained solid promptly obtains carboxyl-content with the dilution heat of sulfuric acid processing.The specific surface of gained molecular sieve is 430m
2/ g, the aperture is 4.3nm.
Medicine absorption: the 1.0g amoxicillin is added in the 200mL water, and making the concentration of amoxicillin is 5.0mg/mL, obtains solution A 1.Get the 0.5g carboxyl-content and be 40.0% functionalized molecule sieve sample and join in the solution A 1 sealing.Stir 2 days after-filtration under the room temperature, will filter the gained solid and place 50 ℃ of dryings down.Promptly obtain sample B1, the medicine adsorbance of carrier is 450mg/g.
Molecular sieve surface methyl is functionalized: according to document J.Phys.Chem.B (physical chemistry magazine B) 2005,109, the described method of 16263-16271, the carboxy-functionalized mesopore molecular sieve B1 that gets 0.5g absorption medicine is tiled on the filter paper, and filter paper is fixed with a homemade circular steel support.Simultaneously, in the poly-tetrafluoro liner of reactor, add 0.5mL HMDS.Metal rack is put in the poly-tetrafluoro liner, and sealing guarantees that sieve sample does not directly contact with liquid reagent HMDS.It is 5.0% that 50 ℃ of reaction 0.5h make trimethyl content, and is adsorbed with the Bifunctionalized mesopore molecular sieve of carboxyl/trimethyl of alkalescent medicine.Promptly get C1 behind 60 ℃ of vacuum drying 12.0h.
Medicament slow release test: get 0.15g sample C1 solid powder or under 3.0MPa pressure resulting tablet, put into 150mL simulated body fluid SBF.37 ℃ of constant temperature.Through after the predefined time, take out a spot of solution and measure the solution drug level, simultaneously the fresh simulation SBF of adding equivalent in the slow-releasing system at once with UV-vis.10.0h medicine discharges substantially fully.
Embodiment 2
Synthetic carboxy-functionalized mesopore molecular sieve: according to document Chem.Mater. (chemical material) 1999,11, the method described in the 3285-3295.At first the 2.0g Surfactant CTAB is joined in the 240mL water, add 1.0g NaOH simultaneously, be stirred to CTAB and all dissolve the back and add 9.5mL inorganic silicon source such as ethyl orthosilicate and 0.5mL and contain the organosilan of cyano group as (CH
3CH
2O)
3SiCH
2CH
2CN is aging behind the stirring 24h under the room temperature.Filter back gained solid and handle with dilution heat of sulfuric acid that promptly to obtain carboxyl-content be 5.0% functional mesoporous molecular sieve.The specific surface of gained molecular sieve is 1250m
2/ g, the aperture is 3.0nm.
Medicine absorption: the 10.0g SIX is added in the 100mL chloroform, and making the concentration of SIX is 100.0mg/mL, obtains solution A 2.Get the 2.0g carboxyl-content and be 5.0% functionalized molecule sieve sample and join in the solution A 2 sealing.Stir 1 day after-filtration under the room temperature, will filter the gained solid and place 80 ℃ of dryings down.Promptly obtain sample B2, the medicine adsorbance of carrier is 240mg/g.
Molecular sieve surface methyl is functionalized: functionalized process is with embodiment 1, the response time be extended for 2.0h sample in the content of trimethyl be 10.0%, the gained sample is C2.
The medicament slow release test: drug release is tested with embodiment 1.Be 28.0h the complete release time of sample C2 Chinese medicine.
Embodiment 3
Synthetic carboxy-functionalized mesopore molecular sieve: according to document Micropor.Mesopor.Mat. (microporous mesoporous material) 2004,72, method described in the 33-42 is got the (CH of 2.0g MCM-48 sample and 3.0mL
3O)
3SiCH
2CH
2CH
2CH
2CN joins in the 100mL toluene, backflow 12.0h.Filter the gained solid and promptly obtain carboxy-functionalized MCM-41 with the dilute sulfuric acid processing.Carboxyl-content is 21.0% in the sample, and the specific surface of molecular sieve is 1100m
2/ g, the aperture is 3.1nm.
Medicine absorption: 10.0g formonitrile HCN amidine amine is added in the 100mL water, and making the concentration of formonitrile HCN amidine amine is 100.0mg/mL, obtains solution A 3.Get the 2.0g carboxyl-content and be 21.0% functionalized molecule sieve sample and join in the solution A 3 sealing.Stir 3 days after-filtration under the room temperature, will filter the gained solid and place under the room temperature dry.Promptly obtain sample B3, the medicine adsorbance of carrier is 310mg/g.
Molecular sieve surface methyl is functionalized: functionalized process is with embodiment 1, and the content of trimethyl is 18.0%, and the gained sample is C3.
The medicament slow release test: drug release is tested with embodiment 1.Be 41.0h the complete release time of sample C3 Chinese medicine.
Embodiment 4
Synthetic sulfonic group functional mesoporous molecular sieve: process changes organosilan into the (CH of 5.0mL with embodiment 1
3CH
2O)
3SiCH
2CH
2CH
2SH, the inorganic silicon source changes the 5.0mL methyl silicate into, filters back gained solid and handles with hydrogen peroxide and dilute sulfuric acid, obtains sulfonic group content and be 50.0% functional mesoporous molecular sieve.The specific surface of molecular sieve is 390m
2/ g, the aperture is 4.4nm.
Medicine absorption: the 0.2g famotidine is added in the 200mL methanol, and making the concentration of famotidine is 1.0mg/mL, obtains solution A 4.Get 0.2g sulfonic group content and be 50.0% functionalized molecule sieve sample and join in the solution A 4 sealing.Stir 0.5 day after-filtration under the room temperature, will filter the gained solid and place 50 ℃ of dryings down.Promptly obtain sample B4, the medicine adsorbance of carrier is 210mg/g.
Molecular sieve surface methyl is functionalized: according to step among the embodiment 1, making dimethyl content with the DMCS post treatment method is 5.0% the Bifunctionalized mesopore molecular sieve of sulfonic group/dimethyl.Promptly get C4 behind 40 ℃ of vacuum drying 12.0h.
The medicament slow release test: drug release is tested with embodiment 1.The 16h medicine discharges substantially fully among the sample C4.
Embodiment 5
Synthetic sulfonic group the functional mesoporous molecular sieve: (CH that organosilan is changed into 5.0mL
3O)
3SiCH
2SH, the inorganic silicon source changes the 5.0mL ethyl orthosilicate into, and all the other processes are with embodiment 4, obtain sulfonic group content and be 50.0% functional mesoporous molecular sieve.The specific surface of molecular sieve is 370m
2/ g, the aperture is 3.9nm.
Medicine absorption: the 2.5g prothionamide is added in the 500mL acetone, and making the concentration of prothionamide is 50.0mg/mL, obtains solution A 5.Get 0.5g sulfonic group content and be 50.0% functionalized molecule sieve sample and join in the solution A 5 sealing.Stir 2 days after-filtration under the room temperature, will filter the gained solid and place 50 ℃ of dryings down.Promptly obtain sample B5, the medicine adsorbance of carrier is 410mg/g.
Molecular sieve surface methyl is functionalized: according to the step among the embodiment 1, making monomethyl content with the TMCS post treatment method is 15.0% the Bifunctionalized mesopore molecular sieve of sulfonic group/monomethyl.Promptly get C5 behind 70 ℃ of vacuum drying 12.0h.
The medicament slow release test: drug release is tested with embodiment 1.The 18h medicine discharges substantially fully among the sample C5.
Embodiment 6
Synthetic sulfonic group functional mesoporous molecular sieve: according to document Micropor.Mesopor.Mat. (microporous mesoporous material) 2004,72, method described in the 33-42 is got the (CH of 1.0g HMS sample and 1.0mL
3O)
3SiCH
2CH
2CH
2CH
2SH joins in the 100mL toluene, backflow 12.0h.Filter the gained solid and obtain the functionalized MCM-41 of sulfonic group with hydrogen peroxide and dilute sulfuric acid processing.Carboxyl-content is 15.0% in the sample, and the specific surface of molecular sieve is 1400m
2/ g, the aperture is 2.6nm.
Medicine absorption: process promptly obtains sample B6 with embodiment 5, and the medicine adsorbance of carrier is 240mg/g.
Molecular sieve surface methyl is functionalized: process is with embodiment 5, and monomethyl content is 15.0% among the Bifunctionalized mesopore molecular sieve C6 of gained sulfonic group/monomethyl.
The medicament slow release test: drug release is tested with embodiment 1.The 17h medicine discharges substantially fully among the sample C6.
Claims (10)
1, a kind of functional mesoporous molecular sieve is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that comprising the steps:
(1), alkalescent medicine is joined in water or the organic solvent, making drug concentrations is 1.0-100.0mg/mL, obtains solution A;
(2), functional mesoporous molecular sieve is joined in the solution A, make functional mesoporous molecular sieve: solution A is 0.1-0.5g:10.0-500.0mL, stir 0.5-3 days after-filtration under the room temperature, place the functional mesoporous molecular sieve B that is drying to obtain the absorption medicine under 40-80 ℃ filtering the gained solid;
(3), the functional mesoporous molecular sieve B that will adsorb medicine adopts the method for post processing at molecular sieve surface graft-CH
3Group can obtain being adsorbed with the Bifunctionalized solid powder of alkalescent medicine.
2, a kind of functional mesoporous molecular sieve as claimed in claim 1 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described solid powder carries out tabletting under 1.0-6.0MPa pressure, promptly get tablet.
3, a kind of functional mesoporous molecular sieve as claimed in claim 1 or 2 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described functional mesoporous molecular sieve is-functionalized SBA-15, SBA-12, MCM-41, MCM-48 or the HMS molecular sieve of COOH-SO
3SBA-15, SBA-12, MCM-41, MCM-48 or HMS molecular sieve that H is functionalized.
4, a kind of functional mesoporous molecular sieve as claimed in claim 3 is applied to the method for alkalescent medicine absorption and slow release, the aperture that it is characterized in that described functional mesoporous molecular sieve in 2.0-8.0nm, specific surface area at 300-1400m
2/ g, functional mesoporous molecular sieve surface-COOH or-SO
3The molar content of H is 5.0-50.0%.
5, a kind of functional mesoporous molecular sieve as claimed in claim 1 or 2 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described alkalescent medicine be meant in the molecular structural formula contain-NH2 ,=alkalescent medicine of NH, ≡ N group.
6, a kind of functional mesoporous molecular sieve as claimed in claim 5 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described alkalescent medicine is Penicillin antibiotics, disulfonamide, treatment digestive system and ulcer class medicine and tuberculosis class medicine.
7, a kind of functional mesoporous molecular sieve as claimed in claim 6 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described Penicillin antibiotics is amoxicillin or benzathine benzylpenicillin; Disulfonamide is SIX or sulfadiazine; Treatment digestive system and ulcer class medicine is famotidine or formonitrile HCN amidine amine; Tuberculosis class medicine is prothionamide or isoniazid.
8, a kind of functional mesoporous molecular sieve as claimed in claim 1 or 2 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described organic solvent is ethanol, acetone or chloroform.
9, a kind of functional mesoporous molecular sieve as claimed in claim 1 or 2 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described-CH
3Be trimethyl, dimethyl or monomethyl.
10, a kind of functional mesoporous molecular sieve as claimed in claim 9 is applied to the method for alkalescent medicine absorption and slow release, it is characterized in that described trimethyl is-Si (CH
3)
3Or-Si (CH
2)
2(CH
3)
3, dimethyl is=Si (CH
3)
2Or=SiCH
2(CH
3)
2, monomethyl is ≡ SiCH
2CH
3Or ≡ SiCH
2CH
2CH
2CH
3
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| CN106913546B (en) * | 2015-12-28 | 2021-06-22 | 山东新时代药业有限公司 | Fast-dissolving minodronic acid tablet and preparation method thereof |
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