CN105769816A - Sustained-release preparation for polypeptide drug, and preparation method thereof - Google Patents
Sustained-release preparation for polypeptide drug, and preparation method thereof Download PDFInfo
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- CN105769816A CN105769816A CN201410813419.9A CN201410813419A CN105769816A CN 105769816 A CN105769816 A CN 105769816A CN 201410813419 A CN201410813419 A CN 201410813419A CN 105769816 A CN105769816 A CN 105769816A
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Abstract
The invention discloses a sustained-release preparation for a polypeptide drug. The preparation uses nanometer cellulose, nanometer carboxymethyl cellulose, or quaternized nanometer cellulose as a carrier material, overcomes the disadvantages that the polypeptide drug has poor stability and is easy to remove, and enables the effect of the polypeptide drug to be long-lasting. The invention also discloses a preparation method for the sustained-release preparation. The preparation method comprises the following steps: adding a solution of the polypeptide drug into an NCC solution, a nanometer carboxymethyl cellulose solution or a quaternized nanometer cellulose solution at a temperature of 0 to 40 DEG C and carrying out incubation for 1 to 48 h; and then adding NaCl flocculated and embedded polypeptide drug-NCC nanoparticles, polypeptide drug-nanometer carboxymethyl cellulose nanoparticles or polypeptide drug-quaternized nanometer cellulose nanoparticles, and carrying out centrifugation. The preparation method has the advantages of easiness and practicability.
Description
Technical field
The present invention relates to a kind of using nano-cellulose and derivant thereof as peptide drugs slow-release preparation of carrier material and preparation method thereof, belong to biomedicine field.
Background technology
Development along with biotechnology, polypeptide drug application clinically is more and more extensive, owing to the physical and chemical stability of polypeptide is poor, Half-life in vivo is short, should not pass through biomembrane, and is quickly eliminated after having intravenous injection or the feature such as degraded, effective route of administration and drug delivery system are restricted, it is that polypeptide drugs are applied to clinical bottleneck (Eur.J.Pharm.2013,713,54 57).Therefore, this area is in the urgent need to a kind of novel pastille slow-release material.Both can there have is the release polypeptide drug of control, and make blood drug level be maintained in the Valid concentration that comparison is steadily lasting, thus increasing the safety of medication, having improved the significance for the treatment of.
Cellulose is polysaccharide the abundantest, reproducible, degradable in the world.Cellulose is nontoxic and has good biocompatibility, it is possible to prepare into the nano-cellulose (being called for short NCC) of medical application.NCC has very big surface area and potential top load, and medicine can be bound in its surface, it is achieved Controlled release.But, have no the nano-cellulose relevant report as sustained-release drug carrier up to now.
Based on this, the present invention, using nano-cellulose and derivant thereof as sustained-release drug carrier, overcomes the difficulty that polypeptide drug easily should not be eliminated or degrade after passing through blood brain barrier and intravenous injection, it is achieved the slow releasing function to polypeptide drug.
Summary of the invention
It is desirable to provide it is a kind of using nano-cellulose and derivant thereof as peptide drugs slow-release preparation of carrier material and preparation method thereof.This carrier material overcomes the deficiency that polypeptide drug self stability is poor, be easily eliminated, and makes polypeptide drugs drug effect more lasting.
Peptide drugs slow-release preparation, it is characterised in that said preparation is using nano-cellulose, carboxymethyl nano-cellulose or quaternized nano-cellulose as carrier material.Described polypeptide drug is interior morphine peptide.
The preparation method of peptide drugs slow-release preparation: when 0～40 DEG C, joins polypeptide drug solution in NCC solution, carboxymethyl nanofiber cellulose solution or quaternized nanofiber cellulose solution and hatches 1～48h；It is subsequently adding NaCl flocculation embedding polypeptide drug-NCC nanoparticle, polypeptide drug-carboxymethyl nano-cellulose nanoparticle or polypeptide drug-quaternized nano-cellulose nanoparticle, centrifugal.
The concentration of described polypeptide drug solution is 1～3mgmL-1, the concentration of NCC solution, carboxymethyl nanofiber cellulose solution and quaternized nanofiber cellulose solution is 2～4mgmL-1, the volume ratio of polypeptide drug solution and NCC solution, carboxymethyl nanofiber cellulose solution and quaternized nanofiber cellulose solution is 1:15～1:5.
Described NaCl flocculation is 1:100 with polypeptide drug mass ratio.
The preparation method of described nano-cellulose: adopt 60% sulphuric acid hydrolysis microcrystalline Cellulose, then neutralizes hydrolyzed solution, adds a large amount of water and removes salt, more centrifugal colloidal suspensions is through dialysing and obtaining NCC.
The preparation method of described carboxymethyl nano-cellulose: after NCC is dissolved, by etherifying reagent by its carboxy methylation, then neutralization, washing, drying carboxymethyl nano-cellulose.
The preparation method of described quaternized nano-cellulose: by NCC ammonification in urea liquid, add 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride again that it is quaternized, then neutralizing, put in bag filter and dialyse 2 days, lyophilization obtains the quaternized nano-cellulose of white sponge.
Nano-cellulose, the extracorporeal releasing experiment of morphine peptide in carboxymethyl nano-cellulose and quaternized nano-cellulose slow release: morphine peptide in 150～350 μ g is embedded in the NCC of 1.5～3.5mg, the interior morphine peptide-NCC nanoparticle of preparation in carboxymethyl nano-cellulose and quaternized nano-cellulose, interior morphine peptide-carboxymethyl nano-cellulose nanoparticle and interior morphine peptide-quaternized nano-cellulose nanoparticle dissolution are in the deionized water of 2～4mL, and it is moved in the bag filter of 3500～12000Da molecular weight, bag filter is put into the deionized water of 20～30mL, the physiological fluid of simulation, intestinal juice and gastric juice discharge.
Intracorporeal active experiment: in 21 ± 1 DEG C of room temperatures, with the constant-temperature hot water of 50 ± 1 DEG C for induced pain source, immerses above for mouse tail tip 5cm in hot water, and record mouse tail enters water to the time contracted between dried up.Mouse tail vein injection respectively organizes medicine carrying 1mL, and experiment measured primary first-order equation every 5 minutes before starting, and excessively sensitive or blunt mice is given it up, and surveyed 3 times altogether, and incubation period based on averaging is generally 3 ~ 5s.After record administration the 5th, 10,15,20,30,45,60,90, the TFL of 120min.For preventing from scalding in experiment, the incubation period recorded, more than 10s, calculates by 10s.Pain sensation adjustment effect utilizes maximum analgesic effect (being called for short MPE) value to evaluate: MPE(%)=100 [(the pain territory after administration-pain territory, basis)]/(pain territory, 10 seconds-basis)].Within this experimental record 90min, the whipping of mice is movable, in crude drug, the nanoparticle of morphine peptide and nano-cellulose, carboxymethyl nano-cellulose and the interior morphine peptide of quaternized nano-cellulose embedding all has paroxysmal pain activity, result shows, the paroxysmal pain activity of interior morphine peptide is better than the nanoparticle of nano-cellulose, carboxymethyl nano-cellulose and the interior morphine peptide of quaternized nano-cellulose embedding, but the slow release effect of interior morphine peptide does not but have morphine peptide nanoparticles in the embedding of various nano-cellulose good.
Accompanying drawing explanation
Fig. 1 is the in-vitro release figure of morphine peptide in NCC-.
Fig. 2 is the in-vitro release figure of carboxymethyl nano-cellulose-Nei morphine peptide.
Fig. 3 is the in-vitro release figure of quaternized nano-cellulose-Nei morphine peptide.
Fig. 4 is the internal releasing trend figure of morphine peptide in NCC-, carboxymethyl nano-cellulose-Nei morphine peptide and quaternized nano-cellulose-Nei morphine peptide.
Detailed description of the invention
Embodiment 1
Weigh 20g microcrystalline Cellulose at 40 DEG C, be slowly added to 60% sulphuric acid 200mL at 80rmin-1When stirring hydrolysis 2h, with in NaOH and after, be diluted with water to 1000mL, stand and remove the supernatant, repeatedly, remove NaSO in solution4, finally centrifugal obtain colloidal suspensions and be nano-cellulose, dialyse 3 days standby.
When 10 DEG C, by 175 μ L, 2mgmL-1Interior morphine peptide solution join 0.5mL, 3.5mgmL-1NCC in hatch 12h after, add morphine peptide-NCC nanoparticle in the NaCl flocculation of 1mmol, centrifugal 10min, pipette the interior morphine peptide that supernatant HPLC detection is free, converted score, calculate embedding rate 84.7%.
Release in vitro: morphine peptide in 294.45 μ g is embedded in the NCC of 1.75mg, the interior morphine peptide-NCC nanoparticle dissolution of preparation is in the deionized water of 4mL, and it is moved in the bag filter of 5000Da, bag filter is put into the deionized water of 20mL, the physiological fluid of simulation, intestinal juice, gastric juice discharges, it is explosion type release at front 2h, is followed by slow releasing, release 237.16 ± 10 μ g after release 12h.
Tail-flick test: in 21 ± 1 DEG C of room temperatures, with the constant-temperature hot water of 50 ± 1 DEG C for induced pain source, immerses above for mouse tail tip 5cm in hot water, and record mouse tail enters water to the time contracted between dried up.Mouse tail vein injection respectively organizes 1mL, and experiment measured primary first-order equation every 5 minutes before starting, and excessively sensitive or blunt mice is given it up, and surveys 3 times altogether, incubation period based on averaging, is generally 3 ~ 5s.After record administration the 5th, 10,15,20,30,45,60,90, the TFL of 120min.For preventing from scalding in experiment, the incubation period recorded, more than 10s, calculates by 10s.Pain sensation adjustment effect utilizes MPE value: the paroxysmal pain activity of interior morphine peptide is better than interior morphine peptide nanoparticles, and the lasting effect of interior morphine peptide does not but have the good of interior morphine peptide-NCC nanoparticle.
Embodiment 2
Weigh 20g microcrystalline Cellulose at 40 DEG C, be slowly added to 60% sulphuric acid 200mL at 80rmin-1When stirring hydrolysis 2h, with in NaOH and after, be diluted with water to 1000mL, stand and remove the supernatant, repeatedly, remove NaSO in solution4, finally centrifugal obtain colloidal suspensions and be nano-cellulose, dialyse 3 days standby.
When 30 DEG C, by 225 μ L, 2mgmL-1Interior morphine peptide solution join 0.5mL, 2.5mgmL-1NCC in hatch 12h after, add morphine peptide-NCC nanoparticle in the NaCl flocculation of 1mmol, centrifugal 10min, pipette the interior morphine peptide that supernatant HPLC detection is free, converted score, calculate embedding rate 70.20%.
Release in vitro: morphine peptide in 245.7 μ g is embedded in the NCC of 1.75mg, the interior morphine peptide-NCC nanoparticle dissolution of preparation is in the deionized water of 4mL, and it is moved in the bag filter of 6000Da, bag filter is put into the deionized water of 20mL, the physiological fluid of simulation, intestinal juice, gastric juice discharges, it is explosion type release at front 2h, is followed by slow releasing, release 196.56 ± 10 μ g after release 12h.
Tail-flick test: concrete grammar is embodiment 1 such as.Pain sensation adjustment effect utilizes MPE value to evaluate: the lasting effect of the interior morphine peptide-NCC nanoparticle obtained as stated above does not but have embodiment 1 good.
Embodiment 3
Weigh 20g microcrystalline Cellulose at 40 DEG C, be slowly added to 60% sulphuric acid 200mL at 80rmin-1When stirring hydrolysis 2h, with in NaOH and after, be diluted with water to 1000mL, stand and remove the supernatant, repeatedly, remove NaSO in solution4, finally centrifugal obtain colloidal suspensions and be nano-cellulose, dialyse 3 days standby.
When 40 DEG C, by 350 μ L, 2mgmL-1Interior morphine peptide join 0.5mL, 3.5mgmL-1NCC in hatch 12h after, add morphine peptide-NCC nanoparticle in the NaCl flocculation of 1mmol, centrifugal 10min, pipette the interior morphine peptide that supernatant HPLC detection is free, converted score, calculate embedding rate 75.43%.
Release in vitro: morphine peptide in 264 μ g is embedded in the NCC of 1.75mg, the interior morphine peptide-NCC nanoparticle dissolution of preparation is in the deionized water of 4mL, and it is moved in the bag filter of 7000Da, bag filter is put into the deionized water of 20mL, the physiological fluid of simulation, intestinal juice, gastric juice discharges, it is explosion type release at front 2h, is followed by slow releasing, release 211.2 ± 10 μ g after release 12h.
Tail-flick test: concrete grammar is embodiment 1 such as.Pain sensation adjustment effect utilizes MPE value to evaluate: the lasting effect of the interior morphine peptide-NCC nanoparticle obtained as stated above is than embodiment the last 2, but does not have embodiment 1 good.
Embodiment 4
Weighing NCC0.22g in round-bottomed flask, the alcoholic solution that 0.22gNaOH is dissolved in 10mL70% exists, and pipettes 7mL in round-bottomed flask, adds the alcoholic solution of 8mL70%, stirring reaction 2.5h at 35 DEG C.Adding 0.1g monoxone, 0.1g potassium iodide, 0.1g sodium acetate adds in reactant liquor after being dissolved in the alcoholic solution of 5mL85%, continues stirring reaction 20min.Then heat to 80 DEG C, add remaining sodium hydroxide-alcoholic solution, etherificate 2h, be neutralized to pH=7 with the hydrochloric acid solution of 2%, with the alcoholic solution washed product 3 × 30min of 10mL95% after sucking filtration, dry carboxymethyl nano-cellulose standby.
When 25 DEG C, by 100 μ L, 2mgmL-1Interior morphine peptide solution join 0.5mL, 4mgmL-1Carboxymethyl nano-cellulose in hatch 12h after, add morphine peptide-carboxymethyl nano-cellulose nanoparticle in the 5%HCl flocculation of 1mmol, centrifugal 10min, pipette the interior morphine peptide that supernatant HPLC detection is free, converted score, calculate embedding rate 64.20%.
Release in vitro: morphine peptide in 128.4ug is embedded in the carboxymethyl nano-cellulose of 2mg, the interior morphine peptide-carboxymethyl nano-cellulose nanoparticle dissolution of preparation is in the deionized water of 4mL, and it is moved in the bag filter of 5000Da, bag filter is put into the deionized water of 20mL, the physiological fluid of simulation, intestinal juice, gastric juice discharges, it is explosion type release at front 2h, is followed by slow releasing, release 102.72 ± 10ug after release 12h.
Tail-flick test: concrete grammar is embodiment 1 such as.Pain sensation adjustment effect utilizes MPE value to evaluate: the slow release effect of the interior morphine peptide-carboxymethyl nano-cellulose nanoparticle obtained as stated above does not have interior morphine peptide-nano-cellulose nanoparticle good.
Embodiment 5
Weighing NCC0.22g in round-bottomed flask, the alcoholic solution that 0.22gNaOH is dissolved in 10mL70% exists, and pipettes 7mL in round-bottomed flask, adds the alcoholic solution of 8mL70%, stirring reaction 2.5h at 35 DEG C.Adding 0.1g monoxone, 0.1g potassium iodide, 0.1g sodium acetate adds in reactant liquor after being dissolved in the alcoholic solution of 5mL85%, continues stirring reaction 20min.Then heat to 80 DEG C, add remaining sodium hydroxide-alcoholic solution, etherificate 2 ~ 5h, be neutralized to pH=7 with the hydrochloric acid solution of 2%, with the alcoholic solution washed product 3 × 30min of 10mL95% after sucking filtration, dry carboxymethyl nano-cellulose standby.
When 25 DEG C, by 50 μ L, 2mgmL-1Interior morphine peptide solution join 0.5mL, 4mgmL-1Carboxymethyl nano-cellulose in hatch 12h after, add morphine peptide-carboxymethyl nano-cellulose nanoparticle in the 5%HCl flocculation of 1mmol, centrifugal 10min, pipette the interior morphine peptide that supernatant HPLC detection is free, converted score, calculate embedding rate 53.20%.
Release in vitro: morphine peptide in 53.20ug is embedded in the carboxymethyl nano-cellulose of 2mg, the interior morphine peptide-carboxymethyl nano-cellulose nanoparticle dissolution of preparation is in the deionized water of 4mL, and it is moved in the bag filter of 3500～12000Da, bag filter is put into the deionized water of 20mL, the physiological fluid of simulation, intestinal juice, gastric juice discharges, it is explosion type release at front 2h, is followed by slow releasing, release 42.56 ± 10ug after release 12h.
Tail-flick test: concrete grammar is embodiment 1 such as.Pain sensation adjustment effect utilizes MPE value to evaluate: the slow release effect of the interior morphine peptide-carboxymethyl nano-cellulose nanoparticle obtained as stated above does not have embodiment 4 good.
Embodiment 6
Configuration H2O:NaOH: carbamide (8.5:1:0.5) dissolves freezing standby, weighs the 2g nano-cellulose dried finely ground, puts into reaction 2 ~ 5min, then 8000 ~ 10000r/min in solution 50 ~ 100mL that above-mentioned configuration is good, centrifugal 10 ~ 30min, removes insoluble matter.Solution is poured in the beaker of 250mL, add etherifying reagent 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride 2 ~ 10g etherificate 12 ~ 24h.With the HCl of 5% be adjusted to neutrality put in bag filter dialyse lyophilization in 4 ~ 7 days obtain white sponge solid, dry quaternized nano-cellulose standby.
When 25 DEG C, by 50 μ L, 2mgmL-1Interior morphine peptide solution join 0.5mL, 4mgmL-1Quaternized nano-cellulose in hatch 12h after, add morphine peptide-quaternized nano-cellulose nanoparticle in the 5%HCl flocculation of 1mmol, centrifugal 10min, pipette the interior morphine peptide that supernatant HPLC detection is free, converted score, calculate embedding rate 89.50%.
Release in vitro: morphine peptide in 89.50ug is embedded in the quaternized nano-cellulose of 2mg, the interior morphine peptide-quaternized nano-cellulose nanoparticle dissolution of preparation is in the deionized water of 4mL, and it is moved in the bag filter of 3500～12000Da, bag filter is put into the deionized water of 20mL, the physiological fluid of simulation, intestinal juice, gastric juice discharges, it is explosion type release at front 2h, is followed by slow releasing, release 71.60 ± 0.1ug after release 12h.
Tail-flick test: concrete grammar is embodiment 1 such as.Pain sensation adjustment effect utilizes MPE value to evaluate: the interior morphine peptide obtained as stated above-quaternized nano-cellulose nanoparticle slow release effect is better than interior morphine peptide-carboxymethyl nano-cellulose nanoparticle and interior morphine peptide-nano-cellulose nanoparticle.
Embodiment 7
Configuration H2O:NaOH: carbamide (8.5:1:0.5) dissolves freezing standby, weighs the 2g nano-cellulose dried finely ground, puts into reaction 2 ~ 5min, then 8000 ~ 10000r/min in solution 50 ~ 100mL that above-mentioned configuration is good, centrifugal 10 ~ 30min, removes insoluble matter.Solution is poured in the beaker of 250mL, add etherifying reagent 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride 2 ~ 10g etherificate 12 ~ 24h.With the HCl of 5% be adjusted to neutrality put in bag filter dialyse lyophilization in 4 ~ 7 days obtain white sponge solid, dry quaternized nano-cellulose standby.
When 25 DEG C, by 100 μ L, 2mgmL-1Interior morphine peptide solution join 0.5mL, 4mgmL-1Quaternized nano-cellulose in hatch 12h after, add morphine peptide-quaternized nano-cellulose nanoparticle in the 5%HCl flocculation of 1mmol, centrifugal 10min, pipette the interior morphine peptide that supernatant HPLC detection is free, converted score, calculate embedding rate 91.20%.
Release in vitro: morphine peptide in 182.4ug is embedded in the quaternized nano-cellulose of 2mg, the interior morphine peptide-quaternized nano-cellulose nanoparticle dissolution of preparation is in the deionized water of 4mL, and it is moved in the bag filter of 3500～12000Da, bag filter is put into the deionized water of 20mL, the physiological fluid of simulation, intestinal juice, gastric juice discharges, it is explosion type release at front 2h, is followed by slow releasing, release 145.92 ± 10ug after release 12h.
Tail-flick test: concrete grammar is embodiment 1 such as.Pain sensation adjustment effect utilizes MPE value to evaluate: the interior morphine peptide obtained as stated above-quaternized nano-cellulose nanoparticle slow release effect is better than embodiment 6.
Claims (8)
1. peptide drugs slow-release preparation, it is characterised in that said preparation is using nano-cellulose, carboxymethyl nano-cellulose or quaternized nano-cellulose as carrier material.
2. peptide drugs slow-release preparation as claimed in claim 1, it is characterised in that described polypeptide drug is interior morphine peptide.
3. the preparation method of peptide drugs slow-release preparation as claimed in claim 1 or 2, it is characterized in that: when 0～40 DEG C, polypeptide drug solution is joined in NCC solution, carboxymethyl nanofiber cellulose solution or quaternized nanofiber cellulose solution and hatch 1～48h；It is subsequently adding NaCl flocculation embedding polypeptide drug-NCC nanoparticle, polypeptide drug-carboxymethyl nano-cellulose nanoparticle or polypeptide drug-quaternized nano-cellulose nanoparticle, centrifugal.
4. preparation method as claimed in claim 3, it is characterised in that: the concentration of described polypeptide drug solution is 1～3mgmL-1, the concentration of NCC solution, carboxymethyl nanofiber cellulose solution and quaternized nanofiber cellulose solution is 2～4mgmL-1, the volume ratio of polypeptide drug solution and NCC solution, carboxymethyl nanofiber cellulose solution and quaternized nanofiber cellulose solution is 1:15～1:5.
5. preparation method as claimed in claim 3, it is characterised in that: described NaCl flocculation is 1:100 with polypeptide drug mass ratio.
6. preparation method as claimed in claim 3, it is characterised in that the preparation method of described nano-cellulose: adopt 60% sulphuric acid hydrolysis microcrystalline Cellulose, then neutralizes hydrolyzed solution, adds a large amount of water and removes salt, more centrifugal colloidal suspensions is through dialysing and obtaining NCC.
7. preparation method as claimed in claim 3, it is characterised in that the preparation method of described carboxymethyl nano-cellulose: after NCC is dissolved, by etherifying reagent by its carboxy methylation, then neutralization, washing, drying carboxymethyl nano-cellulose.
8. preparation method as claimed in claim 3, the preparation method that it is characterized in that described quaternized nano-cellulose: by NCC ammonification in urea liquid, add 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride again that it is quaternized, then neutralize, putting in bag filter and dialyse 2 days, lyophilization obtains the quaternized nano-cellulose of white sponge.
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| CN101942102A (en) * | 2010-09-07 | 2011-01-12 | 东南大学 | Preparation method of powder nano cellulose |
| WO2013009253A1 (en) * | 2011-07-08 | 2013-01-17 | Chalmers Tekniska Högskola Aktiebolag | Microfibrillated cellulose films for controlled release of active agents |
| US20140335132A1 (en) * | 2010-11-23 | 2014-11-13 | Helen Mary Burt | Binding drugs with nanocrystalline cellulose (ncc) |
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- 2014-12-24 CN CN201410813419.9A patent/CN105769816A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101942102A (en) * | 2010-09-07 | 2011-01-12 | 东南大学 | Preparation method of powder nano cellulose |
| US20140335132A1 (en) * | 2010-11-23 | 2014-11-13 | Helen Mary Burt | Binding drugs with nanocrystalline cellulose (ncc) |
| WO2013009253A1 (en) * | 2011-07-08 | 2013-01-17 | Chalmers Tekniska Högskola Aktiebolag | Microfibrillated cellulose films for controlled release of active agents |
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