CN111388427A - Formula and preparation process of specific targeting medicament for treating pancreatic cancer - Google Patents
Formula and preparation process of specific targeting medicament for treating pancreatic cancer Download PDFInfo
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- CN111388427A CN111388427A CN202010271731.5A CN202010271731A CN111388427A CN 111388427 A CN111388427 A CN 111388427A CN 202010271731 A CN202010271731 A CN 202010271731A CN 111388427 A CN111388427 A CN 111388427A
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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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
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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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1611—Inorganic compounds
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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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
The invention discloses a specific targeting medicament formula for treating pancreatic cancer, which comprises the following components: a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide and modified magnetic carboxymethyl chitosan nano-microspheres, wherein the weight ratio of the compound X-76 to the modified magnetic carboxymethyl chitosan nano-microspheres is 1: 15 to 20. The invention can lead the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microsphere to have superparamagnetism, not only can selectively reach and be positioned at a tumor target area to release drugs under the guidance of an external magnetic field through intravenous, arterial catheter, oral administration or direct injection and other ways, but also improves the comprehensive control of temperature, time and stirring speed in the manufacturing process of the targeted therapeutic action of the compound X-76, leads the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microsphere to have smaller diameter (35 +/-2 nm) and good slow release performance, and simultaneously strengthens the targeted therapeutic effect of the drug on pancreatic cancer cells PANC-1.
Description
Technical Field
The invention relates to the technical field of targeted anticancer medicaments, in particular to a specific targeted medicament formula for treating pancreatic cancer and a preparation process thereof.
Background
Pancreatic cancer is a malignant tumor of the digestive tract that is highly malignant and difficult to diagnose and treat, and about 90% of pancreatic cancers are ductal adenocarcinomas originating from the epithelium of the glandular duct. Its morbidity and mortality has increased dramatically in recent years. Survival rate <1% for 5 years is one of the worst-prognosis malignancies. The early diagnosis rate of pancreatic cancer is low, the operative mortality rate is high, and the cure rate is low. The incidence rate of the disease is higher for men than for women, the ratio of men to women is 1.5-2: 1, male patients are far more common than women before menopause, and the incidence rate of postmenopausal women is similar to that of men.
The targeted drug is the most advanced drug for treating cancer at present, and the greatest difference from the traditional drug lies in the action mechanism. The conventional chemotherapy drugs play a role by poisoning cells, and because tumor cells cannot be accurately identified, normal cells can be killed, which is the root of side effects of the chemotherapy drugs. Targeted drugs have been developed against tumor genes, which recognize characteristic sites on tumor cells that are determined by genes specific to the tumor cells. At present, the targeted therapy has very good curative effect on cancers such as colorectal cancer, lung cancer and the like, but the curative effect of the targeted drug therapy on pancreatic cancer is not ideal.
The small-sized magnetic nanoparticles have sizes comparable to the sizes of viruses (20-450 nm), proteins (5-50 nm), DNA or genes (2 nm wide and 10-100 nm long), so when the magnetic nanoparticles are used as magnetic targeting drug carriers, the magnetic nanoparticles can not only enter the target position of a diseased organ or tissue, but also can enter the interior of tumor cells, and can also avoid target embolism. Meanwhile, the magnetic nano-particles have higher surface activity and magnetic property, and have wide application in the aspects of vacuum sealing, lubrication, magnetic recording, targeted medicine, biotechnology and the like.
Disclosure of Invention
The invention aims to solve the defects in the prior art, and provides a specific targeting medicament formula for treating pancreatic cancer and a preparation process thereof.
One of the purposes of the invention is to provide a specific targeting medicament formula for treating pancreatic cancer, which comprises the following components:
a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide and modified magnetic carboxymethyl chitosan nano-microspheres, wherein the weight ratio of the compound X-76 to the modified magnetic carboxymethyl chitosan nano-microspheres is 1: 15 to 20.
Preferably, the preparation of the modified magnetic carboxymethyl chitosan nano drug-loaded microsphere comprises the following specific steps: firstly wrapping oleic acid with magnetic Fe3O4Dispersing nano particles into cyclohexane to serve as an oil phase, adding a carboxymethyl chitosan aqueous solution serving as a water phase into the oil phase, stirring and mixing uniformly under the action of ultrasonic waves to obtain a mixed solution, adding an orthoester cross-linking agent into the mixed solution, and continuously stirring and reacting for 1-3 hours; and then carrying out magnetic separation to collect the lower-layer precipitate, washing with petroleum ether and acetone respectively, and drying to obtain the modified magnetic carboxymethyl chitosan nano-microsphere.
Preferably, the oleic acid-coated magnetic Fe3O4The volume ratio of an oil phase formed by nanoparticles to a water phase formed by a carboxymethyl chitosan aqueous solution is 4-6: 1, and the mass volume concentration of the carboxymethyl chitosan aqueous solution is 1.5-1.8%; the ultrasonic time of the ultrasonic wave is 15-25 min, and the stirring speed is 500-600 rpm.
The invention also aims to provide a preparation process of the specific targeting medicament for treating pancreatic cancer, which comprises the following steps:
s1, dissolving a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide in maleic acid to serve as an organic phase, and preparing the modified magnetic carboxymethyl chitosan nano microspheres into aqueous dispersion serving as an aqueous phase;
s2, adding the organic phase obtained in the step S1 into the water phase while stirring, and stirring for 8-20 hours at 20-40 ℃ to obtain a mixture;
s3, washing the mixture obtained in the step S2 by deionized water, and then collecting microspheres by magnetic separation;
s4, freeze-drying and crushing the microspheres obtained in the step S3 to obtain compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microspheres, namely the specific targeting medicament.
Preferably, in step S1, the concentration of the aqueous dispersion prepared from the modified magnetic carboxymethyl chitosan nanospheres is 0.2 to 0.5%, and the weight ratio of the modified magnetic carboxymethyl chitosan nanospheres to the compound X-76 is 1: 15 to 18.
Preferably, in step S2, the rotation speed of the stirring is 600 to 1500rpm, the stirring time is 9 to 15 hours, and in step S3, the steps of washing with deionized water and magnetic separation are repeated 3 to 5 times.
Preferably, in step S4, the freeze-drying time is 10-15 hours, the freeze-drying temperature is-10 to-15 ℃, and the particle size of the specific targeting agent is 35 ± 2 nm.
Compared with the prior art, the invention has the following beneficial effects:
in the invention, the oleic acid coated magnetic Fe is adopted3O4Nanoparticles instead of conventional magnetic Fe3O4The nano particles are implanted, so that the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microsphere has superparamagnetism, can selectively reach and be positioned at a tumor target region to release drugs under the guidance of an external magnetic field through intravenous, arterial catheter, oral administration or direct injection and the like, and improves the targeted therapeutic effect of the compound X-76. The temperature, time and stirring speed in the preparation process are comprehensively controlled, so that the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microsphere has small diameter (35 +/-2 nm) and good slow release performance, and the targeted treatment effect of the medicament on pancreatic cancer cells PANC-1 is enhanced.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples.
Example 1
S1, dissolving a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide in maleic acid to serve as an organic phase, preparing the modified magnetic carboxymethyl chitosan nano microsphere into an aqueous dispersion to serve as an aqueous phase, wherein the concentration of the aqueous dispersion prepared from the modified magnetic carboxymethyl chitosan nano microsphere is 0.2%, and the weight ratio of the modified magnetic carboxymethyl chitosan nano microsphere to the compound X-76 is 1: 18;
s2, adding the organic phase obtained in the step S1 into the water phase while stirring, and stirring for 8 hours at 20 ℃ at the rotating speed of 600rpm to obtain a mixture;
s3, washing the mixture obtained in the step S2 by deionized water, and then collecting microspheres by magnetic separation, wherein the steps of washing by deionized water and magnetic separation are repeated for 5 times;
s4, freeze-drying the microspheres obtained in the step S3 for 15h at-15 ℃, and crushing to obtain the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microspheres, namely the specific targeting medicament (marked as P1), wherein the particle size of the specific targeting medicament is 37 nm.
Example 2
S1, dissolving a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide in maleic acid to serve as an organic phase, preparing the modified magnetic carboxymethyl chitosan nano microsphere into an aqueous dispersion to serve as an aqueous phase, wherein the concentration of the aqueous dispersion prepared from the modified magnetic carboxymethyl chitosan nano microsphere is 0.2%, and the weight ratio of the modified magnetic carboxymethyl chitosan nano microsphere to the compound X-76 is 1: 20;
the preparation method of the modified magnetic carboxymethyl chitosan nano drug-loaded microsphere comprises the following specific steps: firstly wrapping oleic acid with magnetic Fe3O4The nanoparticles are dispersed into cyclohexane as an oil phase; secondly, adding a carboxymethyl chitosan aqueous solution with the mass volume concentration of 1.5 percent into an oil phase as a water phase, wherein the oleic acid-coated magnetic Fe3O4Volume ratio of oil phase formed by nano particles to water phase formed by carboxymethyl chitosan water solution is 4: 1, stirring and mixing evenly under the action of ultrasonic wavesUniformly stirring, wherein the ultrasonic time of ultrasonic waves is 15min, and the stirring speed is 550rpm to obtain a mixed solution, then adding an orthoester cross-linking agent into the mixed solution, and continuously stirring for reaction for 2 h; then carrying out magnetic separation to collect lower-layer precipitates, washing with petroleum ether and acetone respectively, and drying to obtain modified magnetic carboxymethyl chitosan nano microspheres;
s2, adding the organic phase obtained in the step S1 into the water phase while stirring, and stirring for 8 hours at 20 ℃ at the rotating speed of 500rpm to obtain a mixture;
s3, washing the mixture obtained in the step S2 by deionized water, and then collecting microspheres by magnetic separation, wherein the steps of washing by deionized water and magnetic separation are repeated for 4 times;
s4, freeze-drying the microspheres obtained in the step S3 for 15h at-12 ℃, and crushing to obtain the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microspheres, namely the specific targeting medicament (marked as P2), wherein the particle size of the specific targeting medicament is 36 nm.
Example 3
S1, dissolving a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide in maleic acid to serve as an organic phase, preparing the modified magnetic carboxymethyl chitosan nano microsphere into an aqueous dispersion to serve as an aqueous phase, wherein the concentration of the aqueous dispersion prepared from the modified magnetic carboxymethyl chitosan nano microsphere is 0.2%, and the weight ratio of the modified magnetic carboxymethyl chitosan nano microsphere to the compound X-76 is 1: 16;
the preparation method of the modified magnetic carboxymethyl chitosan nano drug-loaded microsphere comprises the following specific steps: firstly wrapping oleic acid with magnetic Fe3O4The nanoparticles are dispersed into cyclohexane as an oil phase; secondly, adding a carboxymethyl chitosan aqueous solution with the mass volume concentration of 1.8% into an oil phase as a water phase, wherein the oleic acid-coated magnetic Fe3O4Volume ratio of oil phase formed by nano particles to water phase formed by carboxymethyl chitosan water solution 5: 1, stirring and mixing uniformly under the action of ultrasonic waves, wherein the ultrasonic time of the ultrasonic waves is 25min, and the stirring speed is 600rpmObtaining a mixed solution, then adding an orthoester cross-linking agent into the mixed solution, and continuously stirring for reaction for 3 hours; then carrying out magnetic separation to collect lower-layer precipitates, washing with petroleum ether and acetone respectively, and drying to obtain modified magnetic carboxymethyl chitosan nano microspheres;
s2, adding the organic phase obtained in the step S1 into the water phase while stirring, and stirring for 8 hours at the temperature of 30 ℃ and the rotating speed of 700rpm to obtain a mixture;
s3, washing the mixture obtained in the step S2 by deionized water, and then collecting microspheres by magnetic separation, wherein the steps of washing by deionized water and magnetic separation are repeated for 3 times;
s4, freeze-drying the microspheres obtained in the step S3 for 15h at-15 ℃, and crushing to obtain the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microspheres, namely the specific targeting medicament (marked as P3), wherein the particle size of the specific targeting medicament is 34 nm.
Cytotoxicity assays
The tested drugs are: the X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microspheres P1, P2 and P3 prepared in the examples 1-3 are used as experimental groups, and rapamycin is used as a control group.
Human pancreatic cancer PANC-1 was cultured in medium containing 10% fetal bovine serum F12 at 37 ℃ with 5% CO210000 tumor cells/well are inoculated on a 96-well culture plate, after 24h of culture, compounds which are diluted by culture medium to final concentrations of 0.01, 0.1, 1, 5, l0, 20, 25 and 50 mu mol/L are added, rapamycin with the same concentration gradient is used as positive control, no drug is added as blank control, 3 repeated wells are arranged at each concentration, 48h of culture is carried out, cells are fixed by TCA with precooled volume fraction of 10%, the culture solution is left for 1h at 4 ℃, then distilled water is washed for 5 times, natural drying is carried out at room temperature, 0.4% SRB solution prepared by 1% glacial acetic acid is added, the solution is dyed for 15min at room temperature, the culture solution is discarded, the solution is washed for 5 times by 1% acetic acid and is naturally dried at room temperature, finally 10 mmol/L solution (pH10.5) is added, the OD value is measured by an enzyme reader at 540nm wavelength, and the cell proliferation inhibition rate is 1-experimental group (%) (1-experimental group/Tris)Control group) 100%. And calculating the IC of the compound on tumor cells50. And calculating the IC of the compound on tumor cells50。
Inhibition (%) = ((negative control OD value-experimental OD value)/negative control OD value) × 100%
| EXAMPLE 1 group 1 | EXAMPLE 2 group | EXAMPLE 3 group | Control group 1 | |
| Human pancreatic cancer (IC)50） | 20.3±0.2 | 19.7±0.2 | 20.5±0.2 | 25.2±0.3 |
The data results obtained by the cytotoxicity experiments show that the compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microsphere prepared by the invention has stronger lethality on human pancreatic cancer PANC-1 cells than pure rapamycin.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (7)
1. The formula of the specific targeting medicament for treating the pancreatic cancer is characterized by comprising the following components: a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide and modified magnetic carboxymethyl chitosan nano-microspheres, wherein the weight ratio of the compound X-76 to the modified magnetic carboxymethyl chitosan nano-microspheres is 1: 15 to 20.
2. The specific targeting agent formula for treating pancreatic cancer according to claim 1, wherein the modified magnetic carboxymethyl chitosan nano drug-loaded microsphere is prepared by the following specific steps: firstly wrapping oleic acid with magnetic Fe3O4Dispersing nano particles into cyclohexane to serve as an oil phase, adding a carboxymethyl chitosan aqueous solution serving as a water phase into the oil phase, stirring and mixing uniformly under the action of ultrasonic waves to obtain a mixed solution, adding an orthoester cross-linking agent into the mixed solution, and continuously stirring and reacting for 1-3 hours; and then carrying out magnetic separation to collect the lower-layer precipitate, washing with petroleum ether and acetone respectively, and drying to obtain the modified magnetic carboxymethyl chitosan nano-microsphere.
3. The formulation of claim 2, wherein the oleic acid-coated magnetic Fe is used as a carrier of a drug for treating pancreatic cancer3O4The volume ratio of an oil phase formed by nanoparticles to a water phase formed by a carboxymethyl chitosan aqueous solution is 4-6: 1, the mass volume concentration of the carboxymethyl chitosan aqueous solution is 1.5-1.8%, the ultrasonic time of ultrasonic waves is 15-25 min, and the stirring speed is 500-600 rpm.
4. A preparation process of a specific targeting medicament for treating pancreatic cancer comprises the following steps:
s1, dissolving a compound X-76, namely 43-O- (2- (4- (diethylaminomethyl) -1H-1,2, 3-triazole-1-yl) acetyl) rapamycin oxide in maleic acid to serve as an organic phase, and preparing the modified magnetic carboxymethyl chitosan nano microspheres into aqueous dispersion serving as an aqueous phase;
s2, adding the organic phase obtained in the step S1 into the water phase while stirring, and stirring for 8-20 hours at 20-40 ℃ to obtain a mixture;
s3, washing the mixture obtained in the step S2 by deionized water, and then collecting microspheres by magnetic separation;
s4, freeze-drying and crushing the microspheres obtained in the step S3 to obtain compound X-76/modified magnetic carboxymethyl chitosan nano drug-loaded microspheres, namely the specific targeting medicament.
5. The preparation process of the specific targeting medicament for treating pancreatic cancer according to claim 4, wherein in step S1, the concentration of the aqueous dispersion prepared from the modified magnetic carboxymethyl chitosan nano-microsphere is 0.2-0.5%, and the weight ratio of the modified magnetic carboxymethyl chitosan nano-microsphere to the compound X-76 is 1: 15 to 18.
6. The process for preparing a specific targeting agent for treating pancreatic cancer according to claim 4, wherein in step S2, the rotation speed of stirring is 600-1500 rpm, the stirring time is 9-15 h, and in step S3, the steps of washing with deionized water and magnetic separation are repeated 3-5 times.
7. The process for preparing the specific targeting agent for treating pancreatic cancer according to claim 4, wherein in step S4, the freeze-drying time is 10-15 h, the freeze-drying temperature is-10 to-15 ℃, and the particle size of the specific targeting agent is 35 ± 2 nm.
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Cited By (1)
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