CN115120721A - Preparation method of sericin/manganese dioxide compound loaded with phthalocyanine and adriamycin - Google Patents
Preparation method of sericin/manganese dioxide compound loaded with phthalocyanine and adriamycin Download PDFInfo
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- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 title claims abstract description 52
- 108010013296 Sericins Proteins 0.000 title claims abstract description 32
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 title claims abstract description 29
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229940009456 adriamycin Drugs 0.000 title claims abstract description 17
- -1 manganese dioxide compound Chemical class 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
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- 238000000034 method Methods 0.000 claims description 7
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- HPZOOQSXPMEJBV-ODCFVKFUSA-N Tirilazad mesylate Chemical compound CS(O)(=O)=O.O=C([C@@H]1[C@@]2(C)CC=C3[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)CN(CC1)CCN1C(N=1)=CC(N2CCCC2)=NC=1N1CCCC1 HPZOOQSXPMEJBV-ODCFVKFUSA-N 0.000 claims description 3
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 230000005909 tumor killing Effects 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/32—Manganese; Compounds thereof
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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
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
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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
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Abstract
The invention discloses a preparation method of a sericin/manganese dioxide compound loaded phthalocyanine and adriamycin, which mainly comprises the following steps: (1) synthesizing phthalocyanine nanodots (Pc); (2) synthesizing a phthalocyanine-loaded sericin/manganese dioxide composite nanoparticle (SMP) by self-assembling in an ethanol solution; (3) and (3) preparing nanoparticles (SMPD) with Doxorubicin (DOX) loaded on the surfaces of the SMP nanoparticles. The obtained inorganic nanoparticles can form a nanoparticle aqueous solution which is uniformly distributed in water, have the advantages of high stability, low toxic and side effects, good controlled release of the drug and the like, effectively solve the problem of low solubility of hydrophobic drug molecules and provide an efficient drug delivery system.
Description
Technical Field
The invention belongs to the field of drug delivery, and particularly relates to a preparation method of a sericin/manganese dioxide compound loaded phthalocyanine and adriamycin.
Background
Sericin is a hydrophilic glycoprotein extracted from silk, and is composed of 18 kinds of amino acids including serine, glycine, glutamic acid, etc. The chemical element composition is as follows: carbon (46.5%), oxygen (31%), nitrogen (16.5%), hydrogen (6%). Through research, the sericin has various good efficacies of anti-inflammation, antibiosis, antioxidation and the like.
Because the molecular size of the adriamycin medicine is small and the solubility in water is extremely low, the problems of nonspecific selectivity, low medicine utilization rate, high kidney clearance rate, strong toxic and side effects and the like are urgently solved in the medicine delivery process, so that the improvement of the water solubility and the biocompatibility of the adriamycin medicine has important scientific significance.
In order to fully exert the advantage of good biocompatibility of sericin and solve the problems of hypoxia and insufficient efficiency in photodynamic, sericin is self-assembled in an ethanol solution to form nanosphere-coated Pc nanodots, and the nanosphere-coated Pc nanodots are subjected to KMnO 4 The mineralized manganese dioxide is acted, and the chemotherapeutic drug DOX is loaded on the surface of the nanoparticle to obtain the final product SMPD nanoparticle, under the action of EPR, the nanoparticle is passively targeted to a tumor part and is decomposed to generate oxygen under the action of a tumor microenvironment to release the loaded Pc and DOX. The oxygen generation relieves the tumor hypoxia, enhances the photodynamic efficiency of Pc, and realizes the combination of enhanced photodynamic therapy and chemotherapy.
Disclosure of Invention
Aiming at the defects that the existing inorganic nanoparticles have poor selectivity, the loading capacity of the medicine is low, the selective controllable release of the medicine is difficult to ensure and the like, the invention aims to provide a construction method for loading phthalocyanine and adriamycin on a sericin/manganese dioxide compound and application thereof in the field of cancer treatment by medicines.
Sericin is used as a reducing agent and a biological template, self-assembly is carried out in ethanol solution containing phthalocyanine nanodots (Pc) to form nanospheres, the Pc is wrapped in the nanospheres, and then biomineralization is carried out on the surfaces of the nanospheres through oxidation-reduction reaction with potassium permanganateManganese dioxide, finally loading the chemotherapeutic drug doxorubicin DOX on the surface of the nano particles to obtain the final product SS-MnO 2 -Pc @ DOX (SMPD for short). The nanoparticles can be enriched at the tumor part through the EPR effect, the problem of insufficient oxygen concentration in the photodynamic therapy process can be solved, the decomposition of the nanoparticles promotes the release of Pc and DOX, the synergistic proceeding of chemotherapy and enhanced photodynamic is realized, and the treatment efficiency is improved. Meanwhile, manganese dioxide can also react with GSH in the tumor, so that the consumption of the GSH on singlet oxygen is reduced, and the tumor killing effect of the singlet oxygen is improved. Meanwhile, the defects of high toxic and side effects on normal collective tissues and the like of the adriamycin are overcome, and the targeting property and excellent controllable release of the drug-loaded particles are realized.
The technical scheme of the invention is as follows:
a preparation method of a sericin/manganese dioxide compound loaded with phthalocyanine and adriamycin comprises the following steps:
(1) ultrasonically dispersing phthalocyanine in absolute ethyl alcohol, placing the phthalocyanine in a reaction kettle for reaction for 24 hours, ultrasonically dispersing obtained phthalocyanine nanoparticles, removing large particles in a centrifugal mode, and dialyzing with ethanol;
(2) dissolving sericin (SS) in secondary water, adding into absolute ethyl alcohol dropwise under ultrasonic treatment, and continuing ultrasonic treatment to obtain milky white dispersion liquid;
(3) mixing potassium permanganate solution (KMnO) 4 ) Dripping the mixture into the solution obtained in the step (2), reacting under ultrasonic, centrifugally collecting the obtained tan reactant, and washing and dispersing the tan reactant by secondary water;
(4) taking the solution obtained in the step (1), dripping the solution obtained in the step (3) under ultrasound, then adding a potassium permanganate solution with the same volume and mass concentration as the solution obtained in the step (3), reacting under ultrasound, centrifugally collecting a product, and washing and dispersing the product by using secondary water;
(5) putting the particle dispersion liquid obtained in the step (4) into a reaction bottle, dropwise adding a DOX aqueous solution under ultrasound, and performing ultrasonic treatment;
(6) transferring the solution obtained in the step (5) to a stirring table, and stirring in the dark, dialyzing the obtained product for 12h to remove free DOX, and then obtaining the SMPD nano-particle aqueous solution.
Further, the required mass of Pc in step (1) is 20mg, and the mass concentration in ethanol is 0.5mg mL -1 The reaction kettle is set to 180 ℃ for 24 hours.
Further, the required mass of the sericin in the step (2) is 200mg, and the mass concentration in secondary water is 20mg mL -1 (ii) a The absolute ethyl alcohol content was 15 mL.
Further, the mass concentration of potassium permanganate in the step (3) is 6mg mL -1 Take 5 mL.
Further, the required weight of the sericin aqueous solution in the step (4) is 15mg, and the ultrasonic reaction is carried out for 15 minutes.
Further, in the step (5), the mass fraction of the SMPD nanoparticle dispersion liquid is 10mL and is 2mg mL -1 (ii) a 2mL of DOX aqueous solution with the mass concentration of 2.5mg mL -1 。
The main advantages of the invention are:
1. aiming at the problems of the existing inorganic nanoparticle delivery system, the project creatively provides the delivery system of the construction method of loading phthalocyanine and adriamycin on the sericin/manganese dioxide compound, which can effectively achieve the aim of selective release, solve the problems of stability and drug selective controllable release of the existing inorganic nanoparticle delivery system and promote accurate diagnosis and efficient treatment of tumors.
2. In the project, sericin has various effects of good antibiosis, anti-inflammation, oxidation resistance and the like, is a pure natural hydrophilic glycoprotein, and is one of the greatest characteristics of the project for application of sericin.
Drawings
In order to make the purpose, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings:
fig. 1 is a schematic diagram of the synthesis of SMPD in example 1.
Fig. 2 is a particle size distribution diagram of SMPD in example 1.
Fig. 3 is a schematic diagram of the uv-vis absorption spectrum of the SMPD in example 1.
Fig. 4 is an infrared schematic of the SMPD of example 1.
Fig. 5 is a schematic representation of the MTT cytotoxicity assay of SMPD in example 1.
Detailed Description
The following examples are intended to illustrate the invention, but are not intended to limit the scope of the invention.
EXAMPLE 1 preparation of sericin/manganese dioxide Complex Supported with phthalocyanine and Doxorubicin
A preparation schematic diagram of a sericin/manganese dioxide compound nano drug loaded phthalocyanine and adriamycin is shown in figure 1, and mainly comprises the following steps:
(1) ultrasonically dispersing 20mg of phthalocyanine in 40mL of absolute ethyl alcohol for 30min, placing the phthalocyanine in a 100mL reaction kettle for reaction at 180 ℃ for 24h, then ultrasonically dispersing the obtained phthalocyanine nanoparticles again, removing large particles in a centrifugal mode, and dialyzing with ethanol;
(2) dissolving 100mg of sericin in 5mL of secondary water, adding the sericin into 15mL of absolute ethyl alcohol dropwise under ultrasound, and continuing to perform ultrasound for 5min to obtain a milky dispersion liquid;
(3) subsequently, 5mL of 6mg mL -1 Dripping the potassium permanganate solution into the solution obtained in the step (2), reacting for 15min under ultrasonic waves, centrifugally collecting the obtained tan reactant, and washing and dispersing the brown reactant by secondary water;
(4) take 15mL of 0.5mg mL -1 Dripping the solution obtained in the step (1) into the solution obtained in the step (3) under ultrasonic, then adding the potassium permanganate solution with the same amount as that in the step (3), reacting for 15min under ultrasonic, centrifugally collecting the product, and washing and dispersing the product by using secondary water; obtaining phthalocyanine-loaded sericin/manganese dioxide composite nanoparticles (SMP);
(5) 10mL of the solution was taken and 2mg mL of the solution was taken -1 The nanoparticle dispersion liquid obtained in (4) is added into a reaction bottle by dropping 2mL and 2.5mg mL under ultrasound -1 Performing ultrasonic treatment on the DOX aqueous solution for 5 min;
(6) transferring the solution obtained in the step (5) to a stirring table, stirring for 12h in the dark, dialyzing the obtained product for 12h to remove free DOX, and then obtaining the SMPD nano-particle aqueous solution.
Fig. 2 is a schematic diagram of the particle size distribution of SMPD, illustrating successful synthesis of SMPD with good stability.
FIGS. 3 and 4 are UV-VIS spectra and IR spectra of SMPD, SMP, and DOX, respectively, all illustrating the successful synthesis of SMPD.
Fig. 5 is a schematic diagram of MTT cytotoxicity assay of SMPD, demonstrating that SMPD cytotoxicity gradually decreased with increasing drug concentration, and was more effective in combination with photodynamic therapy (SMPD + L).
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (6)
1. A preparation method of a sericin/manganese dioxide compound loaded with phthalocyanine and adriamycin is characterized by comprising the following steps:
(1) ultrasonically dispersing phthalocyanine in absolute ethyl alcohol, placing the phthalocyanine in a reaction kettle for reaction for 24 hours, ultrasonically dispersing obtained phthalocyanine nanoparticles, removing large particles in a centrifugal mode, and dialyzing with ethanol;
(2) dissolving sericin SS in secondary water, adding the sericin SS into absolute ethyl alcohol dropwise under ultrasound, and continuing to perform ultrasound to obtain milky dispersion liquid;
(3) mixing potassium permanganate solution KMnO 4 Dripping the mixture into the solution obtained in the step (2), reacting under ultrasonic wave, centrifugally collecting the obtained tan reactant, and washing and dispersing the brown reactant by secondary water;
(4) taking the solution obtained in the step (1), dripping the solution obtained in the step (3) under ultrasound, then adding a potassium permanganate solution with the same volume and mass concentration as the solution obtained in the step (3), reacting under ultrasound, centrifugally collecting a product, and washing and dispersing the product by using secondary water;
(5) adding the particle dispersion liquid obtained in the step (4) into a reaction bottle, dropwise adding a DOX aqueous solution under ultrasonic treatment, and performing ultrasonic treatment;
(6) transferring the solution obtained in the step (5) to a stirring table, and stirring in the dark, dialyzing the obtained product for 12h to remove free DOX, and then obtaining an SMPD nanoparticle aqueous solution.
2. The method for preparing a sericin/manganese dioxide complex loaded with phthalocyanine and adriamycin according to claim 1, wherein: the mass concentration of the phthalocyanine in the absolute ethyl alcohol in the step (1) is 0.5mg mL -1 The temperature of the reaction kettle is 180 ℃.
3. The method for preparing a sericin/manganese dioxide complex loaded with phthalocyanine and adriamycin according to claim 1, wherein: the mass concentration of the sericin in the secondary water in the step (2) is 20mg mL -1 。
4. The method for preparing a sericin/manganese dioxide complex loaded with phthalocyanine and adriamycin according to claim 1, wherein: the mass concentration of potassium permanganate in the step (3) is 6mg mL -1 。
5. The method for preparing a sericin/manganese dioxide complex loaded with phthalocyanine and adriamycin according to claim 1, wherein: and (4) carrying out ultrasonic reaction for 15 minutes.
6. The method for preparing a sericin/manganese dioxide complex loaded with phthalocyanine and adriamycin according to claim 1, wherein: the mass concentration of the DOX aqueous solution in the step (5) is 2.5mg mL -1 。
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| CN113231105A (en) * | 2021-05-31 | 2021-08-10 | 华中科技大学 | Manganese dioxide loaded metal phthalocyanine composite material, preparation and application in degradation of antibiotics |
| CN113456610A (en) * | 2021-05-21 | 2021-10-01 | 浙江理工大学 | Manganese dioxide/sericin hybrid nano-particles for resisting oxidative stress damage and preparation method thereof |
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| US20210085789A1 (en) * | 2017-04-07 | 2021-03-25 | Seoul National University R&Db Foundation | Pharmaceutical composition for cancer treatment |
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