CN112472818B - Nano material using modified natural melanin as carrier, and preparation method and application thereof - Google Patents

Nano material using modified natural melanin as carrier, and preparation method and application thereof Download PDF

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CN112472818B
CN112472818B CN202011280799.6A CN202011280799A CN112472818B CN 112472818 B CN112472818 B CN 112472818B CN 202011280799 A CN202011280799 A CN 202011280799A CN 112472818 B CN112472818 B CN 112472818B
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melanin
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quercetin
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CN112472818A (en
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孙冬冬
王静媛
汪泽坤
高寅
杨恩东
郭峰
汪维云
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Anhui Agricultural University AHAU
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Abstract

The invention relates to a nano material taking modified natural melanin as a carrier, which comprises a melanin-quercetin nano material, wherein the melanin-quercetin nano material is generated by modifying natural medicine quercetin on the surface of a natural polydopamine nano material through pi-pi bond and covalent bond, the diameter of the melanin-quercetin nano material is 80-100nm, and the application of the nano material taking modified natural melanin as the carrier in the field of nano materials is further provided. Compared with the prior art, the invention utilizes the excellent drug loading capacity of melanin to uniformly wrap the natural flavonoid drug quercetin with antibacterial activity on the surface, so that the quercetin has uniform shape and size and can effectively kill escherichia coli.

Description

Nano material using modified natural melanin as carrier, and preparation method and application thereof
Technical Field
The invention belongs to the technical field of nano materials, and particularly relates to a nano material taking modified natural melanin as a carrier, and a preparation method and application thereof.
Background
With the rapid development of nanotechnology, traditional inorganic nano-drug carrier materials are increasingly unable to meet the increasing demands of patients, and therefore, nano-drug-loaded polymer materials are the key point of research. The nanometer high molecular material has stronger biocompatibility, lower toxicity and easier-to-degrade drug loading, so the nanometer high molecular material is considered to be a promising drug delivery system.
Natural melanin has been found to exhibit a variety of functions in biological systems, including protection of humans and animals from uv light, antibacterial functions, thermoregulation, free radical quenching, and some nervous system involvement. But it aggregates severely, is poorly dispersible, and has poor variability; the properties seriously hinder the research and development of the natural melanin in the field of nano materials and limit the practical application of the natural melanin, and the difficult problems are solved along with the modification and synthesis of the natural melanin into polydopamine, and the polydopamine can be used as a good nano drug-carrying particle.
The flavonoid natural product has antiinflammatory, antioxidant, and antibacterial effects, and has wide medicinal value including protecting nerve, lung, cardiovascular diseases and aging. However, the application of the single traditional natural medicine quercetin as one of flavonoid medicines is greatly limited, because the quercetin is difficult to dissolve in water and has low bioavailability, the utilization rate of the quercetin in the fields of biochemistry and nanomedicine is extremely low. Based on the content, the nanometer material taking modified natural melanin as a carrier, and the preparation method and the application thereof are provided.
Disclosure of Invention
The present invention aims at providing a nanometer material with modified natural melanin as a carrier, a preparation method and an application thereof, so as to solve the problems in the background technology.
The invention realizes the purpose through the following technical scheme:
the invention provides a nano material taking modified natural melanin as a carrier, which comprises a melanin-quercetin nano material, wherein the melanin-quercetin nano material is generated by modifying natural medicine quercetin on the surface of a polydopamine nano material through pi-pi bond and covalent bond.
The invention also provides application of the nano material taking the modified natural melanin as a carrier in the field of antibacterial nano materials.
The invention also provides a preparation method of the nano material by using the modified natural melanin as the carrier, which comprises the following steps:
(1) adding natural melanin polydopamine into an organic solution and a weak alkaline solution, stirring to form a mixed solution, adding a dopamine hydrochloride solution into the mixed solution, continuously stirring under a dark condition, reacting, repeatedly washing for a plurality of times, and dispersing in deionized water again to obtain a material I.
(2) And (2) centrifuging the material I in the step (1) at low temperature, drying to obtain an intermediate, dispersing the intermediate in the organic solution of the natural flavonoid drug under a dark condition, stirring, centrifuging for several times after stirring, and removing the adsorbed organic solution to obtain a material II.
(3) And (3) extruding the second material in the step (2) to homogenize the particle size of the product, so as to obtain the finished product melanin-quercetin nanometer material.
As a further optimization scheme of the invention, the natural melanin nano-material in the step (1) is extracted from the frozen squid.
As a further optimization scheme of the above invention, the weak alkaline solution in step (1) is a mixture of any one or more of sodium carbonate, sodium bicarbonate and ammonia monohydrate.
As a further optimization scheme of the above invention, the organic solvent in the organic solution in steps (1) and (2) is one of ethanol, styrene, trichloroethylene, ethylene glycol ether or triethanolamine.
As a further optimization scheme of the above invention, the natural flavonoid in the step (2) is one of quercetin, rutin, baicalein or baicalin.
As a further optimization scheme of the above invention, the centrifugation conditions of the material one in the step (2) are as follows: the centrifugation temperature is 4-6 ℃, the centrifugation speed is 18000rpm, and the centrifugation time is 10-30 min.
As a further optimization scheme of the invention, in the step (3), a liposome extruder is adopted to homogenize the particle size of the product, and the specific step is that the material II is passed through polycarbonate fiber membranes with the pore diameters of 400nm and 200nm respectively by adopting the liposome extruder and is repeated for a plurality of times.
The invention has the beneficial effects that: the natural melanin used for synthesizing the medicine carrying system is polydopamine, and the natural medicine quercetin is modified on the surface of the polydopamine through pi-pi bonds and covalent bonds to generate melanin-quercetin, so that the quercetin with an antibacterial effect can reach an action position, the release efficiency is greatly improved, compared with the common and traditional antibacterial materials, the natural melanin has the characteristics of quick action, more medicine carrying amount and high biocompatibility, and the natural melanin is easy to synthesize and is suitable for popularization.
Drawings
FIG. 1: (A) transmission electron micrograph of example 1; (B) transmission electron micrograph of comparative example 1; (C) transmission electron micrograph of comparative example 2.
FIG. 2: (A) uv-vis spectra of example 1, comparative examples 1 and 2; (B) fourier Infrared Spectroscopy of example 1, comparative examples 1, 2.
FIG. 3: the effect on colony forming units of E.coli and drug-resistant E.coli after treatment of example 1 (30. mu.g/mL), comparative example 1 (30. mu.g/mL) and comparative example 2 (30. mu.g/mL).
Detailed Description
The present application will now be described in further detail with reference to the drawings, it should be noted that the following detailed description is given for illustrative purposes only and is not to be construed as limiting the scope of the present application, as those skilled in the art will be able to make numerous insubstantial modifications and adaptations to the present application based on the above disclosure.
Example 1
(1) Extracting natural melanin polydopamine from frozen squids into a triangular flask, adding 40mL of ethanol and 90mL of water, adding 30% ammonia monohydrate solution, stirring for 30min, weighing 0.5g of dopamine hydrochloride, dissolving the dopamine hydrochloride in 10mL of deionized water, adding the dopamine monohydrate solution into the mixed solution, continuously stirring for 24h under a dark condition, repeatedly washing the solution for several times after the reaction is finished, and dispersing the dopamine hydrochloride in the deionized water again to obtain a material I;
(2) centrifuging the obtained material I at low temperature of 4 ℃ for 20min at 18000rpm of a centrifuge, drying the material I in a drying oven at 40 ℃, weighing 40mg of the material I, dispersing the material I in 4mL of 20mg/mL quercetin-ethanol solution under the dark condition, stirring the material I for 12h, centrifuging the material I at 18000rpm for 20min, and washing and removing the adsorbed organic solution for multiple times to obtain a material II;
(3) and passing the material through polycarbonate fiber membranes with the pore diameters of 400nm and 200nm by using a liposome extruder for two purposes, and repeating the step three times to obtain a finished product.
Comparative example 1
(1) Extracting natural melanin polydopamine from frozen squids into a triangular flask, adding 40mL of ethanol and 90mL of water, adding 30% ammonia monohydrate solution, stirring for 30min, weighing 0.5g of dopamine hydrochloride, dissolving the dopamine hydrochloride in 10mL of deionized water, adding the dopamine monohydrate solution into the mixed solution, continuously stirring for 24h under a dark condition, repeatedly washing the solution for several times after the reaction is finished, and dispersing the dopamine hydrochloride in the deionized water again to obtain a material I;
(2) centrifuging the obtained material I at low temperature of 4 ℃ for 20min at 18000rpm of a centrifuge, drying the material I in a drying oven at 40 ℃, weighing 40mg of the material I, dispersing the material I in 4mL of 20mg/mL of rutin organic solution under the dark condition, stirring the material I for 12h, centrifuging the material I at 18000rpm for 20min, and washing the adsorbed rutin with the organic solution for multiple times to remove the adsorbed rutin to obtain a material II;
(3) and passing the material through polycarbonate fiber membranes with the pore diameters of 400nm and 200nm by using a liposome extruder for two purposes, and repeating the step three times to obtain a finished product.
Comparative example 2
(1) Extracting natural melanin polydopamine from frozen squids into a triangular flask, adding 40mL of ethanol and 90mL of water, stirring for 30 minutes, standing overnight, washing the solution for several times, and dispersing into deionized water to obtain a material I;
(2) centrifuging the obtained material I at low temperature of 4 ℃ for 20min at 18000rpm of a centrifuge, drying the material I in a drying oven at 40 ℃, weighing 40mg of the material I, dispersing the material I in 4mL of 20mg/mL of rutin organic solution under the dark condition, stirring the material I for 12h, centrifuging the material I at 18000rpm for 20min, and washing the adsorbed rutin with the organic solution for multiple times to remove the adsorbed rutin to obtain a material II;
(3) and passing the material through polycarbonate fiber membranes with the pore diameters of 400nm and 200nm by using a liposome extruder for two purposes, and repeating the step three times to obtain a finished product.
The morphology of the nanomaterials of example 1, comparative example 1 and comparative example 2 was examined using a transmission electron microscope (TEM, TJEOL6300F, tokyo japan, Philips) and a scanning electron microscope (SEMXL-20, Holland, Philips), and TEM images showed that example 1 and comparative example 1 were black spheres having a diameter of about 80 to 120nm, whereas natural melanin was poorly dispersed and aggregated as seen from C in fig. 1, and the synthesized nanoparticles were amorphous, and thus, the synthesized natural melanin polydopamine nanoparticles were more regular in shape and substantially spherical in shape, compared to natural melanin that had not been modified.
Infrared and ultraviolet-visible absorption were performed on example 1, comparative example 1 and comparative example 2 using bruker sensor 27FT-IRDTGS detector (ylacetal.2014, tanetal.2011) and spectrophotometer (JASCO, japan) to obtain product characteristic analysis, as shown in fig. 2, the ultraviolet absorption spectrum of example 1, as can be seen from a in fig. 2, about 240nm and 360nm are characteristic peaks of polydopamine, about 255nm and 375nm are characteristic peaks of rutin, and quercetin and rutin are both natural flavonoid drugs, and characteristic peaks thereof are 260nm and 360 nm; as can be seen from fig. 2A, the characteristic peaks of example 1 and comparative example 1, which are changed at 295nm and 350nm, are the result of quercetin and rutin modification, while comparative example 2, which shows characteristic peaks at about 230nm and 360nm, indicates that it is not surface-modified; b in FIG. 2 shows that polydopamine is present at 1622cm in the infrared absorption spectrum-1And 1505cm-1The stretching vibration peak of C-C on the aromatic ring of the indole and the bending vibration peak of C-N weaker on the indole-5, 6-quinone appear at 1040cm-1The peak is the bending vibration peak in the C-H plane on the polydopamine, the characteristic peaks of the example 1 and the comparative example 1 are consistent with the molecular structure of the polydopamine, while the characteristic peaks of the comparative example 2 are subjected to peak separation and enhancement due to the fact that the unmodified components of the natural melanin are complex; characteristic peaks of quercetin and rutin standard sample in infrared spectrum are 1103cm respectively-1、1514cm-1、3401cm-1And 1655cm-1、1600cm-1、3420cm-1Respectively assigned to antisymmetric and symmetric extensions of ═ C-O-CAs can be seen from the infrared absorption results of example 1, when quercetin was modified with polydopamine nanoparticles synthesized from natural melanin, the characteristic absorptions of polydopamine and quercetin appeared together, but at 1040cm, the peak was observed-1And 1514cm-1The intensity of the peak was reduced due to the pi-pi interaction and chemical bond formation between quercetin and polydopamine during modification, and comparative example 1 was 1600cm-1And 3401cm-1The appearance of characteristic peak can prove that rutin modifies the modified rutin, and the characteristic peak is also 1500cm in comparative example 2-1And 1103cm-1The characteristic peak appears, and is just the result of modifying the characteristic peak by the quercetin.
And (3) testing the antibacterial rate: the strains were subjected to 10 times of the above-mentioned treatment-1，10-2，10-3，10-4，10-5And 10-6Dilution in a gradient followed by dilution 10-6The solution (2) is prepared by extracting 150 mu L of solution, putting the solution into a centrifuge tube, then adding the finished product (30 mu g/mL) of example 1, the finished product (30 mu g/mL) of comparative example 1 and the finished product (30 mu g/mL) of comparative example 2 respectively, and the untreated solution to form a blank group, mixing, incubating for 2h, absorbing 150 mu L of bacterial liquid, dispersing on a solid culture medium for 24h, culturing at 37 ℃, and repeating the experiment for three times. As shown in fig. 3, the experimental group treated in example 1 has the highest bacteriostatic effect and stronger bacteriostatic activity against escherichia coli, and compared with the comparative examples 1 and 2, the example group shows that the natural melanin synthesized polydopamine nanoparticles containing quercetin can effectively improve the drug utilization rate and significantly enhance the antibacterial activity.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention.

Claims (6)

1. A nano material using modified natural melanin as a carrier is characterized by comprising a melanin-quercetin nano material, wherein the melanin-quercetin nano material is generated by modifying natural medicine quercetin on the surface of a natural polydopamine nano material through pi-pi bonds and covalent bonds, the natural polydopamine nano material is synthesized by natural melanin, specifically, the natural melanin is added into an ethanol solution and an ammonia monohydrate solution, the mixed solution is stirred to form a mixed solution, a dopamine hydrochloride solution is added into the mixed solution, the mixed solution is continuously stirred under dark conditions, reacts, is repeatedly washed for a plurality of times, and is dispersed in deionized water again to obtain the natural polydopamine nano material, and the diameter of the melanin-quercetin nano material is 80-100 nm.
2. The use of the nanomaterial of claim 1, wherein the nanomaterial is obtained by modifying natural melanin as a carrier.
3. The method for preparing the nano-material by modifying the natural melanin as the carrier according to claim 1, which comprises the following steps:
(1) adding natural melanin into an ethanol solution and an ammonia monohydrate solution, stirring to form a mixed solution, adding a dopamine hydrochloride solution into the mixed solution, continuously stirring and reacting under a dark condition, repeatedly washing for a plurality of times, and dispersing in deionized water again to obtain a natural polydopamine nano material;
(2) centrifuging the material I in the step (1) at low temperature and drying to obtain an intermediate, dispersing the intermediate in a quercetin ethanol solution under a dark condition, stirring, centrifuging for several times after stirring, and removing adsorbed organic solution to obtain a material II;
(3) and (3) extruding the second material in the step (2) to homogenize the particle size of the product, so as to obtain the finished product melanin-quercetin nanometer material.
4. The method for preparing nano-material by modifying natural melanin as carrier according to claim 3, wherein the natural melanin is extracted from frozen squid in the step (1).
5. The method for preparing nano-materials by modifying natural melanin as a carrier according to claim 3, wherein the centrifugation conditions of the first material in the step (2) are as follows: the centrifugation temperature is 4-6 ℃, the centrifugation speed is 18000rpm, and the centrifugation time is 10-30 min.
6. The method for preparing nano-materials by modifying natural melanin as a carrier according to claim 3, wherein the step (3) is to use a liposome extruder to homogenize the particle size of the product, and the specific step is to repeat the step (2) several times by using the liposome extruder to pass through polycarbonate fiber membranes with the pore diameters of 400nm and 200nm respectively.
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CN114870025B (en) * 2022-04-28 2023-06-30 云南大学 Responsive slow-release polydopamine-Zn-natural polyphenol coordination nano-drug and preparation method thereof
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