CN115475170A - Preparation method of evodiamine derivative superficial fungus-resistant solid lipid nanoparticle gel - Google Patents
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Abstract
The invention discloses a method for preparing evodiamine derivative anti-superficial fungi solid lipid nanoparticle gel. The formula of each prepared 25g of evodiamine derivative solid lipid nanoparticle gel is as follows: 100-300mg of evodiamine derivative, 300-600mg of soybean lecithin, 100-300mg of glyceryl monostearate, 5-10g of PEG-400, 200-500mg of Tween-80200, 100-300mg of carbomer 940, 1-2g of glycerol, 1-2g of propylene glycol, 100-400mg of triethanolamine, 30-50mg of ethylparaben and the balance of ultrapure water. The novel evodiamine derivative emulsifiable paste prepared by the invention is mainly used for superficial fungal infection of skin, such as tinea manuum, tinea pedis, tinea corporis, tinea cruris, eczema and the like.
Description
Technical Field
The invention belongs to the technical field of chemical pharmacy, and particularly relates to a method for preparing evodiamine derivative superficial fungus resistant solid lipid nanoparticle gel, which is an external medicine for treating superficial fungal infection.
Background
Superficial fungal infection refers to fungal infection of skin and outer layer of limbs, mainly including tinea pedis, tinea corporis, tinea cruris, onychomycosis, tinea capitis and the like, has the characteristics of infectivity, repeated attack and the like, affects about 20-25% of the population worldwide, and becomes a public health problem seriously puzzling the health of people of various countries. According to the latest statistics, the incidence rate of the tinea pedis is the highest in China at all ages, the incidence rate of the tinea capitis is the highest in children, and the onychomycosis is mainly concentrated in teenagers and adults. The main pathogens of superficial fungi are filamentous fungi including Trichophyton, epidermophyton, microsporum canis, candida albicans, etc., of which 60% of dermatophyte infections are caused by Trichophyton rubrum. In recent years, the incidence of clinical fungal infections has increased year by year due to the widespread use of broad-spectrum antibiotics, immunosuppressants and anti-malignant tumor drugs. The superficial fungus resistant medicines clinically used at present mainly comprise azoles and allylamines, have relatively single structural skeleton, are easy to generate drug resistance and cross drug resistance, and cause the disease to relapse. The research on new drugs mainly focuses on modification and modification of the structure of the azole. Therefore, it is of great importance to find and develop new drugs with novel skeleton structure, strong antifungal activity, broad antibacterial spectrum and good drug resistance.
The novel evodiamine derivative is obtained by modifying and transforming the structure of evodiamine in the early stage of the subject group, and the preparation method and the application thereof in treating superficial fungal infection are already applied for patent protection (the application of the evodiamine derivative in preparing a medicament for treating superficial fungal infection, CN 202111134080.6). In the long-term research on traditional Chinese medicines, the research team finds that fructus evodiae (originally recorded in Shen nong's herbal Jing) has been used for treating damp-cold beriberi since ancient times. The Chinese medicine dictionary: the evodia rutaecarpa decoction (100%) has strong inhibition effect on vibrio cholerae (agar trenching plate method). The 10% water infusion has inhibitory effect on Epidermophyton floccosum in test tube; 1:3 water infusion inhibits 11 dermatophytes such as Microsporum ozi to varying degrees. The main active ingredient of the fructus evodiae is evodiamine, but the antifungal activity of the fructus evodiae is weak. The early stage of the research team obtains the compound with remarkable antifungal activity by modifying and transforming the evodiamine structure and screening the in vivo and in vitro biological activity comprehensively. The compound has a completely different structure from the antifungal medicines on the market, has novel structure, strong antifungal activity and wide antibacterial spectrum, and has obviously better bactericidal effect on trichophyton rubrum, trichophyton mentagrophytes and candida albicans than ketoconazole which is widely used on the market. In the mechanism, the formation of fungal biomembranes and hyphae is mainly inhibited, the structures of cell walls and cell membranes of the fungi are destroyed, the hydrophobicity of the cell surface is reduced, and the antifungal activity is further exerted.
The medicine is used for treating superficial mycosis, comprises local and systemic medicines, and is mainly used for local medicines clinically. The most common superficial antifungal preparations in the market are cream and gel, and the common defects of the cream and the gel are poor penetration capability of stratum corneum, slow release and skin targeting. The solid lipid nanoparticle gel is prepared by preparing a medicament into solid lipid nanoparticles and dispersing the solid lipid nanoparticles in a gel matrix, and is a popular preparation formulation in recent research, and has the main advantages that: (1) The solid lipid nanoparticles prepared from the medicine can greatly improve the solubility of the insoluble medicine, can promote the medicine to quickly permeate into the horny layer of the skin and be stored in the epidermal layer, and is beneficial to improving the medicine effect and reducing the administration dosage; (2) The diameter (5-100 nm) of the 'screen mesh' of the gel matrix can be adjusted by the content of the thickening agent to adapt to different drug delivery requirements, and the stability of the nano-particles to extreme conditions such as pH value, temperature, gravity and the like can be improved, thereby being beneficial to industrial production and application. (3) The solid lipid nanoparticle gel has certain slow release property and skin targeting property. Therefore, the novel evodiamine derivative is prepared into a cream preparation so as to facilitate the clinical development and application of the medicine.
Disclosure of Invention
The invention aims to provide a preparation method of evodiamine derivative anti-superficial fungi solid lipid nanoparticle gel.
The invention adopts the following technical scheme:
a preparation method of evodiamine derivative emulsifiable paste comprises the following steps of preparing 25g evodiamine derivative solid lipid nanoparticle gel: evodiamine derivative 100-300mg, soybean lecithin 300-600mg, glyceryl monostearate 100-300mg, PEG-400-10 g, tween-80-500 mg, carbomer 940 100-300mg, glycerol 1-2g, propylene glycol 1-2g, triethanolamine 100-400mg, ethylparaben 30-50mg, and the balance of ultrapure water;
the preparation method comprises the following steps:
1) Preparing evodiamine derivative micro powder: grinding evodiamine derivative, and sieving with 300 mesh sieve to obtain medicinal micropowder with diameter less than 50 μm;
2) Preparing evodiamine derivative solid lipid nanoparticles: dissolving evodiamine derivative micro powder, soybean lecithin and glyceryl monostearate according to the formula ratio by using dichloromethane, carrying out rotary evaporation on the solvent under reduced pressure at 55-65 ℃ to form a layer of film, adding a mixed solution of Tween-80 and PEG-400, washing the film, carrying out hydration for 1-2h at 55-65 ℃, and carrying out ultrasonic probe straightening for 15-25min to obtain the evodiamine derivative solid lipid nanoparticles;
3) Preparing a gel matrix: wetting carbomer 940 with glycerol, adding ultrapure water, stirring to swell the carbomer 940 for 12 to 15h, dissolving ethylparaben in propylene glycol, stirring, adding triethanolamine solution dropwise under stirring to prepare a gel matrix;
4) Preparing evodiamine derivative solid lipid nanoparticle gel: slowly adding the evodiamine derivative solid lipid nanoparticles into the gel matrix under stirring, and stirring. The preparation process of the evodiamine derivative solid lipid nanoparticle is shown in figure 1.
The particle diameter and particle diameter distribution of the evodiamine derivative solid lipid nanoparticles are shown in figure 2, and the average particle diameter is 382.5
nm, PDI value 0.498. The microscopic examination of the evodiamine derivative solid lipid nanoparticle gel is shown in figure 4, and particles larger than 180 μm are not detected.
Drawings
FIG. 1 is a flow chart of the preparation of evodiamine derivative solid lipid nanoparticles;
FIG. 2 is a diagram showing the particle size and particle size distribution of evodiamine derivative solid lipid nanoparticles;
FIG. 3 is an appearance diagram of the evodiamine derivative solid lipid nanoparticle gel;
FIG. 4 is a microscopic view of the evodiamine derivative solid lipid nanoparticle gel.
Detailed Description
The technology of the present invention is further illustrated by the following specific examples, which should not be construed as limiting the scope of the invention.
Example 1
A method for preparing evodiamine derivative shallow fungus resistant solid lipid nanoparticle gel comprises the following steps of preparing 25g evodiamine derivative solid lipid nanoparticle gel: 100mg of evodiamine derivative, 300mg of soybean lecithin, 100mg of glycerin monostearate, 5g of PEG-400, 80250 mg of Tween, 200 mg of carbomer 940, 2g of glycerol, 2g of propylene glycol, 250 mg of triethanolamine, 50mg of ethylparaben, and the balance of ultrapure water.
The preparation method comprises the following steps:
1) Preparing evodiamine derivative micro powder: grinding evodiamine derivative, and sieving with 300 mesh sieve to obtain medicinal micropowder with diameter less than 50 μm;
2) Preparing evodiamine derivative solid lipid nanoparticles: dissolving evodiamine derivative micro powder, soybean lecithin and glyceryl monostearate with dichloromethane, performing rotary evaporation at 60 deg.C under reduced pressure to form a layer of film, adding mixed solution of tween-80 and PEG-400, washing the film, hydrating at 60 deg.C for 1h, and ultrasonically finishing particles in ice water for 20min to obtain evodiamine derivative solid lipid nanoparticles;
3) Preparing a gel matrix: wetting carbomer 940 with glycerol, adding ultrapure water, stirring to swell the carbomer 940 for 12h, dissolving ethylparaben in propylene glycol, adding the dissolved ethylparaben under stirring, and dropwise adding triethanolamine solution under stirring to obtain a gel matrix;
4) Preparing evodiamine derivative solid lipid nanoparticle gel: slowly adding the evodiamine derivative solid lipid nanoparticles into the gel matrix under stirring, and stirring.
Example 2
A method for preparing evodiamine derivative shallow fungus resistant solid lipid nanoparticle gel comprises the following steps of preparing 25g evodiamine derivative solid lipid nanoparticle gel: evodiamine derivative 200 mg, soybean lecithin 400mg, glyceryl monostearate 200 mg, PEG-400 g, tween-80500 mg, carbomer 940 mg, glycerol 1g, propylene glycol 1g, triethanolamine 400mg, ethylparaben 30mg, and the balance of ultrapure water. The preparation method is the same as example 1.
Example 3
A method for preparing evodiamine derivative shallow fungus resistant solid lipid nanoparticle gel comprises the following steps of preparing 25g evodiamine derivative solid lipid nanoparticle gel: evodiamine derivative 300mg, soybean lecithin 600mg, glyceryl monostearate 300mg, PEG-400 g, tween-80 mg, carbomer 940 mg, glycerol 2g, propylene glycol 2g, triethanolamine 300mg, ethylparaben 30mg and the balance of ultrapure water. The preparation method is the same as example 1.
The novel evodiamine derivative solid lipid nanoparticle gel is tested according to the following quality standards:
1) Traits
The product is in the form of milky semitransparent gel, as shown in FIG. 3.
2) And (3) identification:
HPLC main peak retention time: in the chromatogram recorded under the content determination item of the evodiamine derivative, the retention time of the main peak of the test solution is consistent with that of the main peak of the reference solution.
3) Examination of
And (3) checking the granularity: according to the first method (microscopy) of 0982 in the general rules of 2020 edition of Chinese pharmacopoeia, a proper amount of solid lipid nanoparticle gel is coated on a glass slide, a cover glass is covered on the glass slide, the glass slide is lightly pressed to be uniform, bubbles are avoided, and particles larger than 180 mu m are not detected.
And (3) pH checking: taking about 1g of the product, adding 9g of fresh boiled and cooled purified water, stirring to dissolve, cooling, and detecting with a pH meter to obtain a pH value of 6.5-7.5.
4) Novel evodiamine derivative content determination method (determination according to 2020 edition Chinese pharmacopoeia high performance liquid chromatography (general rule 0512))
Chromatographic conditions and system applicability test: a chromatographic column: agilent 5HC-C18 (2) column (250X 4.6 mm,5 μm); mobile phase: methanol-water (90; flow rate: 1 mL/min; column temperature: 35 ℃; detection wavelength: λ 274 nm; sample injection amount: 10. mu L; detection time: 15 min; the number of theoretical plates is not less than 5000 according to the peak calculation of the novel evodiamine derivative.
The determination method comprises the following steps: taking the product of about 200 mg, adding a proper amount of methanol, carrying out ultrasonic treatment for 10min, cooling to room temperature, adding methanol to a constant volume of 10 ml, shaking up, filtering with a 0.45-micrometer microporous membrane, and filtering to obtain a filtrate for later use. Precisely measuring 10 μ l of the filtrate, injecting into a liquid chromatograph, and recording chromatogram; and taking an appropriate amount of the novel evodiamine derivative reference substance, precisely weighing, adding methanol for dissolving, quantitatively diluting to prepare a solution containing about 20 mu g of the novel evodiamine derivative in each 1ml, shaking up, measuring by the same method, and calculating by peak area according to an external standard method to obtain the content of the evodiamine derivative in the superficial fungus-resistant solid lipid nanoparticle gel of the evodiamine derivative.
Claims (1)
1. A method for preparing evodiamine derivative superficial fungus resistant solid lipid nanoparticle gel is characterized in that: the formula of the solid lipid nanoparticle gel for preparing 25g evodiamine derivatives is as follows: evodiamine derivative 100-300mg, soybean lecithin 300-600mg, glyceryl monostearate 100-300mg, PEG-400-10 g, tween-80-500 mg, carbomer 940 100-300mg, glycerol 1-2g, propylene glycol 1-2g, triethanolamine 100-400mg, ethylparaben 30-50mg and the balance of ultrapure water;
the preparation method comprises the following steps:
1) Preparing evodiamine derivative micro powder: grinding evodiamine derivative, and sieving with 300 mesh sieve to obtain medicinal micropowder with diameter less than 50 μm;
2) Preparing the evodiamine derivative solid lipid nanoparticles: dissolving evodiamine derivative micro powder, soybean lecithin and glyceryl monostearate according to the formula ratio by using dichloromethane, carrying out rotary evaporation on the solvent under reduced pressure at 55-65 ℃ to form a layer of film, adding a mixed solution of Tween-80 and PEG-400, washing the film, carrying out hydration for 1-2h at 55-65 ℃, and carrying out ultrasonic probe straightening for 15-25min to obtain the evodiamine derivative solid lipid nanoparticles;
3) Preparing a gel matrix: wetting carbomer 940 with glycerol, adding ultrapure water, stirring to swell the carbomer 940 for 12 to 15h, dissolving ethylparaben in propylene glycol, stirring, adding triethanolamine solution dropwise under stirring to prepare a gel matrix;
4) Preparing evodiamine derivative solid lipid nanoparticle gel: slowly adding the evodiamine derivative solid lipid nanoparticles into the gel matrix under stirring, and stirring.
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2022
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| CN101088523A (en) * | 2006-06-12 | 2007-12-19 | 大百汇生物科技（深圳）有限公司 | Nanometer solid lipid particle of active skullcap components and its prepn process and prepn |
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| WO2022064455A1 (en) * | 2020-09-25 | 2022-03-31 | Jyotsnendu Giri | Instant nanogel composition and process of preparation thereof |
| CN113633608A (en) * | 2021-08-26 | 2021-11-12 | 辽宁万嘉医药科技有限公司 | anti-HPV (human papillomavirus) polyphenol slow-release lipid nanoparticle gel and preparation method thereof |
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| 杨兰等: "吴茱萸碱丁酰基衍生物固体脂质纳米粒的体外释放及在体胃肠吸收研究", 《中国药理学通报》, vol. 34, no. 5, pages 724 - 728 * |
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