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Gambogic acid nano preparation based on hydrophobic prodrug and capable of improving long circulation

A nano-preparation, gambogic acid technology, applied in the field of medicine, can solve problems such as leakage, low drug loading efficiency, and drug crystallization

Active Publication Date: 2021-01-05
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, traditional nano-preparations have problems such as low drug loading efficiency, poor stability, and drug crystallization and leakage during storage.

Method used

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  • Gambogic acid nano preparation based on hydrophobic prodrug and capable of improving long circulation
  • Gambogic acid nano preparation based on hydrophobic prodrug and capable of improving long circulation
  • Gambogic acid nano preparation based on hydrophobic prodrug and capable of improving long circulation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of oleyl bromide

[0042]

[0043] Add 1 g of oleyl alcohol to the reaction vessel, add 20 ml of anhydrous dichloromethane to dissolve, then add 504.1 mg of phosphorus tribromide, stir at room temperature for 30 minutes, and separate by silica gel column chromatography to obtain 598.9 mg of a white oily substance.

[0044] of the substance 1 HNMR and MS data are as follows:

[0045] 1 HNMR (CDCl 3,300MHz)δ: 5.46–5.31(m,2H,9-H,10-H),3.43(t,J=6.9Hz,2H,1-H),2.10–1.89(m,4H,8-H, 11-H),1.93–1.80(m,2H,43-H),1.50–1.25(m,22H),0.89(q,J=7.6,6.9Hz,3H).

[0046] MS(ESI) m / z: 663.45[2M+H] +

[0047] The chemical structural formula is as follows: C 18 h 35 Br.

Embodiment 2

[0048] Embodiment 2: the preparation of gambogic acid-oleyl alcohol

[0049]

[0050] Add 1.03g gambogic acid to the reaction vessel, add N,N-dimethylformamide to dissolve, add 598.9mg oleyl alcohol bromide, then add potassium carbonate 113.53mg, stir at room temperature, overnight, silica gel column chromatography, that is Gambogic acid compound shown in formula (I), namely gambogic acid-oleyl alcohol is obtained.

[0051] The 1HNMR and MS data of this substance are as follows:

[0052] 1HNMR (CDCl3, 300MHz) δ: 12.84(s, 1H, 6-OH), 7.53(d, J=6.9Hz, 1H, 10-H), 6.66(d, J=10.2Hz, 1H, 4-H) ,6.05–5.93(m,1H,27-H),5.46(d,1H,3-H),5.355(m,2H,50-H,51-H),5.11–4.98(m,2H,32- H,37-H),3.90–3.71(m,2H,42-H),3.47(dd,J=6.9,4.4Hz,1H,11-H),3.31(dd,J=14.6,8.1Hz,1H ,31-H),3.21–3.10(m,1H,31-H),3.08–2.89(m,2H,26-H),2.51(d,J=9.3Hz,1H,22-H),2.30( dd,J=13.4,4.8Hz,1H,21-H),2.01(q,J=6.9Hz,6H,36-H,49-H,52-H),1.88–1.35(m,28H),1.35 –1.21(m,24H),0.92–0.82(m,3H).

[0053] MS (ESI) m / z (%): 879.58 [M+H]...

Embodiment 3

[0055] Embodiment 3: Preparation of gambogic acid-oleyl alcohol / vitamin E polyethylene glycol succinate nanoparticles (GA-OA / TPGS)

[0056] Weigh 7.15 mg of the gambogic acid-oleyl alcohol prodrug prepared in Example 2 and dissolve 1.0725 mg of vitamin E polyethylene glycol succinate (the molecular weight range of polyethylene glycol is 1000 to 10000) in 800 μl of DMSO. Slowly add the DMSO mixed solution to 10ml of ultrapure water at 37°C, stir while adding, and after standing for 2 hours, dialyze for 2 to 5 days to remove DMSO to obtain gambogic acid-oleyl alcohol / vitamin E polyethylene glycol Succinate nanoparticles (GA-OA / TPGS), the appearance of figure 1 As shown, the particle size distribution diagram is shown in figure 2 As shown, the average particle size is 155.23±3.34nm, the particle size distribution is narrow, the PDI is 0.078±0.027, and the drug loading and encapsulation efficiency are high, which are 56.82% and 65.60%, respectively. Gambogic acid-oleyl alcohol / ...

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Abstract

The invention discloses a gambogic acid nano preparation based on a hydrophobic prodrug and capable of improving long circulation. The nano preparation is a gambogic acid prodrug nano preparation andis gambogic acid oleyl alcohol / polyethylene glycol vitamin E succinate nanoparticles. According to the invention, gambogic acid is modified into an inactive prodrug, and the inactive prodrug is administrated in the form of nanoparticles so that the circulating half-life period of gambogic acid in vivo is improved, the vascular irritation during administration is relieved, and the preparation has important theoretical and practical values for clinical application of gambogic acid.

Description

technical field [0001] The invention belongs to the field of medicine, and specifically relates to a gambogic acid hydrophobic prodrug nano-preparation. The invention also discloses its preparation method, and its role in prolonging the half-life of the drug in rats and improving the blood vessels of gambogic acid administered intravenously. irritating application. Background technique [0002] Gambogic acid (Gambogic acid, GA) is the main active ingredient of Garcinia hanbaryi Hook.f., a plant of Garcinia hanbaryi Hook.f., which has significant antitumor activity and has curative effect on various cancers. However, the solubility of gambogic acid is extremely small, coupled with its rapid clearance in plasma, the half-life of gambogic acid in the body is very short, which limits the clinical application of gambogic acid. The currently reported gambogic acid injections are mainly formulated with borax solution or added with polyoxyethylene castor oil. This method improves ...

Claims

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Application Information

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IPC IPC(8): C07D493/18A61K47/54A61K31/352A61K9/51A61K47/22A61P35/00
CPCC07D493/18A61K47/54A61K31/352A61K9/5146A61P35/00
Inventor 曲玮冯锋王如意柳文媛张仲涛刘博文
Owner CHINA PHARM UNIV
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