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A Hydrophobic Prodrug-Based Gambogic Acid Nanoformulation with Improved Long Circulation

A nano-preparation, gambogic acid technology, applied in the field of medicine, can solve the problems of low drug loading efficiency, drug crystallization, and poor stability, and achieve the effects of improving drugability, reducing side effects, and good stability

Active Publication Date: 2022-05-20
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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  • A Hydrophobic Prodrug-Based Gambogic Acid Nanoformulation with Improved Long Circulation
  • A Hydrophobic Prodrug-Based Gambogic Acid Nanoformulation with Improved Long Circulation
  • A Hydrophobic Prodrug-Based Gambogic Acid Nanoformulation with Improved Long Circulation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of oleyl alcohol 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 598.9 mg of white oily substance by silica gel column chromatography.

[0044] of the substance 1 The 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] Example 2: Preparation of gambogic acid-oleyl alcohol

[0049]

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

[0051] The 1HNMR and MS data of this material 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...

Embodiment 3

[0055] Example 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 1.0725 mg of vitamin E polyethylene glycol succinate (the molecular weight range of the polyethylene glycol contained is 1000-10000) and dissolve it in 800 μl DMSO. Slowly add the DMSO mixed solution to 10 ml of ultrapure water at 37°C, stir while adding, and let stand for 2 h, then dialyze for 2 to 5 days to remove DMSO to obtain gambogic acid-oleyl alcohol / vitamin E polyethylene glycol Succinate nanoparticles (GA-OA / TPGS) with appearance as figure 1 As shown, the particle size distribution is shown in figure 2 As shown, the average particle size was 155.23±3.34nm, the particle size distribution was narrow, the PDI was 0.078±0.027, and the drug loading and encapsulation efficiency were high, 56.82% and 65.60%, respectively. The gambogic acid-oleyl alcohol / v...

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Abstract

The invention discloses a hydrophobic prodrug-based gambogic acid nano-preparation that can improve long circulation. The nano-preparation of the present invention is a gambogic acid prodrug. The nano-preparation is gambogic acid-oleyl alcohol / polyethylene glycol-vitamin E Succinate nanoparticles. The present invention modifies gambogic acid into an inactive prodrug, administers it in the form of nanoparticles, improves the circulation half-life of gambogic acid in the body, and relieves the vascular irritation during administration at the same time, which is beneficial to the clinical application of gambogic acid It has important theoretical and practical value.

Description

technical field [0001] The invention belongs to the field of medicine, and specifically relates to a hydrophobic prodrug nano preparation of gambogic acid. The invention also discloses a preparation method thereof, as well as a method for prolonging the half-life of the drug in rats and improving the blood vessels for intravenous administration of gambogic acid. stimulating application. Background technique [0002] Gambogic acid (GA) is the main active component of Garcinia hanbaryi Hook.f., which has significant antitumor activity and is effective against various cancers. However, the solubility of gambogic acid is extremely small, coupled with its fast 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 prepared by using borax solution or adding polyoxyethylene castor oil. This method improves the solubility of gambogic acid to a ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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