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Application of ursolic acid conjugate having anticancer activity and serving as drug carrier or molecular probe carrier

A technology of ursolic acid conjugates and molecular probes, applied in the field of biomedicine, can solve problems such as other diseases, inflammation of liver and other organs

Inactive Publication Date: 2017-04-26
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a novel carrier-free amphiphilic small molecule nano-drug delivery system to solve the problem that after the nano-carrier transports the drug into cancer cells in the prior art, it needs to be excreted from the body through organs such as the liver. Technical problems that can cause inflammation of organs such as the liver or a range of other conditions;

Method used

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  • Application of ursolic acid conjugate having anticancer activity and serving as drug carrier or molecular probe carrier
  • Application of ursolic acid conjugate having anticancer activity and serving as drug carrier or molecular probe carrier
  • Application of ursolic acid conjugate having anticancer activity and serving as drug carrier or molecular probe carrier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Synthesis of UA-Met, shown in structural formula VI, chemical name: (1S, 2R, 4aS, 6aS, 6bR, 10S, 12aR)-N-(N-(N,N-dimethylcarbamimidoyl)carbamimidoyl)-10-hydroxy-1 ,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b -octadecahydropicene-4a(2H)-carboxamide.

[0082] At room temperature, 200 mg of UA and 181 mg of DCC were stirred and dissolved with 3 ml of THF; 101 mg of NHS previously dissolved in 1.7 ml of acetonitrile was added dropwise to the reaction flask on an ice bath. The reaction was stirred at room temperature for 24 h. After the UA reaction was complete, the insoluble matter was removed by filtration, the solvent was evaporated under reduced pressure, and the activated UA was obtained by column chromatography. 100 mg of activated UA pure product and 30 mg of Met were stirred and dissolved in 5 ml of methanol. After reacting at room temperature for 24 h, the solvent was evaporated under reduced pressure, and the pure product of UA-Met...

Embodiment 2

[0089] Preparation method of UA-Met nanoparticles

[0090] Accurately weigh 0.00586 g of UA-Met powder, dissolve it in 1 ml of methanol, and ultrasonically dissolve it to form a 10 mM solution; take 20 uL of methanol solution and add it dropwise to an EP tube containing 180 uL (Note: drop Vortex during the addition process, 20 uL dropwise addition time is 20s), then. After sonication for 1 min, centrifugation at 12000 rpm for 5 min, the supernatant was UA-Met nanoparticles.

[0091] The average size of the particle diameter of the UA-Met nanoparticle aqueous solution prepared in this embodiment is about 110 nanometers, and the particle diameter diagram is as follows figure 2 shown.

Embodiment 3

[0093] Two parts of 200 ul of the nanoparticle aqueous solution prepared in Example 2 were placed in a cuvette, and then 800 ul of PBS solutions with a pH of 7.0 and a pH of 5.0 were added respectively, and then irradiated with a laser pointer to observe the phenomenon. The results are as follows: image 3 shown.

[0094] Such as image 3 As shown, the results show that the UA-Met nanoparticle aqueous solution maintains its nanostructure in the neutral pH=7.0 solution, and in the acidic condition pH=5.0, the nanoscale aqueous solution appears flocculent and the beam is dispersed. Numerous studies have shown that the tumor microenvironment is weakly acidic, which is necessary for the drug to be released in large quantities after entering the tumor microenvironment and responding to the pH.

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Abstract

The invention discloses application of an ursolic acid conjugate having the anticancer activity and serving as a drug carrier or a molecular probe carrier. The ursolic acid conjugate is characterized by being a conjugate formed by connecting of carboxy groups of ursolic acid or derivatives of ursolic acid with amino groups of guanidine drugs in the form of amido bonds. According to the specific application, a drug or a molecular probe is encapsulated and carried with the ursolic acid conjugate to form nanoparticles. When serving as the carrier, the referred conjugate has a certain anticancer effect without too high cytotoxicity and is easy and convenient to synthesize; the nanoparticles are self-assembled through a solvent exchange method, when the ursolic acid conjugate serves as the carrier of an anticancer drug or a fluorescent material, the problem on water solubility of a series of anticancer drugs is effectively solved.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to the preparation of a novel carrier-free amphiphilic small molecule nanometer drug delivery system and its application in tumor treatment. Background technique [0002] In recent years, with the development of nanotechnology, various carriers have been developed for drug delivery, such as liposomes, micelles, proteins, metal nanoparticles, and inorganic nanoparticles. And excellent properties have attracted the attention of more and more researchers, especially in the field of biomedicine, a variety of liposome and phospholipid-shaped nano-drug delivery systems have entered clinical applications; among them, the use of multifunctional nano-materials for The simultaneous diagnosis and treatment of cancer has gradually received extensive attention, and more and more literature reports have appeared. However, most anticancer drugs have problems such as poor water solubility and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/69A61K47/54A61K49/00A61P35/00A61K31/56
CPCA61K9/1075A61K31/56A61K31/704A61K47/28A61K49/0052A61K49/0082A61K49/0093
Inventor 邵敬伟郑桂容江凯沈志春
Owner FUZHOU UNIV
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