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Preparation and applications of RGD-fatty amine series compound as tumor targeting vector material

A compound and targeting technology, applied in the preparation of targeting carrier materials, the application field of drug carriers in the preparation of targeted drug delivery preparations, can solve the problems of ordinary nano-drug delivery systems not being targeted, and achieve excellent target The effect of tropism, strong stability, and not easy to be degraded by enzymes

Inactive Publication Date: 2009-09-23
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Ordinary nano-drug delivery system is not targeted

Method used

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  • Preparation and applications of RGD-fatty amine series compound as tumor targeting vector material
  • Preparation and applications of RGD-fatty amine series compound as tumor targeting vector material
  • Preparation and applications of RGD-fatty amine series compound as tumor targeting vector material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Boc-Arg (NO 2 )-Gly-OMe Preparation

[0039] 1.595g (5.0mmol) Boc-Arg (NO 2)-OH was dissolved in 20ml of anhydrous DMF, and under ice-cooling conditions, 0.675g (5mmol) of N-hydroxybenzotriazole (HOBt) was added and completely dissolved. After 10 minutes 1.236 g (6 mmol) of dicyclohexylcarbodiimide (DCC) were added. Obtain reaction liquid (I), stand-by. Dissolve 0.628g (5.0mmol) HCL·Gly-OMe (5mmol) in 20ml THF under ice-cooling, then add 1ml N-methylmorpholine (NMM) to adjust the pH to 8-9. Stir for 35 minutes to obtain the reaction solution (II), which is ready for use. The reaction solution (I) was added to the reaction solution (II) under the ice bath, first stirred under the ice bath for 1 h, then stirred at room temperature for 12 h, TLC (chloroform / methanol, 10:1) showed that Boc-Arg (NO 2 )-OH disappears. Dicyclohexylurea (DCU) was filtered off, and the filtrate was blown off of DMF. The residue was dissolved with 50 ml of ethyl acetate. The res...

Embodiment 2

[0040] Example 2 Boc-Arg (NO 2 )-Gly-OH preparation

[0041] 0.780g (2.0mmol) Boc-Arg (NO 2 )-Gly-OMe was dissolved in 10 ml methanol. Adjust pH to 10-11 with NaOH (2N) aqueous solution under ice bath and stir for 4h, TLC (chloroform / methanol, 10:1) showed that Boc-Arg (NO 2 )-Gly-OMe disappears. The reaction mixture was saturated with KHSO 4 Adjust the pH to 7, and concentrate under reduced pressure to remove methanol. The residue was washed with saturated KHSO 4 Adjust the pH to 2, and extract with ethyl acetate (30ml×3). The combined ethyl acetate phases were washed with saturated NaCl aqueous solution to neutral, anhydrous NaCl 2 SO 4 dry. After filtration, the filtrate was concentrated to dryness under reduced pressure to afford 0.591 g (78.7%) of the title compound as a white solid. (ESI-MS(m / z): 375.3[M] - )

Embodiment 3

[0043] 1) Boc-Asp(OBzl)-NHCH 2 (CH 2 ) 6 CH 3 preparation of

[0044] According to Boc-Arg (NO 2 ) The preparation method of Gly-OMe, 1.615g (5mmol) Boc-Asp (OBzl)-OH and 0.541g (4.5mmol) CH 3 (CH 2 ) 6 CH 2 NH 2 1.918 g (98.2%) of a crude beige solid was obtained, and purified by a silica gel column to obtain 1192 g (61.0%) of the title compound as a white solid. (ESI-MS(m / z): 435.7[M] + )

[0045] 2) HCl Asp(OBzl)-NHCH 2 (CH 2 ) 6 CH 3 preparation of

[0046] 0.868g (2.0mmol) Boc-Asp(OBzl)-NHCH 2 (CH 2 ) 6 CH 3 Dissolve in 10ml 4mol / l hydrogen chloride-ethyl acetate solution, stir at room temperature for 4 hours, TLC (chloroform / methanol, 5:1) shows that the raw material point disappears, concentrate under reduced pressure to remove ethyl acetate, add a small amount of ether to the residue repeatedly to reduce Pump dry under pressure to remove hydrogen chloride gas. Finally, a small amount of diethyl ether was added to triturate the residue to obtain 0.6...

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Abstract

The invention relates to the preparation and applications of RGD-fatty amine series compound as tumor targeting vector material, and the compound has a structure as the right formula.

Description

technical field [0001] The present invention relates to the preparation of targeted carrier materials, in particular to a method for constructing a targeted drug delivery system for fat-soluble drugs. The invention also relates to the application of drug carriers in the preparation of targeted drug delivery preparations, belonging to the field of biomedicine. Background technique [0002] The growth and metastasis of malignant tumors is a complex multi-step and multi-link process, and most of them are related to abnormal expression of integrins or changes in molecular structure. Integrins are a large family of transmembrane proteins, consisting of α and β subunits to form heterodimers. At present, it has been found that there are about 18 kinds of α, about 8 kinds of β, and at least 24 kinds of integrin forms of heterodimers. The progression of integrins in tumors may be dual: 1) In the early stage of tumorigenesis, the reduction of integrin expression can weaken the adhesi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/09C07K1/06C07K1/02A61K9/127A61K9/14A61K9/107A61K47/42A61K31/337A61P35/00A61K47/18
Inventor 崔国辉崔纯莹孙怡
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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