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Preparation and uses of tumor-targeted carrier material RGD-fatty alcohol series of compounds

A compound, RGD-O technology, applied in the field of biomedicine, can solve the problem that ordinary nano drug-carrying systems do not have targeting

Inactive Publication Date: 2009-04-08
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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Boc-Arg (NO 2 Preparation of )-Gly-OBzl

[0031] 1.600g (5.0mmol) Boc-Arg (NO 2)-OH was dissolved in 20ml of anhydrous DMF, and 0.675g (5mmol) of N-hydroxybenzotriazole (HOBt) was added to the resulting solution under ice-cooling to completely dissolve. After 10 minutes 1.071 g (6 mmol) of dicyclohexylcarbodiimide (DCC) were added. Obtain reaction liquid (I), stand-by. Suspend 1.685g (5.0mmol) Tos·Gly-OBzl (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 a...

Embodiment 2

[0032] Example 2 Boc-Arg (NO 2 )-Gly-OH preparation

[0033] 0.932g (2.0mmol) Boc-Arg (NO 2 )-Gly-OBzl was dissolved in 10ml methanol. Under ice-cooling, the resulting solution was adjusted to pH 12 with NaOH (2N) aqueous solution and stirred for 2 h. TLC (chloroform / methanol, 5:1) showed that Boc-Arg (NO 2 )-Gly-OBzl 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 aqueous NaCl until neutral, anhydrous NaCl 2 SO 4 dry. After filtration, the filtrate was concentrated to dryness under reduced pressure to afford 0.752 g (84.8%) of the title compound as a white solid. (ESI-MS(m / z): 375.3[M] - )

Embodiment 3

[0035] 1) Boc-Asp(OBzl)-OCH 2 (CH 2 ) 6 CH 3 preparation of

[0036] According to Boc-Arg (NO 2 ) The preparation method of Gly-OBzl is by 1.61g (5mmol) Boc-Asp (Bzl)-OH and 0.65g (5.0mmol) CH 3 (CH 2 ) 6 CH 2 OH obtained 2.24 g (96.1 g) of a beige oily crude product, which was purified on a silica gel column to obtain 1.67 g of the title compound as a colorless oil. ESI-MS (m / z): 458.4[M] +

[0037] 2) HCl Asp(OBzl)-OCH 2 (CH 2 ) 6 CH 3 preparation of

[0038] 0.87g (2.0mmol) Boc-Asp(OBzl)-OCH 2 (CH 2 ) 6 CH 3 Dissolve in 10ml 4mol / l hydrogen chloride-ethyl acetate solution, stir at room temperature for 2 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 Concentrate under reduced pressure to remove hydrogen chloride gas. Finally, a small amount of diethyl ether was added to triturate the residue into ...

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Abstract

The invention discloses a method for preparing RGD-fatty alcohol series compounds as tumor targeting carrier materials and application thereof. The method comprises the following steps: conjugating n-octa alkyl fatty alcohol, decane-based fatty alcohol, dodecyl fatty alcohol, tetradecyl fatty alcohol, hexadecane fatty alcohol, and octadecyl fatty alcohol with RGD peptide segment respectively, and performing hydrophobic modification on the compounds to synthesize a peptide conjugated compound with different amphiphilic long-chain alkyls and RGD, namely Arg-Gly-Asp-O-CnH[2n +1] (n is equal to 8, 10, 12, 14, 16, or 18), and synthesize a compound of Gly-Gly-Asp-O-C4H29 simultaneously, thus the effectiveness of the targeting materials is further confirmed.

Description

technical field [0001] The present invention relates to the preparation and application of RGD-fatty alcohol series compounds, which are tumor targeting carrier materials, and especially relates to the construction method of targeted drug delivery system for fat-soluble drugs. The present 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 many malignant tumors 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 expre...

Claims

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Application Information

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IPC IPC(8): A61K47/42A61K31/337A61K31/704A61K33/24A61K9/127A61K9/14A61K9/107A61P35/00C07K1/107C07K5/08A61K47/18
CPCY02P20/55
Inventor 崔国辉崔纯莹郑雪莲
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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