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Hexose ester, synthetic method thereof and use thereof

A six-carbon sugar ester and synthesis method technology, applied in the field of six-carbon sugar ester, can solve problems such as multi-drug resistance, difficulty in reaching the HIV virus reservoir, and inability to completely eliminate HIV

Inactive Publication Date: 2014-07-30
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still problems that drugs cannot completely eliminate HIV, it is difficult to reach the HIV virus reservoir, and long-term medication is prone to multi-drug resistance.

Method used

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  • Hexose ester, synthetic method thereof and use thereof
  • Hexose ester, synthetic method thereof and use thereof
  • Hexose ester, synthetic method thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1 Preparation of galactose ester

[0043] 1. In N 2 Under protection, 1,4-butanediamine (4.47 g, 50.8 mol) was dissolved in 45 mL of anhydrous CH 2 Cl 2 In 20mL of anhydrous CH 2 Cl 2 Boc anhydride (2.77 g, 12.7 mmol) was added to the reaction liquid, and the ice bath was removed after 2 h of reaction, and stirred at room temperature for 16 h. Add 50mL CH 2 Cl 2 Diluted, the organic layer was washed successively with water (100mL), saturated NaCl solution (100mL), anhydrous NaCl 2 SO4 dry. The solvent was removed under reduced pressure with 0.5% NEt 3 CH 2 Cl 2 / MeOH=9 / 1 column chromatography to obtain colorless oil 1 (tert-butyl-(4-aminobutyl)carbamate, 2.15 g, yield 90%).

[0044] 2. In N 2 Under protection, compound 1 (1.88 g, 10 mmol) was dissolved in 40 mL of anhydrous CH 2 Cl 2 , add NEt under stirring in ice bath 3 (2.78 mL). Cholesterol chloroformate (4.93 g, 11 mmol) was dissolved in 10 mL of anhydrous CH 2 Cl 2 , slowly added dropw...

Embodiment 2

[0049] Example 2 Affinity of galactose ester-modified liposomes to macrophage membranes

[0050] (1) Preparation of fluorescent liposomes modified with galactose esters

[0051] Select doxorubicin (DOX) with a large conjugated system and excited fluorescence stability as a fluorescent probe, encapsulated in liposomes, and ammonium sulfate active drug loading method to prepare galactose ester modified DOX liposomes (DOX- Gal-L). Ordinary DOX liposome (DOX-L) does not contain galactose ester in the prescription.

[0052] (2) Affinity of galactose ester-modified liposomes to macrophage membranes

[0053] Take the RAW 264.7 cells in the logarithmic growth phase, adjust the concentration of the cell suspension, and adjust the cell concentration to 10 with the growth medium after counting the cells. 4 / mL, inoculate in 24-well plate, add 500 μL to each well, in 5% CO 2 After incubating at 37°C for 24 hours, 500 μL of free DOX, DOX-L, and DOX-Gal-L in a series of concentration gr...

Embodiment 3

[0054] Example 3 Biocompatibility of galactose esters

[0055] Take the RAW 264.7 cells in the logarithmic growth phase, adjust the concentration of the cell suspension, and adjust the cell concentration to 10 with the growth medium after counting the cells. 4 / mL, inoculate in 96-well plate, add 200 μL to each well, in 5% CO 2 After incubating at 37°C for 12 hours, a series of concentration-gradient galactose esters were added, and 6 wells were inoculated for each concentration. After continuing to culture for 24 hours, 20 μL of 0.5% MTT solution was added to each well, and cultured for 4 hours. Terminate the culture, and carefully aspirate the culture medium in the well. Add 100 μL of dimethyl sulfoxide to each well, shake on a shaker at low speed for 10 min, and fully dissolve the crystals. An enzyme-linked immunosorbent assay was used to measure the OD value at 570 nm of each well. At the same time set the zero well (medium, cells, dimethyl sulfoxide), control wells (m...

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Abstract

The invention relates to a hexose ester, and concretely relates to the hexose ester, a synthetic method thereof and a use thereof. The molecular general formula of the hexose ester is C36+m+nH60+2m+2nN2O10. The synthetic method comprises the following steps: dissolving an alpha, omega-diamine and a Boc acid anhydride in an organic solvent, and reacting to obtain a compound 1; dissolving the compound 1, cholesteryl chloroformate and an alkali in the organic solvent, and reacting to obtain a compound 2; dissolving acetyl chloride and the compound 2 in the organic solvent, and reacting to obtain a compound 3; dissolving the compound 3 and alpha, omega-dicarboxylic anhydride the an organic solvent, adding the alkali, and reacting to obtain a compound 4; dissolving 2,3,4,6-tetra-O-benzyl-hexose, the compound 4 and a condensing agent in the organic solvent, adding the alkali, and reacting to obtain a compound 5; and dissolving the compound 5 and Pd / C in the organic solvent, and reacting to obtain a compound 6(D-hexose-4[(4-{[(cholane-4-oxo)carbonyl]amino}A)amino]-4-carbonyl B ester).

Description

technical field [0001] The invention relates to a six-carbon sugar ester, in particular to a six-carbon sugar ester and its synthesis method and application. Background technique [0002] Highly active antiretroviral therapy (HAART) can inhibit HIV replication and reduce AIDS morbidity and mortality. However, there are still problems that drugs cannot completely eliminate HIV, are difficult to reach the HIV virus reservoir, and are prone to multi-drug resistance after long-term medication. Finding anti-HIV new drugs with high efficiency and low toxicity, and developing a new drug delivery system for the HIV reservoir is a hot spot and difficulty in current international anti-AIDS research (1. Sosnik A, Chiappetta DA, Carcaboso AM. Drug delivery systems in HIV Pharmacotherapy: What has been done and the challenges standing ahead. Journal of Controlled Release. 2009, 138(1): 2-15; 2. Ojewole E, Mackraj I, Naidoo P, Govender T. Exploring the use of novel drug delivery systems ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J41/00A61K47/28A61K9/127A61K31/7072A61P31/18
Inventor 王秀敏王凌嵩李宇航汤少恒连惠龙杨钦磊李岩秀
Owner XIAMEN UNIV
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