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Cholestrin derivative as nucleoside analog

A technology for cholesterol derivatives and nucleoside analogs, applied in the fields of chemistry and biomedicine, can solve the problems of inability to reach the administration concentration, poor water solubility and lipid solubility, and poor lipid solubility.

Inactive Publication Date: 2005-07-06
INST OF RADIATION MEDICINE ACAD OF MILITARY MEDICAL SCI OF THE PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The currently synthesized nucleoside analogs are generally highly water-soluble and poorly fat-soluble, and some drugs are even poorly water-soluble and fat-soluble
Therefore, their liposome encapsulation rate is low, often unable to reach the administration concentration

Method used

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  • Cholestrin derivative as nucleoside analog
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1. Preparation of Aciclovir Cholesterol Succinate

[0028] This product is the product of acylation of the two ends of the succinic acid molecule with the fatty chain hydroxyl of acyclovir and cholesterol hydroxyl respectively. The English chemical name is Succinic acid 2-(2-amino-6-oxo-1, 6-dihydro-purin-9 -ylmethoxy)-ethyl ester 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16, 17-tetradecahydro-1H-cyclopenta[α]phenanthren-3-yl ester, molecular formula C 39 h 59 N 5 o 6 , molecular weight 693.93. The first synthesis of succinyl acyclovir (C 12 h 15 N 5 o 6 ),Specific steps are as follows. Get Acyclovir (4.5g, 0.02mol), succinic anhydride (10g, 0.1mol), 4-dimethylaminopyridine (DMAP, 0.244g, 2mmol), add 100ml N, N-dimethylformamide ( DMF), filled with nitrogen, sealed, reacted at room temperature for 2 days, evaporated the reactant under reduced pressure to remove most of the solvent, poured the remaining liquid into ice water ...

Embodiment 2

[0032] Embodiment 2. Preparation of didanosine cholesterol oxalate

[0033] This product is the acylation product of the two ends of the oxalic acid molecule with the hydroxyl group of the side chain of the aliphatic ring of didanosine and the hydroxyl group of cholesterol, the chemical name is Oxalic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2, 3, 4, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17-tetradecahydro-1H-cyclopenta[α]phenanthren-3-yl ester 5-(6-oxo-1,6 -dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester, molecular formula C 39 h 56 N 4 o 6 , molecular weight 676.89. The specific synthesis steps are as follows: take cholesterol (3.86g, 10mmol), oxalyl chloride (5ml) and add 100ml of dichloromethane, stir at room temperature for 5h, evaporate most of the solvent under reduced pressure, add didanosine (1.18g, 5mmol) and 50ml of DMF : THF (1:1, v / v), sealed, stirred at room temperature for 10h, evaporated and concentrated under reduced pressure, the remaining solut...

Embodiment 3

[0034] Example 3. Preparation of didanosine cholesterol succinate

[0035] This product is the product of acylation of the two ends of the succinic acid molecule with the hydroxyl group of the side chain of the aliphatic ring of didanosine and the hydroxyl group of cholesterol respectively. The chemical name is Succinic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2 , 3, 4, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17-tetradecahydro-1H-cyclopenta[α]phenanthren-3-yl ester 5-(6-oxo-1, 6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester, molecular formula C 41 h 60 N 4 o 6 , molecular weight 704.9. First, the intermediate cholesterol hemisuccinate was synthesized, and then acylated with didanosine (ddI) to obtain the target product. The specific synthesis steps are as follows: take cholesterol (3.86g, 10mmol), succinic anhydride (3g, 30mmol), DMAP (0.122g, 1mmol) and add 100ml of dichloromethane, stir at 55°C for 3 days, evaporate the solvent to dryness under reduced pressur...

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Abstract

The invention discloses a nucleoside analog cholesterol derivative characterized in that its structure is Nu-L-Ch, wherein Nu is a nucleoside analog group, L is a fatty chain connection group with a carbon number between 2 and 7, Ch is a cholesterol group. A highly dispersed transmission system including liposomes, nonionic surfactant vesicles, nanoparticles and microemulsion or a self-assembly transmission system can be formed from the nucleoside analog cholesterol derivative.

Description

technical field [0001] The present invention relates to the fields of chemistry and biomedicine, in particular to a nucleoside analog cholesterol derivative, from which a highly dispersed delivery system can be prepared, including liposomes, nonionic surfactant vesicles, nanoparticles, microemulsions and self-assembling delivery systems. Background technique [0002] Nucleosides are important chemical components in organisms, and nucleotides and nucleic acids derived from them are carriers of genetic information. The most important genetic materials, DNA and RNA, are assembled from nucleotides. Nucleosides and nucleotides also participate in many important reactions in living organisms. Nucleosides in nature are composed of a purine or pyrimidine base combined with a five-carbon sugar. The bases include adenine, guanine, cytosine, uracil, and thymine, and the five-carbon sugars are ribose and deoxyribose, which are composed of adenosine, guanosine, cytidine, and uridine, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/107A61K9/127A61K9/14A61K47/28C07J9/00
Inventor 金义光艾萍
Owner INST OF RADIATION MEDICINE ACAD OF MILITARY MEDICAL SCI OF THE PLA
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