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Organic functional compound having disulfide chemical bond and steroids skeleton, preparation method thereof and use thereof

A technology of skeleton structure and disulfide chemistry, which is applied in the application field of functional surfactants, can solve the problems of complicated synthesis and lack of in vivo environment responsiveness of the carrier, and achieves simple synthesis method, good biological reducibility, good purity and water solubility. Effect

Inactive Publication Date: 2013-09-25
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, the research and application of cationic organic functional molecules based on the structure of cholesterol is still in the preliminary stage, and it is worthy of further research and development.
On the other hand, from the perspective of practical application as a carrier of drugs or therapeutic gene drugs, the synthesis of organic functional molecules derived from cholesterol-derived gene carriers is relatively cumbersome, and the carrier lacks in vivo environmental responsiveness during the delivery of gene drugs.

Method used

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  • Organic functional compound having disulfide chemical bond and steroids skeleton, preparation method thereof and use thereof
  • Organic functional compound having disulfide chemical bond and steroids skeleton, preparation method thereof and use thereof
  • Organic functional compound having disulfide chemical bond and steroids skeleton, preparation method thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] (1) Compound CS-1

[0041] The first step: Dissolve bis(2-hydroxyethyl)-disulfide compound (14g, 90mmol) in 200ml dry tetrahydrofuran, slowly add 4-nitrate dissolved in 50ml dry tetrahydrofuran dropwise under the catalysis of 20ml triethylamine Phenyl chloroformate (12g, 60mmol), reacted in an ice bath at 0°C for 30h, then distilled off tetrahydrofuran under reduced pressure, purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:1 (v / v )), the monohydroxy disulfide compound intermediate is prepared, and its productive rate is 35%, and the main chemical structure features are as follows:

[0042] 1 H NMR (CDCl 3 , 300MHz): 8.27(m, 2H, ArH), 7.37(m, 2H, ArH), 4.56(t, 2H, J=6.3Hz, CH 2 OCO), 3.91(t, 2H, J=6.6Hz, CH 2 OH), 3.03(t, 2H, J=5.7Hz, CH 2 S), 2.89(t, 2H, J=5.7Hz, CH 2 S).

[0043] ESI-MS: [M + ]=319.1m / z

[0044] The second step: the monohydroxy disulfide intermediate (3.2g, 10mmol) prepared above was dissolved in 30ml of ...

Embodiment 2

[0051]

[0052] (2) Compound CS-2

[0053] The first step: Dissolve two (2-hydroxyethyl)-disulfide compounds (28g, 180mmol) in 500ml of dry anhydrous acetonitrile, and slowly drop them under the catalysis of 10g 4-dimethylaminopyridine (DMAP) to dissolve in advance 4-Nitrochloroformic acid phenol ester (25g, 60mmol) in 50ml of dry chloroform, react at room temperature for 15h and remove chloroform under reduced pressure, through column chromatography (eluent: dichloromethane: petroleum Ether=1: 1 (v / v)) purification, obtains the intermediate containing disulfide chemical bond, and its productive rate is 43%, and main chemical structural feature is as follows:

[0054] 1 H NMR (CDCl 3 , 300MHz): 8.27(m, 2H, ArH), 7.37(m, 2H, ArH), 4.56(t, 2H, J=6.3Hz, CH 2 OCO), 3.91(t, 2H, J=6.6Hz, CH 2 OH), 3.03(t, 2H, J=5.7Hz, CH 2 S), 2.89(t, 2H, J=5.7Hz, CH 2 S).

[0055] ESI-MS: [M + ]=319.1m / z

[0056] The second step: the disulfide intermediate (7g, 13mmol) prepared in the p...

Embodiment 3

[0063]

[0064] (3) Compound CS-3

[0065] The first step: Dissolve bis(2-hydroxyethyl)-disulfide compound (28g, 180mmol) in 500ml dry anhydrous acetonitrile, under the catalysis of 10g 4-dimethylaminopyridine (DMAP), slowly dropwise add Dissolve 4-nitrochloroformic acid phenol ester (25g, 60mmol) in 50ml of dry chloroform, react at room temperature for 15h, remove chloroform by distillation under reduced pressure, and go through column chromatography (eluent: dichloromethane: Petroleum ether=1:1 (v / v)) separation and purification, the intermediate that contains disulfide chemical bond is prepared, and its productive rate is 43%, and main chemical structure characteristic is:

[0066] 1 H NMR (CDCl 3 , 300MHz): 8.27(m, 2H, ArH), 7.37(m, 2H, ArH), 4.56(t, 2H, J=6.3Hz, CH 2 OCO), 3.91(t, 2H, J=6.6Hz, CH 2 OH), 3.03(t, 2H, J=5.7Hz, CH 2 S), 2.89(t, 2H, J=5.7Hz, CH 2 S).

[0067] ESI-MS: [M + ]=319.1m / z

[0068] The second step: the disulfide compound intermediate (7g,...

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Abstract

The invention provides a novel-structure cation organic functional molecule having a disulfide chemical bond and a steroids skeleton, a preparation method thereof and use thereof. The cation organic functional molecule having the disulfide chemical bond and the steroids skeleton provided by the invention has low cellular toxicity and high biocompatibility and the molecular structure of the molecule is amphiphilic, can be efficiently bonded with genes in buffer solution and efficiently expresses target protein through intracellular transfection. The disulfide bond in the novel organic functional molecule provided by the invention can be reduced and broken, so that a loaded gene medicament can be released from an aggregation compound easily; and a fat-soluble cholesterol skeleton provides high biocompatibility and improves the bonding of a cation fragment and genes and the loading capacity of the cation fragment. The novel organic functional molecule provided by the invention is prepared by a simple and convenient method, can be used as a low-toxicity and efficient gene medicament release carrier biological material and can be applied in the preparation formulas of water agents or emulsion cosmetics and personal care supplies as an efficient and low-toxicity cation functional surfactant.

Description

technical field [0001] The invention relates to the field of "smart" organic biological functional materials, in particular to an organic functional compound having both bioreducible disulfide chemical bonds and a steroidal skeleton chemical structure, a preparation method and a controllable slow-release in the preparation environment responsiveness Application of functional surfactants in the preparation of pharmaceuticals and cosmetics. Background technique [0002] Since the 1990s, Biomaterials has become one of the most popular research topics in interdisciplinary fields such as life science and material science. Among them, the carrier biomaterials used for the delivery of drugs and therapeutic functional genes can deliver the loaded drugs and exogenous therapeutic genes to specific cells, tissues or organs in the organism to exert targeted therapeutic effects. At present, most of the gene carrier materials being studied at home and abroad are amphiphilic cationic orga...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J31/00C07K5/09A61K47/28A61K8/63A61K8/64
Inventor 曹阿民盛瑞隆
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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