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Preparation method of biodegradable polyurethane gene transfection reagent

A polyurethane and group technology, applied in the field of nano-biological materials, can solve the problems of unreported, unreported synthesis of cationic polyurethane, and achieve the effects of low cost, low cytotoxicity and low cytotoxicity

Inactive Publication Date: 2015-02-18
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, the synthesis of cationic polyurethanes containing disulfide bonds has not been reported
And the research on cationic polyurethane containing disulfide bond as gene release carrier has not been reported yet.

Method used

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  • Preparation method of biodegradable polyurethane gene transfection reagent
  • Preparation method of biodegradable polyurethane gene transfection reagent
  • Preparation method of biodegradable polyurethane gene transfection reagent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: Synthesis of dithiodiethanol p-nitrophenyl carbonate (DTDE-PNC)

[0058] (1) Add dithiodiethylene glycol (DTDE, 4g) and pyridine (7.4g) at a molar ratio of 1:1, add 40ml of anhydrous dimethylformamide and stir to dissolve for 10-30 minutes, then slowly add p-Nitrophenyl chloroformate (PNC, 10.3g) The molar ratio of p-nitrophenyl chloroformate (PNC) to dithiodiethylene glycol (DTDE) is 1:1.5, react at room temperature for 24 hours ;

[0059] (2) Wash the reaction finished mixture once with disodium hydrogen phosphate solution, then wash with deionized water, and remove the solvent by rotary evaporation; the reaction crude product is separated and purified by silica gel strain to obtain pure light yellow product dithiodiethyl-p-nitrate phenyl carbonate (7.4 g, 58% yield). 1 HNMR (300MHz, CDCl 3 , ppm): δ8.26 (aromatic protons, 4H); 7.37 (aromatic protons, 4H); 4.57 (2×SSCH2CH2, 4H); 3.08 (2×SSCH2CH2, 4H) (see figure 1 ).

Embodiment 2

[0060] Example 2: Synthesis of polyurethane containing 1,4-bis(3-aminopropyl)-piperazine

[0061] (1) Put DTDE-PNC (1.21g) prepared in Example 1 and 1,4-bis(3-aminopropyl)-piperazine (0.5g) in a molar ratio of 1:1 into a round bottom flask ; Dissolved with 5ml chloroform, reacted at room temperature for 5 days;

[0062] (2) the reaction product is dissolved in 10ml deionized water; the pH value is adjusted to 6 with hydrochloric acid and the molecular cut-off is 1000g / mol for dialysis bag dialysis; freeze-drying, obtains solid product containing polyurethane (0.7g, producing disulfide bond) rate of 65%). The degree of polymerization n is 300-350.

[0063] The NMR data of the solid product are: 1 HNMR (D 2 O) δ (ppm) = 4.30 (2 × SSCH2CH2, 4H); 3.4-4.0 (2 × NCH2CH2N, 8H); 3.31 (2 × OCONHCH2, 4H); 3.21 (2 × OCONHCH2CH2, 4H); 2.95 (2 × SSCH2CH2 ,4H); 1.95(2×CH2CH2CH2,4H) (see figure 2 ).

Embodiment 3

[0064] Embodiment 3: Synthetic polyurethane containing three (2-aminoethyl) amines

[0065] (1) DTDE-PNC (1.83g) and two (2-aminoethyl) 2-(tert-butoxycarbonylamino) ethylamine (0.93g) of equimolar ratio are put into flask;

[0066] (2) Dissolve with 5ml dimethylformamide and react at room temperature for 5 days;

[0067] (3) After the reaction is over, add 20ml of trifluoroacetic acid to react for 6h, and depressurize and rotary evaporate the trifluoroacetic acid;

[0068] (4) The reaction product was dissolved with 10ml deionized water, and the pH value was adjusted to 6;

[0069] (5) Dialysis with a dialysis bag with a molecular cut-off of 1000 g / mol;

[0070] (6) Freeze drying to obtain a solid product (0.25 g, yield 18%). The degree of polymerization n is 200-250; 1 HNMR (D 2 O)δ(ppm)=4.33(2×SSCH2CH2,4H); 3.65(CH2CH2NH2,2H); 3.56(2×OCONHCH2,4H); 3.47(CH2N(CH2)CH2,6H); 2.98(2×SSCH2CH2,4H )(See image 3 ).

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Abstract

The invention belongs to the technical field of nano-grade biological materials, and relates to a preparation method of a degradable cationic polyurethane, and the application of the degradable cationic polyurethane as a transfection reagent in transfecting mammalian cell lines. The structural formula of the degradable cationic polyurethane is represented by a formula (1), wherein R group is selected from those with polymerization degree n of 200-400. The reaction reagents adopted in the method have the advantages of no toxicity, no pollution, and low cost. The method can be popularized. In the synthesizing reaction, no special condensation agent and catalyst is required to be added, the reaction conditions are mild, and side reactions are less. With the method, disulfide bond and amine functional groups can be conveniently introduced, such that polyurethane with diverse structures can be obtained. The polyurethane provided by the invention has good biocompatibility and low cytotoxicity.

Description

technical field [0001] The invention belongs to the technical field of nano-biological materials, and relates to a preparation method of a degradable cationic polyurethane and its application as a transfection reagent to transfect mammalian cell lines. Background technique [0002] Gene therapy is a new method of delivering genes with therapeutic functions to human cells and expressing required functional proteins to treat diseases. How to use vectors to introduce exogenous genes into target cells safely, accurately and effectively is the key technology for the success of gene therapy. At present, recombinant viral vectors have been widely used in in vitro gene transfection and clinical gene therapy, but their potential safety issues such as immunogenicity, mutagenesis and tumorigenicity are still a major problem that needs to be solved urgently. In contrast, non-viral gene carriers such as liposomes, polymers, and nanoparticles have better safety, and have the advantages o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G71/00C12N15/63
Inventor 娄博林超程建宋焱艳
Owner TONGJI UNIV
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