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Hydrophobic-modified polyethyleneimine and application thereof as protein carrier

A polyethyleneimine and protein technology, applied in the biological field, can solve the problems of small molecular weight, weak protein binding ability, and inability to form nanoparticles, so as to reduce cytotoxicity, improve the effect of antigen cross-presentation, and improve the effect of immunotherapy. Effect

Inactive Publication Date: 2013-04-24
SHANGHAI JIAO TONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a protein antigen carrier, it is also unable to form nanoparticles due to its small molecular weight and weak ability to bind proteins.

Method used

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  • Hydrophobic-modified polyethyleneimine and application thereof as protein carrier
  • Hydrophobic-modified polyethyleneimine and application thereof as protein carrier
  • Hydrophobic-modified polyethyleneimine and application thereof as protein carrier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The synthetic schematic diagram of the hydrophobically modified polyethyleneimine of the present embodiment is as follows figure 1 As shown, the specific steps are as follows:

[0037] First, polyethyleneimine PEI-423Da is dissolved in a dehydrated and dried organic solvent (which can be dichloromethane, chloroform, tetrahydrofuran, methanol, ethanol, propanol or acetonitrile, dichloromethane is used in this embodiment), and Chain Lipid CH Substituted at Position 1 in Twice the Molar Ratio 3 -(CH 2 ) 11 -Br, the mixture was reacted at 20-100°C for 0.5-50h, then dichloromethane was distilled off under reduced pressure, further precipitated and washed with ether, separated and purified to obtain the structural formula The final product represented is lipid hydrophobically modified polyethyleneimine 2C1 2 -PEI-423Da (C12PEI 423 ). 1 H NMR (CDCl 3 , 300MHz) 4.3 (broad peak, NH), 3.2-2.2 (broad peak, N-CH 2 CH 2 -N, 34H), 1.8-1.15 (broad peak, fatty chain CH 2 , 4...

Embodiment 2

[0046] The materials involved in this embodiment are the same as in Example 1, and the synthesis process of hydrophobically modified polyethylenimine and the composite method of nanoparticles are also the same as in Example 1, except that the chain lipid during synthesis is CH 3 -(CH 2 ) 7 -Br, the final product prepared is lipid hydrophobic modified polyethyleneimine 2C8-PEI-423Da (C8PEI 423 ) such as the structural formula shown. 1 H NMR (CDCl 3 , 300MHz) 4.3 (broad peak, NH), 3.2-2.2 (broad peak, N-CH 2 CH 2 -N, 34H), 1.8-1.15 (broad peak, fatty chain CH 2 , 12H), 0.94-0.72 (triplet, terminal CH 3 , 6H).

[0047] Prepare C in the same way as in Example 1 8 PEI 423 / OVA complex. The measured particle diameter was 205.8 nm, and the Zeta potential was -12.8 mV. Antigen cross-presentation effects such as Figure 4 shown by Figure 4 It can be seen that the prepared C 8 PEI 423 / OVA composite nanoparticles can significantly enhance the cross-presentation of anti...

Embodiment 3

[0049] The materials involved in this embodiment are the same as in Example 1, and the synthesis process of hydrophobically modified polyethylenimine and the composite method of nanoparticles are also the same as in Example 1, except that the chain lipid during synthesis is CH 3 ——(CH 2 ) 19 -CI, the final product prepared is lipid hydrophobic modified polyethyleneimine 2C20-PEI-423Da (C20PEI 423 ), such as the structural formula shown. 1 H NMR (CDCl 3 , 300MHz) 4.3 (broad peak, NH), 3.2-2.2 (broad peak, N-CH 2 CH 2 -N, 34H), 1.8-1.15 (broad peak, fatty chain CH 2 , 72H), 0.94-0.72 (triplet, terminal CH 3 , 6H).

[0050] Prepare C in the same way as in Example 1 20 PEI 423 / OVA complex. The measured particle diameter was 275.8 nm, and the Zeta potential was -9.0 mV. Antigen cross-presentation effects such as Figure 5 shown by Figure 5 It can be seen that the prepared C 20 PEI 423 / OVA composite nanoparticles significantly enhanced the cross-presentation of a...

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Abstract

The invention discloses a hydrophobic-modified polyethyleneimine and application thereof as a protein carrier. The structural general formula of the hydrophobic-modified polyethyleneimine is disclosed in the specification, wherein n is any natural number ranging from 5 to 20, and X is Cl, Br or I. The hydrophobic-modified polyethyleneimine can be compounded with protein to form stable nanoparticles, and thus, can be used as a protein carrier. Compared with the prior art, the hydrophobic-modified polyethyleneimine disclosed by the invention has strong protein binding force, can carry antigen protein, can be recognized by antigen presenting cells, and can initiate immunoreaction; and meanwhile, the hydrophobic-modified polyethyleneimine enhances the antigen cross-presentation effect, obviously lowers the cytotoxicity, is beneficial to enhancing the immunotherapeutic effect, and is an excellent therapeutic tumor vaccine nano carrier system.

Description

technical field [0001] The invention relates to the field of biotechnology, in particular to a hydrophobically modified polyethyleneimine and its use as a protein carrier. Background technique [0002] Therapeutic vaccines aim to break the body's immune tolerance and improve the body's immune response. Its mechanism of action is to fundamentally reawaken the body's immune response to the target antigen by improving and enhancing the intake, expression, processing, presentation and activation of the immune response to the vaccine target antigen. It can induce a specific immune response in a diseased individual, remove pathogens or abnormal cells, and cure the disease. As an emerging vaccine for therapeutic purposes, it has broad prospects for development, especially in tumor treatment. [0003] However, the curative effect of tumor vaccines based on protein antigens is currently limited. One of the important reasons is that the immune response induced by it is humoral immun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/04A61K47/32A61K39/00A61K39/12A61P35/00A61P31/12
Inventor 陈剑王辉徐宇虹盛瑞隆曹阿民
Owner SHANGHAI JIAO TONG UNIV
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