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Hydrophobically modified polyethylenimines and their use as protein carriers

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

Inactive Publication Date: 2016-01-13
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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  • Hydrophobically modified polyethylenimines and their use as protein carriers
  • Hydrophobically modified polyethylenimines and their use as protein carriers
  • Hydrophobically modified polyethylenimines and their use as protein carriers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0037] First, dissolve polyethyleneimine PEI-423Da in a dehydrated and dried organic solvent (dichloromethane, chloroform, tetrahydrofuran, methanol, ethanol, propanol or acetonitrile, dichloromethane is used in this example), and add Two-fold molar ratio of 1-substituted chain lipid CH 3 -(CH 2 ) 11 -Br, the mixture is reacted at 20-100°C for 0.5-50h and then distilled under reduced pressure to remove dichloromethane, and then precipitated and washed with ether, and then separated and purified to obtain the structural formula The final product represented is the lipid hydrophobic modified polyethyleneimine 2C1 2 -PEI-423Da(C12PEI 423 ). 1 HNMR (CDCl 3 , 300MHz) 4.3 (wide peak, NH), 3.2-2.2 (wide peak, N-CH 2 CH 2 -N, 34H), 1.8-1.15 (broad peak, fatty chain CH 2 , 40H), 0.94-0.72 (triplet, terminal CH 3 , 6H).

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Embodiment 2

[0046] The material involved in this example is the same as that of Example 1. The synthesis process of hydrophobically modified polyethyleneimine and the composite method of nanoparticles are also the same as that of Example 1. The difference is that the chain lipid during synthesis is CH 3 -(CH 2 ) 7 -Br, the final product prepared is the lipid hydrophobically modified polyethyleneimine 2C8-PEI-423Da (C8PEI 423 ) Such as structural formula Shown. 1 HNMR (CDCl 3 , 300MHz) 4.3 (wide peak, NH), 3.2-2.2 (wide 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 size is 205.8nm, and the Zeta potential is -12.8mV. Antigen cross-presentation effect such as Figure 4 Shown by Figure 4 It can be seen that: the prepared C 8 PEI 423 / OVA composite nanoparticles have a significant enhancement effect on antigen cross-presentation i...

Embodiment 3

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

[0050] Prepare C in the same way as in Example 1. 20 PEI 423 / OVA complex. The measured particle size is 275.8nm, and the Zeta potential is -9.0mV. Antigen cross-presentation effect such as Figure 5 Shown by Figure 5 It can be seen that: the prepared C 20 PEI 423 / OVA composite nanoparticles have a significant enhancement effect on antigen cross-present...

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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 vaccine is designed to break the body's immune tolerance and improve the body's immune response. Its mechanism of action is to fundamentally re-awaken 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 an already ill individual, remove pathogens or abnormal cells, and cure the disease. As a new therapeutic vaccine, it has broad development prospects, especially in tumor treatment. [0003] However, the curative effect of tumor vaccines based on protein antigens is limited at present. One of the important reasons is that the immune response it induces is humoral immunity, that is, an imm...

Claims

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Application Information

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Patent Type & Authority Patents(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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