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Modified dendritic PAMAM polymer as well as preparation method and application thereof

A polymer and dendritic technology, applied in the field of medical materials, can solve the problems of limited temperature adjustment range and single type of polymer, and achieve the effect of reducing toxicity

Active Publication Date: 2019-01-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Temperature-sensitive smart materials based on PAMAM dendrimers have been reported, but they mainly focus on modifying PAMAM with the constituent units of temperature-sensitive polymers (such as: isobutyramide), and the obtained polymers are single and temperature-adjustable. limited range
It is still a challenge to continue to develop the types of smart PAMAM polymers and enrich their performance control range

Method used

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  • Modified dendritic PAMAM polymer as well as preparation method and application thereof
  • Modified dendritic PAMAM polymer as well as preparation method and application thereof
  • Modified dendritic PAMAM polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Dendrimer G4-PAMAM-DMEA 45 Synthesis

[0053] Dendrimer G4-PAMAM-DMEA 45 It is prepared by reacting the amino group on the surface of G4-PAMAM with the small molecule of tertiary amine activated by CDI (DMEA-CDI). The synthetic route is as follows: figure 1 shown.

[0054] Preparation of CDI-activated DMEA (DMEA-CDI):

[0055] Dissolve DMEA (N,N-dimethylethanolamine) (0.02mol) in 20mL of dichloromethane to obtain a DMEA solution; dissolve CDI (0.05mol) in 40mL of dichloromethane to obtain a CDI solution; drop the DMEA solution into CDI solution (complete dropwise addition within 30 minutes), after the dropwise addition is completed, react at room temperature for 24 hours; after the reaction is completed, wash the product three times with deionized water (collect the lower layer product), remove a small amount of water with anhydrous magnesium sulfate, and spin evaporate Remove the solvent dichloromethane, and then use a vacuum pump to remove a small amoun...

Embodiment 2

[0062] Example 2: Dendrimer G4-PAMAM-DEEA 45 Synthesis

[0063] Dendrimer G4-PAMAM-DEEA 45 It is prepared by reacting a small tertiary amine molecule (DEEA-CDI) activated by CDI with the amino group on the surface of PAMAM. The synthetic route is as follows figure 1 shown.

[0064] The preparation of DEEA activated by CDI, that is, DEEA-CDI: DEEA (N, N-diethylethanolamine) replaces DMEA (N, N-dimethylethanolamine) in Example 1, and other conditions and steps are the same as in Example 1, DEEA- The NMR results of CDI are shown in Fig. 3(b).

[0065] G4-PAMAM-DEEA 45 Preparation of:

[0066] (1) In 1.5ml of anhydrous DMSO, react 25mg of fourth-generation PAMAM (G4-PAMAM) with 71mg of DEEA-CDI in an oil bath at 40°C for 24 hours, the molar ratio of DEEA-CDI to the terminal amino group of G4-PAMAM The ratio is 3:1, and the product is obtained;

[0067] (2) Concentrate the product to about 0.5-1.0mL with a vacuum pump, pass through a Sephadex LH20 column, use methanol as the...

Embodiment 3

[0071] Example 3: Dendrimer G4-PAMAM-DPEA 45 Synthesis

[0072] Preparation of small molecules of N,N-dipropylethanolamine (DPEA) tertiary amine:

[0073] Dissolve ethanolamine (0.05 mol) and bromopropane (0.1 mol) in 100 mL of acetonitrile, add sodium carbonate (0.15 mol), and react under airtight conditions for 4 days at room temperature; filter the solution after the reaction to remove excess sodium carbonate and by-products Sodium bromide salt, the solvent was removed by rotary evaporation; the product was dissolved in dichloromethane, and then washed three times with saturated brine, the organic phase was collected, and the organic solvent was removed under reduced pressure. Colorless transparent liquid product with a yield of 44%. The NMR results of N,N-dipropylethanolamine (DPEA) are shown in Fig. 2(a).

[0074] The preparation of DPEA activated by CDI, that is, DPEA-CDI: DPEA (N, N-dipropylethanolamine) replaces DMEA (N, N-dimethylethanolamine) in Example 1, and oth...

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Abstract

The invention belongs to the technical field of medical materials, and discloses a modified dendritic PAMAM polymer as well as a preparation method and application thereof. The structure formula of the modified dendritic PAMAM polymer is PAMAM-(NH-C(O)-O-R)n, wherein R is tertiary amine group substituted alkyl; -NH- in the structure is amido-NH2 at the terminal of the PAMAM polymer; n is an integer greater than 0; the PAMAM polymer is preferably the fourth generation or the fifth generation PAMAM polymer. The modified dendritic PAMAM polymer has the temperature response, pH response and carbondioxide response performances; compared with a non-modified PAMAM, the modified dendritic PAMAM polymer has the advantage that the toxicity is obviously reduced. The invention further discloses application of the modified dendritic PAMAM polymer in a medicine carrier.

Description

technical field [0001] The invention belongs to the technical field of medical materials, and in particular relates to a modified dendritic PAMAM polymer and its preparation method and application. Background technique [0002] Polyamidoamine (PAMAM, polyamidoamine) is a class of dendrimer macromolecules commonly used in the field of biomedical materials. It has a clear chemical structure and a regular three-dimensional space structure. It contains a cavity inside and a large number of primary amine groups on the surface, which provides the possibility for physical loading and chemical bonding of drug molecules. In addition, the cationic primary amine groups on the surface of PAMAM can be combined with nucleic acid drugs such as DNA or siRNA to serve as delivery carriers for nucleic acid drugs and improve drug delivery efficiency. However, high algebraic PAMAM dendrimers can cause greater toxicity to cells and animals, which limits its application in the biomedical field to...

Claims

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Application Information

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IPC IPC(8): C08G73/02A61K47/34
CPCA61K47/34C08G73/028
Inventor 杜金志童其松徐炜黄华王均
Owner SOUTH CHINA UNIV OF TECH
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