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PH-sensitive amphipathic graft copolymer POEAd-g-MPEG, preparation method and application of graft copolymer

A graft copolymer, poead-g-nh2 technology, applied in the field of synthesis of new pH-sensitive amphiphilic graft copolymers, can solve the problems of weak acid sensitivity, low stability, and limitations

Active Publication Date: 2016-09-21
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The first type has low stability at pH 7.4 and its extracellular drug release in tumor cells limits its further application. Although the second type has tumor tissue sensitivity, its acid sensitivity is weak, and further research is needed to improve it.

Method used

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  • PH-sensitive amphipathic graft copolymer POEAd-g-MPEG, preparation method and application of graft copolymer
  • PH-sensitive amphipathic graft copolymer POEAd-g-MPEG, preparation method and application of graft copolymer
  • PH-sensitive amphipathic graft copolymer POEAd-g-MPEG, preparation method and application of graft copolymer

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Experimental program
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Effect test

Embodiment 1

[0029] Polyorthoester Copolymer POEAd-g-COF 3 The synthetic method of is realized through the following steps:

[0030] Under a nitrogen atmosphere, add 1.01g (3.28MmoL) 4,4'-dimethethyleneoxy-bis-(2-aminoethoxy-1,3-dioxolane) to a 50ml eggplant-shaped bottle, 1.90 g (3.28Mmol) 2-N-trifluoroacetyl-1,3-di-(4'-succinimidyl succinate) propylene glycol ester, 1.5mL triethylamine, 10mL anhydrous N,N-di Methylformamide was reacted at 30°C for 7 days, a small amount of dichloromethane was added, and anhydrous ether was settled twice to obtain 1.87 g of a white solid product with a yield of 86.6%. 1 H NMR (400MHz, CDCl 3 ,δ,ppm):2.55-2.61(m,8H,OOC-CH2-CH2-COO),3.41(s,4H,H2N-CH2),3.55-3.78(m,8H,N-CH2-CH2-O, CH-CH2-O),4.02-4.13(m,8H,O-CH2-CH,NH-CH-CH2-O),4.31-4.47(m,4H,O-CH2-CH2-CH-O),5.82 -5.83(d,2H,CH-(O)3),6.47(s,3H,OC-NH)( figure 1 ).

Embodiment 2

[0032] Polyorthoester copolymer POEAd-g-NH with side chain amino group 2 , the synthetic method is realized through the following steps:

[0033] 1.87g main chain polyorthoester copolymer POEAd-g-COF 3 Dissolve with 50mL tetrahydrofuran, add to 300mL 7% sodium carbonate aqueous solution, magnetically stir and react for 6 hours, remove tetrahydrofuran by distillation under reduced pressure, and then use a 3500Da dialysis belt to dialyze in a small amount of triethylamine aqueous solution for 48 hours (change every six hours) dialysate), and finally freeze-dried to obtain the target polymer POEAd-g-NH 2 1.52 g, yield 81.3%. 1 HNMR (400MHz, DMSO-d 6 ):δ(ppm)2.27-2.38(m,8H,OOC-CH 2 -CH 2 -COO),3.15-3.20(m,4H,H 2 N-CH 2 ),3.41-3.66(m,8H,N-CH 2 -CH 2 -O,CH-CH 2 -O),4.02-4.06(t,8H,O-CH 2-CH,NH-CH-CH 2 -O),4.20-4.40(m,4H,O-CH 2 -CH 2 -CH-O),5.83-5.85(d,2H,CH-(O) 3 )( figure 2 ).

Embodiment 3

[0035] The synthetic method of pH sensitive amphiphilic graft copolymer POEAd-g-MPEG550, realizes by following steps: the copolymer POEAd-g-NH 2 0.56g, polyethylene glycol monomethyl ether active ester (molecular weight: 550) 2.73g, 4.57Mmol, 1mL triethylamine, accurately weighed and put into a dry eggplant-shaped reaction bottle, and then the reaction bottle was placed in a 30°C React in an oil bath. After 24 hours of reaction, use a 3500Da dialysis belt to dialyze in an aqueous solution with a small amount of triethylamine for 48 hours (change the dialysate every six hours), and finally freeze-dry to obtain the target polymer. 1 HNMR (400MHz, DMSO-d 6 ):δ(ppm)2.29-2.43(m,8H,OOC-CH 2 -CH 2 -COO),3.06-3.10(m,4H,H 2 N-CH 2 ),3.18-3.21(m,8H,N-CH 2 -CH 2 -O,CH-CH 2 -O),3.24(s,3H,PEG-OCH 3 ), 3.51(s, MPEG), 4.02-4.06(t, 8H, O-CH 2 -CH,NH-CH-CH 2 -O),4.20-4.40(m,4H,O-CH 2 -CH 2 -CH-O),5.83-5.85(d,2H,CH-(O) 3 )( image 3 ).

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Abstract

The invention discloses a pH-sensitive amphipathic graft copolymer POEAd-g-MPEG, a preparation method and an application of the graft copolymer. The copolymer has acid sensitivity, biocompatibility and biodegradability, can self-organize in an aqueous solution, and forms a drug carrier with a shell-core structure. The copolymer has bright application prospects in the field of tumor treatment.

Description

technical field [0001] The invention relates to a synthesis method of a novel pH-sensitive amphiphilic graft copolymer containing orthoester groups in the main chain and drug delivery thereof. The invention belongs to the technical field of biological material and drug controlled release. Background technique [0002] At present, chemotherapy is an important means of clinical treatment of cancer, but the further application of chemotherapy is limited due to the toxicity of chemotherapy drugs and tumor targeting. In order to solve these limiting factors, combined with the characteristics of tumor tissue itself, nano-drug carriers have been extensively studied. Among them, PEGylated stimuli-responsive nano-drug carriers can prolong the delivery time of drugs in vivo and enhance tumor targeting. been extensively studied. Among stimuli-responsive nanocarriers, acid sensitivity is the most studied stimulus in recent years. However, at present, a large number of acid-sensitive ...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08G69/44C08G69/48A61K9/107A61K47/34A61K45/06A61P35/00
CPCA61K9/1075A61K45/06A61K47/34C08G69/44C08G69/48C08G81/00
Inventor 唐汝培闫国卿
Owner ANHUI UNIVERSITY
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