Functional single-chain cyclic poly (beta-amino ester) as well as preparation method and gene delivery drug application thereof
A functional, aminoester technology, applied in the field of functional single-chain cyclic polymer and its preparation, gene delivery drug application field, can solve the problems of no way, limited clinical approval and large-scale application, achieve narrow PDI, charge The effect of easy adjustment of density and composition, good biocompatibility
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[0038] A synthetic method of a class of functional single-chain cyclic poly(β-amino ester) disclosed by the present invention, the synthetic route can be found in figure 1 , including the following steps:
[0039]1) A linear poly(β-amino ester) with a double bond is obtained through a Michael addition reaction between a diacrylate monomer and a small molecule organic amine;
[0040] 2) The linear poly(β-amino ester) with double bond prepared in step 1) is subjected to reversible addition-fragmentation chain transfer polymerization to obtain a single-chain polycyclic poly(β-amino ester) with controllable structure and composition ;
[0041] 3) Adding a functional end-capping agent to the single-chain polycyclic poly(β-amino ester) prepared in step 2) for functional end-capping treatment to prepare a functional single-chain cyclic poly(β-amino ester).
[0042] Specifically, the following steps are included:
[0043] 1) Add a certain amount of diacrylate monomer and small mole...
Embodiment 1
[0064] The reaction ratio of 2,2-dithiodiethanol diacrylate and dodecylamine is 2:1, react at 60°C for 5h; add 0.5 equivalent of 2,2-dithiodiethanol diacrylate, After 48 hours of reaction, the obtained low molecular weight linear poly(β-amino ester) had a molecular weight of 3000 Da.
[0065] Low molecular weight linear poly(β-amino ester), chain transfer agent and AIBN reaction feed ratio is 300:1:1, react at 50°C for 50h, then add 4 equivalents of N-(2-aminoethyl)morpholine, After reacting at 25°C for 48 hours, the obtained single-chain polycyclic poly(β-amino ester) had a molecular weight of 30,000 Da.
[0066] figure 2 It is a solution state in which the single-chain polycyclic poly(β-amino ester) with a molecular weight of 30,000 Da prepared in this example is dissolved in dimethyl sulfoxide. image 3 The H NMR spectrum of the single-chain polycyclic poly(β-amino ester) with a molecular weight of 30,000 Da prepared for this example.
[0067] see Figure 4 , Figure ...
Embodiment 2
[0069] The reaction ratio of bisphenol A polyoxyethylene ether diacrylate and dodecylamine is 0.5:1, react at 60°C for 2h; add 1 equivalent of bisphenol A polyoxyethylene ether diacrylate, react at 25°C for 48h , to obtain a linear poly(β-amino ester) with a molecular weight of 2800 Da.
[0070] Low molecular weight linear poly(β-amino ester), chain transfer agent and AIBN reaction ratio is 200:5:1, react at 50℃ for 96h, then add 5 equivalents of 1,11-diamino-3,6,9 - Trioxaundecane, reacted at 25° C. for 48 hours, and the molecular weight of the obtained single-chain polycyclic poly(β-amino ester) was 40000 Da.
[0071] see Figure 4 , Figure 4 (b) is the purified gel permeation chromatography (GPC) curve of the single-chain polycyclic poly(β-amino ester) with a molecular weight of about 40,000 Da prepared in this example.
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