Antiserum and low cytotoxicity polyamino acid gene delivery carrier material with transmembrane activity and nuclear localization function
A polyamino acid and cytotoxic technology, which is applied in gene therapy, medical preparations of non-active ingredients, drug delivery, etc., to achieve high-efficiency targeted delivery, low cytotoxicity, and good antiserum ability
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[0102] The present invention also provides a method for preparing the above-mentioned polyamino acid gene delivery carrier material, comprising the following steps: (1) synthesizing an esterified product of glutamic acid at the γ-position; (2) preparing step (1) corresponding to the esterified product (3) N-carboxyl cyclic anhydride (NCAs) monomers were ring-opened to prepare polyamino acids; (4) side chains containing both primary amine groups and oligomers were prepared by photoclick reaction Polyamino acid of ethylene glycol; (5) Converting the side chain amino group into guanidine group to obtain a polyamino acid gene delivery vector.
[0103] Specifically, the above-mentioned preparation method comprises the following steps:
[0104] (1) Make α,ω-enol, α,ω-alkynol, oligoethylene glycol containing α,ω-enol end group, or oligoethylene glycol containing α,ω-alkynol end group It undergoes esterification reaction with the γ-position carboxyl group of glutamic acid to synthesi...
Embodiment 1
[0112] Example 1: Ring cPALG and Linear L Synthesis of PALG
[0113] Weigh 34 moles of L-glutamic acid and 153 moles of propenyl alcohol, mix them evenly in a flask, slowly add 41 moles of concentrated sulfuric acid dropwise under ice bath conditions, and complete the dropwise addition within 30 min. After cooling for 1 h, the ice bath was removed and the temperature was raised to room temperature, and the reaction was continued for 48 h. After the reaction is completed, a sufficient amount of triethylamine is added to the system for neutralization, then a sufficient amount of acetone is added to stir, and the precipitate is obtained by filtration. The precipitate was dried in a vacuum oven at room temperature overnight, and the crude product was recrystallized from isopropanol / water, filtered, washed with sufficient cold acetone, and dried in vacuo. The product γ-allyl-L-glutamate was a white flake crystal with a yield of 47%.
[0114] Suspend 10 mole parts of γ-allyl-L-gl...
Embodiment 2
[0131] Example 2: Synthesis of cPALGgAET
[0132] Weigh the ring-shaped cPALG prepared in Example 1 containing 0.59 mole parts of C=C bond and dissolve it in 3 parts by volume of DMF, stir to dissolve it completely, and then add 1.18 mole parts of -SH bond to the mercaptoethylamine hydrochloride; Weigh 12.3 parts by mass of benzoin dimethyl ether (Irgacure 651) and add it to the reaction solution, react under ultraviolet flashlight irradiation (λmax=365nm, the intensity is 3-5mW cm -2 ) at room temperature for 120 min. After the reaction, the obtained reaction solution was put into a dialysis bag (1000 Mw) for dialysis for two days. Freeze-dried to give a nearly white solid, named cPALGgAET, yield 92%, 1 H NMR see attached image 3 , the structural formula is as follows:
[0133]
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