DO3A-containing diolefin crosslinking agent and application thereof for preparing nano-polymer-based contrast medium
A nano-polymer and diolefin technology, which can be used in preparations for in vivo testing, medical preparations with inactive ingredients, and capsule delivery, etc. Enhanced penetration and retention
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Embodiment 1
[0051] Embodiment 1: the preparation of the double olefin cross-linking agent containing DO3A
[0052] The preparation method of the double olefin crosslinking agent containing DO3A in the present embodiment is as follows:
[0053] 1. Add 5g of 5-aminoisophthalic acid and an organic solvent into the reactor, then add 11g of aminoethyl methacrylate and 7g of triethylamine, stir for 15 minutes to remove the triethylamine salt, and the filtrate is protected under nitrogen 14g of dicyclohexylcarbodiimide (DCC) and 3g of 4-dimethylaminopyridine (DMAP) were added under low temperature, and the reaction was stirred at room temperature for 10-12 hours; after the reaction was completed, the filtrate was collected by filtration, and after removing the solvent under high vacuum Separation by silica gel powder chromatography (eluent is n-hexane: ethyl acetate = 1:1, v / v) to obtain reaction intermediate I——5-amino-(1,3-ethyl methacrylate di benzamide);
[0054] The structural formula of ...
Embodiment 2
[0061] Embodiment 2: the preparation of the double olefin cross-linking agent containing DO3A
[0062] 1. Add 5-aminoisophthalic acid (5.08g, 28.04mmol) and 70ml N,N-dimethylformamide into the reactor, then add aminoethyl methacrylate (11.15g, 67.30mmol) and three Ethylamine (7.34g, 72.91mmol), stirring for 15 minutes to remove the triethylamine salt, the filtrate was added dicyclohexylcarbodiimide (13.88g, 67.30mmol)) and 4-dimethylaminopyridine under nitrogen protection (2.74g, 22.43mmol), stirred and reacted at room temperature for 10-12 hours; after the reaction, the filtrate was collected by filtration, and the solvent was removed under high vacuum and then separated by silica gel powder chromatography (eluent was n-hexane: ethyl acetate Esters=1:1, v / v) to obtain 2.52 g of reaction intermediate I——5-amino-(1,3-ethyl methacrylate dibenzamide), with a yield of 22%.
[0063] 1 H NMR (DMSO-d 6 ):δ8.49(t,2H,J=5.6Hz),7.35(s,1H),7.11(s,2H),6.05(s,2H),5.67(s,2H),5.45(s,2H) ,...
Embodiment 3
[0068] Example 3: Loading of Drugs
[0069] 4. Drop chain transfer agent 4-cyano-4-(thiobenzoyl)valeric acid (43.3mg, 0.155mmol) and oligoethylene glycol methacrylate (4.42g, 14.73mmol), azobisisobutyronitrile (5.1mg, 31.0μmol) and solvent DMF5.0ml, under the condition of liquid nitrogen freezing solution, constantly fill in a large amount of nitrogen and use vacuum pump to remove trace oxygen in the system solution, Repeated three times, and then reacted in an oil bath at 70°C. During the reaction, samples were taken intermittently for NMR to determine the conversion rate of the monomer. When the conversion rate of polyethylene glycol methacrylate reached 80%, the polymerization was terminated, and the reaction liquid After adding into n-hexane for sedimentation and vacuum drying, a macromolecular chain transfer agent is obtained.
[0070] 1 H NMR (CDCl 3 ):δ4.06(br,C(O)OCH 2 ),3.64(br,CH 2 OCH 2 ),3.36(br,CH 2 OCH 3 ),1.76(br,C(CH 3 )CH 2 ),0.86(br,C(CH 3 )CH 2 ). ...
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