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Cystamine diisocyanate monomer, cystamine diisocyanate monomer based polymers as well as preparation method and application of cystamine diisocyanate monomer

A cystamine diisocyanate and dihydroxy compound technology, which is applied in the preparation of hydrogenated polysulfides/polysulfides, medical preparations without active ingredients, and medical preparations containing active ingredients, etc., can solve the application of unfavorable biomedical materials. and other problems, to achieve the effect of enriching varieties, reducing cumbersome steps and facilitating preparation

Active Publication Date: 2016-02-24
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the existing monomers dithiodiethanol and 3,3'-disulfane disubstituted dipropyl-1,2-diol may cause the synthesized polymers to have varying degrees of cytotoxicity, which is not conducive to biological Application of medical materials

Method used

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  • Cystamine diisocyanate monomer, cystamine diisocyanate monomer based polymers as well as preparation method and application of cystamine diisocyanate monomer
  • Cystamine diisocyanate monomer, cystamine diisocyanate monomer based polymers as well as preparation method and application of cystamine diisocyanate monomer
  • Cystamine diisocyanate monomer, cystamine diisocyanate monomer based polymers as well as preparation method and application of cystamine diisocyanate monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of Cystamine Diisocyanate Monomer

[0046]

[0047] Under nitrogen atmosphere, cystamine dihydrochloride (11.25g, 0.05mol) and pyridine (23.73g, 0.3mol) were dissolved in 120mL of anhydrous dichloromethane, and poured into a 500mL three-neck flask. Dissolve triphosgene (8.91g, 0.03mol) in 40mL of anhydrous dichloromethane and add it to a 50mL constant pressure dropping funnel. Submerge the three-necked flask in an ice-salt bath, and when the temperature of the system drops to -10-15°C, under magnetic stirring, start to add triphosgene to the three-necked flask from a constant pressure dropping funnel to maintain the temperature of the system at - Reaction at 10°C for 6h.

[0048] After the reaction, extract three times with 0.1N glacial hydrochloric acid, take the organic phase, add anhydrous MgSO 4 Dry overnight, then filter with suction and concentrate by rotary evaporation to obtain a crude product, which is purified by distillation under reduced press...

Embodiment 2

[0051] Cystamine diisocyanate monomer (CDI) undergoes polycondensation reaction with polycaprolactone (OCL) with hydroxyl groups at both ends to generate reductive and degradable polycaprolactone (SSPCL) containing disulfide bonds. The process is as follows:

[0052]

[0053] By changing the feed ratio of CDI and OCL, a series of SSPCLs with different molecular weights can be prepared. The raw material composition and GPC characterization results of the polymers are shown in Table 1.

[0054] Take the synthesis of SSPCL (Table 1, Polymer 1) as an example: under nitrogen protection, dissolve 0.210g cystamine diisocyanate in 1mL anhydrous DMF and then transfer to a closed reactor, then add 2.6mL to dissolve 0.530g OCL ( Mn=530g / mol) of anhydrous DMF, finally add a catalytic amount of dibutyltin dilaurate (7mg), and seal the reactor, put it in a 60°C oil bath for 24h, then add the end-capping agent 2-butene -1,4-diol continued to react for 12h. After the reaction, precipitate...

Embodiment 3

[0059] Cystamine diisocyanate monomer (CDI) undergoes polycondensation reaction with oligoethylene glycol (OEG) whose terminal group is a hydroxyl group to prepare reductively degradable polyethylene glycol (SSPEG) containing a disulfide bond. The process is as follows:

[0060]

[0061] A series of SSPEGs with different molecular weights can be prepared by changing the feed ratio of cystamine diisocyanate and oligoethylene glycol with hydroxyl-terminated groups. The raw material composition and GPC characterization results of the polymers are shown in Table 2.

[0062] Take the synthesis of SSPEG (Table 2, polymer 4) as an example: under the protection of nitrogen, dissolve 0.210g cystamine diisocyanate in 1mL anhydrous DMF and add to the closed reactor, then add 0.40g OEG (Mn=400g / mol) Dissolve in 2.1mL of anhydrous DMF and add to the closed reactor, finally add a catalytic amount of dibutyltin dilaurate (6mg), and seal the closed reactor, put it in an oil bath at 60°C, an...

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Abstract

The invention discloses a cystamine diisocyanate monomer, cystamine diisocyanate monomer based polymers as well as a preparation method and an application of the cystamine diisocyanate monomer. The cystamine diisocyanate monomer contains a reductive breakable disulfide bond, and the chemical structural formula is shown in the specification; the cystamine diisocyanate monomer can produce linear reductive degradable polyurethane or polyuria through polycondensation with a dihydroxyl compound or a diamino compound, can also produce a reticulated reductive degradable polyurethane through polycondensation with a trihydroxyl compound and can be taken as a coupling agent to connect two polymers with different structures for preparation of a reductive sensitive block polymer. The reductive degradable polymers synthesized from cystamine diisocyanate and containing the disulfide bond can be applied to drug-delivery carriers.

Description

technical field [0001] The invention belongs to the technical field of material science, and relates to a reducing degradable material and a monomer thereof; in particular, it relates to a cystamine diisocyanate monomer, a polymer based on the monomer, and a preparation method and application thereof. Background technique [0002] Reductively degradable polymer materials have attracted extensive attention in the intracellular release of drugs and genes due to their unique reductive degradation properties. Reduction-degradable polymeric materials remain stable under non-reducing conditions (such as the blood circulation system and extracellular environment), but rapidly degrade under high glutathione concentrations (2-10 mM) in the cytoplasm or nucleus. This rapid degradation behavior at high glutathione concentrations is completely different from the usual slow hydrolysis of polyester or polycarbonate. Works from different research groups have demonstrated that nanomedicine...

Claims

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Application Information

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IPC IPC(8): C07C319/22C07C323/25C08G18/77C08G18/42C08G18/48C08G18/32C08G81/00A61K47/34A61K9/14A61K31/704
CPCA61K9/146A61K31/704A61K47/34C07C319/22C07C323/25C08G18/3206C08G18/3218C08G18/3228C08G18/4277C08G18/4833C08G18/775C08G81/00
Inventor 程茹王秀秀钟志远
Owner SUZHOU UNIV
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