Sulfydryl modified high-molecular compound, and preparation method and application thereof

Abstract

The invention relates to a sulfydryl modified high-molecular compound, and a preparation method and application thereof. The sulfydryl modified high-molecular compound is prepared from an acryloyl derivative modified high-molecular compound and a multi-sulfydryl compound through a Michael addition reaction of mercaptan and conjugated double bonds. The preparation method not only can realize the structure target of the sulfydryl modified high-molecular compound disclosed by the invention, but also has the following advantages: the structure and composition of the synthetic product, the variety and content of a large number of compound molecular functional groups and the like can be flexibly and effectively controlled; a reagent with high biocompatibility is adopted, so that the production cost is effectively controlled, and the toxicity in the synthesis process is reduced; and under the condition that a safe reagent and simple reaction steps are adopted, the obtained sulfydryl modified biocompatible polymer series compound which can be used as an extracellular matrix material and has good raw material structure and biological activity and adjustable functional group type and content according to needs can be obtained, and various clinical application requirements are met.

Description

technical field [0001] The invention belongs to the field of polymer materials, and in particular relates to a mercapto-modified polymer compound and its preparation method and application. Background technique [0002] Biocompatible polymers have many important physiological functions. Common biocompatible polymers include: polysaccharides, proteins, and synthetic polymers. Among them, the typical natural biocompatible polymer is hyaluronic acid. In 1934, Professor Karl Mayer extracted natural hyaluronic acid from the vitreous body of the bull's eye for the first time. Natural hyaluronic acid is composed of D-glucuronic acid and N-acetyl A natural heteropolysaccharide composed of alternating units of D-glucosamine. After decades of research, it was found that it widely exists in the connective tissues of humans and other vertebrates, such as intercellular spaces, sports joint tissues, umbilical cords, skin, cartilage, blood vessel walls, synovial fluid, and cockscombs and ...

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Problems solved by technology

Specifically, the method overcomes the following shortcomings and deficiencies in the prior art: 1) The modification reagent needs to be synthesized through multi-step reactions, such as: dithiodihydrazide method and modified dithiodihydrazide method; 2) In the synthesis process of the modification reagent, highly toxic organic substances such as hydrazine hydrate need to be used, which does not meet the development needs of green chemistry or an environment-friendly society; 3) The thiol modification method involving the EDCI coupling agent needs to maintain the pH of the reaction system during the activation stage = 4.75, after entering the gel stage, it is impossible to achieve a stable and uniform reaction system through homogenization such as stirring, and the industrial operation is difficult; 4) The synthesis of HA-SH by the Ethylene sulfide method needs to be carried out under the condition of pH=10, and hyaluronic acid cannot be avoided Degradation reactions that occurred during the synthesis process; in addition, thiocycloethane is a flammable, toxic and dangerous product, and its solubility in water is low, which limits the possibility of obtaining a higher degree of substitution by this method; 5) Traut's reagent hydrazide hyaluronic acid derivative The substance modification method is limited by the high cost of raw materials and cannot be produced on a large scale; 6) Since thiols and amino groups are highly active nucleophiles, β-mercaptoethylamine and thiols such as ethyl cysteine ​​can be directly The modification process has the main condensation reaction of amino group and carboxyl group and the side reaction of condensation of thiol and carboxyl group, and this side reaction is difficult to completely avoid by changing the reaction conditions

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