Crosslinking of Chitosan with Dialdehyde Derivatives of Nucleosides and Nucleotides. Mechanism and Comparison with Glutaraldehyde

S. Mikhailov, A. Zakharova, M. Drenichev, Andrey V. Ershov, M. A. Kasatkina, L. Vladimirov, V. Novikov, N. Kildeeva
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引用次数: 25

Abstract

ABSTRACT In medical and pharmaceutical applications, chitosan is used as a component of hydrogels–macromolecular networks swollen in water. Chemical hydrogels are formed by covalent links between the crosslinking reagents and amino functionalities of chitosan. To date, the most commonly used chitosan crosslinkers are dialdehydes, such as glutaraldehyde (GA). We have developed novel GA like crosslinkers with additional functional groups–dialdehyde derivatives of uridine (oUrd) and nucleotides (oUMP and oAMP)–leading to chitosan-based biomaterials with new properties. The process of chitosan crosslinking was investigated in details and compared to crosslinking with GA. The rates of crosslinking with oUMP, oAMP, and GA were essentially the same, though much higher than in the case of oUrd. The remarkable difference in the crosslinking properties of nucleoside and nucleotide dialdehydes can be clearly attributed to the presence of the phosphate group in nucleotides that participates in the gelation process through ionic interactions with the amino groups of chitosan. Using NMR spectroscopy, we have not observed the formation of aldimine bonds. It can be concluded that the real number of crosslinks needed to cause gelation of chitosan chains may be less than 1%.
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壳聚糖与核苷和核苷酸双醛衍生物的交联。戊二醛的作用机理及比较
在医疗和制药领域,壳聚糖被用作水凝胶-在水中膨胀的大分子网络的组成部分。化学水凝胶是由交联试剂和壳聚糖的氨基官能团之间的共价连接形成的。迄今为止,最常用的壳聚糖交联剂是二醛,如戊二醛(GA)。我们已经开发出具有附加官能团的新型GA类交联剂-尿苷的双醛衍生物(oUrd)和核苷酸(oUMP和oAMP) -导致具有新性能的壳聚糖基生物材料。对壳聚糖交联过程进行了详细的研究,并与GA交联进行了比较。与oUMP、oAMP和GA的交联率基本相同,但比oUrd的交联率高得多。核苷和核苷酸二醛交联性能的显著差异可以清楚地归因于核苷酸中磷酸基团的存在,磷酸基团通过与壳聚糖的氨基离子相互作用参与凝胶化过程。利用核磁共振波谱,我们没有观察到醛胺键的形成。由此可见,引起壳聚糖链凝胶化所需的实际交联数可能小于1%。
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