Dynamic Glycopeptide Dendrimers: Synthesis and Their Controllable Self-Assembly into Varied Glyco-Nanostructures for the Biomimicry of Glycans

• DOI: 10.1021/acs.biomac.1c01137
• Publication Date: 2021-12-09T12:49:08Z
• Authors: Feihu Bi; Jin Zhang; Zengming Wei; Deshui Yu; Shuai Zheng; Jie Wang; Hongyu Li; Zan Hua; Hui Zhang; Guang Yang
• Keywords: Dendrimers; Polysaccharides; Glycopeptides; 02 engineering and technology; 0210 nano-technology; 01 natural sciences; Micelles; Nanostructures; 0104 chemical sciences

A library of 14 dynamic glycopeptide amphiphilic dendrimers composed hydrophilic and bioactive saccharides (seven kinds) as dendrons 7 hydrophobic peptides (di- tetrapeptides) arms with β-cyclodextrin (CD) a core were facially designed synthesized in several steps. Fourteen first conjugated to the C-2 C-3 positions CD, forming glycodendrons. Subsequently, seven oligopeptide introduced at C-6 CD moiety by an acylhydrazone covalent bond, resulting unique Janus precise varied molecular structures. The kinds parts easily prepare series dendrimers. Intriguingly, these obtained showcased very different self-assembly behaviors from traditional linear block-copolymers self-assembled into glyco-nanostructures controllable morphologies including glycospheres, worm-like micelles, fibers depending upon repeat unit ratio phenylalanine. Both glycodendrons assemblies displayed strong specific recognitions C-type mannose-specific lectin. Moreover, nanomaterials can encapsulate exemplary molecules such Nile red (NR). dye-loaded nanostructures showed pH-controllable release behavior around physiological acidic tumor environment. Furthermore, cell experiments demonstrated that further facilitate functions model drug pyridone agent reduce expression monocyte chemotactic protein-1 (MCP-1) interleukin -1beta (IL-1β) primary peritoneal macrophages via encapsulating drugs. Considering all abovementioned advantages structures, bioactivity, targeting, cargo release, we believe findings not only enrich glycopeptides but also provide new avenue fabrication smart structure-controllable glyco-nanomaterials which hold great potential biological applications targeted delivery therapeutic molecules.