Synthesis of Poly(acyclic orthoester)s: Acid‐Sensitive Biomaterials for Enhancing Immune Responses of Protein Vaccine. (9th March 2020)

• Record Type: Journal Article
• Authors: Xing, Yumeng; Xu, Zunkai; Liu, Tao; Shi, Linqi; Kohane, Daniel; Guo, Shutao
• Is Part Of: Angewandte Chemie. Volume 132:Number 18(2020)
• Page Start: 7302
• Page End: 7306
• Publication Date: 2020-03-09
• Subjects: Biomaterialien -- Wirkstofftransport -- Ester -- Nanopartikel -- Polymere; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202001169
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: While poly(acyclic orthoester)s (PAOEs) have many appealing features for drug delivery, their application is significantly hindered by a lack of facile synthetic methods. Reported here is a simple method for synthesizing acyclic diketene acetal monomers from diols and vinyl ether, and their polymerization with a diol to first synthesize PAOEs. The PAOEs rapidly hydrolyze at lysosomal pH. With the help of a cationic lipid, ovalbumin, a model vaccine antigen was efficiently loaded into PAOEs nanoparticles using a double emulsion method. These nanoparticles efficiently delivered ovalbumin into the cytosol of dendritic cells and demonstrated enhanced antigen presentation over poly(lactic‐ co ‐glycolic acid) (PLGA) nanoparticles. PAOEs are promising vehicles for intracellular delivery of biopharmaceuticals and could increase the utility of poly(orthoesters) in biomedical research. Abstract : Wirkstofftransport : Eine einfache Synthese von acyclischen Polyorthoestern gelingt durch Polykondensation von acyclischen Diketenacetalen und Diolen. Nanopartikel von acyclischen Polyorthoestern setzen Antigene in das Zytoplasma frei und verbessern die Effizienz der Antigenpräsentation, was potenzielle Anwendungen in protein‐ und genbasierten Therapien aufzeigt.