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Design, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte-specific targeting

Bernardes, GJL and Kikkeri, R and Maglinao, M and Laurino, P and Collot, M and Hong, SY and Lepenies, B and Seeberger, PH (2010) Design, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte-specific targeting. Organic & Biomolecular Chemistry, 8. pp. 4987-4996. ISSN 1477-0520

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Abstract

Targeting glycan-binding receptors is an attractive strategy for cell-specific drug and gene delivery. The C-type lectin asialoglycoprotein receptor (ASGPR) is particularly suitable for liver-specific delivery due to its exclusive expression by parenchymal hepatocytes. In this study, we designed and developed an efficient synthesis of carbohydrate-functionalized [small beta]-cyclodextrins ([small beta]CDs) and liposomes for hepatocyte-specific delivery. For targeting of ASGPR, rhodamine B-loaded [small beta]CDs were functionalized with glycodendrimers. Liposomes were equipped with synthetic glycolipids containing a terminal d-GalNAc residue to mediate binding to ASGPR. Uptake studies in the human hepatocellular carcinoma cell line HepG2 demonstrated that [small beta]CDs and liposomes displaying terminal d-Gal/d-GalNAc residues were preferentially endocytosed. In contrast, uptake of [small beta]CDs and liposomes with terminal d-Man or D-GlcNAc residues was markedly reduced. The d-Gal/d-GalNAc-functionalized [small beta]CDs and liposomes presented here enable hepatocyte-specific targeting. Gal-functionalized [small beta]CDs are efficient molecular carriers to deliver doxorubicin in vitro into hepatocytes and induce apoptosis.

Item Type: Article
Subjects: UNSPECIFIED
Divisions: UNSPECIFIED
Depositing User: Cron Job
Date Deposited: 19 Jun 2019 20:24
Last Modified: 22 Apr 2021 06:50
DOI: