Hyaluronic Acid Surface Modified Liposomes Prepared via Orthogonal Aminoxy Coupling: Synthesis of Nontoxic Aminoxylipids Based on Symmetrically α-Branched Fatty Acids, Preparation of Liposomes by Microfluidic Mixing, and Targeting to Cancer Cells Expressing CD44
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- Hyaluronan Receptors analysis metabolism MeSH
- Antineoplastic Agents administration & dosage MeSH
- Cell Line MeSH
- Endocytosis MeSH
- Fluorescent Dyes MeSH
- Hyaluronic Acid chemistry metabolism MeSH
- Humans MeSH
- Lipids chemical synthesis MeSH
- Liposomes chemistry therapeutic use MeSH
- Microfluidics MeSH
- Neoplasms drug therapy MeSH
- Drug Delivery Systems methods MeSH
- Microscopy, Electron, Transmission MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Hyaluronan Receptors MeSH
- Antineoplastic Agents MeSH
- CD44 protein, human MeSH Browser
- Fluorescent Dyes MeSH
- Hyaluronic Acid MeSH
- Lipids MeSH
- Liposomes MeSH
New synthetic aminoxy lipids are designed and synthesized as building blocks for the formulation of functionalized nanoliposomes by microfluidization using a NanoAssemblr. Orthogonal binding of hyaluronic acid onto the outer surface of functionalized nanoliposomes via aminoxy coupling ( N-oxy ligation) is achieved at hemiacetal function of hyaluronic acid and the structure of hyaluronic acid-liposomes is visualized by transmission electron microscopy and cryotransmission electron microscopy. Observed structures are in a good correlation with data obtained by dynamic light scattering (size and ζ-potential). In vitro experiments on cell lines expressing CD44 receptors demonstrate selective internalization of fluorochrome-labeled hyaluronic acid-liposomes, while cells with down regulated CD44 receptor levels exhibit very low internalization of hyaluronic acid-liposomes. A method based on microfluidization mixing was developed for preparation of monodispersive unilamellar liposomes containing aminoxy lipids and orthogonal binding of hyaluronic acid onto the liposomal surface was demonstrated. These hyaluronic acid-liposomes represent a potentially new drug delivery platform for CD44-targeted anticancer drugs as well as for immunotherapeutics and vaccines.
APIGENEX s r o Poděbradská 173 5 Prague 9 190 00 Czech Republic
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