Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems

Title
Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
Publication Date
2009
Author(s)
Daines, Alison M
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Hayman, Colin M
Hook, Sarah M
McBurney, Warren T
Rades, Thomas
Rendle, Phillip M
Sims, Ian M
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Pergamon Press
Place of publication
United Kingdom
DOI
10.1016/j.bmc.2009.05.043
UNE publication id
une:8167
Abstract
Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed.
Link
Citation
Bioorganic & Medicinal Chemistry, 17(14), p. 5207-5218
ISSN
1464-3391
0968-0896
Start page
5207
End page
5218

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