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Title: Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
Contributor(s): Daines, Alison M (author); Greatrex, Ben  (author)orcid ; Hayman, Colin M (author); Hook, Sarah M (author); McBurney, Warren T (author); Rades, Thomas (author); Rendle, Phillip M (author); Sims, Ian M (author)
Publication Date: 2009
DOI: 10.1016/j.bmc.2009.05.043
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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.
Publication Type: Journal Article
Source of Publication: Bioorganic & Medicinal Chemistry, 17(14), p. 5207-5218
Publisher: Pergamon
Place of Publication: United Kingdom
ISSN: 1464-3391
Field of Research (FOR): 030405 Molecular Medicine
030401 Biologically Active Molecules
030503 Organic Chemical Synthesis
Socio-Economic Objective (SEO): 970103 Expanding Knowledge in the Chemical Sciences
970106 Expanding Knowledge in the Biological Sciences
920108 Immune System and Allergy
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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