Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems.
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.
Daines
Alison M
AM
Industrial Research Limited, PO Box 31-310, Lower Hutt 5040, New Zealand.
Greatrex
Ben W
BW
Hayman
Colin M
CM
Hook
Sarah M
SM
McBurney
Warren T
WT
Rades
Thomas
T
Rendle
Phillip M
PM
Sims
Ian M
IM
D000818:Animals; D002784:Cholesterol / Q000737:chemistry; D003713:Dendritic Cells / Q000166:cytology; D006031:Glycosylation; D019695:Glycyrrhizic Acid / Q000737:chemistry*; D006410:Hematopoiesis / Q000187:drug effects; D006412:Hematopoietic Stem Cells / Q000166:cytology / Q000187:drug effects; D016882:ISCOMs / Q000737:chemistry* / Q000494:pharmacology*; D051379:Mice; D008810:Mice, Inbred C57BL; D046529:Microscopy, Electron, Transmission; D049329:Nanostructures / Q000737:chemistry; D009828:Oleanolic Acid / Q000737:chemistry*; D010743:Phospholipids / Q000737:chemistry; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology*
D016882:ISCOMs; D010743:Phospholipids; D012503:Saponins; D019695:Glycyrrhizic Acid; D009828:Oleanolic Acid; D002784:Cholesterol