Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
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Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems. / Daines, Alison M; Greatrex, Ben W; Hayman, Colin M; Hook, Sarah M; McBurney, Warren T; Rades, Thomas; Rendle, Phillip M; Sims, Ian M.
In: Bioorganic & Medicinal Chemistry Letters, Vol. 17, No. 14, 2009, p. 5207-18.Research output: Contribution to journal › Journal article › peer-review
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TY - JOUR
T1 - Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
AU - Daines, Alison M
AU - Greatrex, Ben W
AU - Hayman, Colin M
AU - Hook, Sarah M
AU - McBurney, Warren T
AU - Rades, Thomas
AU - Rendle, Phillip M
AU - Sims, Ian M
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
U2 - 10.1016/j.bmc.2009.05.043
DO - 10.1016/j.bmc.2009.05.043
M3 - Journal article
C2 - 19502067
VL - 17
SP - 5207
EP - 5218
JO - Bioorganic & Medicinal Chemistry Letters
JF - Bioorganic & Medicinal Chemistry Letters
SN - 0960-894X
IS - 14
ER -
ID: 40353558