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

Research output: Contribution to journalJournal articlepeer-review

Standard

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 journalJournal articlepeer-review

Harvard

Daines, AM, Greatrex, BW, Hayman, CM, Hook, SM, McBurney, WT, Rades, T, Rendle, PM & Sims, IM 2009, 'Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems', Bioorganic & Medicinal Chemistry Letters, vol. 17, no. 14, pp. 5207-18. https://doi.org/10.1016/j.bmc.2009.05.043

APA

Daines, A. M., Greatrex, B. W., Hayman, C. M., Hook, S. M., McBurney, W. T., Rades, T., Rendle, P. M., & Sims, I. M. (2009). Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems. Bioorganic & Medicinal Chemistry Letters, 17(14), 5207-18. https://doi.org/10.1016/j.bmc.2009.05.043

Vancouver

Daines AM, Greatrex BW, Hayman CM, Hook SM, McBurney WT, Rades T et al. Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems. Bioorganic & Medicinal Chemistry Letters. 2009;17(14):5207-18. https://doi.org/10.1016/j.bmc.2009.05.043

Author

Daines, Alison M ; Greatrex, Ben W ; Hayman, Colin M ; Hook, Sarah M ; McBurney, Warren T ; Rades, Thomas ; Rendle, Phillip M ; Sims, Ian M. / Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems. In: Bioorganic & Medicinal Chemistry Letters. 2009 ; Vol. 17, No. 14. pp. 5207-18.

Bibtex

@article{b0b76514e9a942a3853b330b41fa893d,
title = "Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems",
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.",
author = "Daines, {Alison M} and Greatrex, {Ben W} and Hayman, {Colin M} and Hook, {Sarah M} and McBurney, {Warren T} and Thomas Rades and Rendle, {Phillip M} and Sims, {Ian M}",
year = "2009",
doi = "10.1016/j.bmc.2009.05.043",
language = "English",
volume = "17",
pages = "5207--18",
journal = "Bioorganic & Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Pergamon Press",
number = "14",

}

RIS

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