Synthesis and Evaluation of QS-21-Based Immunoadjuvants with a Terminal-Functionalized Side Chain Incorporated in the West Wing Trisaccharide

Pengfei Wang*, Dattatray A. Devalankar, Qipu Dai, Ping Zhang, Suzanne M. Michalek

*此作品的通讯作者

科研成果: 期刊稿件文章同行评审

17 引用 (Scopus)

摘要

Three QS-21-based vaccine adjuvant candidates with a terminal-functionalized side chain incorporated in the west wing trisaccharide have been synthesized. The terminal polar functional group serves to increase the solubility of these analogues in water. Two of the synthetic analogues have been shown to have adjuvant activity comparable to that of GPI-0100. The stand-alone adjuvant activity of the new synthetic analogues again confirmed that it is a feasible way to develop new saponin-based vaccine adjuvants through derivatizing at the west wing branched trisaccharide domain. Inclusion of an additional polar functional group such as a carboxyl group (as in 3x) or a monosaccharide (as in 4x and 5x) is sufficient to increase the water solubility of the corresponding synthetic analogues to a level comparable to that of GPI-0100 and suitable for immunological studies and clinical application. The structure of the incorporated side chain has a significant impact on the adjuvant activity in terms of the magnitude and nature of the host's responses.

源语言英语
页(从-至)9560-9566
页数7
期刊Journal of Organic Chemistry
81
20
DOI
出版状态已出版 - 21 10月 2016
已对外发布

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