Synthesis and Evaluation of QS-21-Based Immunoadjuvants with a Terminal-Functionalized Side Chain Incorporated in the West Wing Trisaccharide.
Synthesis and Evaluation of QS-21-Based Immunoadjuvants with a Terminal-Functionalized Side Chain Incorporated in the West Wing Trisaccharide.
复制标题
西翼三糖中纳入终端功能的侧链的基于QS-21的免疫补充的合成和评估。
DOI：
10.1021/acs.joc.6b00922
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发表时间：
2016-10-21
期刊：
影响因子：
--
通讯作者：
Michalek SM
中科院分区：
文献类型：
--
作者：
Wang P;Devalankar DA;Dai Q;Zhang P;Michalek SM
已经合成了三种基于QS-21的疫苗佐剂候选物，其具有掺入西翼三糖中的末端官能化侧链。末端极性官能团用于增加这些类似物在水中的溶解度。两种合成类似物已显示具有与GPI-0100相当的佐剂活性。新合成类似物的独立佐剂活性再次证实，通过在西翼分支三糖结构域衍生化来开发新的基于皂苷的疫苗佐剂是可行的方式。包含另外的极性官能团如羧基（如在3x中）或单糖（如在4x和5x中）足以将相应的合成类似物的水溶性增加到与GPI-0100相当的水平，并且适合于免疫学研究和临床应用。掺入的侧链的结构在宿主应答的大小和性质方面对佐剂活性具有显著影响。
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.
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