对映选择合成
小分子
手性(物理)
化学
对映体
免疫系统
内化
分子
立体化学
抗原
受体
生物
生物化学
催化作用
免疫学
物理
对称性破坏
量子力学
手征对称破缺
有机化学
Nambu–Jona Lasinio模型
作者
Zhen Zhou,Yufang Zhang,Hongyu Ji,Yu Jin,Sisi Chen,Pengfei Duan,Ye Liu
标识
DOI:10.1002/anie.202301085
摘要
Abstract Although numerous chiral small molecules have been discovered and synthesized, the investigation on their enantioselective immunological effects remains limited. In this study, we designed and synthesized a pair of small molecule enantiomers ( R / S ‐ResP) by covalently bonding two immunostimulators (resiquimod/Res) onto a planar chiral framework (paracyclophane/P). Notably, we found that S ‐ResP exhibits a 4.05‐fold higher affinity for toll‐like receptor 7 (TLR7) than R ‐ResP, thereby more effectively enhancing the functions of dendritic cells and macrophages in cytokine secretion and antigen internalization. Furthermore, we observed that S ‐ResP significantly enhances RBD antigen‐induced cross‐neutralization against various SARS‐CoV‐2 strains compared to R ‐ResP. These findings demonstrate the enantioselective effects of small molecules on regulating vaccine‐induced immune responses and emphasize the significance of chirality in designing small molecular adjuvants.
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