两亲性
芘
小泡
唾液酸
超分子化学
选择性
组合化学
共轭体系
化学
细胞毒性
膜
生物物理学
材料科学
有机化学
生物化学
共聚物
体外
分子
生物
聚合物
催化作用
作者
Jiwon Hwang,Ye Rim Kim,Jung Yeon Park,Woo Hyun Nam,Jehan Kim,Jinhan Cho,Yongju Kim
标识
DOI:10.1021/acsami.2c02922
摘要
N-Acetylneuraminic acid (Neu5Ac), one of the abundant types of sialic acid, is an emerging anticancer agent owing to its ability to target selectins in the plasma membrane of cancer cells. Considering the functionality of Neu5Ac, obtaining novel Neu5Ac-conjugated materials with a selective and an enhanced antitumor activity has remained a challenge. Herein, we report the supramolecular materials of three novel amphiphiles composed of Neu5Ac as a hydrophilic segment and pyrene or adamantane as a hydrophobic segment. The synthetic amphiphiles 1, 2, and 3 self-assembled into ribbons, vesicles, and irregular aggregates in an aqueous solution, respectively. Among the materials, vesicles of amphiphile 2 showed the most substantial selectivity toward cancer cells, followed by cell death due to the production of reactive oxygen species by the pyrene group. The dual advantage of Neu5Ac-selectivity and the pyrene-cytotoxicity of vesicles of amphiphile 2 can provide a strategy for effective anticancer materials.
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