A Simple Synthesis of Tetraamino-[60]Fullerene Epoxides as Potential Antitumor Drug Candidates  

作　　者：Yicheng Lu Jie Li Xiaolong Liu Dan He Libin Yang Wei Zhou Xie Wang Shanshan Chen Shiliang Chen Yating Liu Xin Wang Jiao Li Jiawei Huo Yang Liu Zehu Wang Meihan Liu Yijun Wang Yamin Li Fuwen Zhao Shumu Li Jinchao Wei Jianan Liu Wei Li Chunru Wang 

机构地区：[1]Key Laboratory of Molecular Nanostructure and Nanotechnology,Institute of Chemistry,Chinese Academy of Sciences,Beijing 100190 [2]University of Chinese Academy of Sciences,Beijing 100190 [3]The National Center for Nanoscience and Technology,Beijing 100190 [4]Central South University,Changsha,410082 Hunan [5]Hangzhou Institute of Medicine(HIM),Chinese Academy of Sciences,Hangzhou,310092 Zhejiang [6]Cancer Center,Beijing Tongren Hospital,Capital Medical University,Beijing 100069 [7]Technical Institute of Physics and Chemistry,Chinese Academy of Sciences,Beijing 100190 [8]Beijing FULLCAN Biotechnology Co.,Beijing 100085

出　　处：《CCS Chemistry》2024年第10期2392-2399,共8页中国化学会会刊（英文）

基　　金：supported by the major research project of the National Natural Science Foundation of China(grant no.52272049);the National Key Research and Development Program of China(grant no.2022YFA1205900).

摘　　要：Amphiphilic aminated fullerenes have a broad margin of safety and significant antitumor effects.Herein,we develop a simple and versatile synthesis strategy for tetraamino-[60]fullerene epoxide(C_(60)(NR^(1)R^(2))_(4)O)using C_(60)Cl_(6)as a precursor,which notably reduces the reaction time to less than 1 h while retaining a high yield of over 80%with both cyclic and linear secondary amine substrates even at the gram level.The molecular structure of C_(60)(NR^(1)R^(2))_(4)O is first validated by single-crystal diffraction,and a two-step reaction mechanism comprising nucleophilic substitution of Cl and the oxidative elimination of Cl_(2)is proposed based on experimental verification and density functional theory simulation.A set of water-soluble aminated C_(60)(NR^(1)R^(2))_(4)O was prepared in large quantities,and in vitro antitumor evaluation unveiled the critical role that terminal primary amino moieties of C_(60)(NR^(1)R^(2))_(4)O play in their antineoplastic effects.This work provides an effective synthesis method for aminated C_(60)(NR^(1)R^(2))_(4)O,facilitating the development of fullerene-derived tumor-targeted drugs.

关 键 词：fullerene epoxides simple synthesis C_(60)Cl_(6) water-soluble aminated fullerene ANTITUMOR 

分 类 号：O62[理学—有机化学]