Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1599-1606.DOI: 10.6023/cjoc202008015 Previous Articles     Next Articles



戎瑞雪a,b, 李基民a, 李耀文a, 郭啸宇a, 王冲b, 李艳军c, 李金梅d, 韩宝君c, 曹志然a, 王克让b,*(), 李小六b,*()   

  1. a 河北大学基础医学院 河北省炎性自身免疫性疾病发病机制及防治重点实验室 河北保定 071000
    b 河北大学化学与环境科学学院 药物化学与分子诊断教育部重点实验室 河北省化学生物学重点实验室 河北保定 071002
    c 保定市第一中心医院骨四科 河北保定 071000
    d 保定市第一中心医院病理科 河北保定 071000
  • 收稿日期:2020-08-11 修回日期:2020-09-15 发布日期:2020-12-31
  • 通讯作者: 王克让, 李小六
  • 基金资助:
    国家自然科学基金(21572044); 国家自然科学基金(21778013); 河北省自然科学基金(B2017201193); 河北省卫生健康委员会基金(20202217); 大学生创新项目(201910075009); 大学生创新项目(2020338); 河北大学高层次人才科研启动基金(521000981311)

Synthesis and Anti-tumor Effects of Naphthalimide Derivatives Targeted in Cell Nucleus

Ruixue Ronga,b, Jimin Lia, Yaowen Lia, Xiaoyu Guoa, Chong Wangb, Yanjun Lic, Jinmei Lid, Baojun Hanc, Zhiran Caoa, Kerang Wangb,*(), Xiaoliu Lib,*()   

  1. a College of Basic Medicine, Key Laboratory of Pathogenesis Mechanism and Control of Inflammatory-autoimmune Diseases in Hebei Province, Hebei University, Baoding, Hebei 071000
    b College of Chemistry and Environmental Science, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis (Ministry of Education), Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002
    c Forth Department of Orthopedic, Baoding First Central Hospital, Baoding, Hebei 071000
    d Department of Pathology, Baoding First Central Hospital, Baoding, Hebei 071000
  • Received:2020-08-11 Revised:2020-09-15 Published:2020-12-31
  • Contact: Kerang Wang, Xiaoliu Li
  • About author:
    * Corresponding authors. E-mail: ;
  • Supported by:
    National Natural Science Foundation of China(21572044); National Natural Science Foundation of China(21778013); Natural Science Foundation of Hebei Province(B2017201193); Foundation of Health Commission of Hebei Province(20202217); Innovation Project of Students(201910075009); Innovation Project of Students(2020338); Hebei University High-level Talent Research Startup Project(521000981311)

A series of novel chiral amino alcohol modified naphthalimide derivatives NI1~NI8 were designed and synthesized by nucleophilic substitution reaction. Furthermore, their cytotoxicities were studied by thiazolyl blue tetrazolium bromide (MTT) method. The cytotoxicity of the R-type isomer in the naphthalimide derivatives with primary hydroxyl amino alcohol modification was better than that of the S-type isomer. In addition, deoxyribonucleic acid (DNA) binding interactions and fluorescence imaging of (R)-2-(2-(dimethylamino)ethyl)-6-((1-hydroxypropan-2-yl)amino)-naphthalimide (NI1) and (S)-2-(2-(dimethylamino)ethyl)-6-((1-hydroxypropan-2-yl)amino)-naphthalimid (NI2) with Ct-DNA and HeLa cells were investigated. NI1 and NI2 showed strong binding interactions with Ct-DNA with a bonding constant of 104 L/mol. And NI1 and NI2 exhibited nucleus-targeting imaging for HeLa cells. NI1 and NI2 mainly arrested the S phase. Moreover, the hematoxic results of NI1in mice showed no significant effects on the red blood cells, white blood cells and platelets in the blood.

Key words: naphthalimide, nucleus, chiral, cell cycle