A 4-aminonaphthalimide-based fluorescent traceable prodrug with excellent photoinduced cytotoxicity

Jing Liu; Shilong Zhong; Lingling Zhang; Mengwen Yi; Xiangjun Liu; Tao Bing; Nan Zhang; Dihua Shangguan

doi:10.1039/d1cc01847g

A 4-aminonaphthalimide-based fluorescent traceable prodrug with excellent photoinduced cytotoxicity

Chem Commun (Camb). 2021 Jul 1;57(53):6558-6561. doi: 10.1039/d1cc01847g.

Authors

Jing Liu¹, Shilong Zhong², Lingling Zhang², Mengwen Yi², Xiangjun Liu¹, Tao Bing¹, Nan Zhang¹, Dihua Shangguan³

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. xjliu@iccas.ac.cn sgdh@iccas.ac.cn and University of Chinese Academy of Sciences, Beijing, 100049, China.
² Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. xjliu@iccas.ac.cn sgdh@iccas.ac.cn.
³ Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. xjliu@iccas.ac.cn sgdh@iccas.ac.cn and University of Chinese Academy of Sciences, Beijing, 100049, China and School of Molecular Medicine, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou, 310013, China.

PMID: 34113937
DOI: 10.1039/d1cc01847g

Abstract

A blue light activated anti-cancer prodrug, NST, was designed based on a photoactive 4-aminonaphthalimide derivative and an anticancer drug, 10-hydroxycamptothecin. NST was hard to be taken up by living cells and showed negligible dark cytotoxicity. The irradiation caused photocleavage of NST and resulted in high cytotoxicity.

MeSH terms

Antineoplastic Agents / metabolism
Camptothecin / analogs & derivatives
Camptothecin / metabolism
Cell Line, Tumor
Humans
Light*
Phthalimides / chemistry*
Phthalimides / metabolism
Phthalimides / pharmacology*
Prodrugs / chemistry*
Prodrugs / metabolism
Prodrugs / pharmacology*

Substances

Antineoplastic Agents
Phthalimides
Prodrugs
phthalimide
10-hydroxycamptothecin
Camptothecin