One-step synthesis, self-assembly and bioimaging applications of adenosine triphosphate containing amphiphilies with aggregation-induced emission feature.
Amphiphilic molecules with aggregation-induced emission (AIE) characteristics have attracted intensive interest for biological imaging applications for their self-assembly into nanostructures and obvious enhanced fluorescence intensity in aqueous solution. Although many AIE-active fluorescent organic nanoparticles (FONs) have been fabricated recently, the direct linkage of hydrophilic small molecules and hydrophobic AIE dyes has rarely been reported. In this work, we reported a one-pot strategy for preparation of adenosine triphosphate (ATP) containing molecules that conjugated the amino group of ATP and aldehyde-terminated AIE dye (PhCHO) based on mercaptoacetic acid locking imine (MALI) reaction. These AIE-active ATP-PhCHO showed amphiphilic properties and could self-assemble into micelles, which displayed high water dispersibility, strong yellow fluorescence, good biocompatibility and biological imaging capability. These advantages make ATP-PhCHO FONs promising for biomedical applications.
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.
Zi
Z
Long
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.
Meiying
M
Liu
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.
Liucheng
L
Mao
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.
Guangjian
G
Zeng
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.
Qiang
Q
Huang
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.
Hongye
H
Huang
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China. Electronic address: fengjiedeng@aliyun.com.
Fengjie
F
Deng
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China.
Yiqun
Y
Wan
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China. Electronic address: xiaoyongzhang1980@gmail.com.
Xiaoyong
X
Zhang
Department of Chemistry, The Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, China. Electronic address: weiyen@tsinghua.edu.cn.
Yen
Y
Wei
D000255:Adenosine Triphosphate / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D002470:Cell Survival; D004396:Coloring Agents / Q000737:chemistry; D003952:Diagnostic Imaging; D006367:HeLa Cells; D006801:Humans; D008422:Materials Testing / Q000379:methods*; D053758:Nanoparticles / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*
D000447:Aldehydes; D004396:Coloring Agents; D013501:Surface-Active Agents; D000255:Adenosine Triphosphate
Aggregation-induced emission; Biocompatibility; Biological imaging; Self-assembly