Acta Chim. Sinica ›› 2016, Vol. 74 ›› Issue (11): 910-916.DOI: 10.6023/A16070342 Previous Articles     Next Articles



王俊, 武英龙, 孙立和, 曾钫, 吴水珠   

  1. 华南理工大学发光材料与器件国家重点实验室 华南理工大学材料科学与工程学院 广州 510640
  • 投稿日期:2016-07-14 发布日期:2016-09-06
  • 通讯作者: 吴水珠
  • 基金资助:


NIR AIE System for Tracking Release of Taurine and ROS Scavenging

Wang Jun, Wu Yinglong, Sun Lihe, Zeng Fang, Wu Shuizhu   

  1. South China University of Technology, State Key Laboratory of Luminescent Materials & Devices, College of Material Science and Engineering, GuangZhou 510640
  • Received:2016-07-14 Published:2016-09-06
  • Supported by:

    Project supported by the National Key Basic Research Program of China (Project No. 2013CB834702), and the National Natural Science Foundation of China (Nos. 21574044 and 21474031).

Fluorophores with aggregation-induced emission (AIE) feature are favorable tools for both chemical sensing and bioimaging. Inflammatory cells excessively express hydrolytic enzymes (esterase, protease and phosphatase) and are usually exposed to elevated levels of reactive oxygen species (ROS). Overexpression of ROS and the insufficient neutralization by antioxidants may give rise to the development of oxidative stress and chronic inflammation. Taurine (2-aminoethanesulfonic acid), as an effective antioxidant, can protect tissues from oxidative stress associated with various inflammatory diseases. Moreover, it has been recently reported that the incorporation of taurine can amazingly boost the cellular uptake for intracellular accumulation. Herein, we designed and synthesized a new near-infrared (NIR) AIE fluorophore DTPE. We anticipate that, the combination of the hydrophilic taurine with the NIR AIE fluorophore through an ester bond could be a remarkable method for extending the applications of AIE-active fluorophores e.g. as a trackable visualized therapeutic system featuring both imaging esterase-activated taurine release and ROS scavenging. Then we obtained the AIE probe system DTPE-Tau by incorporating taurine with the fluorophore through carbamate bond. The hydrophilic taurine moiety endows the system with enhanced water solubility and cellular uptake ability. The system is characterized by several advantages, such as large Stokes shift (225 nm), low cytotoxicity, and good photostability. The ester bond can be hydrolysed by the overexpressed esterase in inflammatory cells, thereby releasing a taurine moiety for ROS scavenging and in the meantime the AIE fluorophore moiety acts as a reporter for tracking esterase-activated taurine release. The enhancement of emission could serve as the reporting signal. The release rate is determined to be 75% for esterase at 0.05 mg/mL, calculated based on the fluorescence-intensity working curve. Also, the probe has been successfully utilized for tracking esterase-activated release of taurine and scavenging intracellular ROS in RAW264.7 cell line, which shows great potential for trackable visualized therapy.

Key words: aggregation induced emission, taurine, near-infrared fluorescence imaging, esterase, tetraphenylethylene