Visualizing Drug Release from a Stimuli-Responsive Soft Material Based on Amine-Thiol Displacement

Tianhong Wu, Shiqing Huang, Xing Feng, Xiaogang Liu, Tony D. James, Xiaolong Sun, Xuhong Qian

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Abstract

In this research, we developed a photoluminescent platform using amine-coupled fluorophores, generated from a single conjugate acceptor containing bis-vinylogous thioesters. Based on the experimental and computational results, the fluorescence turn-on mechanism was proposed to be charge separated induced energy radiative transition for the amine-coupled fluorophore, while the sulfur-containing precursor was not fluorescent since the energy internal conversion occurred through vibrational 2RS- (R represents alkyl groups) as energy acceptor(s). Further utilizing the conjugate acceptor, we establish a new fluorogenic approach via a highly cross-linked soft material to selectively detect cysteine under neutral aqueous conditions. Turn-on fluorescence emission and macroscopic degradation occurred in the presence of cysteine as the stimuli, which can be visually tracked due to the generation of an optical indicator and the cleavage of linkers within the matrix. Furthermore, a novel drug delivery system was constructed, achieving controlled release of sulfhydryl drug (6-mercaptopurine) which was tracked by photoluminescence and high-performance liquid chromatography. The photoluminescent molecules developed herein are suitable for visualizing polymeric degradation, making them suitable for additional “smart” material applications.

Original languageEnglish
Pages (from-to)22967-22976
JournalACS Applied Materials and Interfaces
Volume15
Issue number19
Early online date5 May 2023
DOIs
Publication statusPublished - 17 May 2023

Bibliographical note

Funding Information:
X.S. thanks the National Natural Science Foundation of China (Nos. 21907080 and 22278330) and Youth Innovative Team (No. xtr052022012) from Xi’an Jiaotong University. T.D.J. thanks the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01). We also thank Professor Eric V. Anslyn (UT Austin) and Amilra De Silva (Queen’s University Belfast) for the discussions and suggestions.

Keywords

  • amine−thiol displacement induced emission
  • drug release
  • fluorescence sensing
  • macromolecular degradation
  • single crystal

ASJC Scopus subject areas

  • General Materials Science

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