Biological deoxycholic acid-coumarin conjugates: photo-switchable structures and self-assembly morphology

TETRAHEDRON LETTERS

卷:57

Article

Sun, Jinzhi¹  Xiang, Shuaishuai¹  Xu, Xiang¹  Li, Weina¹  Shi, Jinsheng¹ 

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

关键词: Biological conjugates;    Photo-switchable;    Supramolecular assembly;    Amphiphilic cavity;    Deoxycholic acid;   

DOI  :  10.1016/j.tetlet.2016.04.013

来源: Elsevier

【 摘 要 】

Construction of functional materials and supramolecular chemistry systems using biological molecules has been paid considerable attention. In this Letter, a deoxycholic acid-coumarin (DAC) conjugate with both segments originating from biological molecules was developed. The photo-induced structure transformation was thoroughly investigated. This method can provide a simple and highly-efficient strategy to construct complex bile acid derivatives. With the amphiphilic rigid steroidal skeleton, the DAC conjugates and their corresponding dimers exhibit excellent self-assembly properties, which can also be conveniently adjusted by the photo-induced conversion process. Interestingly, both hydrophilic and hydrophobic binding cavities were demonstrated to exist in the assemblies, leading to the possibility to introduce various functional molecules into the systems simultaneously. Additionally, the fluorescence intensity of DAC can also be adjusted with the structure conversion. Based on these properties, this biologically originated molecule can be used as controlled-release materials and has the potential to observe the real-time condition in living cells. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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