Synthesis of gemini surfactants with twelve symmetric fluorine atoms and one singlet F MR signal as novel F MRI agents |
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| Authors: | Yu Li Bijaya Thapa Hua Zhang Xuefei Li Fanghua Yu Eun-Kee Jeong Zhigang Yang Zhong-Xing Jiang |
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| Institution: | 1. Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, PR China;2. Department of Physics, University of Utah, Salt Lake City 84108, USA;3. Department of Radiology, University of Utah, Salt Lake City 84108, USA;4. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China;5. Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Wuhan University, Ministry of Education, Wuhan 430071, PR China |
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| Abstract: | A family of fluorinated gemini surfactants derived from perfluoropinacol has been synthesized as novel 19F magnetic resonance imaging (19F MRI) agents. These fluorinated surfactants with 12 symmetric fluorine atoms and one singlet 19F MR peak can be conveniently prepared from perfluoropinacol and oligo(ethylene glycols) on multi-gram scales. Solubility, hydrophilicity (log P), and critical micelle concentration (CMC) measurements of these fluorinated surfactants indicated that high aqueous solubility can be achieved by introducing oligo(ethylene glycols) with appropriate length into perfluoropinacol, i.e., manipulating the fluorine content (F%). One of these fluorinated surfactants with high aqueous solubility and excellent 19F MR properties has been identified by 19F MRI phantom experiments as a promising 19F MRI agent. |
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| Keywords: | 19F MRI Perfluoropinacol Gemini surfactant Imaging agent Oligo(ethylene glycols) (OEG) |
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