Hexaphyrin as a Potential Theranostic Dye for Photothermal Therapy and 19F Magnetic Resonance Imaging |
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| Authors: | Dr Tomohiro Higashino Hirotaka Nakatsuji Ryosuke Fukuda Haruki Okamoto Dr Hirohiko Imai Prof?Dr Tetsuya Matsuda Prof?Dr Hidehito Tochio Prof?Dr Masahiro Shirakawa Prof?Dr Nikolai V Tkachenko Prof?Dr Mitsuru Hashida Prof?Dr Tatsuya Murakami Prof?Dr Hiroshi Imahori |
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| Affiliation: | 1. Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyoto, Japan;2. Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Kyoto, Japan;3. Department of Systems Science, Graduate School of Informatics, Kyoto University, Kyoto, Japan;4. Department of Biophysics, Graduate School of Science, Kyoto University, Kyoto, Japan;5. Department of Chemistry and Bioengineering, Tampere University of Technology, Tampere, Finland;6. Department of Drug Delivery Research, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto, Japan;7. Current address: Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Imizu, Toyama, Japan |
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| Abstract: | Two features of meso‐Aryl‐substituted expanded porphyrins suggest suitability as theranostic agents. They have excellent absorption in near infrared (NIR) region, and they offer the possibility of introduction of multiple fluorine atoms at structurally equivalent positions. Here, hexaphyrin (hexa) was synthesized from 2,6‐bis(trifluoromethyl)‐4‐formyl benzoate and pyrrole and evaluated as a novel expanded porphyrin with the above features. Under NIR illumination hexa showed intense photothermal and weak photodynamic effects, which were most likely due to its low excited states, close to singlet oxygen. The sustained photothermal effect caused ablation of cancer cells more effectively than the photodynamic effect of indocyanine green (a clinical dye). In addition, hexa showed potential for use in the visualization of tumors by 19F magnetic resonance imaging (MRI), because of the multiple fluorine atoms. Our results strongly support the utility of expanded porphyrins as theranostic agents in both photothermal therapy and 19F MRI. |
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| Keywords: | expanded porphyrin fluorine MRI NMR spectroscopy photochemistry theranostics |
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