title: Hexaphyrin as a Potential Theranostic Dye for Photothermal Therapy and19F Magnetic Resonance Imaging.
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 by19F 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 and19F MRI.
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Higashino
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Nakatsuji
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Fukuda
authors.affiliation: Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Sakyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Haruki
authors.initials: H
authors.lastname: Okamoto
authors.affiliation: Department of Systems Science, Graduate School of Informatics, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan.
authors.forename: Hirohiko
authors.initials: H
authors.lastname: Imai
authors.affiliation: Department of Systems Science, Graduate School of Informatics, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Matsuda
authors.affiliation: Department of Biophysics, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
authors.forename: Hidehito
authors.initials: H
authors.lastname: Tochio
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Shirakawa
authors.affiliation: Department of Chemistry and Bioengineering, Tampere University of Technology, P. O. Box 541, 33101, Tampere, Finland.
authors.forename: Nikolai V
authors.initials: NV
authors.lastname: Tkachenko
authors.affiliation: Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Sakyo-ku, Kyoto, 615-8510, Japan.|Department of Drug Delivery Research, Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan.
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Hashida
authors.affiliation: Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Sakyo-ku, Kyoto, 615-8510, Japan.|Current address: Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Murakami
authors.affiliation: Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.|Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Sakyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Hiroshi
authors.identifier: 0000-0003-3506-5608
authors.initials: H
authors.lastname: Imahori
mesh_terms: D002470:Cell Survival; D066235:Fluorine-19 Magnetic Resonance Imaging / Q000379:methods*; D006801:Humans; D006979:Hyperthermia, Induced; D010789:Phototherapy; D011166:Porphyrins / Q000737:chemistry*; D019265:Spectroscopy, Near-Infrared; D000068936:Theranostic Nanomedicine; D014407:Tumor Cells, Cultured; D001749:Urinary Bladder Neoplasms / Q000000981:diagnostic imaging / Q000378:metabolism / Q000473:pathology / Q000628:therapy*
chemical_list: D011166:Porphyrins
keywords: MRI; NMR spectroscopy; expanded porphyrin; fluorine; photochemistry; theranostics