Premium
Hexaphyrin as a Potential Theranostic Dye for Photothermal Therapy and 19 F Magnetic Resonance Imaging
Author(s) -
Higashino Tomohiro,
Nakatsuji Hirotaka,
Fukuda Ryosuke,
Okamoto Haruki,
Imai Hirohiko,
Matsuda Tetsuya,
Tochio Hidehito,
Shirakawa Masahiro,
Tkachenko Nikolai V.,
Hashida Mitsuru,
Murakami Tatsuya,
Imahori Hiroshi
Publication year - 2017
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201700071
Subject(s) - photothermal therapy , singlet oxygen , photodynamic therapy , hexa , photochemistry , porphyrin , chemistry , rose bengal , magnetic resonance imaging , nuclear magnetic resonance , materials science , nanotechnology , oxygen , organic chemistry , crystallography , radiology , medicine , physics
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 19 F 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 19 F MRI.