Maintaining of the Green Fluorescence Emission of 9‑Aminoanthracene for Bioimaging Applications

• Published in: ACS omega 2017-07, Vol.2 (7), p.3371-3379
• Main Authors: Uchiyama, Yosuke, Watanabe, Ryo, Kurotaki, Takanori, Kuniya, Suguru, Kimura, Shinobu, Sawamura, Yukihiro, Ohtsuki, Takemaru, Kikuchi, Yuichi, Matsuzawa, Hideyo, Uchiyama, Koji, Itakura, Makoto, Kawakami, Fumitaka, Maruyama, Hiroko
• Format: Article
• Language: English
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.7b00711

The green fluorescence emission of 9-aminoanthracence (9AA) was maintained by controlling the oxidation of 9AA with oxygen in the solid state and in solution. The solid-state fluorescence of 9AA was maintained for a longer time when lauric acid was used because the equilibrium between 9AA and 9-anthrylammonium salt (9AAH + ) inclines toward the right-hand side in the presence of an acid. A solution of 9AA in CDCl3, to which nitrogen had been bubbled through for 5 min, continued to emit green fluorescence for more than 3 days, whereas the fluorescence emission disappeared within 3 days for the solution that had been bubbled with oxygen for 5 min. 9AA is oxidized by oxygen in MeOH under dark conditions to give almost nongreen fluorescent anthraquinone monoimine (AQNH), whereas dimerization of 9AA occurs under UV irradiation at 365 nm, much faster than the generation of AQNH. These results suggest that 9AA is oxidized by the triplet rather than the singlet oxygen in MeOH. Some of the organic molecules, proteins, and biological tissues were successfully stained with 9AA on microscope slides within 10 min because the green fluorescence emission of 9AA was successfully maintained in the presence of an acid and under hypoxic conditions of the used materials.