Multiple deuteration of triphenylphosphine and live-cell Raman imaging of deuterium-incorporated Mito-Q

Shogo Moriyama; Miyu Mae; Daiki Shibata; Hiroyuki Yamakoshi; Shinji Kajimoto; Takakazu Nakabayashi; Takayoshi Ishimoto; Kaiki Mogi; Hironao Sajiki; Shuji Akai; Yoshinari Sawama

doi:10.1039/D3CC04410F

Multiple deuteration of triphenylphosphine and live-cell Raman imaging of deuterium-incorporated Mito-Q†

Shogo Moriyama,^a Miyu Mae,^a Daiki Shibata,

^b Hiroyuki Yamakoshi,^b Shinji Kajimoto,

^bc Takakazu Nakabayashi,

^b Takayoshi Ishimoto,

^d Kaiki Mogi,^e Hironao Sajiki,

^e Shuji Akai

^a and Yoshinari Sawama

*^af

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan
E-mail: sawama@phs.osaka-u.ac.jp

^b Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, Japan

^c JST PRESTO, 4-1-8 Hon-cho, Kawaguchi, Saitama 332-0012, Japan

^d Graduate School of Advanced Science and Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan

^e Gifu Pharmaceutical University, 1-25-4-Daigaku-nishi, Gifu 501-1196, Japan

^f Deuterium Science Research Unit, Center for the Promotion of Interdisciplinary Education and Research, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

All aromatic C–H bonds of triphenylphosphine (PPh₃) were efficiently replaced by C–D bonds using Ru/C and Ir/C co-catalysts in 2-PrOH and D₂O, an inexpensive deuterium source. Furthermore, non-radioactive and safe deuterium-incorporated Mito-Q (drug candidate) was prepared from deuterated PPh₃ and used for the live-cell Raman imaging to evaluate the mitochondrial uptake.

Chemical Communications

Multiple deuteration of triphenylphosphine and live-cell Raman imaging of deuterium-incorporated Mito-Q†

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Multiple deuteration of triphenylphosphine and live-cell Raman imaging of deuterium-incorporated Mito-Q

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