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

Chem Commun (Camb). 2023 Oct 10;59(81):12100-12103. doi: 10.1039/d3cc04410f.

Authors

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan. [email protected].
² Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
³ JST PRESTO, 4-1-8 Hon-cho, Kawaguchi, Saitama 332-0012, Japan.
⁴ Graduate School of Advanced Science and Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan.
⁵ Gifu Pharmaceutical University, 1-25-4-Daigaku-nishi, Gifu 501-1196, Japan.
⁶ Deuterium Science Research Unit, Center for the Promotion of Interdisciplinary Education and Research, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 37721453
DOI: 10.1039/d3cc04410f

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.