Synthesis of deuterated γ-linolenic acid and application for biological studies: metabolic tuning and Raman imaging. Issue 17 (2nd February 2021)

• Record Type: Journal Article
• Authors: Dodo, Kosuke; Sato, Ayato; Tamura, Yuki; Egoshi, Syusuke; Fujiwara, Koichi; Oonuma, Kana; Nakao, Shuhei; Terayama, Naoki; Sodeoka, Mikiko
• Is Part Of: Chemical communications. Volume 57:Issue 17(2021)
• Page Start: 2180
• Page End: 2183
• Publication Date: 2021-02-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc07824g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : γ-Linolenic acid (GLA) is reported to show tumor-selective cytotoxicity via unidentified mechanisms. We introduced deuterium into GLA as a dual functional tag for metabolic inhibition and Raman imaging and applied for mechanistic studies. Abstract : γ-Linolenic acid (GLA) is reported to show tumor-selective cytotoxicity through unidentified mechanisms. Here, to assess the involvement of oxidized metabolites of GLA, we synthesized several deuterated GLAs and evaluated their metabolism and cytotoxicity towards normal human fibroblast WI-38 cells and VA-13 tumor cells generated from WI-38 by transformation with SV40 virus. Deuteration of GLA suppressed both metabolism and cytotoxicity towards WI-38 cells and increased the selectivity for VA-13 cells. Fully deuterated GLA was visualized by Raman imaging, which indicated that GLA is accumulated in intracellular lipid droplets of VA-13 cells. Our results suggest the tumor-selective cytotoxicity is due to GLA itself, not its oxidized metabolites.