Issue 17, 2021

Synthesis of deuterated γ-linolenic acid and application for biological studies: metabolic tuning and Raman imaging

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.

Graphical abstract: Synthesis of deuterated γ-linolenic acid and application for biological studies: metabolic tuning and Raman imaging

Supplementary files

Article information

Article type
Communication
Submitted
01 Dec 2020
Accepted
26 Jan 2021
First published
29 Jan 2021

Chem. Commun., 2021,57, 2180-2183

Synthesis of deuterated γ-linolenic acid and application for biological studies: metabolic tuning and Raman imaging

K. Dodo, A. Sato, Y. Tamura, S. Egoshi, K. Fujiwara, K. Oonuma, S. Nakao, N. Terayama and M. Sodeoka, Chem. Commun., 2021, 57, 2180 DOI: 10.1039/D0CC07824G

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