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Synthesis of deuterated γ-linolenic acid and application for biological studies: metabolic tuning and Raman imaging.
Dodo, Kosuke; Sato, Ayato; Tamura, Yuki; Egoshi, Syusuke; Fujiwara, Koichi; Oonuma, Kana; Nakao, Shuhei; Terayama, Naoki; Sodeoka, Mikiko.
Afiliación
  • Dodo K; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and Sodeoka Live Cell Chemistry Project, ERATO, Japan Sciences and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan and AMED-CREST,
  • Sato A; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and Sodeoka Live Cell Chemistry Project, ERATO, Japan Sciences and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • Tamura Y; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and Sodeoka Live Cell Chemistry Project, ERATO, Japan Sciences and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • Egoshi S; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and AMED-CREST, Japan Agency for Medical Research and Development, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • Fujiwara K; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and AMED-CREST, Japan Agency for Medical Research and Development, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • Oonuma K; RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • Nakao S; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and AMED-CREST, Japan Agency for Medical Research and Development, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • Terayama N; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and AMED-CREST, Japan Agency for Medical Research and Development, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan and RIKEN Center for Sustainable R
  • Sodeoka M; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. sodeoka@riken.jp dodo@riken.jp and Sodeoka Live Cell Chemistry Project, ERATO, Japan Sciences and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan and AMED-CREST,
Chem Commun (Camb) ; 57(17): 2180-2183, 2021 Mar 01.
Article en En | MEDLINE | ID: mdl-33527102
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácido gammalinolénico Límite: Humans Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article
Texto completo
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XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácido gammalinolénico Límite: Humans Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article