Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities

Rie Sakane, Kimito Kimura, Yoshihisa Hirota, Michiyasu Ishizawa, Yuta Takagi, Akimori Wada, Shigefumi Kuwahara, Makoto Makishima, Yoshitomo Suhara

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4 Citations (Scopus)

Abstract

Vitamin K is an essential cofactor of γ-glutamylcarboxylase as related to blood coagulation and bone formation. Menaquinone-4, one of the vitamin K homologues, is biosynthesized in the body and has various biological activities such as being a ligand for steroid and xenobiotic receptors, protection of neuronal cells from oxidative stress, and so on. From this background, we focused on the role of menaquinone in the differentiation activity of progenitor cells into neuronal cells and we synthesized novel vitamin K derivatives with modification of the ω-terminal side chain. We report here new vitamin K analogues, which introduced an alkylated phenyl group at the ω-terminal side chain. These compounds exhibited potent differentiation activity as compared to control.

Original languageEnglish
Pages (from-to)4881-4884
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume27
Issue number21
DOIs
Publication statusPublished - 2017 Nov 1

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Keywords

  • Menaquinone-4
  • Neuronal cells
  • SXR
  • Transcriptional activity
  • Vitamin K

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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