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

Research output: Contribution to journalArticle

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.

LanguageEnglish
Pages4881-4884
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume27
Issue number21
DOIs
StatePublished - 2017 Nov 1

Fingerprint

Vitamin K
Derivatives
Vitamin K 2
Oxidative stress
Bioactivity
Coagulation
Bone
Blood
Ligands

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

Cite this

Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities. / Sakane, Rie; Kimura, Kimito; Hirota, Yoshihisa; Ishizawa, Michiyasu; Takagi, Yuta; Wada, Akimori; Kuwahara, Shigefumi; Makishima, Makoto; Suhara, Yoshitomo.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 27, No. 21, 01.11.2017, p. 4881-4884.

Research output: Contribution to journalArticle

Sakane, Rie ; Kimura, Kimito ; Hirota, Yoshihisa ; Ishizawa, Michiyasu ; Takagi, Yuta ; Wada, Akimori ; Kuwahara, Shigefumi ; Makishima, Makoto ; Suhara, Yoshitomo. / Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities. In: Bioorganic and Medicinal Chemistry Letters. 2017 ; Vol. 27, No. 21. pp. 4881-4884
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