Synthesis of novel vitamin K2 analogues with modification at the Ω-terminal position and their biological evaluation as potent steroid and xenobiotic receptor (SXR) agonists

Yoshitomo Suhara, Masato Watanabe, Kimie Nakagawa, Akimori Wada, Yoichi Ito, Kazuyoshi Takeda, Kazuhiko Takahashi, Toshio Okano

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Abstract

Vitamin K2 is a ligand for a nuclear receptor, steroid and xenobiotic receptor (SXR), that induces the gene expressions of CYP3A4. We synthesized vitamin K2 analogues with hydroxyl or phenyl groups at the Ω-terminal of the side chain. The up-regulation of SXR-mediated transcription of the target gene by the analogues was dependent on the length of the side chain and the hydrophobicity of the Ω-terminal residues. Phenyl analogue menaquinone-3 was as active as the known SXR ligand rifampicin.

Original languageEnglish
Pages (from-to)4269-4273
Number of pages5
JournalJournal of Medicinal Chemistry
Volume54
Issue number12
DOIs
Publication statusPublished - 2011 Jun 23

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ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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