Synthesis of new vitamin K analogues as steroid and xenobiotic receptor (SXR) agonists: insights into the biological role of the side chain part of vitamin K.

Yoshitomo Suhara, Masato Watanabe, Sayaka Motoyoshi, Kimie Nakagawa, Akimori Wada, Kazuyoshi Takeda, Kazuhiko Takahashi, Hiroaki Tokiwa, Toshio Okano

Index: J. Med. Chem. 54 , 4918-22, (2011)

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Abstract

Vitamin K(2) has been demonstrated to induce gene expression related to bone formation through a nuclear steroid and xenobiotic receptor (SXR). We synthesized new vitamin K analogues with the same isoprene side chains symmetrically introduced at the 2 and 3 positions of 1,4-naphthoquinone and evaluated the transcriptional activity of the target gene. The transcriptional activity was related to the length of the side chain which allowed optimal interaction with ligand-binding domain of SXR.