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

doi:10.1021/jm200025f

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

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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 language	English
Pages (from-to)	4269-4273
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	54
Issue number	12
DOIs	https://doi.org/10.1021/jm200025f
Publication status	Published - 2011 Jun 23
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm200025f

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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. / Suhara, Yoshitomo; Watanabe, Masato; Nakagawa, Kimie et al.
In: Journal of Medicinal Chemistry, Vol. 54, No. 12, 23.06.2011, p. 4269-4273.

Research output: Contribution to journal › Article › peer-review

Suhara, Y, Watanabe, M, Nakagawa, K, Wada, A, Ito, Y, Takeda, K, Takahashi, K & Okano, T 2011, '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', Journal of Medicinal Chemistry, vol. 54, no. 12, pp. 4269-4273. https://doi.org/10.1021/jm200025f

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AU - Wada, Akimori

AU - Ito, Yoichi

AU - Takeda, Kazuyoshi

AU - Takahashi, Kazuhiko

AU - Okano, Toshio

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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

Abstract

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