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 journalArticle

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

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Cite this

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; Wada, Akimori; Ito, Yoichi; Takeda, Kazuyoshi; Takahashi, Kazuhiko; Okano, Toshio.

In: Journal of Medicinal Chemistry, Vol. 54, No. 12, 23.06.2011, p. 4269-4273.

Research output: Contribution to journalArticle

Suhara, Yoshitomo ; Watanabe, Masato ; Nakagawa, Kimie ; Wada, Akimori ; Ito, Yoichi ; Takeda, Kazuyoshi ; Takahashi, Kazuhiko ; Okano, Toshio. / 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. In: Journal of Medicinal Chemistry. 2011 ; Vol. 54, No. 12. pp. 4269-4273.
@article{98857ad0182f4eb6b6d874e2b2ea3710,
title = "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 = "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.",
author = "Yoshitomo Suhara and Masato Watanabe and Kimie Nakagawa and Akimori Wada and Yoichi Ito and Kazuyoshi Takeda and Kazuhiko Takahashi and Toshio Okano",
year = "2011",
month = "6",
day = "23",
doi = "10.1021/jm200025f",
language = "English",
volume = "54",
pages = "4269--4273",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "12",

}

TY - JOUR

T1 - 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

AU - Suhara, Yoshitomo

AU - Watanabe, Masato

AU - Nakagawa, Kimie

AU - Wada, Akimori

AU - Ito, Yoichi

AU - Takeda, Kazuyoshi

AU - Takahashi, Kazuhiko

AU - Okano, Toshio

PY - 2011/6/23

Y1 - 2011/6/23

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=79959479006&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79959479006&partnerID=8YFLogxK

U2 - 10.1021/jm200025f

DO - 10.1021/jm200025f

M3 - Article

VL - 54

SP - 4269

EP - 4273

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 12

ER -