Structure-activity relationship of novel menaquinone-4 analogues: Modification of the side chain affects their biological activities

Yoshitomo Suhara; Norika Hanada; Takashi Okitsu; Miho Sakai; Masato Watanabe; Kimie Nakagawa; Akimori Wada; Kazuyoshi Takeda; Kazuhiko Takahashi; Hiroaki Tokiwa; Toshio Okano

doi:10.1021/jm2013166

Structure-activity relationship of novel menaquinone-4 analogues: Modification of the side chain affects their biological activities

Yoshitomo Suhara, Norika Hanada, Takashi Okitsu, Miho Sakai, Masato Watanabe, Kimie Nakagawa, Akimori Wada, Kazuyoshi Takeda, Kazuhiko Takahashi, Hiroaki Tokiwa, Toshio Okano

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

12 Citations (Scopus)

Abstract

We synthesized new vitamin K analogues with demethylation or reduction of the double bonds of the side chain of menaquinone-4 (MK-4) and evaluated their SXR-mediated transcriptional activity as well as the extent of their conversion to MK-4. The results indicated that the analogue with the methyl group deleted at the 7′ site of the side chain part affected conversion activity to MK-4. In contrast, a decrease in the number of the double bonds in the side chain moiety appeared to decrease the SXR-mediated transcriptional activity.

Original language	English
Pages (from-to)	1553-1558
Number of pages	6
Journal	Journal of Medicinal Chemistry
Volume	55
Issue number	4
DOIs	https://doi.org/10.1021/jm2013166
Publication status	Published - 2012 Feb 23
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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abstract = "We synthesized new vitamin K analogues with demethylation or reduction of the double bonds of the side chain of menaquinone-4 (MK-4) and evaluated their SXR-mediated transcriptional activity as well as the extent of their conversion to MK-4. The results indicated that the analogue with the methyl group deleted at the 7′ site of the side chain part affected conversion activity to MK-4. In contrast, a decrease in the number of the double bonds in the side chain moiety appeared to decrease the SXR-mediated transcriptional activity.",

author = "Yoshitomo Suhara and Norika Hanada and Takashi Okitsu and Miho Sakai and Masato Watanabe and Kimie Nakagawa and Akimori Wada and Kazuyoshi Takeda and Kazuhiko Takahashi and Hiroaki Tokiwa and Toshio Okano",

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T1 - Structure-activity relationship of novel menaquinone-4 analogues

T2 - Modification of the side chain affects their biological activities

AU - Suhara, Yoshitomo

AU - Hanada, Norika

AU - Okitsu, Takashi

AU - Sakai, Miho

AU - Watanabe, Masato

AU - Nakagawa, Kimie

AU - Wada, Akimori

AU - Takeda, Kazuyoshi

AU - Takahashi, Kazuhiko

AU - Tokiwa, Hiroaki

AU - Okano, Toshio

PY - 2012/2/23

Y1 - 2012/2/23

N2 - We synthesized new vitamin K analogues with demethylation or reduction of the double bonds of the side chain of menaquinone-4 (MK-4) and evaluated their SXR-mediated transcriptional activity as well as the extent of their conversion to MK-4. The results indicated that the analogue with the methyl group deleted at the 7′ site of the side chain part affected conversion activity to MK-4. In contrast, a decrease in the number of the double bonds in the side chain moiety appeared to decrease the SXR-mediated transcriptional activity.

AB - We synthesized new vitamin K analogues with demethylation or reduction of the double bonds of the side chain of menaquinone-4 (MK-4) and evaluated their SXR-mediated transcriptional activity as well as the extent of their conversion to MK-4. The results indicated that the analogue with the methyl group deleted at the 7′ site of the side chain part affected conversion activity to MK-4. In contrast, a decrease in the number of the double bonds in the side chain moiety appeared to decrease the SXR-mediated transcriptional activity.

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Structure-activity relationship of novel menaquinone-4 analogues: Modification of the side chain affects their biological activities

Abstract

ASJC Scopus subject areas

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