Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities

Rie Sakane; Kimito Kimura; Yoshihisa Hirota; Michiyasu Ishizawa; Yuta Takagi; Akimori Wada; Shigefumi Kuwahara; Makoto Makishima; Yoshitomo Suhara

doi:10.1016/j.bmcl.2017.09.038

Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities

Rie Sakane, Kimito Kimura, Yoshihisa Hirota, Michiyasu Ishizawa, Yuta Takagi, Akimori Wada, Shigefumi Kuwahara, Makoto Makishima, Yoshitomo Suhara

研究成果: Article › 査読

6 被引用数 (Scopus)

抄録

Vitamin K is an essential cofactor of γ-glutamylcarboxylase as related to blood coagulation and bone formation. Menaquinone-4, one of the vitamin K homologues, is biosynthesized in the body and has various biological activities such as being a ligand for steroid and xenobiotic receptors, protection of neuronal cells from oxidative stress, and so on. From this background, we focused on the role of menaquinone in the differentiation activity of progenitor cells into neuronal cells and we synthesized novel vitamin K derivatives with modification of the ω-terminal side chain. We report here new vitamin K analogues, which introduced an alkylated phenyl group at the ω-terminal side chain. These compounds exhibited potent differentiation activity as compared to control.

本文言語	English
ページ（範囲）	4881-4884
ページ数	4
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	27
号	21
DOI	https://doi.org/10.1016/j.bmcl.2017.09.038
出版ステータス	Published - 2017 11月 1

ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

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10.1016/j.bmcl.2017.09.038

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引用スタイル

Sakane, R., Kimura, K., Hirota, Y., Ishizawa, M., Takagi, Y., Wada, A., Kuwahara, S., Makishima, M., & Suhara, Y. (2017). Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities. Bioorganic and Medicinal Chemistry Letters, 27(21), 4881-4884. https://doi.org/10.1016/j.bmcl.2017.09.038

Sakane, R, Kimura, K, Hirota, Y, Ishizawa, M, Takagi, Y, Wada, A, Kuwahara, S, Makishima, M & Suhara, Y 2017, 'Synthesis of novel vitamin K derivatives with alkylated phenyl groups introduced at the ω-terminal side chain and evaluation of their neural differentiation activities', Bioorganic and Medicinal Chemistry Letters, vol. 27, no. 21, pp. 4881-4884. https://doi.org/10.1016/j.bmcl.2017.09.038

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abstract = "Vitamin K is an essential cofactor of γ-glutamylcarboxylase as related to blood coagulation and bone formation. Menaquinone-4, one of the vitamin K homologues, is biosynthesized in the body and has various biological activities such as being a ligand for steroid and xenobiotic receptors, protection of neuronal cells from oxidative stress, and so on. From this background, we focused on the role of menaquinone in the differentiation activity of progenitor cells into neuronal cells and we synthesized novel vitamin K derivatives with modification of the ω-terminal side chain. We report here new vitamin K analogues, which introduced an alkylated phenyl group at the ω-terminal side chain. These compounds exhibited potent differentiation activity as compared to control.",

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author = "Rie Sakane and Kimito Kimura and Yoshihisa Hirota and Michiyasu Ishizawa and Yuta Takagi and Akimori Wada and Shigefumi Kuwahara and Makoto Makishima and Yoshitomo Suhara",

note = "Funding Information: We are grateful to The Naito Foundation (Y.S.) and the Fuji Foundation for Protein Research (Y.H.), Japan Food Chemical Research Foundation (Y.H.). This study was financially supported in part by a Grant-in-aid for Scientific Research < KAKENHI > (C) (grant number 16K08325 to Y.S.) and a Grant-in-aid for Scientific Research Young Scientists (B) (grant number 16K18924 to Y.H.) from Japan Society for Promotion of Science . Publisher Copyright: {\textcopyright} 2017 The Author(s)",

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AU - Sakane, Rie

AU - Kimura, Kimito

AU - Hirota, Yoshihisa

AU - Ishizawa, Michiyasu

AU - Takagi, Yuta

AU - Wada, Akimori

AU - Kuwahara, Shigefumi

AU - Makishima, Makoto

AU - Suhara, Yoshitomo

N1 - Funding Information: We are grateful to The Naito Foundation (Y.S.) and the Fuji Foundation for Protein Research (Y.H.), Japan Food Chemical Research Foundation (Y.H.). This study was financially supported in part by a Grant-in-aid for Scientific Research < KAKENHI > (C) (grant number 16K08325 to Y.S.) and a Grant-in-aid for Scientific Research Young Scientists (B) (grant number 16K18924 to Y.H.) from Japan Society for Promotion of Science . Publisher Copyright: © 2017 The Author(s)

PY - 2017/11/1

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N2 - Vitamin K is an essential cofactor of γ-glutamylcarboxylase as related to blood coagulation and bone formation. Menaquinone-4, one of the vitamin K homologues, is biosynthesized in the body and has various biological activities such as being a ligand for steroid and xenobiotic receptors, protection of neuronal cells from oxidative stress, and so on. From this background, we focused on the role of menaquinone in the differentiation activity of progenitor cells into neuronal cells and we synthesized novel vitamin K derivatives with modification of the ω-terminal side chain. We report here new vitamin K analogues, which introduced an alkylated phenyl group at the ω-terminal side chain. These compounds exhibited potent differentiation activity as compared to control.

AB - Vitamin K is an essential cofactor of γ-glutamylcarboxylase as related to blood coagulation and bone formation. Menaquinone-4, one of the vitamin K homologues, is biosynthesized in the body and has various biological activities such as being a ligand for steroid and xenobiotic receptors, protection of neuronal cells from oxidative stress, and so on. From this background, we focused on the role of menaquinone in the differentiation activity of progenitor cells into neuronal cells and we synthesized novel vitamin K derivatives with modification of the ω-terminal side chain. We report here new vitamin K analogues, which introduced an alkylated phenyl group at the ω-terminal side chain. These compounds exhibited potent differentiation activity as compared to control.

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