The difference between 14-epi-previtamin D 3 and 14-epi-19-norprevitamin D 3: Their synthesis and binding affinity for human VDR

Daisuke Sawada; Tomoyuki Katayama; Yuya Tsukuda; Nozomi Saito; Hiroshi Saito; Shinji Kakuda; Midori Takimoto-Kamimura; Kazuya Takenouchi; Atsushi Kittaka

The difference between 14-epi-previtamin D ₃ and 14-epi-19-norprevitamin D ₃: Their synthesis and binding affinity for human VDR

Daisuke Sawada, Tomoyuki Katayama, Yuya Tsukuda, Nozomi Saito, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Kazuya Takenouchi, Atsushi Kittaka

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

1 Citation (Scopus)

Abstract

The synthesis of 14-epi-1α,25(OH) ₂previtamin D ₃, 14-epi-19-nor-1α,25(OH) ₂previtamin D ₃, and their 2-substituted analogs is described. The vitamin D receptor (VDR) binding affinity was further evaluated and 2α-methyl substituted 14-epi-1α,25(OH) ₂previtamin D ₃ had 17-fold more potent affinity than 14-epi-1α25(OH) ₂previtamin D ₃. In the comparison of these compounds, the effects of thermal equilibrium, with or without 19-carbon at the A-ring, and their CD-ring structures are discussed.

Original language	English
Pages (from-to)	319-326
Number of pages	8
Journal	Anticancer research
Volume	32
Issue number	1 PART 2
Publication status	Published - Jan 1 2012
Externally published	Yes

Keywords

14-Epi-19-norprevitamin D
14-Epi-previtamin D
VDR binding affinity

ASJC Scopus subject areas

Oncology
Cancer Research

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Cite this

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title = "The difference between 14-epi-previtamin D 3 and 14-epi-19-norprevitamin D 3: Their synthesis and binding affinity for human VDR",

abstract = "The synthesis of 14-epi-1α,25(OH) 2previtamin D 3, 14-epi-19-nor-1α,25(OH) 2previtamin D 3, and their 2-substituted analogs is described. The vitamin D receptor (VDR) binding affinity was further evaluated and 2α-methyl substituted 14-epi-1α,25(OH) 2previtamin D 3 had 17-fold more potent affinity than 14-epi-1α25(OH) 2previtamin D 3. In the comparison of these compounds, the effects of thermal equilibrium, with or without 19-carbon at the A-ring, and their CD-ring structures are discussed.",

keywords = "14-Epi-19-norprevitamin D, 14-Epi-previtamin D, VDR binding affinity",

author = "Daisuke Sawada and Tomoyuki Katayama and Yuya Tsukuda and Nozomi Saito and Hiroshi Saito and Shinji Kakuda and Midori Takimoto-Kamimura and Kazuya Takenouchi and Atsushi Kittaka",

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T1 - The difference between 14-epi-previtamin D 3 and 14-epi-19-norprevitamin D 3

T2 - Their synthesis and binding affinity for human VDR

AU - Sawada, Daisuke

AU - Katayama, Tomoyuki

AU - Tsukuda, Yuya

AU - Saito, Nozomi

AU - Saito, Hiroshi

AU - Kakuda, Shinji

AU - Takimoto-Kamimura, Midori

AU - Takenouchi, Kazuya

AU - Kittaka, Atsushi

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N2 - The synthesis of 14-epi-1α,25(OH) 2previtamin D 3, 14-epi-19-nor-1α,25(OH) 2previtamin D 3, and their 2-substituted analogs is described. The vitamin D receptor (VDR) binding affinity was further evaluated and 2α-methyl substituted 14-epi-1α,25(OH) 2previtamin D 3 had 17-fold more potent affinity than 14-epi-1α25(OH) 2previtamin D 3. In the comparison of these compounds, the effects of thermal equilibrium, with or without 19-carbon at the A-ring, and their CD-ring structures are discussed.

AB - The synthesis of 14-epi-1α,25(OH) 2previtamin D 3, 14-epi-19-nor-1α,25(OH) 2previtamin D 3, and their 2-substituted analogs is described. The vitamin D receptor (VDR) binding affinity was further evaluated and 2α-methyl substituted 14-epi-1α,25(OH) 2previtamin D 3 had 17-fold more potent affinity than 14-epi-1α25(OH) 2previtamin D 3. In the comparison of these compounds, the effects of thermal equilibrium, with or without 19-carbon at the A-ring, and their CD-ring structures are discussed.

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KW - 14-Epi-previtamin D

KW - VDR binding affinity

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