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

The difference between 14-epi-previtamin D ₃ and 14-epi-19-norprevitamin D ₃ : Their synthesis and binding affinity for human VDR. / Sawada, Daisuke; Katayama, Tomoyuki; Tsukuda, Yuya; Saito, Nozomi; Saito, Hiroshi; Kakuda, Shinji; Takimoto-Kamimura, Midori; Takenouchi, Kazuya; Kittaka, Atsushi.

In: Anticancer research, Vol. 32, No. 1 PART 2, 01.01.2012, p. 319-326.

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

Sawada, Daisuke ; Katayama, Tomoyuki ; Tsukuda, Yuya ; Saito, Nozomi ; Saito, Hiroshi ; Kakuda, Shinji ; Takimoto-Kamimura, Midori ; Takenouchi, Kazuya ; Kittaka, Atsushi. / The difference between 14-epi-previtamin D ₃ and 14-epi-19-norprevitamin D ₃ : Their synthesis and binding affinity for human VDR. In: Anticancer research. 2012 ; Vol. 32, No. 1 PART 2. pp. 319-326.

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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.",

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