Synthesis and biological evaluation of 4-substituted vitamin D and 14-epi-previtamin D analogs

Daisuke Sawada; Yuya Tsukuda; Hiroshi Saito; Ken Ichiro Takagi; Kyouhei Horie; Eiji Ochiai; Kazuya Takenouchi; Atsushi Kittaka

doi:10.1248/cpb.57.1431

Synthesis and biological evaluation of 4-substituted vitamin D and 14-epi-previtamin D analogs

Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Ken Ichiro Takagi, Kyouhei Horie, Eiji Ochiai, Kazuya Takenouchi, Atsushi Kittaka

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

7 Citations (Scopus)

Abstract

We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D3 (1α,25(OH)₂D₃, 1) and its C14-epimer with the previtamin D3 form of 14-epi-1α,25(OH)₂preD₃ (14-epi-pre1). Their vitamin D receptor (VDR) binding affinity and osteocalcin promoter transactivation activity in HOS cells were evaluated, and had lower activity than the natural hormone (1) and 14-epi-pre1, respectively.

Original language	English
Pages (from-to)	1431-1433
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	57
Issue number	12
DOIs	https://doi.org/10.1248/cpb.57.1431
Publication status	Published - Dec 2009
Externally published	Yes

Keywords

C4-modified seco-steroid
Osteocalcin
Previtamin D
Vitamin D
Vitamin D receptor

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.57.1431

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abstract = "We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D3 (1α,25(OH)2D3, 1) and its C14-epimer with the previtamin D3 form of 14-epi-1α,25(OH)2preD3 (14-epi-pre1). Their vitamin D receptor (VDR) binding affinity and osteocalcin promoter transactivation activity in HOS cells were evaluated, and had lower activity than the natural hormone (1) and 14-epi-pre1, respectively.",

keywords = "C4-modified seco-steroid, Osteocalcin, Previtamin D, Vitamin D, Vitamin D receptor",

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T1 - Synthesis and biological evaluation of 4-substituted vitamin D and 14-epi-previtamin D analogs

AU - Sawada, Daisuke

AU - Tsukuda, Yuya

AU - Saito, Hiroshi

AU - Takagi, Ken Ichiro

AU - Horie, Kyouhei

AU - Ochiai, Eiji

AU - Takenouchi, Kazuya

AU - Kittaka, Atsushi

PY - 2009/12

Y1 - 2009/12

N2 - We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D3 (1α,25(OH)2D3, 1) and its C14-epimer with the previtamin D3 form of 14-epi-1α,25(OH)2preD3 (14-epi-pre1). Their vitamin D receptor (VDR) binding affinity and osteocalcin promoter transactivation activity in HOS cells were evaluated, and had lower activity than the natural hormone (1) and 14-epi-pre1, respectively.

AB - We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D3 (1α,25(OH)2D3, 1) and its C14-epimer with the previtamin D3 form of 14-epi-1α,25(OH)2preD3 (14-epi-pre1). Their vitamin D receptor (VDR) binding affinity and osteocalcin promoter transactivation activity in HOS cells were evaluated, and had lower activity than the natural hormone (1) and 14-epi-pre1, respectively.

KW - C4-modified seco-steroid

KW - Osteocalcin

KW - Previtamin D

KW - Vitamin D

KW - Vitamin D receptor

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Synthesis and biological evaluation of 4-substituted vitamin D and 14-epi-previtamin D analogs

Abstract

Keywords

ASJC Scopus subject areas

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