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

Chem Pharm Bull (Tokyo). 2009 Dec;57(12):1431-3. doi: 10.1248/cpb.57.1431.

Authors

Daisuke Sawada¹, Yuya Tsukuda, Hiroshi Saito, Ken-ichiro Takagi, Kyouhei Horie, Eiji Ochiai, Kazuya Takenouchi, Atsushi Kittaka

Affiliation

¹ Teikyo University, Sagamiko, Kanagawa, Japan.

PMID: 19952459
DOI: 10.1248/cpb.57.1431

Abstract

We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D(3) (1alpha,25(OH)(2)D(3), 1) and its C14-epimer with the previtamin D(3) form of 14-epi-1alpha,25(OH)(2)preD(3) (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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Binding Sites
Cholecalciferol / chemical synthesis*
Cholecalciferol / genetics
Cholecalciferol / metabolism
Humans
Molecular Structure
Osteoblasts / metabolism
Receptors, Calcitriol / chemistry
Receptors, Calcitriol / metabolism
Vitamin D / analogs & derivatives*
Vitamin D / chemistry

Substances

Receptors, Calcitriol
Vitamin D
Cholecalciferol