Synthesis of 2alpha-substituted-14-epi-previtamin D3 and its genomic activity

Daisuke Sawada; Tomoyuki Katayama; Yuya Tsukuda; Nozomi Saito; Masashi Takano; Hiroshi Saito; Ken-Ichiro Takagi; Eiji Ochiai; Seiichi Ishizuka; Kazuya Takenouchi; Atsushi Kittaka

doi:10.1016/j.bmcl.2009.07.112

Synthesis of 2alpha-substituted-14-epi-previtamin D3 and its genomic activity

Bioorg Med Chem Lett. 2009 Sep 15;19(18):5397-400. doi: 10.1016/j.bmcl.2009.07.112. Epub 2009 Jul 28.

Authors

Daisuke Sawada¹, Tomoyuki Katayama, Yuya Tsukuda, Nozomi Saito, Masashi Takano, Hiroshi Saito, Ken-Ichiro Takagi, Eiji Ochiai, Seiichi Ishizuka, Kazuya Takenouchi, Atsushi Kittaka

Affiliation

¹ Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 229-0195, Japan.

PMID: 19692243
DOI: 10.1016/j.bmcl.2009.07.112

Abstract

We synthesized and isolated 2 alpha-substituted analogs of 14-epi-previtamin D3 after thermal isomerization at 80 degrees C for the first time. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were evaluated, and the 2 alpha-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D3.

Publication types

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

MeSH terms

Cell Line, Tumor
Cholecalciferol / analogs & derivatives*
Cholecalciferol / chemical synthesis
Cholecalciferol / chemistry
Cholecalciferol / pharmacology
Humans
Osteocalcin / genetics*
Promoter Regions, Genetic / drug effects*
Protein Binding
Receptors, Calcitriol / metabolism*
Vitamins / chemical synthesis
Vitamins / chemistry*
Vitamins / pharmacology*

Substances

Receptors, Calcitriol
Vitamins
Osteocalcin
Cholecalciferol
previtamin D(3)