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 journalArticle

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 languageEnglish
Pages (from-to)319-326
Number of pages8
JournalAnticancer research
Volume32
Issue number1 PART 2
Publication statusPublished - Jan 1 2012
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Oncology
  • Cancer Research

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    Sawada, D., Katayama, T., Tsukuda, Y., Saito, N., Saito, H., Kakuda, S., Takimoto-Kamimura, M., Takenouchi, K., & Kittaka, A. (2012). The difference between 14-epi-previtamin D 3 and 14-epi-19-norprevitamin D 3: Their synthesis and binding affinity for human VDR. Anticancer research, 32(1 PART 2), 319-326.