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

Fingerprint Dive into the research topics of 'The difference between 14-epi-previtamin D <sub>3</sub> and 14-epi-19-norprevitamin D <sub>3</sub>: Their synthesis and binding affinity for human VDR'. Together they form a unique fingerprint.

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.

@article{738b82c0790b457e82c66a748d3f8dbb,

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.",

keywords = "14-Epi-19-norprevitamin D, 14-Epi-previtamin D, VDR binding affinity",

author = "Daisuke Sawada and Tomoyuki Katayama and Yuya Tsukuda and Nozomi Saito and Hiroshi Saito and Shinji Kakuda and Midori Takimoto-Kamimura and Kazuya Takenouchi and Atsushi Kittaka",

year = "2012",

month = jan,

day = "1",

language = "English",

volume = "32",

pages = "319--326",

journal = "Anticancer Research",

issn = "0250-7005",

publisher = "International Institute of Anticancer Research",

number = "1 PART 2",

}

TY - JOUR

T1 - The difference between 14-epi-previtamin D 3 and 14-epi-19-norprevitamin D 3

T2 - Their synthesis and binding affinity for human VDR

AU - Sawada, Daisuke

AU - Katayama, Tomoyuki

AU - Tsukuda, Yuya

AU - Saito, Nozomi

AU - Saito, Hiroshi

AU - Kakuda, Shinji

AU - Takimoto-Kamimura, Midori

AU - Takenouchi, Kazuya

AU - Kittaka, Atsushi

PY - 2012/1/1

Y1 - 2012/1/1

N2 - 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.

AB - 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.

KW - 14-Epi-19-norprevitamin D

KW - 14-Epi-previtamin D

KW - VDR binding affinity

UR - http://www.scopus.com/inward/record.url?scp=84856015543&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84856015543&partnerID=8YFLogxK

M3 - Article

C2 - 22213322

AN - SCOPUS:84856015543

VL - 32

SP - 319

EP - 326

JO - Anticancer Research

JF - Anticancer Research

SN - 0250-7005

IS - 1 PART 2