Synthesis of 2α-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 2α-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

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

14 Citations (Scopus)

Abstract

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

Original language	English
Pages (from-to)	5397-5400
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2009.07.112
Publication status	Published - Sept 15 2009
Externally published	Yes

Keywords

14-Epi-previtamin D
Osteocalcin
Vitamin D
Vitamin D receptor

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2009.07.112

Cite this

@article{ea69652d3c5e47a5a3b2bfadf1a42c67,

title = "Synthesis of 2α-substituted-14-epi-previtamin D3 and its genomic activity",

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

keywords = "14-Epi-previtamin D, Osteocalcin, Vitamin D, Vitamin D receptor",

author = "Daisuke Sawada and Tomoyuki Katayama and Yuya Tsukuda and Nozomi Saito and Masashi Takano and Hiroshi Saito and Takagi, {Ken ichiro} and Eiji Ochiai and Seiichi Ishizuka and Kazuya Takenouchi and Atsushi Kittaka",

note = "Funding Information: We are grateful to Ms. Junko Shimode and Ms. Ayako Kawaji (Teikyo University) for the spectroscopic measurements. This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan (to D.S and N.S.) and by a Grant-in-Aid from the Japan Society for the Promotion of Science (to A.K.). ",

year = "2009",

month = sep,

day = "15",

doi = "10.1016/j.bmcl.2009.07.112",

language = "English",

volume = "19",

pages = "5397--5400",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "18",

}

TY - JOUR

T1 - Synthesis of 2α-substituted-14-epi-previtamin D3 and its genomic activity

AU - Sawada, Daisuke

AU - Katayama, Tomoyuki

AU - Tsukuda, Yuya

AU - Saito, Nozomi

AU - Takano, Masashi

AU - Saito, Hiroshi

AU - Takagi, Ken ichiro

AU - Ochiai, Eiji

AU - Ishizuka, Seiichi

AU - Takenouchi, Kazuya

AU - Kittaka, Atsushi

N1 - Funding Information: We are grateful to Ms. Junko Shimode and Ms. Ayako Kawaji (Teikyo University) for the spectroscopic measurements. This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan (to D.S and N.S.) and by a Grant-in-Aid from the Japan Society for the Promotion of Science (to A.K.).

PY - 2009/9/15

Y1 - 2009/9/15

N2 - We synthesized and isolated 2α-substituted analogs of 14-epi-previtamin D3 after thermal isomerization at 80 °C for the first time. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were evaluated, and the 2α-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D3.

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

KW - 14-Epi-previtamin D

KW - Osteocalcin

KW - Vitamin D

KW - Vitamin D receptor

UR - http://www.scopus.com/inward/record.url?scp=68949092027&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=68949092027&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2009.07.112

DO - 10.1016/j.bmcl.2009.07.112

M3 - Article

C2 - 19692243

AN - SCOPUS:68949092027

SN - 0960-894X

VL - 19

SP - 5397

EP - 5400

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 18

ER -