Synthesis of 25-hydroxy-19-norvitamin D3 analogs and their antiproliferative activities on prostate cells

Midori A. Arai; Ryuji Tsutsumi; Hideki Hara; Tai C. Chen; Toshiyuki Sakaki; Naoko Urushino; Kuniyo Inouye; Atsushi Kittaka

doi:10.3987/com-05-s(k)56

Synthesis of 25-hydroxy-19-norvitamin D₃ analogs and their antiproliferative activities on prostate cells

Midori A. Arai, Ryuji Tsutsumi, Hideki Hara, Tai C. Chen, Toshiyuki Sakaki, Naoko Urushino, Kuniyo Inouye, Atsushi Kittaka

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

15 Citations (Scopus)

Abstract

Synthesis of 25-hydroxy-19-norvitamin D₃ derivatives as prohormone type agents for anti-prostate diseases was accomplished utilizing Julia-type olefination. Synthesized compounds showed potent antiproliferative activity on an immortalized normal prostate cell line, PZ-HPV-7, which has high 1α-hydroxylase activity. Furthermore, we demonstrated that 25-hydroxy-19-norvitamin D₃ was hydroxylated at the 1α position to form 1α,25-dihydroxy-19-norvitamin D₃ by a recombinant human 1α-hydroxylase (CYP27B1) in a cell-free system.

Original language	English
Pages (from-to)	469-479
Number of pages	11
Journal	Heterocycles
Volume	66
Issue number	1
DOIs	https://doi.org/10.3987/com-05-s(k)56
Publication status	Published - 2005 Dec 31
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.3987/com-05-s(k)56

Cite this

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title = "Synthesis of 25-hydroxy-19-norvitamin D3 analogs and their antiproliferative activities on prostate cells",

abstract = "Synthesis of 25-hydroxy-19-norvitamin D3 derivatives as prohormone type agents for anti-prostate diseases was accomplished utilizing Julia-type olefination. Synthesized compounds showed potent antiproliferative activity on an immortalized normal prostate cell line, PZ-HPV-7, which has high 1α-hydroxylase activity. Furthermore, we demonstrated that 25-hydroxy-19-norvitamin D3 was hydroxylated at the 1α position to form 1α,25-dihydroxy-19-norvitamin D3 by a recombinant human 1α-hydroxylase (CYP27B1) in a cell-free system.",

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T1 - Synthesis of 25-hydroxy-19-norvitamin D3 analogs and their antiproliferative activities on prostate cells

AU - Arai, Midori A.

AU - Tsutsumi, Ryuji

AU - Hara, Hideki

AU - Chen, Tai C.

AU - Sakaki, Toshiyuki

AU - Urushino, Naoko

AU - Inouye, Kuniyo

AU - Kittaka, Atsushi

PY - 2005/12/31

Y1 - 2005/12/31

N2 - Synthesis of 25-hydroxy-19-norvitamin D3 derivatives as prohormone type agents for anti-prostate diseases was accomplished utilizing Julia-type olefination. Synthesized compounds showed potent antiproliferative activity on an immortalized normal prostate cell line, PZ-HPV-7, which has high 1α-hydroxylase activity. Furthermore, we demonstrated that 25-hydroxy-19-norvitamin D3 was hydroxylated at the 1α position to form 1α,25-dihydroxy-19-norvitamin D3 by a recombinant human 1α-hydroxylase (CYP27B1) in a cell-free system.

AB - Synthesis of 25-hydroxy-19-norvitamin D3 derivatives as prohormone type agents for anti-prostate diseases was accomplished utilizing Julia-type olefination. Synthesized compounds showed potent antiproliferative activity on an immortalized normal prostate cell line, PZ-HPV-7, which has high 1α-hydroxylase activity. Furthermore, we demonstrated that 25-hydroxy-19-norvitamin D3 was hydroxylated at the 1α position to form 1α,25-dihydroxy-19-norvitamin D3 by a recombinant human 1α-hydroxylase (CYP27B1) in a cell-free system.

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