Structure-activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines

Yoshitomo Suhara, Akimori Wada, Yoji Tachibana, Masato Watanabe, Kanae Nakamura, Kimie Nakagawa, Toshio Okano

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

To reveal an essential biological role of menaquinone-4, we have clarified that dietary PK was converted to menaquinone-4 (MK-4) in animal tissues using deuterated vitamin K analogues. However, the kinds of analogue converted into MK-4 have not been elucidated. In this study, we examined structure-activity relationships in the conversion of several vitamin K analogues, with a substituted side chain, into MK-4 using cultured human cell lines. The results differed with the side chain of the analogues, that is, (1) the length of the isoprene unit and (2) the number of double bonds in the side chain. These findings would be useful for clarifying the mechanism of conversion of other vitamin K homologs into MK-4 as well as related enzymes.

Original languageEnglish
Pages (from-to)3116-3124
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number9
DOIs
Publication statusPublished - 2010 May 1
Externally publishedYes

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Vitamin K
Cells
Substrates
Animals
Tissue
Enzymes
menatetrenone

Keywords

  • Analogues
  • Conversion
  • Deuterated compound
  • Menaquinone-4
  • Structure-activity relationships
  • Vitamin K

ASJC Scopus subject areas

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

Cite this

Structure-activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines. / Suhara, Yoshitomo; Wada, Akimori; Tachibana, Yoji; Watanabe, Masato; Nakamura, Kanae; Nakagawa, Kimie; Okano, Toshio.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 9, 01.05.2010, p. 3116-3124.

Research output: Contribution to journalArticle

Suhara, Yoshitomo ; Wada, Akimori ; Tachibana, Yoji ; Watanabe, Masato ; Nakamura, Kanae ; Nakagawa, Kimie ; Okano, Toshio. / Structure-activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines. In: Bioorganic and Medicinal Chemistry. 2010 ; Vol. 18, No. 9. pp. 3116-3124.
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