Fungal metabolite, epoxyquinol B, crosslinks proteins by epoxy-thiol conjugation

Hiroshi Kamiyama, Takeo Usui, Masakazu Uramoto, Hiroshi Takagi, Mitsuru Shoji, Yujiro Hayashi, Hideaki Kakeya, Hiroyuki Osada

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Epoxyquinol B (EPQB) is a fungal metabolite, containing two α,/β-epoxy ketones. We previously showed that EPQB inhibited the signal transduction involved in angiogenesis through the binding to cysteine residues of receptor kinases. However, the inhibitory mechanism was undefined. In this report, we found that one EPQB molecule is covalently bound to two X-cysteine molecules through two epoxide residues on EPQB. Furthermore, EPQB crosslinked binding proteins through the cysteine residues. These results suggest that EPQB inhibits receptor kinases by crosslinking with other protein or by intramolecular crosslinking.

Original languageEnglish
Pages (from-to)94-97
Number of pages4
JournalJournal of Antibiotics
Volume61
Issue number2
DOIs
Publication statusPublished - 2008 Feb
Externally publishedYes

Fingerprint

Sulfhydryl Compounds
Cysteine
Proteins
Phosphotransferases
Epoxy Compounds
Ketones
epoxyquinol B
Signal Transduction
Carrier Proteins

Keywords

  • Crosslink
  • Cysteine
  • Epoxide
  • Epoxyquinoid
  • Epoxyquinol B
  • Fungal metabolite

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Molecular Medicine

Cite this

Kamiyama, H., Usui, T., Uramoto, M., Takagi, H., Shoji, M., Hayashi, Y., ... Osada, H. (2008). Fungal metabolite, epoxyquinol B, crosslinks proteins by epoxy-thiol conjugation. Journal of Antibiotics, 61(2), 94-97. https://doi.org/10.1038/ja.2008.117

Fungal metabolite, epoxyquinol B, crosslinks proteins by epoxy-thiol conjugation. / Kamiyama, Hiroshi; Usui, Takeo; Uramoto, Masakazu; Takagi, Hiroshi; Shoji, Mitsuru; Hayashi, Yujiro; Kakeya, Hideaki; Osada, Hiroyuki.

In: Journal of Antibiotics, Vol. 61, No. 2, 02.2008, p. 94-97.

Research output: Contribution to journalArticle

Kamiyama, H, Usui, T, Uramoto, M, Takagi, H, Shoji, M, Hayashi, Y, Kakeya, H & Osada, H 2008, 'Fungal metabolite, epoxyquinol B, crosslinks proteins by epoxy-thiol conjugation', Journal of Antibiotics, vol. 61, no. 2, pp. 94-97. https://doi.org/10.1038/ja.2008.117
Kamiyama H, Usui T, Uramoto M, Takagi H, Shoji M, Hayashi Y et al. Fungal metabolite, epoxyquinol B, crosslinks proteins by epoxy-thiol conjugation. Journal of Antibiotics. 2008 Feb;61(2):94-97. https://doi.org/10.1038/ja.2008.117
Kamiyama, Hiroshi ; Usui, Takeo ; Uramoto, Masakazu ; Takagi, Hiroshi ; Shoji, Mitsuru ; Hayashi, Yujiro ; Kakeya, Hideaki ; Osada, Hiroyuki. / Fungal metabolite, epoxyquinol B, crosslinks proteins by epoxy-thiol conjugation. In: Journal of Antibiotics. 2008 ; Vol. 61, No. 2. pp. 94-97.
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