Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution

Naoto Kojima, Takekuni Morioka, Daisuke Urabe, Masahiro Yano, Yuki Suga, Naoyoshi Maezaki, Ayako Ohashi-Kobayashi, Yasuyuki Fujimoto, Masatomo Maeda, Takao Yamori, Takehiko Yoshimitsu, Tetsuaki Tanaka

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an α,β-unsaturated γ-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria.

Original languageEnglish
Pages (from-to)8630-8641
Number of pages12
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number24
DOIs
Publication statusPublished - Dec 15 2010
Externally publishedYes

Fingerprint

Acetogenins
Benzethonium
Alkynes
Visualization
Fluorescence
Mitochondria
Lactones
Hydrocarbons
Fluorescent Dyes
Human Activities
Assays
Cells
Cell Line
Growth
Neoplasms

Keywords

  • Annonaceous acetogenins
  • Antitumor agents
  • Cell distribution
  • Convergent synthesis
  • Fluorescence-labeled analogues

ASJC Scopus subject areas

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

Cite this

Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution. / Kojima, Naoto; Morioka, Takekuni; Urabe, Daisuke; Yano, Masahiro; Suga, Yuki; Maezaki, Naoyoshi; Ohashi-Kobayashi, Ayako; Fujimoto, Yasuyuki; Maeda, Masatomo; Yamori, Takao; Yoshimitsu, Takehiko; Tanaka, Tetsuaki.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 24, 15.12.2010, p. 8630-8641.

Research output: Contribution to journalArticle

Kojima, N, Morioka, T, Urabe, D, Yano, M, Suga, Y, Maezaki, N, Ohashi-Kobayashi, A, Fujimoto, Y, Maeda, M, Yamori, T, Yoshimitsu, T & Tanaka, T 2010, 'Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution', Bioorganic and Medicinal Chemistry, vol. 18, no. 24, pp. 8630-8641. https://doi.org/10.1016/j.bmc.2010.10.004
Kojima, Naoto ; Morioka, Takekuni ; Urabe, Daisuke ; Yano, Masahiro ; Suga, Yuki ; Maezaki, Naoyoshi ; Ohashi-Kobayashi, Ayako ; Fujimoto, Yasuyuki ; Maeda, Masatomo ; Yamori, Takao ; Yoshimitsu, Takehiko ; Tanaka, Tetsuaki. / Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution. In: Bioorganic and Medicinal Chemistry. 2010 ; Vol. 18, No. 24. pp. 8630-8641.
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