Systematic synthesis of low-molecular weight fucoidan derivatives and their effect on cancer cells

Akihiro Kasai, Shinsuke Arafuka, Nozomi Koshiba, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Low-molecular weight type I and II fucoidan derivatives with different sulfation patterns were designed and systematically synthesized from the corresponding common key intermediate and their anti-proliferative activities and apoptosis-inducing activities against human breast cancer (MCF-7) and human cervical epithelioid carcinoma (HeLa) cells were evaluated. Our results demonstrated that one of the type II fucoidan derivatives, 9, effectively reduced the number of viable MCF-7 and HeLa cells in a dose-dependent manner without causing cytotoxicity toward normal WI-38 cells, and that the anti-proliferative activity of 9 was comparable to that of fucoidan 2 isolated from Fucus vesiculosus. Moreover, it was found that both 2 and 9 exhibited similar apoptosis-inducing activities through activation of caspase-8 and -9 on MCF-7 and HeLa cells, respectively.

Original languageEnglish
Pages (from-to)10556-10568
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number42
DOIs
Publication statusPublished - 2015

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low molecular weights
HeLa Cells
Molecular Weight
cancer
Molecular weight
MCF-7 Cells
Cells
Derivatives
apoptosis
synthesis
Fucus
cells
Apoptosis
Neoplasms
Caspase 9
Caspase 8
sulfation
Cytotoxicity
Human Activities
Chemical activation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Systematic synthesis of low-molecular weight fucoidan derivatives and their effect on cancer cells. / Kasai, Akihiro; Arafuka, Shinsuke; Koshiba, Nozomi; Takahashi, Daisuke; Toshima, Kazunobu.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 42, 2015, p. 10556-10568.

Research output: Contribution to journalArticle

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