Biological activities of novel derivatives of differentiation-inducing factor 3 from Dictyostelium discoideum

Katsunori Takahashi, Haruhisa Kikuchi, Van Hai Nguyen, Yoshiteru Oshima, Hirotaka Ishigaki, Junko Nakajima-Shimada, Yuzuru Kubohara

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


Differentiation-inducing factor-3 (DIF-3; 1-(3-chloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one), which is found in the cellular slime mold Dictyostelium discoideum, is a potential candidate compound for the development of new medicines; DIF-3 and its derivatives possess several beneficial biological activities, including anti-tumor, anti-Trypanosoma cruzi, and immunoregulatory effects. To assess the relationship between the biological activities of DIF-3 and its chemical structure, particularly in regard to its alkoxy group and the length of the alkyl chains at the acyl group, we synthesized two derivatives of DIF-3, 1-(3-chloro-2,6-dihydroxy-4-methoxyphenyl)octan-1-one (DIF-3(+3)) and 1-(3-chloro-2,6-dihydroxy-4-butoxyphenyl)-hexan- 1-one (Hex-DIF-3), and investigated their biological activities in vitro. At micro-molar levels, DIF-3(+3) and Hex-DIF-3 exhibited strong anti-proliferative effects in tumor cell cultures, but their anti-T. cruzi activities at 1 μM in vitro were not as strong as those of other known DIF derivatives. In addition, Hex-DIF-3 at 5 μM significantly suppressed mitogen-induced interleukin-2 production in vitro in Jurkat T cells. These results suggest that DIF-3(+3) and Hex-DIF-3 are promising leads for the development of anti-cancer and immunosuppressive agents.

Original languageEnglish
Pages (from-to)1941-1947
Number of pages7
JournalBiological and Pharmaceutical Bulletin
Issue number11
Publication statusPublished - 2017
Externally publishedYes


  • Anti-tumor agent
  • Dictyostelium discoideum
  • Interleukin-2
  • Jurkat cell
  • Trypanosoma cruzi

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science


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