Biological Activities of Novel Derivatives of Differentiation-Inducing Factor 3 from Dictyostelium discoideum

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  • Takahashi Katsunori
    Department of Medical Technology, Faculty of Health Science, Gunma Paz College
  • Kikuchi Haruhisa
    Laboratory of Natural Product Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
  • Nguyen Van Hai
    Laboratory of Natural Product Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
  • Oshima Yoshiteru
    Laboratory of Natural Product Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
  • Ishigaki Hirotaka
    Department of Medical Technology, Faculty of Health Science, Gunma Paz College
  • Nakajima-Shimada Junko
    Department of Molecular and Cellular Parasitology, Graduate School of Health Sciences, Gunma University
  • Kubohara Yuzuru
    Laboratory of Health and Life Science, Graduate School of Heath and Sports Science, Juntendo University

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  • Biological Activities of Novel Derivatives of Differentiation-Inducing Factor 3 from <i>Dictyostelium discoideum</i>

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<p>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.</p>

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