Synthesis and Biological Activities of (-)-6-n-Octyl-indolactam-V, a New Potent Analogue of the Tumor Promoter (-)-Indolactam-V

Yu Nakagawa, Kazuhiro Irie, Yoshimasa Nakamura, Hajime Ohigashi, Hideo Hayashi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

(-)-Indolactam-V (1) without a hydrophobic chain at positions 6 and 7 of the indole ring is a weak tumor promoter compared with teleocidin Bs. To investigate the effects of the hydrophobic substituent at position 6 of teleocidin Bs, we synthesized (-)-6-n-octyl-indolactam-V (2) by a palladium-catalyzed coupling reaction from (-)-6-bromo-indolactam-V (7) which had been obtained by microbial conversion with Streptoverticillium blastmyceticum NA34-17 as the key step. (-)-7-n-Octyl-indolactam-V (3) with potent biological activities comparable to those of teleocidin Bs was similarly synthesized from (-)-7-bromo-indolactam-V as a positive control. Compound 2 showed similar biological activities to those of 3, indicating that the effect of the hydrophobic substituent at position 6 of 1 was identical to that at position 7.

Original languageEnglish
Pages (from-to)1568-1573
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Volume62
Issue number8
Publication statusPublished - Aug 1998
Externally publishedYes

Fingerprint

Bioactivity
Streptomyces blastmyceticus
Carcinogens
bioactive properties
Tumors
palladium
neoplasms
synthesis
indoles
Palladium
teleocidins
indolactam V
6-n-octyl-indolactam V

Keywords

  • (-)-6-n-octyl-indolactam-V
  • Epstein-Barr virus
  • Protein kinase C
  • Teleocidin
  • Tumor promoter

ASJC Scopus subject areas

  • Food Science
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biotechnology
  • Chemistry (miscellaneous)
  • Applied Microbiology and Biotechnology
  • Bioengineering

Cite this

Synthesis and Biological Activities of (-)-6-n-Octyl-indolactam-V, a New Potent Analogue of the Tumor Promoter (-)-Indolactam-V. / Nakagawa, Yu; Irie, Kazuhiro; Nakamura, Yoshimasa; Ohigashi, Hajime; Hayashi, Hideo.

In: Bioscience, Biotechnology and Biochemistry, Vol. 62, No. 8, 08.1998, p. 1568-1573.

Research output: Contribution to journalArticle

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