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 language | English |
|---|---|
| Pages (from-to) | 1568-1573 |
| Number of pages | 6 |
| Journal | Bioscience, Biotechnology and Biochemistry |
| Volume | 62 |
| Issue number | 8 |
| Publication status | Published - Aug 1998 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Synthesis and Biological Activities of (-)-6-n-Octyl-indolactam-V, a New Potent Analogue of the Tumor Promoter (-)-Indolactam-V
AU - Nakagawa, Yu
AU - Irie, Kazuhiro
AU - Nakamura, Yoshimasa
AU - Ohigashi, Hajime
AU - Hayashi, Hideo
PY - 1998/8
Y1 - 1998/8
N2 - (-)-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.
AB - (-)-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.
KW - (-)-6-n-octyl-indolactam-V
KW - Epstein-Barr virus
KW - Protein kinase C
KW - Teleocidin
KW - Tumor promoter
UR - http://www.scopus.com/inward/record.url?scp=0032133181&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0032133181&partnerID=8YFLogxK
M3 - Article
C2 - 9757563
AN - SCOPUS:0032133181
VL - 62
SP - 1568
EP - 1573
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
SN - 0916-8451
IS - 8
ER -