Biological activities and cellular uptake studies of fluorescent derivatives of indole alkaloid tumor promoter teleocidin
✍ Scribed by Kazuhiro Irie; Shigenori Okuno; Koichi Koshimizu; Harukuni Tokuda; Hoyoku Nishino; Akio Iwashima
- Book ID
- 102868561
- Publisher
- John Wiley and Sons
- Year
- 1989
- Tongue
- French
- Weight
- 997 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0020-7136
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✦ Synopsis
To investigate the interaction between tumor promoters and their cellular targets, 6 new fluorescent derivatives of indole alkaloid tumor promoter teleocidin were synthesized from (-)-indolactam V, and examined for induction of Epstein-Barr virus, binding ability to the TPA receptor on mouse skin and activation of protein kinase C. ( -) -7 -( 2 -N -Dansylaminoethyl)indolactam V (dansyl-ILV) had strong activities and proved to be a potent tumor promoter in a 2stage carcinogenesis experiment. (-)-2-Formyl-7-decanoylindolactam V (FD-ILV) showed a weak but significant activity. The other 4 derivatives had little activity. Treatment of HeLa cells with dansyl-ILV and FD-ILV resulted in intense fluorescence in the entire cytoplasm and on the nuclear membrane.
Inactive or less active derivatives with hydrophobicity similar to that of dansyl-ILV showed significant cytoplasmic fluorescence, and those far less hydrophobic than dansyl-ILV or far more hydrophobic than FD-ILV showed little fluorescence. This suggested that hydrophobicity rather than biological activity determines the cellular uptake of these fluorescent probes.
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