Synthesis and biological activities of chaetocin and its derivatives

Chaetocin, a natural product isolated from fungi of species, is a member of the epipolythiodiketopiperazines (ETPs), which have various biological activities, including cytostatic and anticancer activities. Recently, the inhibitory activity toward histone methyltransferases (HMTs) was discovered for...

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Bibliographic Details
Published in:Pure and applied chemistry 2012-04, Vol.84 (6), p.1369-1378
Main Authors: Sodeoka, Mikiko, Dodo, Kosuke, Teng, Yuou, Iuchi, Katsuya, Hamashima, Yoshitaka, Iwasa, Eriko, Fujishiro, Shinya
Format: Article
Language:English
Subjects:
anticancer activity
Anticancer properties
antitumor activity
Apoptosis
bioactive molecules
chaetocin
Derivatives
Enantiomers
histone methyltransferase
Natural products
Synthesis
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Summary:Chaetocin, a natural product isolated from fungi of species, is a member of the epipolythiodiketopiperazines (ETPs), which have various biological activities, including cytostatic and anticancer activities. Recently, the inhibitory activity toward histone methyltransferases (HMTs) was discovered for chaetocin. We previously reported the first total synthesis of chaetocin and various derivatives. During studies on the structure–activity relationship for HMT inhibition, we found that the enantiomer of chaetocin ( -chaetocin) is a more potent apoptosis inducer than natural chaetocin in human leukemia HL-60 cells. Mechanistic studies showed that -chaetocin induces apoptosis through the caspase-8/caspase-3 pathway.
ISSN:0033-4545
1365-3075
DOI:10.1351/PAC-CON-11-10-31