A novel potent cell cycle inhibitor dehydrophenylahistin--enzymatic synthesis and inhibitory activity toward sea urchin embryo.
A novel dehydrogenated cyclic dipeptide named as dehydrophenylahistin (deltaPLH) was effectively prepared from a fungal metabolite (-)-phenylahistin by the enzymatic conversion catalyzed by the cell-free extract of Streptomyces albulus KO-23, an albonoursin-producing actinomycete. deltaPLH exhibited more than 1,000 times as high potent inhibitory activity toward the first cleavage of sea urchin embryos as (-)-phenylahisitn which has been reported to be a cell cycle inhibitor and more than 10,000 as high as albonoursin, indicating that deltaPLH is a promising leading compound for anticancer drugs.
Kanzaki
Hiroshi
H
Laboratory of Bioresources Chemistry, Faculty of Agriculture, Okayama University, Okayama 700-8530, Japan. hkanzaki@cc.okayama-u.ac.jp
Yanagisawa
Satohiro
S
Kanoh
Kaneo
K
Nitoda
Teruhiko
T
D000818:Animals; D002453:Cell Cycle / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D054659:Diketopiperazines; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004625:Embryo, Nonmammalian / Q000166:cytology / Q000187:drug effects; D004798:Enzymes / Q000378:metabolism; D020128:Inhibitory Concentration 50; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D010879:Piperazines / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D012617:Sea Urchins / Q000187:drug effects / Q000196:embryology*; D013302:Streptomyces / Q000201:enzymology
D054659:Diketopiperazines; D004798:Enzymes; D010456:Peptides, Cyclic; D010879:Piperazines; C472173:dehydrophenylahistin; C119340:phenylahistin; C006442:albonoursin