Synthesis and biological activities of reveromycin A and spirofungin A derivatives.
Various derivatives of reveromycin A, an inhibitor of eukaryotic cell growth, and spirofungin A, focusing on the 5S hydroxyl group and C18 hemisuccinyl group, were synthesized and their inhibitory effects on both the isoleucyl-tRNA synthetase activity and the survival of osteoclasts, and activities on the morphological reversion of src(ts)-NRK cells were examined. It was found that 2,3-dihydroreveromycin A is the promising derivative of reveromycin A based on the activity and stability.
Shimizu
Takeshi
T
Synthetic Organic Chemistry Laboratory, RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. tshimizu@riken.jp
Usui
Takeo
T
Fujikura
Makoto
M
Kawatani
Makoto
M
Satoh
Tomoharu
T
Machida
Kiyotaka
K
Kanoh
Naoki
N
Woo
Je-Tae
JT
Osada
Hiroyuki
H
Sodeoka
Mikiko
M
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002453:Cell Cycle; D002626:Chemistry, Pharmaceutical / Q000379:methods; D020128:Inhibitory Concentration 50; D007533:Isoleucine-tRNA Ligase / Q000737:chemistry; D007668:Kidney / Q000166:cytology; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D010010:Osteoclasts / Q000378:metabolism*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013302:Streptomyces / Q000378:metabolism; D013386:Succinates / Q000737:chemistry
D000900:Anti-Bacterial Agents; D011714:Pyrans; D013141:Spiro Compounds; D013386:Succinates; C114877:spirofungin A; C068098:reveromycin A; D007533:Isoleucine-tRNA Ligase