Synthesis and biological property of carba and 20-deoxo analogues of arenastatin A.
The carba analogue, in which a methylene group is substituted for the oxygen atom linked to C-15, and 20-deoxo analogue of arenastatin A, a potent cytotoxic spongean depsipeptide, were synthesized. Both analogues lacking the 15,20-ester function, which was easily metabolized in serum, showed good stability in serum as well as moderate cytotoxic activity against KB cells and better solubility.
Murakami
N
N
Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Japan.
Wang
W
W
Tamura
S
S
Kobayashi
M
M
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects; D003500:Cyclization; D047630:Depsipeptides; D004355:Drug Stability; D006801:Humans; D007624:KB Cells; D051379:Mice; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*
C418103:15-carbaarenastatin A; C418104:20-deoxoarenastatin A; D000970:Antineoplastic Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C096566:arenastatin A