Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens.
To obtain information of structure-activity relationships (SARs) of 13-deoxytedanolide, its chemical transformation has been carried out, targeting on such functional groups as an epoxide, hydroxyls, ketones, and olefins. A total of 10 derivatives have been prepared and their cytotoxicity against P388 murine leukemia cells and inhibitory activity of polypeptide elongation in yeast cell lysate provided some important SARs; the southern hemisphere comprises the pharmacophore, while the epoxide-bearing side chain is essential for the activity.
Nishimura
Shinichi
S
Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
Matsunaga
Shigeki
S
Yoshida
Satoru
S
Nakao
Yoichi
Y
Hirota
Hiroshi
H
Fusetani
Nobuhiro
N
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D018942:Macrolides / Q000737:chemistry* / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D011161:Porifera; D011500:Protein Synthesis Inhibitors / Q000737:chemistry / Q000494:pharmacology; D012441:Saccharomyces cerevisiae; D013329:Structure-Activity Relationship
C409106:13-deoxytedanolide; D000970:Antineoplastic Agents; D018942:Macrolides; D011500:Protein Synthesis Inhibitors