Synthesis and biological activities of the marine bryozoan alkaloids convolutamines A, C and F, and lutamides A and C.
Synthesis of convolutamines and lutamides, new 2,4,6-tribromo-3-methoxyphenethylamine alkaloids isolated from Floridian marine bryozoan Amathia convoluta, was accomplished by a sequence of reactions starting from 3-hydroxyphenethylamines. Cytotoxities of the synthetic lutamides, convolutamines and their de-O-methyl derivatives were examined using drug-sensitive and -resistant P388 as well as KB cell lines. The bioassay suggests that the 2,4,6-tribromo-3-methoxyphenethylamine is an indispensable unit for detection of the activities. Additionally, a reversal of drug resistance by those alkaloids is recognized.
Hashima
H
H
Department of Biological Science, Kanagawa University, Hiratsuka, Japan.
Hayashi
M
M
Kamano
Y
Y
Sato
N
N
D000470:Alkaloids / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D002013:Bryozoa / Q000737:chemistry*; D002455:Cell Division / Q000187:drug effects; D004317:Doxorubicin / Q000494:pharmacology; D019008:Drug Resistance, Neoplasm; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D010063:Ovum / Q000166:cytology / Q000187:drug effects; D010627:Phenethylamines / Q000138:chemical synthesis / Q000494:pharmacology*; D012617:Sea Urchins / Q000166:cytology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D014750:Vincristine / Q000494:pharmacology
D000470:Alkaloids; D000970:Antineoplastic Agents; D010627:Phenethylamines; D014750:Vincristine; D004317:Doxorubicin