Synthesis and biological activity of fatty acid derivatives of quinine.
Derivatives of quinine with fatty acids including polyunsaturated fatty acids were prepared. They showed moderate antimalarial activity as compared with quinine itself using Plasmodium falciparum. The activities were not dependent on whether the fatty acyl group was saturated or unsaturated. On the other hand, the derivatives showed significantly higher cytotoxicity against a mammary tumor cell line FM3A than quinine itself. Calculating from these data, an acetyl derivative of quinine with the shortest acyl group was found to give the highest selectivity.
Kumura
Naokazu
N
Department of Biofunctional Chemistry, Graduate School of Natural Science and Technology, Okayama University, Japan.
Izumi
Minoru
M
Nakajima
Shuhei
S
Shimizu
Sakayu
S
Kim
Hye-Sook
HS
Wataya
Yusuke
Y
Baba
Naomichi
N
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001943:Breast Neoplasms / Q000188:drug therapy / Q000473:pathology; D045744:Cell Line, Tumor; D005227:Fatty Acids / Q000737:chemistry*; D005260:Female; D051379:Mice; D010963:Plasmodium falciparum / Q000187:drug effects; D011803:Quinine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000962:Antimalarials; D000970:Antineoplastic Agents; D005227:Fatty Acids; D011803:Quinine