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...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2005, Vol.69 (11), p.2250-2253
Main Authors: Kumura, N.(Okayama Univ. (Japan)), Izumi, M, Nakajima, S, Shimizu, S, Kim, H.S, Wataya, Y, Baba, N
Format: Article
Language:English
Subjects:
ACIDE GRAS
ACIDOS GRASOS
ALCALOIDE QUINOLIQUE
ALCALOIDES DE LA QUINOLINA
Animals
ANTIBIOTICOS
ANTIBIOTICS
ANTIBIOTIQUE
antimalarial activity
Antimalarials - chemical synthesis
Antimalarials - pharmacology
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Biological and medical sciences
Breast Neoplasms - drug therapy
Breast Neoplasms - pathology
Cell Line, Tumor
CHEMICAL SYNTHESIS
COMPLEXACION
COMPLEXATION
COMPLEXING
COMPOSE ORGANIQUE
COMPUESTOS ORGANICOS
fatty acid
FATTY ACIDS
Fatty Acids - chemistry
Female
Fundamental and applied biological sciences. Psychology
MALARIA
Mice
NEOPLASMAS
NEOPLASME
NEOPLASMS
ORGANIC COMPOUNDS
PLASMODIUM FALCIPARUM
Plasmodium falciparum - drug effects
quinine
Quinine - analogs & derivatives
Quinine - chemical synthesis
Quinine - pharmacology
QUINOLINE ALKALOIDS
SINTESIS QUIMICA
Structure-Activity Relationship
SYNTHESE CHIMIQUE
TOXICIDAD
TOXICITE
TOXICITY
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Description
Summary: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.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.69.2250