Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: effect of phosphate group and environment of the ammonium cation on their biological activity.
A series of dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimethylammonium bromide have been synthesized. The prepared compounds exhibit significant cytotoxic, antifungal and antiprotozoal activities. Alkylphosphocholines possess higher antifungal activity against Candida albicans in comparison with quaternary ammonium compounds. However, quaternary ammonium compounds exhibit significant higher activity against human tumor cells and Acanthamoeba lugdunensis compared to alkylphosphocholines. In addition, their haemolytic toxicity has been investigated. The relationship between structure and biological activity of the tested compounds is discussed.
Lukác
Milos
M
Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Kalinciakova 8, 832 32 Bratislava, Slovakia. lukac@fpharm.uniba.sk
Mojzis
Ján
J
Mojzisová
Gabriela
G
Mrva
Martin
M
Ondriska
Frantisek
F
Valentová
Jindra
J
Lacko
Ivan
I
Bukovský
Marián
M
Devínsky
Ferdinand
F
Karlovská
Janka
J
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D002412:Cations; D045744:Cell Line, Tumor; D000077286:Cetrimonium; D002593:Cetrimonium Compounds / Q000737:chemistry* / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D010767:Phosphorylcholine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000644:Quaternary Ammonium Compounds / Q000737:chemistry
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D002412:Cations; D002593:Cetrimonium Compounds; D006571:Heterocyclic Compounds; D010710:Phosphates; D000644:Quaternary Ammonium Compounds; D010767:Phosphorylcholine; C039128:miltefosine; D009584:Nitrogen; D000077286:Cetrimonium