title: Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: effect of phosphate group and environment of the ammonium cation on their biological activity.
abstract: 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.
authors.affiliation: Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Kalinciakova 8, 832 32 Bratislava, Slovakia. lukac@fpharm.uniba.sk
authors.forename: Milos
authors.initials: M
authors.lastname: Lukác
authors.forename: Ján
authors.initials: J
authors.lastname: Mojzis
authors.forename: Gabriela
authors.initials: G
authors.lastname: Mojzisová
authors.forename: Martin
authors.initials: M
authors.lastname: Mrva
authors.forename: Frantisek
authors.initials: F
authors.lastname: Ondriska
authors.forename: Jindra
authors.initials: J
authors.lastname: Valentová
authors.forename: Ivan
authors.initials: I
authors.lastname: Lacko
authors.forename: Marián
authors.initials: M
authors.lastname: Bukovský
authors.forename: Ferdinand
authors.initials: F
authors.lastname: Devínsky
authors.forename: Janka
authors.initials: J
authors.lastname: Karlovská
mesh_terms: 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
chemical_list: 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