title: Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride.
abstract: A series of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride have been synthesized. Their physicochemical properties were also investigated. The critical micelle concentration (cmc), the surface tension value at the cmc (γcmc), and the surface area at the surface saturation per head group (Acmc) were determined by means of surface tension measurements. The prepared compounds exhibit significant cytotoxic, antifungal and antiprotozoal activities. Alkylphosphocholines and alkylphosphohomocholines possess higher antifungal activity against Candida albicans in comparison with quaternary ammonium compounds in general. However, quaternary ammonium compounds exhibit significantly higher activity against human tumor cells and pathogenic free-living amoebae Acanthamoeba lugdunensis and Acanthamoeba quina compared to alkylphosphocholines. The relationship between structure, physicochemical properties and biological activity of the tested compounds is discussed.
authors.affiliation: Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Kalinčiakova 8, 832 32 Bratislava, Slovakia. lukac@fpharm.uniba.sk
authors.forename: Miloš
authors.initials: M
authors.lastname: Lukáč
authors.forename: Martin
authors.initials: M
authors.lastname: Mrva
authors.forename: Mária
authors.initials: M
authors.lastname: Garajová
authors.forename: Gabriela
authors.initials: G
authors.lastname: Mojžišová
authors.forename: Lenka
authors.initials: L
authors.lastname: Varinská
authors.forename: Ján
authors.initials: J
authors.lastname: Mojžiš
authors.forename: Marián
authors.initials: M
authors.lastname: Sabol
authors.forename: Janka
authors.initials: J
authors.lastname: Kubincová
authors.forename: Hana
authors.initials: H
authors.lastname: Haragová
authors.forename: František
authors.initials: F
authors.lastname: Ondriska
authors.forename: Ferdinand
authors.initials: F
authors.lastname: Devínsky
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001548:Benzalkonium Compounds / Q000737:chemistry*; D001558:Benzethonium / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D000077286:Cetrimonium; D002593:Cetrimonium Compounds / Q000737:chemistry*; D002594:Cetylpyridinium / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D006801:Humans; D008823:Micelles; D010767:Phosphorylcholine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013499:Surface Properties
chemical_list: D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001548:Benzalkonium Compounds; D002593:Cetrimonium Compounds; D008823:Micelles; D010767:Phosphorylcholine; D001558:Benzethonium; D002594:Cetylpyridinium; D000077286:Cetrimonium
keywords: Acanthamoeba; Alkylphosphocholines; Candida albicans; Critical micelle concentration; Cytotoxic activity; Quaternary ammonium compounds