Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride
| Autor: | Mária Garajová, Janka Kubincová, Gabriela Mojžišová, Ferdinand Devínsky, Marián Sabol, Ján Mojžiš, Hana Haragová, Miloš Lukáč, Lenka Varinská, Martin Mrva, František Ondriska |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Antifungal Agents
Surface Properties medicine.drug_class Phosphorylcholine Antineoplastic Agents Cetylpyridinium Chemistry Techniques Synthetic Alkylphosphocholine Structure-Activity Relationship chemistry.chemical_compound Bromide Cell Line Tumor Candida albicans Drug Discovery medicine Humans Organic chemistry Micelles Cell Proliferation Pharmacology biology Cetrimonium Benzethonium chloride Organic Chemistry Biological activity General Medicine biology.organism_classification Acanthamoeba chemistry Critical micelle concentration Benzethonium Cetrimonium Compounds Antiprotozoal Benzalkonium Compounds Nuclear chemistry |
| Zdroj: | European Journal of Medicinal Chemistry. 66:46-55 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2013.05.033 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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