title: The chemical synthesis and cytotoxicity of new sulfur analogues of 2-methoxy-lysophosphatidylcholine.
abstract: The chemical synthesis of phosphorothioate/phosphorodithioate analogues of 2-methoxy-lysophosphatidylcholine has been described. For the preparation of new sulfur derivatives of lysophosphatidylcholine both oxathiaphospholane and dithiaphospholane approaches have been employed. Each lysophospholipid analogue was synthesized as a series of five compounds, bearing different fatty acid residues both saturated (12:0, 14:0, 16:0, 18:0) and unsaturated (18:1). The methylation of glycerol 2-hydroxyl function was applied in order to increase the stability of prepared analogues by preventing 1 → 2 acyl migration. The cellular toxicity of newly synthesized 2-methoxy-lysophosphatidylcholine derivatives was measured using MTT viability assay and lactate dehydrogenase release method.
authors.affiliation: Institute of Technical Biochemistry, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Stefanowskiego 4/10, 90-924 Lodz, Poland.
authors.forename: Przemysław
authors.initials: P
authors.lastname: Rytczak
authors.forename: Anna
authors.initials: A
authors.lastname: Drzazga
authors.forename: Edyta
authors.initials: E
authors.lastname: Gendaszewska-Darmach
authors.forename: Andrzej
authors.initials: A
authors.lastname: Okruszek
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005227:Fatty Acids / Q000737:chemistry; D008244:Lysophosphatidylcholines / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D051379:Mice; D013329:Structure-Activity Relationship; D013455:Sulfur / Q000737:chemistry*
chemical_list: D005227:Fatty Acids; D008244:Lysophosphatidylcholines; D013455:Sulfur
keywords: 2-Methoxylation; Cytotoxicity; Lysophosphatidylcholine analogues; Phosphorodithioates; Phosphorothioates