149576-40-9Relevant academic research and scientific papers
Synthesis of Phosphocholine and Quaternary Amine Ether Lipids and Evaluation of in Vitro Antineoplastic Activity
Morris-Natschke, Susan L.,Gumus, Fatma,Marasco, Canio J.,Meyer, Karen L.,Marx, Michael,et al.
, p. 2018 - 2025 (2007/10/02)
The in vitro antineoplastic activity of many phosphorus-containing (e.g., phosphocholines) and non-phosphorus-containing (e.g., quaternary ammonium salts) ether lipids has been evaluated in the HL-60 promyelocytic cell line.These compounds are analogues of ET-18-OMe (1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine).Structural modification of 1-(alkylamido)-, -(alkylthio)-, and -(alkyloxy)propyl backbones has provided further insight into the structure-activity relationships of these lipids.In this study, a long saturated C-1 chain and a three-carbon backbone with a single short C-2 substituent were preferred.At the positively charged nitrogen of phosphocholines, fewer than three substituents caused a significant loss of activity, and substituents larger than methyl decreased activity slightly.In the nonphosphorus compounds, many nitrogen heterocycles and also a sulfonium moiety were incorporated without changing the degree of activity; however, a thiazolium group decreased activity.The most active compound, 29 -3-(hydroxymethyl)pyridinium bromide>, was approximately twice as active as the reference standard, ET-18-OMe, in a trypan blue dye exclusion assay.
