Chemical syntheses of novel fluorescent-labelled fatty acids, phosphatidylcholines and cholesterol esters.

The synthesis of a novel class of fluorescent-labelled fatty acids of different chain lengths and unsaturation, phospholipids and cholesterol esters has been developed. The following omega-anthracene-labelled cis-unsaturated fatty acids have been synthesized: omega-(9-anthryl)-6c-octenoic, -7c-nonenoic, -10c-dodecenoic, -6c,9c-undecadienoic, -10c,13c-pentadecadienoic acid. They have been introduced into the 2-position of 1-stearoyl- and 1-linoleoyl-3-sn-glycerophosphocholine and cholesterol. Mass spectroscopy, 1H-NMR, IR and fluorescence spectroscopy and different chromatographic procedures have been applied to confirm and characterize their structures. The properties of the different fluorescent-labelled phosphatidylcholines in monomolecular films have been determined by the Langmuir technique.