title: Synthesis and characterization of fluorescent neutral lipid analogs containing N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-aminohexanoic acid.
abstract: The synthesis, identification and characterization of neutral lipid analogs containing N-(7-nitro-2,1,3-benzoxadiazoi-4-yl)-aminocaproic acid are reported. The acyl-imidazole derivative of the fluorescent fatty acid was used to esterify L-alpha-glycerophosphorylcholine. Fluorescent phosphatidylcholines were converted to the corresponding diacylglycerols by phospholipase C digestion. Triacylglycerols were formed by esterification with either fluorescent fatty acid-imidazole or non-fluorescent fatty acid anhydride. The 11 compounds synthesized were identified by a combination of thin layer chromatography, liquid secondary ion mass spectrometry and enzymatic digestion. A solvent system for identifying all eleven analogs by thin layer chromatography is presented. The fluorescence characteristics of these analogs are consistent with previously observed parameters of NBD-lipid analogs, including the density-dependent quenching of analogs containing multiple NBD fluorophores. These analogs mimic native lipids, as evidenced by digestions with the enzymes, porcine pancreatic lipase, phospholipase C and phospholipase A2.
authors.affiliation: Department of Molecular Genetics, Biochemistry and Microbiology, University of Cincinnati College of Medicine, OH 45267-0524.
authors.forename: J C
authors.initials: JC
authors.lastname: McIntyre
authors.forename: D
authors.initials: D
authors.lastname: Watson
authors.forename: R G
authors.initials: RG
authors.lastname: Sleight
mesh_terms: D009327:4-Chloro-7-nitrobenzofurazan / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000614:Aminocaproates; D015119:Aminocaproic Acid / Q000138:chemical synthesis; D000818:Animals; D001692:Biological Transport; D002855:Chromatography, Thin Layer; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D005990:Glycerol / Q000378:metabolism; D050356:Lipid Metabolism; D008055:Lipids / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D013058:Mass Spectrometry; D013552:Swine
chemical_list: D000614:Aminocaproates; D005456:Fluorescent Dyes; D008055:Lipids; C072800:7-nitrobenzoxadiazole-6-aminohexanoic acid; D009327:4-Chloro-7-nitrobenzofurazan; D005990:Glycerol; D015119:Aminocaproic Acid