J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M500493-JLR200 on December 20, 2005

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Journal of Lipid Research, Vol. 47, 633-642, March 2006
Copyright © 2006 by American Society for Biochemistry and Molecular Biology

Synthesis and biological properties of the fluorescent ether lipid precursor 1-O-[9'-(1''-pyrenyl)]nonyl-sn-glycerol

Hongying Zheng1,*, Richard I. Duclos, Jr.2,*, Conor C. Smith{dagger}, Harrison W. Farber{dagger} and Raphael A. Zoeller3,*

* Department of Physiology and Biophysics, Boston University School of Medicine, Boston, MA 02118-2526
{dagger} Pulmonary Center, Boston University School of Medicine, Boston, MA 02118-2526

Published, JLR Papers in Press, December 20, 2005.

1 Present address of H. Zheng: Division of Investigative Pathology, Scott & White Memorial Hospital, Texas A&M University System Health Science Center College of Medicine, 1901 South 1st Street, Building 205, Temple, TX 76508.

2 Present address of R. I. Duclos, Jr.: Center for Drug Discovery, Northeastern University, 360 Huntington Avenue, Boston, MA 02115.

3 To whom correspondence should be addressed. e-mail: rzoeller{at}bu.edu

The synthesis of an {omega}-pyrene-labeled 1-O-alkyl-sn-glycerol was performed using a chirospecific method starting from R-(–)-2,3-O-isopropylidene-sn-glycerol. The product, 1-O-[9'-(1''-pyrenyl)]nonyl-sn-glycerol (pAG), is a fluorescent ether lipid that has a pyrene moiety covalently attached at the alkyl chain terminus. pAG was taken into CHO-K1 cells and a plasmalogen-deficient variant of CHO-K1, NRel-4. This variant is defective in dihydroxyacetonephosphate acyltransferase, which catalyzes the first step in plasmenylethanolamine (PlsEtn) biosynthesis. pAG was incorporated primarily into ethanolamine and choline phospholipids as well as a neutral lipid fraction tentatively identified as alkyldiacylglycerol. NRel-4 accumulated more fluorescence in the phospholipid fraction than CHO-K1, specifically in the ethanolamine phospholipids. Analysis of the fluorescent lipids showed that 93% of the pAG was incorporated into glycerolipids with the ether bond intact. Although the addition of 20 µM 1-O-hexadecyl-sn-glycerol to the medium fully restored PlsEtn biosynthesis in NRel-4 cells, pAG only partially restored PlsEtn synthesis. Incubation of cells with pAG followed by irradiation with long-wavelength (>300 nm) ultraviolet light resulted in cytotoxicity. NRel-4 cells displayed an increased sensitivity to this treatment compared with CHO-K1 cells. This photodynamic cytotoxicity approach could be used to select for mutants that are defective in downstream steps in ether lipid biosynthesis.

Supplementary key words pyrene • fluorescence • chemical synthesis • ether lipid • plasmalogen • alkylglycerol

Abbreviations: ADG, alkyldiacylglycerol; bT, bath temperature; DHAPAT, dihydroxyacetonephosphate acyltransferase; HG, 1-O-hexadecyl-sn-glycerol; pAG, 1-O-[9'-(1''-pyrenyl)]nonyl-sn-glycerol; Pi, inorganic phosphate; PlsCho, plasmenylcholine; PlsEtn, plasmenylethanolamine; P9OH, 9-(1'-pyrenyl)-1-nonanol; PtdEtn, phosphatidylethanolamine; TEA, triethylamine; UV, ultraviolet


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