Enzymic studies of glycol and glycerol lipids containing O-alkyl bonds in liver and tumor tissues

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Abstract

The utilization of [1-14C]hexadecyl-[2-3H]ethyleneglycol and [1-14C]hexadecyl-[2-3H]glycerol as substrates for acyltransferase, phosphotransferase, phosphorylcholine, and phosphorylethanolamine transferase, and O-alkyl cleavage activities in cell-free preparations from normal rat liver and preputial gland tumors of mice was investigated. Our studies demonstrate that alkylethyleneglycols, like alkylglycerols, can serve as substrates for acyltransferases in both the liver and tumor microsomes; the product alkylacylethyleneglycerol can be readily deacylated by pancreatic lipase. A polar lipid was formed from the alkylethyleneglycol by the tumor homogenates in the presence of ATP and Mg2+; although the small quantities formed precluded absolute identification, its thin-layer Chromatographic behavior in acidic and basic solvent systems indicated that a free phosphate group was present. As expected, phosphorylbase transferases in these preparations did not utilize either the alkylethyleneglycol or alkylglycerol as substrates. The O-alkyl moiety of hexadecyl-ethyleneglycol was oxidized to hexadecanal by a tetrahydropteridine-dependent cleavage enzyme in rat liver microsomes, whereas in the tumor microsomes this activity was not present. We conclude that alkylethyleneglycols are metabolized in a manner similar to alkylglycerols and perhaps by identical enzymes.

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This work was supported in part by the United States Atomic Energy Commission; American Cancer Society, Grant BC-70E; National Cancer Institute, National Institutes of Health, Grant CA11949.04; and the National Institute of Arthritis, Metabolism and Digestive Diseases, National Institutes of Health, Grant AM-15172-10.

2

Author to whom inquires should be made: Dr. Fred Snyder, Medical Division, Oak Ridge Associated Universities, P. O. Box 117, Oak Ridge, Tennessee 37830.

3

Department of Medicinal Chemistry, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27514.

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