Synthesis and properties of radioiodinated phospholipid analogues that spontaneously undergo vesicle-vesicle and vesicle-cell transfer

Alan J. Schroit, John W. Madsen

Research output: Contribution to journalArticle

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Abstract

An efficient method for the synthesis and purification of a variety of iodinated phospholipid analogues is described. 1-Acyl-2-[[[3-(3-[ 125I]iodo-4-hydroxyphenyl)propionyl]amino]caproyl]phosphatidylcholine (125I-PC) was prepared by alkylation of 1-acyl-2-(aminocaproyl)phosphatidylcholine with monoiodinated Bolton-Hunter reagent. 125I-Labeled phosphatidic acid, phosphatidylethanolamine, and phosphatidylserine were produced from 125I-PC by phospholipase D catalyzed base exchange in the presence of ethanolamine or L-serine. All of these lipid analogues transferred readily from donor vesicles into recipient membranes. When an excess of acceptor vesicles was mixed with a population of donor vesicles containing the iodinated analogues, approximately 50% of the 125I-labeled lipids transferred to the acceptor vesicle population. In addition, under appropriate incubation conditions, these lipids were observed to transfer from vesicles to mammalian cells. Autoradiographic analysis of 125I-labeled lipids extracted from the cells after incubation with vesicles at 2°C for 60 min revealed that a large proportion of the 125I-labeled phosphatidic acid was metabolized to 125I-labeled diglyceride and 125I-labeled phosphatidylcholine, whereas no metabolism of exogenously supplied 125I-labeled phosphatidylethanolamine or 125I-labeled phosphatidylcholine could be detected.

Original languageEnglish (US)
Pages (from-to)3617-3623
Number of pages7
JournalBiochemistry
Volume22
Issue number15
StatePublished - 1983

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Phosphatidylcholines
Phospholipids
Lipids
Phosphatidic Acids
Phospholipase D
Ethanolamine
Phosphatidylserines
Diglycerides
Alkylation
Metabolism
Serine
Population
Purification
Cells
Membranes
phosphatidylethanolamine

ASJC Scopus subject areas

  • Biochemistry

Cite this

Synthesis and properties of radioiodinated phospholipid analogues that spontaneously undergo vesicle-vesicle and vesicle-cell transfer. / Schroit, Alan J.; Madsen, John W.

In: Biochemistry, Vol. 22, No. 15, 1983, p. 3617-3623.

Research output: Contribution to journalArticle

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