Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.

In recent studies we showed that the phospholipid analogue hexadecylphosphocholine inhibits phosphatidylcholine biosynthesis by affecting the translocation of the rate-limiting enzyme of phosphatidylcholine biosynthesis, CTP:phosphocholine cytidylyltransferase (EC 2.7.7.15), to membranes, where it i...

Full description

Bibliographic Details
Main Authors: C.C. Geilen, A. Haase, T. Wieder, D. Arndt, R. Zeisig, W. Reutter
Format: Article
Language:English
Published: Elsevier 1994-04-01
Series:Journal of Lipid Research
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520411769
_version_ 1818676257421787136
author C.C. Geilen
A. Haase
T. Wieder
D. Arndt
R. Zeisig
W. Reutter
author_facet C.C. Geilen
A. Haase
T. Wieder
D. Arndt
R. Zeisig
W. Reutter
author_sort C.C. Geilen
collection DOAJ
description In recent studies we showed that the phospholipid analogue hexadecylphosphocholine inhibits phosphatidylcholine biosynthesis by affecting the translocation of the rate-limiting enzyme of phosphatidylcholine biosynthesis, CTP:phosphocholine cytidylyltransferase (EC 2.7.7.15), to membranes, where it is active (Geilen et al. 1992. J. Biol. Chem. 267: 6719-6724). The present study was performed to investigate the structure-dependency of this effect. It is shown that the inhibitory properties of phospholipid analogues are dependent on their alkyl side chain length (dodecylphosphocholine < tetradecylphosphocholine < hexadecylphosphocholine < heptadecylphosphocholine < octadecylphosphocholine > eicosadecylphosphocholine). Furthermore, it is demonstrated that this inhibition of phosphatidylcholine biosynthesis by phospholipid analogues is also dependent on the polar head group (hexadecylphosphocholine > hexadecylphosphoethanolamine = hexadecylphosphoserine). These effects result from an inhibition of the CTP:phosphocholine cytidylyltransferase and are not due to an inhibition of choline uptake or differences in the cellular uptake of the phospholipid analogues investigated.
first_indexed 2024-12-17T08:40:36Z
format Article
id doaj.art-0349bd2374224340a9231a5ba15c4cc2
institution Directory Open Access Journal
issn 0022-2275
language English
last_indexed 2024-12-17T08:40:36Z
publishDate 1994-04-01
publisher Elsevier
record_format Article
series Journal of Lipid Research
spelling doaj.art-0349bd2374224340a9231a5ba15c4cc22022-12-21T21:56:21ZengElsevierJournal of Lipid Research0022-22751994-04-01354625632Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.C.C. Geilen0A. Haase1T. Wieder2D. Arndt3R. Zeisig4W. Reutter5Institut für Molekularbiologie und Biochemie der Freien Universität Berlin, Germany.Institut für Molekularbiologie und Biochemie der Freien Universität Berlin, Germany.Institut für Molekularbiologie und Biochemie der Freien Universität Berlin, Germany.Institut für Molekularbiologie und Biochemie der Freien Universität Berlin, Germany.Institut für Molekularbiologie und Biochemie der Freien Universität Berlin, Germany.Institut für Molekularbiologie und Biochemie der Freien Universität Berlin, Germany.In recent studies we showed that the phospholipid analogue hexadecylphosphocholine inhibits phosphatidylcholine biosynthesis by affecting the translocation of the rate-limiting enzyme of phosphatidylcholine biosynthesis, CTP:phosphocholine cytidylyltransferase (EC 2.7.7.15), to membranes, where it is active (Geilen et al. 1992. J. Biol. Chem. 267: 6719-6724). The present study was performed to investigate the structure-dependency of this effect. It is shown that the inhibitory properties of phospholipid analogues are dependent on their alkyl side chain length (dodecylphosphocholine < tetradecylphosphocholine < hexadecylphosphocholine < heptadecylphosphocholine < octadecylphosphocholine > eicosadecylphosphocholine). Furthermore, it is demonstrated that this inhibition of phosphatidylcholine biosynthesis by phospholipid analogues is also dependent on the polar head group (hexadecylphosphocholine > hexadecylphosphoethanolamine = hexadecylphosphoserine). These effects result from an inhibition of the CTP:phosphocholine cytidylyltransferase and are not due to an inhibition of choline uptake or differences in the cellular uptake of the phospholipid analogues investigated.http://www.sciencedirect.com/science/article/pii/S0022227520411769
spellingShingle C.C. Geilen
A. Haase
T. Wieder
D. Arndt
R. Zeisig
W. Reutter
Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.
Journal of Lipid Research
title Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.
title_full Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.
title_fullStr Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.
title_full_unstemmed Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.
title_short Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis.
title_sort phospholipid analogues side chain and polar head group dependent effects on phosphatidylcholine biosynthesis
url http://www.sciencedirect.com/science/article/pii/S0022227520411769
work_keys_str_mv AT ccgeilen phospholipidanaloguessidechainandpolarheadgroupdependenteffectsonphosphatidylcholinebiosynthesis
AT ahaase phospholipidanaloguessidechainandpolarheadgroupdependenteffectsonphosphatidylcholinebiosynthesis
AT twieder phospholipidanaloguessidechainandpolarheadgroupdependenteffectsonphosphatidylcholinebiosynthesis
AT darndt phospholipidanaloguessidechainandpolarheadgroupdependenteffectsonphosphatidylcholinebiosynthesis
AT rzeisig phospholipidanaloguessidechainandpolarheadgroupdependenteffectsonphosphatidylcholinebiosynthesis
AT wreutter phospholipidanaloguessidechainandpolarheadgroupdependenteffectsonphosphatidylcholinebiosynthesis