Role of head group structure in the phase behavior of amino phospholipids. 2. Lamellar and nonlamellar phases of unsaturated phosphatidylethanolamine analogs
- 1 July 1986
- journal article
- research article
- Published by American Chemical Society (ACS) in Biochemistry
- Vol. 25 (15), 4259-4267
- https://doi.org/10.1021/bi00363a013
Abstract
Three types of analogues of unsaturated phosphatidylethanolamines (PE) have been prepared: phosphatidyl-.omega.-amino-1-alkanols, N-alkyl-PE''s, and C2-alkyl-PE''s, with alkyl substitution of carbon-2 of the ethanolamine head group. The physical properties of dioleoyl, dielaidoyl, and 1-palmitoyl-2-oleoyl phospholipids with these head groups have been examined by calorimetry, 31P NMR, freeze-fracture electron microscopy, and X-ray diffraction. N-Alkylation of PE, or substitution of the ethanolamine moiety by 3-amino-1-propanol or 4-amino-1-butanol, decreases the transition temperature of the hydrated gel phase (Tc) and considerably increases the temperature of the lamellar to hexagonal II transition (TH). The pattern of these effects for various PE analogues suggests that head group size and hydrophobicity as well as hydrogen bonding are important determinants of the phase behavior of these lipids. C2-Alkylated PE analogues exhibit several rather surpising properties, notably the ready formation of a quasi-crystalline "high-melting" solid phase even for di-cis-unsaturated species and substantially lower TH values than are observed for the parent PE species. The behavior of these compounds suggests that "hydration forces" can be more important than considerations of lipid "dynamic shape" in predicting the relative stabilities of lamellar vs. nonlamellar phases for at least some zwitterionic phospholipids.This publication has 18 references indexed in Scilit:
- Studies on the thermotropic behavior of aqueous phosphatidylethanolaminesBiochimica et Biophysica Acta (BBA) - Biomembranes, 1983
- The existence of a highly ordered phase in fully hydrated dilauroylphosphatidylethanolamineBiochimica et Biophysica Acta (BBA) - Biomembranes, 1983
- Phase equilibria, molecular conformation, and dynamics in phosphatidylcholine/phosphatidylethanolamine bilayersBiochemistry, 1982
- Characterization of the sub-transition of hydrated dipalmitoylphosphatidylcholine bilayersBiochimica et Biophysica Acta (BBA) - Biomembranes, 1982
- INTERACTIONS BETWEEN NEUTRAL PHOSPHOLIPID-BILAYER MEMBRANES1982
- Intra- and intermolecular interactions of phospholipid headgroups within a two-dimensional hexagonal latticeChemistry and Physics of Lipids, 1981
- Temperature-dependent morphological and phase behavior of sphingomyelinBiochimica et Biophysica Acta (BBA) - Biomembranes, 1980
- The polymorphic phase behaviour of phosphatidylethanolamines of natural and synthetic origin. A 31P NMR studyBiochimica et Biophysica Acta (BBA) - Biomembranes, 1978
- Investigation of phosphatidylethanolamine bilayers by deuterium and phosphorus-31 nuclear magnetic resonanceBiochemistry, 1976
- Isolation and characterization of subcellular membranes with altered phospholipid composition from cultured fibroblasts.Journal of Biological Chemistry, 1976