PMID: 3756138Jul 29, 1986Paper

Role of head group structure in the phase behavior of amino phospholipids. 2. Lamellar and nonlamellar phases of unsaturated phosphatidylethanolamine analogues

Biochemistry
P M BrownJ R Silvius

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 surprising 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 mo...Continue Reading

Citations

May 1, 1989·Lipids·M K JacobsohnG M Jacobsohn
Mar 1, 1991·Chemistry and Physics of Lipids·M W TateS M Gruner
Mar 1, 1991·Chemistry and Physics of Lipids·J R Silvius
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Nov 13, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·Mariya ChavarhaStephen B Hall
Oct 10, 2009·Journal of Colloid and Interface Science·Carlos Rodríguez-AbreuConxita Solans
Nov 3, 2015·Biochimica Et Biophysica Acta·Tomasz Rog, Artturi Koivuniemi
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Apr 4, 2017·Biochimica Et Biophysica Acta. Biomembranes·Hitoshi MatsukiShoji Kaneshina
May 12, 2021·Biochimica Et Biophysica Acta. Molecular and Cell Biology of Lipids·Ziqiang Guan, Howard Goldfine
Feb 12, 2013·Journal of Chemical Theory and Computation·Giulia PalermoMarco De Vivo
Apr 26, 2018·Nano Letters·Rebecca L BallKathryn A Whitehead

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