Relation between the Molecular Structure of Phosphatidyl Nucleosides and the Morphology of their Supramolecular and Mesoscopic Aggregates

Bonaccio, Silvio; Wessicken, Michaela; Berti, Debora; Walde, Peter; Luisi, Pier Luigi

doi:10.1021/la960315l

Cited by 29 publications

(27 citation statements)

References 17 publications

(19 reference statements)

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“…From these images, it is clear that the liposomes aggregate into spherical closed liposomes. In the previous studies performed by Yanagawa [6] and Luisi, [7] phosphatidyl nucleosides were demonstrated to aggregate and to have morphologies such as super-helical strands, rings, and flat disks. We observed the same spherical morphologies for all the liposomes of nucleoside-based phospholipids, even though they feature different nucleobases.…”

Section: Resultsmentioning

confidence: 99%

“…Like the phosphatidyl nucleosides, [6,7] the monomers of these nucleoside-based phospholipids can aggregate together, but the morphologies of these aggregates differ substantially. The liposomes of these nucleoside-based phospholipids have spherical morphologies, which we believe are affected primarily by the lengths of the alkyl chains of nucleoside-based phospholipid monomers.…”

Section: Resultsmentioning

confidence: 99%

“…[5] The authors demonstrated that this modified phospholipid exhibits physical properties that differ from those of its glycerolbased analogues; this indicates the importance that the constitution of the backbone has for the nature of the bilayer structure. The morphologies of some phosphatidyl nucleosides have already been reported by Yanagawa [6] and Luisi, [7] who were the first to investigate the self-association of this family of lipids. Intrigued by these interesting results, we have designed and synthesized novel nucleoside-based phospholipids.…”

Section: Introductionmentioning

confidence: 84%

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Nucleoside‐Based Phospholipids and Their Liposomes Formed in Water

Choi

Jung

et al. 2005

ChemBioChem

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Phospholipids and liposomes have been the subjects of considerable attention because of their importance in biological systems. We have efficiently synthesized novel nucleoside-based phospholipids in six-step sequences starting from their corresponding nucleosides. These nucleoside-based phospholipids self-assemble into liposome-like structures in aqueous solutions. We have analyzed the structures of these liposomes by dynamic light scattering, transmission electron microscopy, and confocal microscopy.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 84%

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Nucleoside‐Based Phospholipids and Their Liposomes Formed in Water

Choi

Jung

et al. 2005

ChemBioChem

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“…Bonaccio et al found that using partially unsaturated chains in phosphatidyl-nucleosides resulted in the formation of nonchiral liposomes due to the depression of the melting temperature below ambient. 158 They also reported an interesting disk morphology in mixtures of cytidine and inosine phospholipids.…”

Section: Nucleotidesmentioning

confidence: 95%

Chiral Molecular Self‐Assembly

Spector¹,

Selinger²,

Schnur³

2003

Topics in Stereochemistry

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“…A few selected examples are mentioned: (i) Chiral phospholiponucleosides (like 1,2-dimyristoyl-sn-glycero-3-phosphocytidine, see Figure 4) in aqueous solution below T m form helical strands (Yanagawa et al, 1989;Itojima et al, 1992), while vesicles are formed from these type of lipids above T m (Bonaccio et al, 1994;Bonaccio et al, 1996). A comparable behavior has been observed more recently with chiral double-chain nucleolipids like DPUPC (1,2-dipalmitoyluridinophosphocholine, see Figure 4), as shown in Figure 6 (Moreau et al, 2004).…”

Section: The Formation Of Chiral Aggregates From Chiral Surfactantsmentioning

confidence: 99%

Surfactant Assemblies and their Various Possible Roles for the Origin(S) of Life

Walde

2006

Orig Life Evol Biosph

Self Cite

138

110

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A large number of surfactants (surface active molecules) are chemically simple compounds that can be obtained by simple chemical reactions, in some cases even under presumably prebiotic conditions. Surfactant assemblies are self-organized polymolecular aggregates of surfactants, in the simplest case micelles, vesicles, hexagonal and cubic phases. It may be that these different types of surfactant assemblies have played various, so-far underestimated important roles in the processes that led to the formation of the first living systems. Although nucleic acids are key players in the formation of cells as we know them today (RNA world hypothesis), it is still unclear how RNA could have been formed under prebiotic conditions. Surfactants with their self-organizing properties may have assisted, controlled and compartimentalized some of the chemical reactions that eventually led to the formation of molecules like RNA. Therefore, surfactants were possibly very important in prebiotic times in the sense that they may have been involved in different physical and chemical processes that finally led to a transformation of non-living matter to the first cellular form(s) of life. This hypothesis is based on four main experimental observations: (i) Surfactant aggregation can lead to cell-like compartimentation (vesicles). (ii) Surfactant assemblies can provide local reaction conditions that are very different from the bulk medium, which may lead to a dramatic change in the rate of chemical reactions and to a change in reaction product distributions. (iii) The surface properties of surfactant assemblies that may be liquid- or solid-like, charged or neutral, and the elasticity and packing density of surfactant assemblies depend on the chemical structure of the surfactants, on the presence of other molecules, and on the overall environmental conditions (e. g. temperature). This wide range of surface characteristics of surfactant assemblies may allow a control of surface-bound chemical reactions not only by the charge or hydrophobicity of the surface but also by its "softness". (iv) Chiral polymolecular assemblies (helices) may form from chiral surfactants. There are many examples that illustrate the different roles and potential roles of surfactant assemblies in different research areas outside of the field of the origin(s) of life, most importantly in investigations of contemporary living systems, in nanotechnology applications, and in the development of drug delivery systems. Concepts and ideas behind many of these applications may have relevance also in connection to the different unsolved problems in understanding the origin(s) of life.

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Relation between the Molecular Structure of Phosphatidyl Nucleosides and the Morphology of their Supramolecular and Mesoscopic Aggregates

Cited by 29 publications

References 17 publications

Nucleoside‐Based Phospholipids and Their Liposomes Formed in Water

Nucleoside‐Based Phospholipids and Their Liposomes Formed in Water

Chiral Molecular Self‐Assembly

Surfactant Assemblies and their Various Possible Roles for the Origin(S) of Life

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