Liposomes Containing Purine and Pyrimidine Bases: Stable Unilamellar Liposomes from Phosphatidyl Nucleosides

Bonaccio, Silvio; Walde, Peter; Luisi, Pier Luigi

doi:10.1021/j100077a036

Cited by 25 publications

(22 citation statements)

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“…These concepts of molecular recognition with nucleolipids were initially applied to a supramolecular film at the air-water interface.27 , 44 ,45 More recently, base-pairing between complementary nucleolipids at mesoscopic interfaces such as those found in vesicular and micellar systems have been investigated. 28,29,[46][47][48][49][50][51] The data collected from several techniques (Langmuir-Blodgett, UVvis, FTIR, ATR, etc. ), provided direct evidence for the formation of multiple hydrogen bonds between the base pairs.…”

Section: Supramolecular Assemblies Of Nucleolipidsmentioning

confidence: 99%

Nucleoside, nucleotide and oligonucleotide based amphiphiles: a successful marriage of nucleic acids with lipids

et al. 2008

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Section: Supramolecular Assemblies Of Nucleolipidsmentioning

confidence: 99%

Nucleoside, nucleotide and oligonucleotide based amphiphiles: a successful marriage of nucleic acids with lipids

et al. 2008

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“…Some authors have reported studies of complementary binding in micelles, where the competition of the protic solvent is overcome by the compartmentalization of the partners into a micellar hydrophobic core. A challenging approach to combine the lipid compartmentalization with the nucleotide structures has been developed, and phosphatidylnucleosides, which are able to form stable liposomes, have been prepared …”

Section: Introductionmentioning

confidence: 99%

Molecular Recognition in Monolayers. Complementary Base Pairing in Dioleoylphosphatidyl Derivatives of Adenosine, Uridine, and Cytidine

et al. 1997

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Chemical recognition by base complementarity in DNA and RNA is strictly related to their stereochemical order. The way in which this high stereoregular order has been achieved in a prebiotic world is not fully understood yet. More primitive systems that display complementary base recognition as a prerequisite to information and, eventually, self-replication might represent a possible route. This study investigates phosphatidylnucleosides bearing complementary bases, adenine and uridine, that can mutually recognize each other, giving mixed structures with features characteristic of complementary base pairing. Dioleoylphosphatidyl derivatives of adenosine (DOP-adenosine), uridine (DOP-uridine), and cytidine (DOP-Cytidine) have been studied at the water-air interface as a function of pH and subphase composition. When monovalent cations (Li + , Na + , and K + ) are dissolved in the subphase, the phosphatidyl derivative monolayers show expansion or compression depending on the cation nature. In particular DOP-adenosine shows a preferential interaction with Li + . The properties of mixtures of the DOP-adenosine/DOPuridine complementary bases were investigated and compared to those of the non-complementary bases (DOP-adenosine/DOP-cytidine). The results indicate a preferential interaction in a hydrophilic environment only for complementary nucleophospholipids at physiological pH, suggesting that the specific interfacial orientation of the phospholiponucleoside imposed by the interface promotes the molecular recognition between the two complementary bases in a way that resembles the Watson-Crick pairing in natural nucleic acids. Moreover, mixed monolayers of adenosine-uridine derivatives show a minimum of the free energy of mixing for DOP-uridine rich mixtures (around the DOP-adenosine/DOP-uridine ) 0.2-0.3 mole fraction) close to the stoichiometry of the trimeric adduct (uridine) 2‚adenosine that forms in highly concentrated solutions of uridine and adenosine, where adenosine displays simultaneously the Watson-Crick and the Hoogsten hydrogen bond patterns.

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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

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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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Liposomes Containing Purine and Pyrimidine Bases: Stable Unilamellar Liposomes from Phosphatidyl Nucleosides

Cited by 25 publications

References 0 publications

Nucleoside, nucleotide and oligonucleotide based amphiphiles: a successful marriage of nucleic acids with lipids

Nucleoside, nucleotide and oligonucleotide based amphiphiles: a successful marriage of nucleic acids with lipids

Molecular Recognition in Monolayers. Complementary Base Pairing in Dioleoylphosphatidyl Derivatives of Adenosine, Uridine, and Cytidine

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

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