Physico-chemical interactions between compartment-forming lipids and other prebiotically relevant biomolecules

Olasagasti, Felix; Maurel, M.C.; Deamer, David W.

doi:10.1051/bioconf/20140205001

Cited by 4 publications

(2 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Single-chain lipid amphiphiles attract wide interest across fundamental and applied science, including fields such as molecular evolution, medicine, disinfectants and preservatives, renewable chemicals, food science, and biofuel production. , While the lipid bilayers of biological membranes are typically composed of double-chain glycerophospholipid molecules, it is believed that biological life originated from the self-assembly of simpler building blocks such as short-chain fatty acids and monoglycerides into early cellular compartments. − Furthermore, single-chain amphiphiles have important biological functions (e.g., antimicrobial activity, cell signaling), and are also known to interact with phospholipid bilayers, the latter of which has also inspired antimicrobial strategies aimed at destabilizing the lipid bilayers surrounding bacterial cells. , Indeed, amidst the growing rise of antibiotic-resistant bacteria, free fatty acids and monoglycerides have emerged as promising antibacterial agents, both in the free form as preservatives and disinfectants as well as encapsulated within nanoscale drug delivery carriers as potential therapeutics . From another perspective, the interaction of phospholipid membranes with free fatty acids is also important for the fermentative production of fatty acids for renewable chemical and biofuel production because high concentrations of fatty acids can damage bacterial cell membranes. , …”

Section: Introductionmentioning

confidence: 99%

Correlating Membrane Morphological Responses with Micellar Aggregation Behavior of Capric Acid and Monocaprin

et al. 2017

View full text Add to dashboard Cite

The interaction of single-chain lipid amphiphiles with phospholipid membranes is relevant to many scientific fields, including molecular evolution, medicine, and biofuels. Two widely studied compounds within this class are the medium-chain saturated fatty acid, capric acid, and its monoglyceride derivative, monocaprin. To date, most studies about these compounds have involved in vitro evaluation of their biological activities, while mechanistic details of how capric acid and monocaprin interact with phospholipid bilayers remain elusive. Herein, we investigated the effect of these two compounds on the morphological and fluidic properties of prefabricated, supported lipid bilayers (SLBs). The critical micelle concentration (CMC) of each compound was determined by fluorescence spectroscopy measurements. At or above its CMC, capric acid induced the formation of elongated tubules protruding from the SLB, as determined by quartz crystal microbalance-dissipation and fluorescence microscopy experiments. By contrast, monocaprin induced the formation of elongated tubules or membrane buds below and above its CMC, respectively. Fluorescence recovery after photobleaching (FRAP) experiments indicated that capric acid increased bilayer fluidity only above its CMC, whereas monocaprin increased bilayer fluidity both above and below its CMC. We discuss these findings in the context of the two compounds' structural properties, including net charge, molecular length and hydrogen-bonding capacity. Collectively, the findings demonstrate that capric acid and monocaprin differentially affect the morphological and fluidic properties of SLBs, and that the aggregation state of the compounds plays a critical role in modulating their interactions with phospholipid membranes.

show abstract

Section: Introductionmentioning

confidence: 99%

Correlating Membrane Morphological Responses with Micellar Aggregation Behavior of Capric Acid and Monocaprin

et al. 2017

View full text Add to dashboard Cite

show abstract

“…In addition to being relevant in the context of prebiotic research [66,67] and technological applications [68,69], these lipids present a number of key advantages compared to e.g. DPPC for a computational investigation of lipid phase transitions: (i) the presence of only one aliphatic tail per headgroup, leading to a faster relaxation; (ii) the limited role of electrostatic interactions (uncharged, non-zwitterionic and moderately polar headgroup); (iii) the absence of a ripple phase [70] as an intermediate state between the GL and LC phases; and (iv) the availability of experimental structural and thermodynamic data [14,68,69,[71][72][73][74][75][76][77].…”

Section: Introductionmentioning

confidence: 99%

Long-timescale motions in glycerol-monopalmitate lipid bilayers investigated using molecular dynamics simulation

Laner¹,

Horta²,

Hünenberger³

2015

Journal of Molecular Graphics and Modelling

View full text Add to dashboard Cite

Effect of the cosolutes trehalose and methanol on the equilibrium and phase-transition properties of glycerol-monopalmitate lipid bilayers investigated using molecular dynamics simulations

2014

View full text Add to dashboard Cite

The influence of the cosolutes trehalose and methanol on the structural, dynamic and thermodynamic properties of a glycerol-1-monopalmitate (GMP) bilayer and on its main transition temperature [Formula: see text] is investigated using atomistic molecular dynamics simulations (600 ns) of a GMP bilayer patch (2 × 8 × 8 lipids) at different temperatures in the range of 302 to 338 K and considering three different cosolute concentrations. Depending on the environment and temperature, these simulations present no or a single GL[Formula: see text]LC, LC[Formula: see text]GL or LC[Formula: see text]ID transition, where LC, GL and ID are the liquid crystal, gel and interdigitated phases, respectively. The trehalose molecules form a coating layer at the bilayer surface, promote the hydrogen-bonded bridging of the lipid headgroups, preserve the interaction of the headgroups with trapped water and induce a slight lateral expansion of the bilayer in the LC phase, observations that may have implications for the phenomenon of anhydrobiosis. However, this cosolute does not affect [Formula: see text] and its dependence on hydration in the concentration range considered. On the other hand, methanol molecules intercalate between the lipid headgroups, promote a lateral expansion of the bilayer in the LC phase and induce a concentration dependent decrease of [Formula: see text], observations that may have implications for the phenomenon of anesthesia. The occurrence of an ID phase in the presence of this cosolute may be viewed as an extreme consequence of lateral expansion. The analysis of the simulations also suggests the existence of two basic conservation principles: (1) the hydrogen-bond saturation principle rests on the observation that for all species present in the different systems, the total numbers of hydrogen-bonds per molecule is essentially constant, the only factor of variability being their distribution among different partners; (2) the densest packing principle rests on the observation that the effective volume per methylene group in the interior of the bilayer is only weakly sensitive to the environment, with values comparable to those for liquid (LC) and solid (ID) alkanes, or intermediate (GL).

show abstract

Physico-chemical interactions between compartment-forming lipids and other prebiotically relevant biomolecules

Cited by 4 publications

References 36 publications

Correlating Membrane Morphological Responses with Micellar Aggregation Behavior of Capric Acid and Monocaprin

Correlating Membrane Morphological Responses with Micellar Aggregation Behavior of Capric Acid and Monocaprin

Long-timescale motions in glycerol-monopalmitate lipid bilayers investigated using molecular dynamics simulation

Effect of the cosolutes trehalose and methanol on the equilibrium and phase-transition properties of glycerol-monopalmitate lipid bilayers investigated using molecular dynamics simulations

Contact Info

Product

Resources

About