Molecular Dynamics Simulation Study of the Interaction of Cationic Biocides with Lipid Bilayers: Aggregation Effects and Bilayer Damage

Hill, Eric H.; Stratton, Kelly; Whitten, David G.; Evans, Deborah G.

doi:10.1021/la303158c

Cited by 45 publications

(81 citation statements)

References 29 publications

(41 reference statements)

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“…32 Recent all-atom molecular dynamics simulations on the micro-second timescale reveal that OPE-3 can cause membrane damage that results in water leakage, which may be the initial step that subsequently lead to membrane failure. 38 Our multi-scale characterization of the dark membrane perturbation activity of the CPEs and OPEs using model E. coli plasma membranes so far support a carpet or detergent-like mechanism 9, 24 by which these antimicrobial compounds induce membrane collapse and phase transitions.…”

Section: Resultsmentioning

confidence: 64%

Understanding the Dark and Light-Enhanced Bactericidal Action of Cationic Conjugated Polyelectrolytes and Oligomers

Jett²,

et al. 2013

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A multiscale investigation was carried out to study the dark and light-enhanced bactericidal mechanisms of poly(phenylene ethynylene) (PPE)-based cationic conjugated polyelectrolytes (CPEs) and oligo-phenylene ethynylenes (OPEs). On the morphological scale, Gram-negative E. coli cells exposed to CPE and OPE compounds in the dark show damage to the cell envelope, plasma membrane, and in some cases the cytoplasm, while with UV-irradiation, E. coli sustained catastrophic damages to both the cell envelope and cytoplasm. In contrast, the Gram-positive S. epi bacteria appeared intact when exposed to CPE and OPE compounds in the dark but showed damages to the cell envelope with UV-irradiation. To better understand the molecular basis of CPE and OPE induced morphological changes and damages to bacteria, we investigated the effect of these compounds on model bacterial plasma membrane, and bacterial proteins and plasmid DNA. Measurements of dark membrane perturbation activity of the CPEs and OPEs using model lipid membranes support a carpet or detergent-like mechanism by which the antimicrobial compounds induce membrane collapse and phase transitions. Under UV-irradiation, E. coli bacteria exposed to CPEs and OPEs showed covalent modifications and damages to both cellular protein and plasmid DNA, likely through oxidative pathways mediated by singlet oxygen and subsequent reactive oxygen species sensitized by the CPE and OPE compounds. Our finding thus show that the antimicrobial polymers and oligomers exert toxicity towards Gram-negative bacteria by disrupting the morphology and structures of cell envelope and cytoplasm, including cellular components such as proteins and DNA while exert toxicity towards Gram-positive bacteria by binding to and disrupting just the cell wall.

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Section: Resultsmentioning

confidence: 64%

Understanding the Dark and Light-Enhanced Bactericidal Action of Cationic Conjugated Polyelectrolytes and Oligomers

Jett²,

et al. 2013

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“…Hill et al performed atomistic MD simulations of polyelectrolyte oligomers and a model bacterial membrane consisting of both zwitterionic (DOPE) and negatively charged (DOPG) phospholipids [93]. Simulations showed that individual cationic oligomers can bind the lipid bilayer surface, driven by the electrostatic interactions with the lipid phosphate groups.…”

Section: Linear Polyelectrolitesmentioning

confidence: 99%

Simulating the interaction of lipid membranes with polymer and ligand-coated nanoparticles

Rossi

Monticelli

2016

Advances in Physics: X

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Nanoscience and nanotechnology are undergoing rapid expansion owing to the promise of breakthroughs in key sectors, such as energy and medicine. As for medicine, interaction of nanomaterials with biological membranes is a key issue, both for the development of drug and gene delivery vectors and for understanding the molecular basis of nanoparticle (NP) biological activity. NP-membrane interactions are often studied with the aid of molecular simulations of model membranes, allowing to overcome the limitations in temporal and spatial resolution generally encountered by experimental techniques applied to fluid membranes. In the present review we summarize the current literature on simulations of NP-membrane interactions, focusing on small polymeric and ligand-coated NPs. Open questions emerging from experiments concern the effect of NP size, surface charge, and ligand arrangement on NP partitioning into and permeation across membranes. While simulations are contributing to significant progress in this area, some challenges remain, namely regarding the representation of the complexity of biological environments and the cooperative behavior of NPs (e.g. aggregation), as well as methodological challenges to tackle the intrinsically multi-scale nature of nano-bio interactions.

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“…Polyphilic molecules are compounds that consist of fragments of different philicity. The molecules used here feature many possibilities of functionalization to tailor the interactions with the membranes toward different goals.…”

Section: Introductionmentioning

confidence: 99%

Conformational Space of a Polyphilic Molecule with a Fluorophilic Side Chain Integrated in a DPPC Bilayer

et al. 2017

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We investigate the conformational space of a polyphilic molecule with hydrophilic, lipophilic and fluorophilic parts inserted as a transmembrane agent into a dipalmitoylphosphatidylcholine bilayer by means of all-atom molecular dynamics simulations. Special focus is put on the competing structural driving forces arising from the hydrophilic, lipophilic and fluorophilic side chains and the aromatic backbone of the polyphile. We observe a significant difference between the lipophilic and the fluorophilic side chains regarding their intramembrane distribution. While the lipophilic groups remain membrane-centered, the fluorophilic parts tend to orient toward the phosphate headgroups. This trend is important for understanding the influence of polyphile agents on the properties of phospholipid membranes. From a fundamental point of view, our computed distribution functions of the side chains are related to the interplay of sterical, enthalpic and entropic driving forces. Our findings illustrate the potential of rationally designed membrane additives which can be exploited to tune the properties of phospholipid membranes. © 2017 Wiley Periodicals, Inc.

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Molecular Dynamics Simulation Study of the Interaction of Cationic Biocides with Lipid Bilayers: Aggregation Effects and Bilayer Damage

Cited by 45 publications

References 29 publications

Understanding the Dark and Light-Enhanced Bactericidal Action of Cationic Conjugated Polyelectrolytes and Oligomers

Understanding the Dark and Light-Enhanced Bactericidal Action of Cationic Conjugated Polyelectrolytes and Oligomers

Simulating the interaction of lipid membranes with polymer and ligand-coated nanoparticles

Conformational Space of a Polyphilic Molecule with a Fluorophilic Side Chain Integrated in a DPPC Bilayer

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