Interaction of <scp>l</scp>-Phenylalanine with a Phospholipid Monolayer at the Water–Air Interface

Griffith, Elizabeth C.; Perkins, Russell; Telesford, Dana-Marie; Adams, Ellen M.; Ćwiklik, Łukasz; Allen, Heather C.; Roeselová, Martina; Vaida, Veronica

doi:10.1021/jp508473w

Cited by 50 publications

(97 citation statements)

References 73 publications

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“…Follow-up studies demonstrated the ability of amino acid amyloids to bind to lipid membranes (Griffith et al 2014;Cutró et al 2015;R o s ae ta l .2015; Sankaranarayanan 2015), just as observed with protein amyloids (Terzi et al 1997;Jayasinghe and Langen 2007). Therefore, it appears that the phenylalanine amyloids not only share the same morphology and chemical-physical characteristics as protein amyloid but also their specificity toward biological targets.…”

Section: Nonproteinaceous Amyloidsmentioning

confidence: 90%

Metabolite amyloids: a new paradigm for inborn error of metabolism disorders

Gazit

2016

J of Inher Metab Disea

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The formation of ordered amyloid assemblies is associated with major human degenerative disorders, including Alzheimer's disease, Parkinson's disease, and type 2 diabetes. Amyloid fibrils are elongated nanoscale structures that bind to specific dyes (including thioflavin T and Congo red). Amyloid fibrillar assemblies or their early intermediates are known to induce apoptotic cytotoxic effect. Until recently, amyloid fiber formation was observed only with proteins and peptides. We reported in 2012 that a single amino acid, phenylalanine, could also form typical amyloid fibrils with the same morphology, dye-binding specificity, and electron diffraction pattern as protein amyloids. X-ray crystallography demonstrated the formation of supramolecular β-sheet-like organization by phenylalanine at its zwitterionic form. Metabolite amyloids had pronounced cytotoxicity that could be depleted by treatment with antibodies raised against the phenylalanine structures. We suggested that the observed amyloid formation could explain some of the symptoms observed in phenylketonuria (PKU) upon the accumulation of phenylalanine. Follow-up studies by other groups revealed the ability of phenylalanine amyloids to bind to membranes, as observed with protein amyloids. Furthermore, the doxycycline amyloid formation inhibitor was shown to also affect the formation of phenylalanine amyloids. In 2015, it was reported that other metabolites involved in metabolic disorders, including adenine, uracil, tyrosine, and orotic acid, could form amyloid-like assemblies. It was further demonstrated that the assemblies induce apoptotic cell death. Taken together, we suggest a new hypothesis to understand the etiology of degenerative processes observed in inborn error of metabolism disorders and indicate new avenues for treatment.

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Section: Nonproteinaceous Amyloidsmentioning

confidence: 90%

Metabolite amyloids: a new paradigm for inborn error of metabolism disorders

Gazit

2016

J of Inher Metab Disea

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“…29,30 Interestingly, studies seeking to replicate microbial blooms in a controlled manner (using informed representative organic species for each stage of the bloom) showed that N 2 O 5 uptake on SSA did not differ significantly from simplistic laboratory-generated NaCl particles (see Figure 3b). 31 This implies either (1) the complex nature of the organic species result in loose surface packing 20,32 or (2) the organic species are well mixed or present in low enough concentrations so as not to impact uptake. Both have significant implications for understanding how chemical changes dictate aerosol climate properties (i.e., heterogeneous reactivity, hygroscopicity, and interaction with solar radiation).…”

Section: ■ Chemistry-driven Interactions Betweenmentioning

confidence: 99%

Sea Spray Aerosol: The Chemical Link between the Oceans, Atmosphere, and Climate

et al. 2017

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The oceans, atmosphere, and clouds are all interconnected through the release and deposition of chemical species, which provide critical feedback in controlling the composition of our atmosphere and climate. To better understand the couplings between the ocean and atmosphere, it is critical to improve our understanding of the processes that control sea spray aerosol (SSA) composition and which ones plays the dominate role in regulating atmospheric chemistry and climate.

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“…There have been several studies in which various groups, including ours, have used MD simulations to investigate the solubilisation of various small molecules in surfactant micelles. [8][9][10][11][12][13][14] However, very little has been performed using MD simulations to investigate the interaction of drug molecules with soluble surfactant monolayers, and the research that has been undertaken has been focused on drugs interacting with lipid monolayers, including thymol with dipalmitoylphosphatidylcholine (DPPC) monolayers, 15 Lphenylalanine with DPPC monolayers, 16 nalidixate calixarene with cholesterol monolayers, 17 and piroxicam with dimyristoylphosphatidylcholine (DMPC) monolayers. 18 To our knowledge, this is the first paper in which molecular dynamics simulations have been used to investigate the interactions between a drug molecule and a soluble surfactant monolayer.…”

Section: Introductionmentioning

confidence: 99%

Towards optimised drug delivery: structure and composition of testosterone enanthate in sodium dodecyl sulfate monolayers

et al. 2018

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Surface tension and specular neutron reflectivity measurements have been used, for the first time to systematically study both the interfacial structure and composition of monolayers of the soluble surfactant, sodium dodecyl sulfate containing a low-dose, poorly water soluble drug, testosterone enanthate. Modelling of the specular neutron reflectivity data suggests that the hydrophobic testosterone enanthate was adsorbed in the C12 hydrophobic tail region of the surfactant monolayer, regardless of the concentration of surfactant at the interface and whether or not additional drug was added to the interface. The location of the hydrophobic drug in the tail region of the surfactant monolayer is supported by the results of classical, large-scale molecular dynamics simulations. The thickness of the surfactant monolayer obtained, in the presence and absence of drug, using molecular dynamics simulations was in good agreement with the corresponding values obtained from the specular neutron reflectivity measurements. The stoichiometry of surfactant:drug at the air-water interface at sodium dodecyl sulfate concentrations above the critical micelle concentration was determined from specular neutron reflectivity measurements to be approximately 3 : 1, and remained constant after the spreading of further testosterone enanthate at the interface. Significantly, this stoichiometry was the same as that obtained in the micelles from bulk solubilisation studies. Important insights into the preferred location of drug in surfactant monolayers at the air-water interface as well as its effect on the structure of the monolayer have been obtained from our combined use of experimental and simulation techniques.

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Interaction of l-Phenylalanine with a Phospholipid Monolayer at the Water–Air Interface

Cited by 50 publications

References 73 publications

Metabolite amyloids: a new paradigm for inborn error of metabolism disorders

Metabolite amyloids: a new paradigm for inborn error of metabolism disorders

Sea Spray Aerosol: The Chemical Link between the Oceans, Atmosphere, and Climate

Towards optimised drug delivery: structure and composition of testosterone enanthate in sodium dodecyl sulfate monolayers

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