Microscopic Structure and Solvation in Dry and Wet Octanol

Chen, Bin; Siepmann, J. Ilja

doi:10.1021/jp0548164

Cited by 138 publications

(193 citation statements)

References 45 publications

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“…The suitability of the octanol-water logP is due to the amphiphilic nature of octanol, that allow to mimic, for instance, the biological membrane environment [18]. The agreement of the obtained results using these association of methodologies will be discussed.…”

Section: Introductionmentioning

confidence: 81%

A combination of techniques to evaluate photodynamic efficiency of photosensitizers

et al. 2009

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Photodynamic therapy, used mainly for cancer treatment and microorganisms inactivation, is based on production of reactive oxygen species by light irradiation of a sensitizer. Hematoporphyrin derivatives as Photofrin (PF), Photogem (PG) and Photosan (PF), and chlorin-e6-derivatives as Photodithazine (PZ), have suitable sensitizing properties. The present study provides a way to make a fast previous evaluation of photosensitizers efficacy by a combination of techniques: a) use of bovine serum albumin and uric acid as chemical dosimeters; b) photo-hemolysis of red blood cells used as a cell membrane interaction model, and c) octanol/phosphate buffer partition to assess the relative lipophilicity of the compounds. The results suggest the photodynamic efficient ranking: PZ > PG ≥ PF > PS. These results agree with the cytotoxicity of the photosensitizers as well as to chromatographic separation of the HpDs, both performed in our group, showing that the more lipophilic is the dye, the more acute is the damage to the RBC membrane and the oxidation of indol, which is immersed in the hydrophobic region of albumin.

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Section: Introductionmentioning

confidence: 81%

A combination of techniques to evaluate photodynamic efficiency of photosensitizers

et al. 2009

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“…Frenkel and Smit [11] point out that the time required for each molecule of an ice-water interfacial system to fully sample all environments would be much longer than any plausible equilibration time. The water-acetonitrile liquid mixture is another case where the local structure of the fluid makes the ergodic convergence time much longer than a useful "equilibration time."…”

Section: Resultsmentioning

confidence: 99%

Ergodic Convergence Times for Molecular Liquids

Mountain

2010

Int J Thermophys

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A problem common to all molecular dynamics and Monte Carlo simulations used to estimate fluid properties is how to decide when adequate sampling of the phase space of the system has been realized. One procedure for addressing the sampling question is to construct the energy metric for the system. The energy metric provides an indication of when the time-averaged energies of the individual molecules converge to a common value (self-averaging). The time required for the value of the energy metric to decrease to 1 % of its initial value is a useful indication that adequate sampling has been realized. The energy metric based ergodic convergence times for the molecular liquids water, acetonitrile, methanol, and carbon dioxide plus mixtures of water and methanol and of water and acetonitrile are reported. The convergence time τ for water is about 100 ps at ambient conditions; for carbon dioxide it is about 300 ps while for methanol it is about 800 ps. The convergence times for water/acetonitrile mixtures are much longer due to the microheterogeneous structure of the mixtures. The ergodic convergence time is an increasing function of the mole fraction of methanol in the mixtures. The convergence times for water along the liquid side of the liquid-vapor coexistence curve are found to decrease strongly as the temperature increases.

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“…The validity of using octanol to mimic the cell membrane interior has recently been questioned. Wet octanol saturates at ~20 mol% water which collects into nanoscale aggregates [51,52]. This suggests that water saturated octanol is actually not as hydrophobic as the membrane interior.…”

Section: Oligoargininementioning

confidence: 99%

Current Understanding of the Mechanisms by which Membrane-Active Peptides Permeate and Disrupt Model Lipid Membranes

Sun

Forsman²,

Woodward

2015

CTMC

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Link to publicationCitation for published version (APA): Sun, D., Forsman, J., & Woodward, C. E. (2016). Current understanding of the mechanisms by which membrane-active peptides permeate and disrupt model lipid membranes. Current Topics in Medicinal Chemistry, 16(2), 170-186. DOI: 10.2174/1568026615666150812121241 General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal translocation, but associated with this, is membrane rupture to form large pores, which are subsequently stabilized by peptide adsorption to the pore edges. This disruption to the membrane is presumably responsible for cell death. Amyloidal peptides also show evidence of stable large pore formation, however, the mechanism for pore stabilization appears linked with their ability to form fibrils and prefibrillar aggregates and oligomers. There is some evidence that pores and membrane defects in fact act as nucleation sites for these structures. Where possible we have related the experimental and theoretical work to our own simulation findings in an effort to produce a comprehensive, albeit speculative picture for the mechanisms of action for this important group of peptides. Keywords:Membrane active peptides; anti-microbial peptides; cell-penetrating peptides; amyloid peptides; lipid membrane; pore-formation 3 Graphical AbstractWe review the modes of activity of three classes of membrane active peptides: cell penetrating; antimicrobial, and amyloid peptides.4

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Microscopic Structure and Solvation in Dry and Wet Octanol

Cited by 138 publications

References 45 publications

A combination of techniques to evaluate photodynamic efficiency of photosensitizers

A combination of techniques to evaluate photodynamic efficiency of photosensitizers

Ergodic Convergence Times for Molecular Liquids

Current Understanding of the Mechanisms by which Membrane-Active Peptides Permeate and Disrupt Model Lipid Membranes

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