Amphipathic Solvation of Indole: Implications for the Role of Tryptophan in Membrane Proteins

Johnston, Andrew James; Zhang, Yapei; Büsch, Sebastian; Pardo, Luis Carlos; Imberti, Silvia; McLain, Sylvia E.

doi:10.1021/acs.jpcb.5b02476

Cited by 36 publications

(69 citation statements)

References 62 publications

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“…[8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] Neutron diffraction experiments have been used to study an aqueous solution of 30 mol% PG, containing 200 mM of 1,2-dipropionyl-sn-glycero-3-phosphocholine (C 3 -PC). The neutron diffraction experiments were performed on the SAN-DALS diffractometer at the ISIS neutron facility, UK.…”

Section: A Neutron Diffractionmentioning

confidence: 99%

“…Empirical Potential Structure Refinement (EPSR) modeling 7 can be used to create a model which 'fits' the measured diffraction data and has been used for a variety of systems to gain a better understanding of the structure of molecules in solution. [11][12][13][14][19][20][21][22] EPSR is Monte Carlo-based simulation which begins with a set of established potentials and then refines these potentials iteratively until a good fit between the measured data and the model is achieved. The EPSR simulation box here contained 10 C 3 -PC lipids, 750 PG molecules (375 R-and 375 S-) and 1750 water molecules (Fig.…”

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confidence: 99%

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On the solvation of the phosphocholine headgroup in an aqueous propylene glycol solution

Rhys

al-Badri

Ziolek

et al. 2018

The Journal of Chemical Physics

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The atomic-scale structure of the phosphocholine (PC) headgroup in 30 mol% propylene glycol (PG) in aqueous solution has been investigated using a combination of neutron diffraction with isotopic substitution experiments and computer simulation techniques -Molecular Dynamics and Empirical Potential Structure Refinement. Here, the hydration of the PC headgroup remains largely intact compared with the hydration of this group in a bilayer and in a bulk water solution, with the PG molecules showing limited interactions with the headgroup. When direct PG interactions with PC do occur, they are most likely to coordinate to the N(CH 3 ) + 3 motifs. Further, PG does not affect the bulk water structure and the addition of PC does not perturb the PG-solvent interactions. This suggests that the reason why PG is able to penetrate into membranes easily is that it does not form stronghydrogen bonding or electrostatic interactions with the headgroup allowing it to easily move across the membrane barrier.

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Section: A Neutron Diffractionmentioning

confidence: 99%

mentioning

confidence: 99%

On the solvation of the phosphocholine headgroup in an aqueous propylene glycol solution

Rhys

al-Badri

Ziolek

et al. 2018

The Journal of Chemical Physics

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“…This new set of charges for indole was based on previous ab initio calculations for indole 13 and have successfully been used previously for EPSR investigations of indole in methanol water solutions. 9 The labeling scheme of the atoms is shown in Figure 1 and the parameters for all of the atoms in the simulations are shown in Table 1.…”

Section: Molecular Dynamicsmentioning

confidence: 99%

“…This ratio of solvents has been chosen because it allows its comparison with previous neutron diffraction experiments where neither the solute (indole) nor the solvents have negligible contributions to the total diffraction pattern. 9 In addition, MD simulations have been performed on indole at 'infinite dilution', in both methanol and water separately. Measurement of indole as a single molecule in these solutions allows the local ordering of solvents around indole to be investigated without the complicating effects of indole-indole interactions.…”

Section: Introductionmentioning

confidence: 99%

On the positional and orientational order of water and methanol around indole: a study on the microscopic origin of solubility

Henao

Johnston

Guàrdia

et al. 2016

Phys. Chem. Chem. Phys.

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Although they are both highly polar liquids, there are a number of compounds, such as many pharmaceuticals, which show vastly different solubilities in methanol compared with water. From theories of the hydrophobic effect, it might be predicted that this enhanced solubility is due to association between drugs and the less polar -CH 3 groups on methanol. In this work, detailed analysis on the atomic structural interactions between water, methanol and the small molecule indole -which is a precursor to many drugs and is sparingly soluble in water yet highly soluble in methanol -reveal that indole preferentially interacts with both water and methanol via electrostatic interactions rather than with direction interactions to the -CH 3 groups. The presence of methanol hydrogen bonds with π electrons of the benzene ring of indole can explain the increase in solubility of indole in methanol relative to water. In addition, the excess entropy calculations performed here suggest that this solvation is enthalpically rather than entropically driven.

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“…The highest density of neighboring molecules is subsequently plotted 46,47 in the form of Spatial Density Maps (SDMs). 48,49 In the work presented here, five coordinate systems were placed on each DOPC headgroup, three on each ceramide headgroup and one on each of the water molecules. These coordinate systems are used as a frame of reference to generate summed interaction patterns for the location of molecules around the defined groups on the lipids.…”

Section: B Angula Analysismentioning

confidence: 99%

Comparative atomic-scale hydration of the ceramide and phosphocholine headgroup in solution and bilayer environments

Gillams

Lorenz

McLain

2016

The Journal of Chemical Physics

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Previous studies have used neutron diffraction to elucidate the hydration of the ceramide and the phosphatidylcholine headgroup in solution. These solution studies provide bond-length resolution information on the system, but are limited to liquid samples. The work presented here investigates how the hydration of ceramide and phosphatidylcholine headgroups in a solution compares with that found in a lipid bilayer. This work shows that the hydration patterns seen in the solution samples provide valuable insight into the preferential location of hydrating water molecules in the bilayer. There are certain subtle differences in the distribution, which result from a combination of the lipid conformation and the lipid-lipid interactions within the bilayer environment. The lipid-lipid interactions in the bilayer will be dependent on the composition of the bilayer, whereas the restricted exploration of conformational space is likely to be applicable in all membrane environments. The generalized description of hydration gathered from the neutron diffraction studies thus provides good initial estimation for the hydration pattern, but this can be further refined for specific systems. Published by AIP Publishing. [http://dx

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Amphipathic Solvation of Indole: Implications for the Role of Tryptophan in Membrane Proteins

Cited by 36 publications

References 62 publications

On the solvation of the phosphocholine headgroup in an aqueous propylene glycol solution

On the solvation of the phosphocholine headgroup in an aqueous propylene glycol solution

On the positional and orientational order of water and methanol around indole: a study on the microscopic origin of solubility

Comparative atomic-scale hydration of the ceramide and phosphocholine headgroup in solution and bilayer environments

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