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Indoles at interfaces: Calculations of electrostatic effects with density functional and molecular dynamics methods

1999; Wiley; Volume: 75; Issue: 3 Linguagem: Inglês

10.1002/(sici)1097-461x(1999)75

1097-461X

Thomas B. Woolf, Alan Grossfield, John G. Pearson,

Molecular Sensors and Ion Detection

International Journal of Quantum ChemistryVolume 75, Issue 3 p. 197-206 Indoles at interfaces: Calculations of electrostatic effects with density functional and molecular dynamics methods Thomas B. Woolf, Corresponding Author Thomas B. Woolf Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Search for more papers by this authorAlan Grossfield, Alan Grossfield Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Search for more papers by this authorJohn G. Pearson, John G. Pearson Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Search for more papers by this author Thomas B. Woolf, Corresponding Author Thomas B. Woolf Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Search for more papers by this authorAlan Grossfield, Alan Grossfield Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Search for more papers by this authorJohn G. Pearson, John G. Pearson Departments of Physiology and of Biophysics and Biophysical Chemistry, Johns Hopkins University, School of Medicine, Baltimore, Maryland 21205Search for more papers by this author First published: 21 September 1999 https://doi.org/10.1002/(SICI)1097-461X(1999)75:3 3.0.CO;2-8Citations: 25AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract Cation–π interactions have been suggested as a key determinant of aromatic amino acid behavior. These interactions can be modeled as an electrostatic quadrupole moment from the atoms of the ring interacting with the environment. The preference of aromatic amino acids for the interface of membrane bilayers has been suggested as an example of a cation–π effect. Recently, molecular dynamics simulations of indole and N-methylindole in an explicit POPC (palmitoyl oleoyl phosphatidylcholine) membrane bilayer have been performed, using the CHARMM potential function. The CHARMM potential does not explicitly contain cation–π interactions: The electrostatic model involves only point charges at the atomic centers. A proper interpretation of the molecular dynamics calculations requires an assessment of the accuracy of the electrostatic effects present in the CHARMM parameter set. The current study compares the electrostatic interaction energy from CHARMM with calculations using the density functional program deMon. The calculations were performed for the case of a single point charge approaching indole along the x, y, or z directions. Additional calculations used snapshots from the molecular dynamics trajectories of indole and N-methylindole to compare CHARMM and deMon electrostatic energies. The results suggest that much of the cation–π interactions for indole is effectively included within the CHARMM potential function. ©1999 John Wiley & Sons, Inc. Int J Quant Chem 75: 197–206, 1999 Citing Literature Volume75, Issue3Special Issue: Biophysics Quarterly: In Memory of Bernard Pullman1999Pages 197-206 RelatedInformation