The Partitioning of Small Aromatic Molecules to Air-Water and Phospholipid Interfaces Mediated by Non-Hydrophobic Interactions

0468642 - ÚFCH JH 2017 RIV US eng J - Journal Article
Perkins, R.J. - Kukharchuk, Alexandra - Delcroix, Pauline - Shoemaker, R. K. - Roeselová, Martina - Cwiklik, Lukasz - Vaida, V.
The Partitioning of Small Aromatic Molecules to Air-Water and Phospholipid Interfaces Mediated by Non-Hydrophobic Interactions.
Journal of Physical Chemistry B. Roč. 120, č. 30 (2016), s. 7408-7422. ISSN 1520-6106. E-ISSN 1520-5207
R&D Projects: GA ČR GA15-14292S
Institutional support: RVO:61388955 ; RVO:61388963
Keywords : Nuclear magnetic resonance spectroscopy * Biological systems * Mass spectrometry
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 3.177, year: 2016
Method of publishing: Open access

Phenylalanine has an important role both in normal biological function and in disease states such as phenylketonuria (PKU) and amyloid fibril diseases. Two crucial aspects of phenylalanine behavior in biological systems are its preferential partitioning into membranes and its propensity to cluster. In order to examine the intermolecular interactions that give rise to this behavior, the surface partitioning behavior was investigated for a series of molecules structurally related to phenylalanine (phenylglycine, phenylacetic acid, and tyrosine) both experimentally and by molecular dynamics simulations. Surface tension measurements were performed over time for aromatic solutions both in the presence and in the absence of 1,2-dipalmitoyl-sn-glycero-3-phosphatidykholine (DPPC) monolayer films, which functioned as simple model membranes. The observed trends in surface activity defy simple predictions based on solubility and hydrophobicity. The,possibility of clustering is investigated through a combination of Langmuir trough, nuclear magnetic resonance (NMR), fluorescence self-quenching, and mass spectroscopy measurements. It is concluded that clustering does not occur in solution to a significant extent for these molecules, but interfacial clustering is likely. An explanation for observed trends in surface activity is presented on the basis of cluster stability and molecular conformational flexibility.
Permanent Link: http://hdl.handle.net/11104/0266450