Rashid, A, Vakurov, A, Mohamadi, S et al. (2 more authors) (2017) Substituents modulate biphenyl penetration into lipid membranes. Biochimica et Biophysica Acta (BBA) - Biomembranes, 1859 (5). pp. 712-721. ISSN 0005-2736
Abstract
Electrochemical impedance techniques and fluorescence spectroscopic methods have been applied to the study of the interaction of ortho (o)-, meta (m)- and para (p)-Cl-, o-, m- and p-HO-, p-H3CO-, p-H3C-, p-NC- and p-O3− S- substituted biphenyls (BPs) with Hg supported dioleoyl phosphatidylcholine (DOPC) monolayers and DOPC vesicles. Non-planar o-substituted BPs exhibit the weakest interactions whereas planar p-substituted BPs interact to the greatest extent with the DOPC layers. The substituted BP/DOPC monolayer and bilayer interaction depends on the effect of the substituent on the aromatic electron density, which is related to the substituents’ mesomeric Hammetts constants. Substituted BPs with increased ring electron density do not increase the DOPC monolayer thickness on Hg and penetrate the DOPC vesicle membranes to the greatest extent. Substituted BPs with lower ring electron density can cause an increase in the monolayer’s thickness on Hg depending on their location and they remain in the interfacial and superficial layer of the free standing DOPC membranes. Quantum mechanical calculations correlate the binding energy between the substituted BP rings and methyl acetate, as a model for the –CH2-(CO)O-CH2- fragment of a DOPC molecule, with the location of BPs within the DOPC monolayer.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2017 Elsevier B.V. This is an author produced version of a paper published in Biochimica et Biophysica Acta (BBA) - Biomembranes. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | Electrochemical impedance; Fluorescence quenching; Phospholipid monolayers/bilayers; Monosubstituted biphenyls; Hammetts constants |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Biological Sciences (Leeds) > School of Biomedical Sciences (Leeds) The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Physical Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 30 Jan 2017 16:39 |
Last Modified: | 24 Jan 2018 01:38 |
Published Version: | https://doi.org/10.1016/j.bbamem.2017.01.023 |
Status: | Published |
Publisher: | Elsevier |
Identification Number: | 10.1016/j.bbamem.2017.01.023 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:111422 |