The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity

Kleinwächter, Isabel S.; Pannwitt, Stefanie; Centi, Alessia; Hellmann, Nadja; Thines, Eckhard; Bereau, Tristan; Schneider, Dirk

doi:10.3390/membranes11040254

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The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity

Isabel S. Kleinwächter

¹,

¹,

²,

¹,

³,

^2,4

and

Dirk Schneider

^1,2,*

Department of Chemistry, Biochemistry, Johannes Gutenberg University Mainz, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, Germany

Max Planck Institute for Polymer Research, 55128 Mainz, Germany

Institute of Molecular Physiology, Johannes Gutenberg University, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, Germany

⁴

Van ‘t Hoff Institute for Molecular Sciences and Informatics Institute, University of Amsterdam, 1098 XH Amsterdam, The Netherlands

Author to whom correspondence should be addressed.

Academic Editor: Luis Octavio Regasini

Membranes 2021, 11(4), 254; https://doi.org/10.3390/membranes11040254

Received: 9 March 2021 / Revised: 25 March 2021 / Accepted: 26 March 2021 / Published: 31 March 2021

(This article belongs to the Special Issue Biological Membranes as Targets for Natural and Synthetic Compounds)

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Abstract

The hydrophobic tails of aliphatic primary alcohols do insert into the hydrophobic core of a lipid bilayer. Thereby, they disrupt hydrophobic interactions between the lipid molecules, resulting in a decreased lipid order, i.e., an increased membrane fluidity. While aromatic alcohols, such as 2-phenylethanol, also insert into lipid bilayers and disturb the membrane organization, the impact of aromatic alcohols on the structure of biological membranes, as well as the potential physiological implication of membrane incorporation has only been studied to a limited extent. Although diverse targets are discussed to be causing the bacteriostatic and bactericidal activity of 2-phenylethanol, it is clear that 2-phenylethanol severely affects the structure of biomembranes, which has been linked to its bacteriostatic activity. Yet, in fungi some 2-phenylethanol derivatives are also produced, some of which appear to also have bacteriostatic activities. We showed that the 2-phenylethanol derivatives phenylacetic acid, phenyllactic acid, and methyl phenylacetate, but not Tyrosol, were fully incorporated into model membranes and affected the membrane organization. Furthermore, we observed that the propensity of the herein-analyzed molecules to partition into biomembranes positively correlated with their respective bacteriostatic activity, which clearly linked the bacteriotoxic activity of the substances to biomembranes. View Full-Text

Keywords: 2-phenylethanol; phenylacetic acid; phenyllactic acid; methyl phenylacetate; Tyrosol; biomembranes; membrane interaction; bacteriotoxic

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MDPI and ACS Style

Kleinwächter, I.S.; Pannwitt, S.; Centi, A.; Hellmann, N.; Thines, E.; Bereau, T.; Schneider, D. The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity. Membranes 2021, 11, 254. https://doi.org/10.3390/membranes11040254

AMA Style

Kleinwächter IS, Pannwitt S, Centi A, Hellmann N, Thines E, Bereau T, Schneider D. The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity. Membranes. 2021; 11(4):254. https://doi.org/10.3390/membranes11040254

Chicago/Turabian Style

Kleinwächter, Isabel S., Stefanie Pannwitt, Alessia Centi, Nadja Hellmann, Eckhard Thines, Tristan Bereau, and Dirk Schneider. 2021. "The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity" Membranes 11, no. 4: 254. https://doi.org/10.3390/membranes11040254

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The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity

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