The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity
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-pheny...
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| Format: | Article |
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MDPI AG
2021-03-01
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| Series: | Membranes |
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| Online Access: | https://www.mdpi.com/2077-0375/11/4/254 |
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| author | Isabel S. Kleinwächter Stefanie Pannwitt Alessia Centi Nadja Hellmann Eckhard Thines Tristan Bereau Dirk Schneider |
| author_facet | Isabel S. Kleinwächter Stefanie Pannwitt Alessia Centi Nadja Hellmann Eckhard Thines Tristan Bereau Dirk Schneider |
| author_sort | Isabel S. Kleinwächter |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T12:44:13Z |
| format | Article |
| id | doaj.art-25d9d09325cd42f69cda206deb986fb9 |
| institution | Directory Open Access Journal |
| issn | 2077-0375 |
| language | English |
| last_indexed | 2024-03-10T12:44:13Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Membranes |
| spelling | doaj.art-25d9d09325cd42f69cda206deb986fb92023-11-21T13:38:34ZengMDPI AGMembranes2077-03752021-03-0111425410.3390/membranes11040254The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding AffinityIsabel S. Kleinwächter0Stefanie Pannwitt1Alessia Centi2Nadja Hellmann3Eckhard Thines4Tristan Bereau5Dirk Schneider6Department of Chemistry, Biochemistry, Johannes Gutenberg University Mainz, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, GermanyDepartment of Chemistry, Biochemistry, Johannes Gutenberg University Mainz, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, GermanyMax Planck Institute for Polymer Research, 55128 Mainz, GermanyDepartment of Chemistry, Biochemistry, Johannes Gutenberg University Mainz, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, GermanyInstitute of Molecular Physiology, Johannes Gutenberg University, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, GermanyMax Planck Institute for Polymer Research, 55128 Mainz, GermanyDepartment of Chemistry, Biochemistry, Johannes Gutenberg University Mainz, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, GermanyThe 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.https://www.mdpi.com/2077-0375/11/4/2542-phenylethanolphenylacetic acidphenyllactic acidmethyl phenylacetateTyrosolbiomembranes |
| spellingShingle | Isabel S. Kleinwächter Stefanie Pannwitt Alessia Centi Nadja Hellmann Eckhard Thines Tristan Bereau Dirk Schneider The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity Membranes 2-phenylethanol phenylacetic acid phenyllactic acid methyl phenylacetate Tyrosol biomembranes |
| title | The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity |
| title_full | The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity |
| title_fullStr | The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity |
| title_full_unstemmed | The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity |
| title_short | The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity |
| title_sort | bacteriostatic activity of 2 phenylethanol derivatives correlates with membrane binding affinity |
| topic | 2-phenylethanol phenylacetic acid phenyllactic acid methyl phenylacetate Tyrosol biomembranes |
| url | https://www.mdpi.com/2077-0375/11/4/254 |
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