The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Isabel S Kleinwaechter
- Stefanie Pannwitt
- Alessia Centi
- Nadja Hellmann
- Eckhard Thines
- Tristan Bereau
- Dirk Schneider
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000643244400001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.3390/membranes11040254
- eISSN
- 2077-0375
- Externe Identifier
- Clarivate Analytics Document Solution ID: RR6ZV
- PubMed Identifier: 33807437
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- MEMBRANES
- Schlüsselwörter
- 2-phenylethanol
- phenylacetic acid
- phenyllactic acid
- methyl phenylacetate
- Tyrosol
- biomembranes
- membrane interaction
- bacteriotoxic
- Artikelnummer
- ARTN 254
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Titel
- The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity
- Sub types
- Article
- Ausgabe der Zeitschrift
- 11
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:p>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.</jats:p>
- Autoren
- Isabel S Kleinwächter
- Stefanie Pannwitt
- Alessia Centi
- Nadja Hellmann
- Eckhard Thines
- Tristan Bereau
- Dirk Schneider
- DOI
- 10.3390/membranes11040254
- eISSN
- 2077-0375
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Membranes
- Sprache
- en
- Online publication date
- 2021
- Paginierung
- 254 - 254
- Status
- Published online
- Herausgeber
- MDPI AG
- Herausgeber URL
- http://dx.doi.org/10.3390/membranes11040254
- Datum der Datenerfassung
- 2021
- Titel
- The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity
- Ausgabe der Zeitschrift
- 11
Datenquelle: Crossref
- 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.
- Addresses
- Department of Chemistry, Biochemistry, Johannes Gutenberg University Mainz, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, Germany.
- Autoren
- Isabel S Kleinwächter
- Stefanie Pannwitt
- Alessia Centi
- Nadja Hellmann
- Eckhard Thines
- Tristan Bereau
- Dirk Schneider
- DOI
- 10.3390/membranes11040254
- eISSN
- 2077-0375
- Externe Identifier
- PubMed Identifier: 33807437
- PubMed Central ID: PMC8067230
- Funding acknowledgements
- Deutsche Forschungsgemeinschaft: Emmy Noether Program
- DynaMem (state of Rhineland-Palatinate): N/A
- DynaMem: N/A
- Open access
- true
- ISSN
- 2077-0375
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Membranes
- Sprache
- eng
- Medium
- Electronic
- Online publication date
- 2021
- Open access status
- Open Access
- Paginierung
- 254
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Publisher licence
- CC BY
- Datum der Datenerfassung
- 2021
- Titel
- The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity.
- Sub types
- research-article
- Journal Article
- Ausgabe der Zeitschrift
- 11
Files
https://www.mdpi.com/2077-0375/11/4/254/pdf?version=1617938778 https://europepmc.org/articles/PMC8067230?pdf=render
Datenquelle: Europe PubMed Central
- 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.
- Date of acceptance
- 2021
- Autoren
- Isabel S Kleinwächter
- Stefanie Pannwitt
- Alessia Centi
- Nadja Hellmann
- Eckhard Thines
- Tristan Bereau
- Dirk Schneider
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/33807437
- DOI
- 10.3390/membranes11040254
- Externe Identifier
- PubMed Central ID: PMC8067230
- Funding acknowledgements
- DynaMem (state of Rhineland-Palatinate): N/A
- Deutsche Forschungsgemeinschaft: Emmy Noether Program
- ISSN
- 2077-0375
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Membranes (Basel)
- Schlüsselwörter
- 2-phenylethanol
- Tyrosol
- bacteriotoxic
- biomembranes
- membrane interaction
- methyl phenylacetate
- phenylacetic acid
- phenyllactic acid
- Sprache
- eng
- Country
- Switzerland
- PII
- membranes11040254
- Datum der Veröffentlichung
- 2021
- Status
- Published online
- Titel
- The Bacteriostatic Activity of 2-Phenylethanol Derivatives Correlates with Membrane Binding Affinity.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 11
Datenquelle: PubMed
- Author's licence
- CC-BY
- Autoren
- Isabel S Kleinwächter
- Stefanie Pannwitt
- Alessia Centi
- Nadja Hellmann
- Eckhard Thines
- Tristan Bereau
- Dirk Schneider
- Hosting institution
- Universitätsbibliothek Mainz
- Sammlungen
- JGU-Publikationen
- Resource version
- Published version
- DOI
- 10.3390/membranes11040254
- Funding acknowledgements
- Open Access-Publizieren Universität Mainz / Universitätsmedizin Mainz
- File(s) embargoed
- false
- Open access
- true
- ISSN
- 2077-0375
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Membranes
- Schlüsselwörter
- 540 Chemie
- 540 Chemistry and allied sciences
- Sprache
- eng
- Open access status
- Open Access
- Paginierung
- 254
- Datum der Veröffentlichung
- 2021
- Public URL
- https://openscience.ub.uni-mainz.de/handle/20.500.12030/6487
- Herausgeber
- MDPI
- Herausgeber URL
- https://doi.org/10.3390/membranes11040254
- Datum der Datenerfassung
- 2021
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2021
- Zugang
- Public
- Titel
- The bacteriostatic activity of 2-phenylethanol derivatives correlates with membrane binding affinity
- Ausgabe der Zeitschrift
- 11
Files
kleinwächter_isabel_s.-the_bacteriost-20211109122146804.pdf
Datenquelle: OPENSCIENCE.UB
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