Permeation through the cell membrane of a boron-based β-lactamase inhibitor.

Bacteria express beta-lactamases to counteract the beneficial action of antibiotics. Benzo[b]-thiophene-2-boronic acid (BZB) derivatives are β-lactamase inhibitors and, as such, promising compounds to be associated with β-lactam antibacterial therapies. The uncharged form of BZB, in particular, is s...

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Autores principales:	Manuela Minozzi, Gianluca Lattanzi, Roland Benz, Maria P Costi, Alberto Venturelli, Paolo Carloni
Formato:	article
Lenguaje:	EN
Publicado:	Public Library of Science (PLoS) 2011
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/92660a032c3f4a1581d416a3b117cc21
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spelling	oai:doaj.org-article:92660a032c3f4a1581d416a3b117cc212021-11-18T06:47:50ZPermeation through the cell membrane of a boron-based β-lactamase inhibitor.1932-620310.1371/journal.pone.0023187https://doaj.org/article/92660a032c3f4a1581d416a3b117cc212011-01-01T00:00:00Zhttps://www.ncbi.nlm.nih.gov/pmc/articles/pmid/21858024/pdf/?tool=EBIhttps://doaj.org/toc/1932-6203Bacteria express beta-lactamases to counteract the beneficial action of antibiotics. Benzo[b]-thiophene-2-boronic acid (BZB) derivatives are β-lactamase inhibitors and, as such, promising compounds to be associated with β-lactam antibacterial therapies. The uncharged form of BZB, in particular, is suggested to diffuse through the outer membrane of gram negative bacteria. In this study, through the combination of electrophysiological experiments across reconstituted PC/n-decane bilayers and metadynamics-based free energy calculations, we investigate the permeation mechanism of boronic compounds. Our experimental data establish that BZB passes through the membrane, while computer simulations provide hints for the existence of an aqueous, water-filled monomolecular channel. These findings provide new perspectives for the design of boronic acid derivatives with high membrane permeability.Manuela MinozziGianluca LattanziRoland BenzMaria P CostiAlberto VenturelliPaolo CarloniPublic Library of Science (PLoS)articleMedicineRScienceQENPLoS ONE, Vol 6, Iss 8, p e23187 (2011)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Manuela Minozzi Gianluca Lattanzi Roland Benz Maria P Costi Alberto Venturelli Paolo Carloni Permeation through the cell membrane of a boron-based β-lactamase inhibitor.
description	Bacteria express beta-lactamases to counteract the beneficial action of antibiotics. Benzo[b]-thiophene-2-boronic acid (BZB) derivatives are β-lactamase inhibitors and, as such, promising compounds to be associated with β-lactam antibacterial therapies. The uncharged form of BZB, in particular, is suggested to diffuse through the outer membrane of gram negative bacteria. In this study, through the combination of electrophysiological experiments across reconstituted PC/n-decane bilayers and metadynamics-based free energy calculations, we investigate the permeation mechanism of boronic compounds. Our experimental data establish that BZB passes through the membrane, while computer simulations provide hints for the existence of an aqueous, water-filled monomolecular channel. These findings provide new perspectives for the design of boronic acid derivatives with high membrane permeability.
format	article
author	Manuela Minozzi Gianluca Lattanzi Roland Benz Maria P Costi Alberto Venturelli Paolo Carloni
author_facet	Manuela Minozzi Gianluca Lattanzi Roland Benz Maria P Costi Alberto Venturelli Paolo Carloni
author_sort	Manuela Minozzi
title	Permeation through the cell membrane of a boron-based β-lactamase inhibitor.
title_short	Permeation through the cell membrane of a boron-based β-lactamase inhibitor.
title_full	Permeation through the cell membrane of a boron-based β-lactamase inhibitor.
title_fullStr	Permeation through the cell membrane of a boron-based β-lactamase inhibitor.
title_full_unstemmed	Permeation through the cell membrane of a boron-based β-lactamase inhibitor.
title_sort	permeation through the cell membrane of a boron-based β-lactamase inhibitor.
publisher	Public Library of Science (PLoS)
publishDate	2011
url	https://doaj.org/article/92660a032c3f4a1581d416a3b117cc21
work_keys_str_mv	AT manuelaminozzi permeationthroughthecellmembraneofaboronbasedblactamaseinhibitor AT gianlucalattanzi permeationthroughthecellmembraneofaboronbasedblactamaseinhibitor AT rolandbenz permeationthroughthecellmembraneofaboronbasedblactamaseinhibitor AT mariapcosti permeationthroughthecellmembraneofaboronbasedblactamaseinhibitor AT albertoventurelli permeationthroughthecellmembraneofaboronbasedblactamaseinhibitor AT paolocarloni permeationthroughthecellmembraneofaboronbasedblactamaseinhibitor
_version_	1718424366068269056

Permeation through the cell membrane of a boron-based β-lactamase inhibitor.

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