Cargando…

Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids

Synthetic molecules that target specific lipids serve as powerful tools for understanding membrane biology and may also enable new applications in biotechnology and medicine. For example, selective recognition of bacterial lipids may give rise to novel antibiotics, as well as diagnostic methods for...

Descripción completa

Detalles Bibliográficos
Autores principales: Bandyopadhyay, Anupam, McCarthy, Kelly A., Kelly, Michael A., Gao, Jianmin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4363082/
https://www.ncbi.nlm.nih.gov/pubmed/25761996
http://dx.doi.org/10.1038/ncomms7561
_version_ 1782361876883046400
author Bandyopadhyay, Anupam
McCarthy, Kelly A.
Kelly, Michael A.
Gao, Jianmin
author_facet Bandyopadhyay, Anupam
McCarthy, Kelly A.
Kelly, Michael A.
Gao, Jianmin
author_sort Bandyopadhyay, Anupam
collection PubMed
description Synthetic molecules that target specific lipids serve as powerful tools for understanding membrane biology and may also enable new applications in biotechnology and medicine. For example, selective recognition of bacterial lipids may give rise to novel antibiotics, as well as diagnostic methods for bacterial infection. Currently known lipid-binding molecules primarily rely on noncovalent interactions to achieve lipid selectivity. Here we show that targeted recognition of lipids can be realized by selectively modifying the lipid of interest via covalent bond formation. Specifically, we report an unnatural amino acid that preferentially labels amine-presenting lipids via iminoboronate formation under physiological conditions. By targeting phosphatidylethanolamine and lysylphosphatidylglycerol, the two lipids enriched on bacterial cell surfaces, the iminoboronate chemistry allows potent labeling of Gram-positive bacteria even in presence of 10% serum, while bypassing mammalian cells and Gram-negative bacteria. The covalent strategy for lipid recognition should be extendable to other important membrane lipids.
format Online
Article
Text
id pubmed-4363082
institution National Center for Biotechnology Information
language English
publishDate 2015
record_format MEDLINE/PubMed
spelling pubmed-43630822015-09-12 Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids Bandyopadhyay, Anupam McCarthy, Kelly A. Kelly, Michael A. Gao, Jianmin Nat Commun Article Synthetic molecules that target specific lipids serve as powerful tools for understanding membrane biology and may also enable new applications in biotechnology and medicine. For example, selective recognition of bacterial lipids may give rise to novel antibiotics, as well as diagnostic methods for bacterial infection. Currently known lipid-binding molecules primarily rely on noncovalent interactions to achieve lipid selectivity. Here we show that targeted recognition of lipids can be realized by selectively modifying the lipid of interest via covalent bond formation. Specifically, we report an unnatural amino acid that preferentially labels amine-presenting lipids via iminoboronate formation under physiological conditions. By targeting phosphatidylethanolamine and lysylphosphatidylglycerol, the two lipids enriched on bacterial cell surfaces, the iminoboronate chemistry allows potent labeling of Gram-positive bacteria even in presence of 10% serum, while bypassing mammalian cells and Gram-negative bacteria. The covalent strategy for lipid recognition should be extendable to other important membrane lipids. 2015-03-12 /pmc/articles/PMC4363082/ /pubmed/25761996 http://dx.doi.org/10.1038/ncomms7561 Text en http://www.nature.com/authors/editorial_policies/license.html#terms Users may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use:http://www.nature.com/authors/editorial_policies/license.html#terms
spellingShingle Article
Bandyopadhyay, Anupam
McCarthy, Kelly A.
Kelly, Michael A.
Gao, Jianmin
Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids
title Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids
title_full Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids
title_fullStr Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids
title_full_unstemmed Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids
title_short Targeting Bacteria via Iminoboronate Chemistry of Amine-Presenting Lipids
title_sort targeting bacteria via iminoboronate chemistry of amine-presenting lipids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4363082/
https://www.ncbi.nlm.nih.gov/pubmed/25761996
http://dx.doi.org/10.1038/ncomms7561
work_keys_str_mv AT bandyopadhyayanupam targetingbacteriaviaiminoboronatechemistryofaminepresentinglipids
AT mccarthykellya targetingbacteriaviaiminoboronatechemistryofaminepresentinglipids
AT kellymichaela targetingbacteriaviaiminoboronatechemistryofaminepresentinglipids
AT gaojianmin targetingbacteriaviaiminoboronatechemistryofaminepresentinglipids