Targeting bacteria via iminoboronate chemistry of amine-presenting lipids
| Autor: | Kelly A. McCarthy, Anupam Bandyopadhyay, Michael A. Kelly, Jianmin Gao |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Magnetic Resonance Spectroscopy
General Physics and Astronomy iminoboronate 01 natural sciences Mass Spectrometry Bacterial cell structure Jurkat Cells chemistry.chemical_compound lysylphosphatidylglycerol (Lys-PG) Non-covalent interactions Amines bacterial imaging chemistry.chemical_classification Microscopy Confocal Multidisciplinary biology Chemistry Phosphatidylglycerols Lipids Anti-Bacterial Agents Sphingomyelins 3. Good health Amino acid Biochemistry Covalent bond Phosphatidylcholines lipids (amino acids peptides and proteins) phosphatidylethanolamine (PE) Bacillus subtilis Biotechnology Boron Compounds Membrane lipids Membrane biology Phosphatidylserines 010402 general chemistry Article General Biochemistry Genetics and Molecular Biology Membrane Lipids covalent recognition Escherichia coli Humans Phosphatidylethanolamine Dose-Response Relationship Drug 010405 organic chemistry Lysine Phosphatidylethanolamines General Chemistry biology.organism_classification Coculture Techniques 0104 chemical sciences Bacteria |
| Zdroj: | Nature communications |
| ISSN: | 2041-1723 |
| Popis: | 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 labelling of Gram-positive bacteria even in the 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. |
| Databáze: | OpenAIRE |
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