Targeting bacteria via iminoboronate chemistry of amine-presenting lipids.
Targeting bacteria via iminoboronate chemistry of amine-presenting lipids.
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DOI：
10.1038/ncomms7561
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发表时间：
2015-03-12
影响因子：
16.6
通讯作者：
Gao, Jianmin
中科院分区：
文献类型：
--
作者：
Bandyopadhyay, Anupam;McCarthy, Kelly A.;Kelly, Michael A.;Gao, Jianmin
针对特定脂质的合成分子可以作为理解膜生物学的强大工具，并且还可以在生物技术和医学中实现新的应用。例如，选择性识别细菌脂质可能会产生新型抗生素以及细菌感染的诊断方法。目前已知的脂质结合分子主要依靠非共价相互作用来实现脂质选择性。在这里，我们表明，通过共价键形成选择性修饰感兴趣的脂质，可以实现脂质的靶向识别。具体来说，我们报道了一种非天然氨基酸，它在生理条件下通过亚氨基硼酸盐的形成优先标记胺呈递的脂质。通过靶向富集在细菌细胞表面的磷脂酰乙醇胺和赖氨酰磷脂酰甘油这两种脂质，亚氨基硼酸盐化学物质即使在 10% 血清存在的情况下也能有效标记革兰氏阳性细菌，同时绕过哺乳动物细胞和革兰氏阴性细菌。脂质识别的共价策略应该可以扩展到其他重要的膜脂质。
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.
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DOI：
10.1002/anie.201403349
发表时间：
2014-09-15
期刊：
Angewandte Chemie (International ed. in English)
影响因子：
--
作者：
Erdmann RS;Takakura H;Thompson AD;Rivera-Molina F;Allgeyer ES;Bewersdorf J;Toomre D;Schepartz A
通讯作者：
Schepartz A
影响因子：
3.6
作者：
Lozada, Jerome;Liu, Zhibo;Perrin, David M.
通讯作者：
Perrin, David M.
影响因子：
4.3
作者：
Hutin, Marie;Bernardinelli, Gerald;Nitschke, Jonathan R.
通讯作者：
Nitschke, Jonathan R.
DOI：
10.1073/pnas.97.17.9367
发表时间：
2000-08-15
影响因子：
11.1
作者：
Erlanson, DA;Braisted, AC;Wells, JA
通讯作者：
Wells, JA
影响因子：
2.1
作者：
Gonzalez, Rodrigo;Albericio, Fernando;Iannucci, Nancy B.
通讯作者：
Iannucci, Nancy B.