免疫调节与群体感应分子 3-氧代-C12-高丝氨酸内酯：化学支架对于探针开发的重要性。
Immunomodulation and the quorum sensing molecule 3-oxo-C12-homoserine lactone: the importance of chemical scaffolding for probe development.
机构信息
Department of Chemistry, The Skaggs Institute for Chemical Biology and The Worm Institute for Research and Medicine, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
出版信息
Chem Commun (Camb). 2013 Feb 21;49(15):1515-7. doi: 10.1039/c3cc38851d.
Abstract
As a guide for chemical probe design, focused analogue synthetic studies were undertaken upon the lactone ring of 3-oxo-C(12)-homoserine lactone. We have concluded that hydrolytic instability of the heterocyclic ring is pivotal for its ability to modulate immune signaling and probe preparation was aligned with these findings.
摘要
作为化学探针设计的指南，我们对 3-氧代-C(12)-同型丝氨酸内酯的内酯环进行了集中的类似物合成研究。我们得出结论，杂环的水解不稳定性对于其调节免疫信号的能力至关重要，探针的制备也符合这些发现。
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本文引用的文献
1
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2
Thiolactone modulators of quorum sensing revealed through library design and screening.通过文库设计和筛选发现群体感应的硫内酯调节剂。
Bioorg Med Chem. 2011 Aug 15;19(16):4820-8. doi: 10.1016/j.bmc.2011.06.071. Epub 2011 Jul 1.
3
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4
Synthesis of 'clickable' acylhomoserine lactone quorum sensing probes: unanticipated effects on mammalian cell activation.'点击化学'酰基高丝氨酸内酯群体感应探针的合成：对哺乳动物细胞激活的意外影响。
Bioorg Med Chem Lett. 2011 May 1;21(9):2702-5. doi: 10.1016/j.bmcl.2010.11.122. Epub 2010 Dec 4.
5
Small molecules that modulate quorum sensing and control virulence in Pseudomonas aeruginosa.调节铜绿假单胞菌群体感应并控制其毒力的小分子。
J Org Chem. 2010 Oct 15;75(20):6737-46. doi: 10.1021/jo101237e.
6
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J Med Chem. 2010 Nov 11;53(21):7467-89. doi: 10.1021/jm901742e.
7
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9
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