无标签光活性群体感应探针中物种选择性重氮化合物定位。
Species selective diazirine positioning in tag-free photoactive quorum sensing probes.
机构信息
Department of Chemistry and the National Institute for Biotechnology in the Negev, Ben-Gurion University of the Negev, Be'er-Sheva 84105, Israel.
出版信息
Chem Commun (Camb). 2013 Jul 4;49(52):5826-8. doi: 10.1039/c3cc43092h. Epub 2013 May 24.
Abstract
The synthesis and comparison of activities of 'tag-free' probes with diazirines at various positions are described. Remarkable differences in their effects on P. aeruginosa and on human bronchial epithelial cells were observed, supporting the efforts to isolate and identify receptors for N-acyl homoserine lactones.
摘要
描述了在不同位置带有重氮化合物的“无标签”探针的合成和比较。观察到它们对铜绿假单胞菌和人支气管上皮细胞的影响有显著差异，这支持了分离和鉴定 N-酰基高丝氨酸内酯受体的努力。
相似文献
1
Species selective diazirine positioning in tag-free photoactive quorum sensing probes.
Chem Commun (Camb). 2013 Jul 4;49(52):5826-8. doi: 10.1039/c3cc43092h. Epub 2013 May 24.
2
Design and Synthesis of Lactams Derived from Mucochloric and Mucobromic Acids as Quorum Sensing Inhibitors.
Molecules. 2018 May 7;23(5):1106. doi: 10.3390/molecules23051106.
3
Rosmarinic acid is a homoserine lactone mimic produced by plants that activates a bacterial quorum-sensing regulator.
Sci Signal. 2016 Jan 5;9(409):ra1. doi: 10.1126/scisignal.aaa8271.
4
Identification of five structurally unrelated quorum-sensing inhibitors of Pseudomonas aeruginosa from a natural-derivative database.
Antimicrob Agents Chemother. 2013 Nov;57(11):5629-41. doi: 10.1128/AAC.00955-13. Epub 2013 Sep 3.
5
Structural determinants driving homoserine lactone ligand selection in the LasR quorum-sensing receptor.
Proc Natl Acad Sci U S A. 2019 Jan 2;116(1):245-254. doi: 10.1073/pnas.1817239116. Epub 2018 Dec 17.
6
Quorum Sensing Inhibitory Potential and Molecular Docking Studies of Phyllanthus emblica Phytochemicals Against Pseudomonas aeruginosa.
Appl Biochem Biotechnol. 2022 Jan;194(1):434-444. doi: 10.1007/s12010-021-03683-w. Epub 2021 Oct 6.
7
Synthesis and validation of a probe to identify quorum sensing receptors.
Chem Commun (Camb). 2009 Dec 21(47):7378-80. doi: 10.1039/b917507e. Epub 2009 Oct 28.
8
Molecular basis for the recognition of structurally distinct autoinducer mimics by the Pseudomonas aeruginosa LasR quorum-sensing signaling receptor.
Chem Biol. 2009 Sep 25;16(9):961-70. doi: 10.1016/j.chembiol.2009.09.001.
9
Molecular insights into quorum sensing in the human pathogen Pseudomonas aeruginosa from the structure of the virulence regulator LasR bound to its autoinducer.
J Biol Chem. 2007 May 4;282(18):13592-600. doi: 10.1074/jbc.M700556200. Epub 2007 Mar 15.
10
Theoretical and structural analysis of the active site of the transcriptional regulators LasR and TraR, using molecular docking methodology for identifying potential analogues of acyl homoserine lactones (AHLs) with anti-quorum sensing activity.
Eur J Med Chem. 2010 Feb;45(2):608-15. doi: 10.1016/j.ejmech.2009.11.004. Epub 2009 Nov 6.
引用本文的文献
1
Monitoring host-pathogen interactions using chemical proteomics.
RSC Chem Biol. 2023 Nov 10;5(2):73-89. doi: 10.1039/d3cb00135k. eCollection 2024 Feb 7.
2
Chemical biology tools for protein labelling: insights into cell-cell communication.
Biochem J. 2023 Sep 27;480(18):1445-1457. doi: 10.1042/BCJ20220309.
3
A Bacterial Quorum Sensing Molecule Elicits a General Stress Response in .
Front Microbiol. 2021 Sep 16;12:632658. doi: 10.3389/fmicb.2021.632658. eCollection 2021.
4
Immunoediting role for major vault protein in apoptotic signaling induced by bacterial -acyl homoserine lactones.
Proc Natl Acad Sci U S A. 2021 Mar 23;118(12). doi: 10.1073/pnas.2012529118.
5
Proteome-wide mapping of PQS-interacting proteins in .
Chem Sci. 2018 Jan 19;9(8):2290-2294. doi: 10.1039/c7sc04287f. eCollection 2018 Feb 28.
6
Identification of new quorum sensing autoinducer binding partners in using photoaffinity probes.
Chem Sci. 2017 Nov 1;8(11):7403-7411. doi: 10.1039/c7sc01270e. Epub 2017 Aug 29.
7
Chemical proteomics approaches for identifying the cellular targets of natural products.
Nat Prod Rep. 2016 May 4;33(5):681-708. doi: 10.1039/c6np00001k.
8
Quorum sensing communication between bacteria and human cells: signals, targets, and functions.
Front Plant Sci. 2014 Jun 26;5:309. doi: 10.3389/fpls.2014.00309. eCollection 2014.
本文引用的文献
1
The bacterial quorum-sensing signal molecule N-3-oxo-dodecanoyl-L-homoserine lactone reciprocally modulates pro- and anti-inflammatory cytokines in activated macrophages.
J Immunol. 2013 Jul 1;191(1):337-44. doi: 10.4049/jimmunol.1300368. Epub 2013 May 29.
2
The Pseudomonas aeruginosa N-acylhomoserine lactone quorum sensing molecules target IQGAP1 and modulate epithelial cell migration.
PLoS Pathog. 2012;8(10):e1002953. doi: 10.1371/journal.ppat.1002953. Epub 2012 Oct 11.
3
The Pseudomonas aeruginosa quorum sensing signal molecule N-(3-oxododecanoyl) homoserine lactone enhances keratinocyte migration and induces Mmp13 gene expression in vitro.
Biochem Biophys Res Commun. 2012 Oct 19;427(2):273-9. doi: 10.1016/j.bbrc.2012.09.037. Epub 2012 Sep 16.
4
Expression of PPARγ and paraoxonase 2 correlated with Pseudomonas aeruginosa infection in cystic fibrosis.
PLoS One. 2012;7(7):e42241. doi: 10.1371/journal.pone.0042241. Epub 2012 Jul 31.
5
Diazirine based photoaffinity labeling.
Bioorg Med Chem. 2012 Jan 15;20(2):554-70. doi: 10.1016/j.bmc.2011.06.066. Epub 2011 Jun 29.
6
Synthesis and application of an N-acylated l-homoserine lactone derivatized affinity matrix for the isolation of quorum sensing signal receptors.
Bioorg Med Chem Lett. 2011 Sep 1;21(17):5054-7. doi: 10.1016/j.bmcl.2011.04.062. Epub 2011 Apr 22.
7
Perception and degradation of N-acyl homoserine lactone quorum sensing signals by mammalian and plant cells.
Chem Rev. 2011 Jan 12;111(1):100-16. doi: 10.1021/cr100045m. Epub 2010 Jun 10.
8
Pseudomonas signal molecule 3-oxo-C12-homoserine lactone interferes with binding of rosiglitazone to human PPARgamma.
Microbes Infect. 2010 Mar;12(3):231-7. doi: 10.1016/j.micinf.2009.12.009. Epub 2010 Jan 13.
9
Synthesis and validation of a probe to identify quorum sensing receptors.
Chem Commun (Camb). 2009 Dec 21(47):7378-80. doi: 10.1039/b917507e. Epub 2009 Oct 28.
10
Modulation of gene expression via disruption of NF-kappaB signaling by a bacterial small molecule.
Science. 2008 Jul 11;321(5886):259-63. doi: 10.1126/science.1156499. Epub 2008 Jun 19.
Zotero 插件