Side-chain-to-tail thiolactone peptide inhibitors of the staphylococcal quorum-sensing system
The expression of many staphylococcal virulence factors are regulated by the agr locus via a two-component signal transduction system (TCSTS), which is activated in response to a secreted autoinducer peptide (AIP). By exploiting the unique chemical architecture of the naturally occurring AIP-1, seve...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 13; no. 15; pp. 2449 - 2453 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Oxford
Elsevier Ltd
04.08.2003
Elsevier |
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| Online Access | Get full text |
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| Abstract | The expression of many staphylococcal virulence factors are regulated by the
agr locus via a two-component signal transduction system (TCSTS), which is activated in response to a secreted autoinducer peptide (AIP). By exploiting the unique chemical architecture of the naturally occurring AIP-1, several potent inhibitors of staphylococcal TCSTS were designed and synthesized using either a linear or branched solid-phase approach. These inhibitors are competitive binders and contain the crucial 16-membered side-chain-to-tail thiolactone peptide pharmacophore.
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| AbstractList | The expression of many staphylococcal virulence factors are regulated by the agr locus via a two-component signal transduction system (TCSTS), which is activated in response to a secreted autoinducer peptide (AIP). By exploiting the unique chemical architecture of the naturally occurring AIP-1, several potent inhibitors of staphylococcal TCSTS were designed and synthesized using either a linear or branched solid-phase approach. These inhibitors are competitive binders and contain the crucial 16-membered side-chain-to-tail thiolactone peptide pharmacophore. The expression of many staphylococcal virulence factors are regulated by the agr locus via a two-component signal transduction system (TCSTS), which is activated in response to a secreted autoinducer peptide (AIP). By exploiting the unique chemical architecture of the naturally occurring AIP-1, several potent inhibitors of staphylococcal TCSTS were designed and synthesized using either a linear or branched solid-phase approach. These inhibitors are competitive binders and contain the crucial 16-membered side-chain-to-tail thiolactone peptide pharmacophore. Graphic |
| Author | Cockayne, Alan Chan, Weng C Bycroft, Barrie W Lian, Lu-Yun Muharram, S.Hanna Wood, Stewart J Williams, Paul Scott, R.John |
| Author_xml | – sequence: 1 givenname: R.John surname: Scott fullname: Scott, R.John organization: School of Pharmaceutical Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK – sequence: 2 givenname: Lu-Yun surname: Lian fullname: Lian, Lu-Yun organization: Department of Biomolecular Sciences, University of Manchester Institute of Science & Technology, The Mill, Sackville Street, Manchester M60 1QD, UK – sequence: 3 givenname: S.Hanna surname: Muharram fullname: Muharram, S.Hanna organization: Institute of Infection, Immunity & Inflammation, University of Nottingham, University Park, Nottingham NG7 2RD, UK – sequence: 4 givenname: Alan surname: Cockayne fullname: Cockayne, Alan organization: Institute of Infection, Immunity & Inflammation, University of Nottingham, University Park, Nottingham NG7 2RD, UK – sequence: 5 givenname: Stewart J surname: Wood fullname: Wood, Stewart J organization: School of Pharmaceutical Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK – sequence: 6 givenname: Barrie W surname: Bycroft fullname: Bycroft, Barrie W organization: School of Pharmaceutical Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK – sequence: 7 givenname: Paul surname: Williams fullname: Williams, Paul organization: School of Pharmaceutical Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK – sequence: 8 givenname: Weng C surname: Chan fullname: Chan, Weng C email: weng.chan@nottingham.ac.uk organization: School of Pharmaceutical Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK |
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| Keywords | Cyclic peptides Virulence Staphylococcus Pseudopeptide Signal transduction Structure activity relation Bacteria Micrococcales Micrococcaceae Peptide synthesis Inhibition Solid phase Chemical synthesis |
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| Snippet | The expression of many staphylococcal virulence factors are regulated by the
agr locus via a two-component signal transduction system (TCSTS), which is... The expression of many staphylococcal virulence factors are regulated by the agr locus via a two-component signal transduction system (TCSTS), which is... |
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| SubjectTerms | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Bacterial Proteins - genetics Bacteriology Biological and medical sciences Cyclization Dose-Response Relationship, Drug Drug Design Fundamental and applied biological sciences. Psychology Genes, Reporter - genetics Indicators and Reagents Lactones - antagonists & inhibitors Medical sciences Microbiology Pathogenicity, virulence, toxins, bacteriocins, pyrogens, host-bacteria relations, miscellaneous strains Peptides - antagonists & inhibitors Pharmacology. Drug treatments Signal Transduction - physiology Staphylococcus - drug effects Staphylococcus - genetics Staphylococcus - physiology Structure-Activity Relationship Trans-Activators - genetics Tyrosine |
| Title | Side-chain-to-tail thiolactone peptide inhibitors of the staphylococcal quorum-sensing system |
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