The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological Activity
Quorum sensing (QS) signaling system is important for bacterial growth, adhesion, and biofilm formation resulting in numerous infectious diseases. Dihydropyrrol-2-ones (DHPs) represent a novel class of antimicrobial agents that inhibit QS, and are less prone to develop bacterial resistance due to th...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/14/2676 |
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| author | Aditi Taunk Renxun Chen George Iskander Kitty K. K. Ho Basmah Almohaywi David StClair Black Mark D. P. Willcox Naresh Kumar |
| author_facet | Aditi Taunk Renxun Chen George Iskander Kitty K. K. Ho Basmah Almohaywi David StClair Black Mark D. P. Willcox Naresh Kumar |
| author_sort | Aditi Taunk |
| collection | DOAJ |
| description | Quorum sensing (QS) signaling system is important for bacterial growth, adhesion, and biofilm formation resulting in numerous infectious diseases. Dihydropyrrol-2-ones (DHPs) represent a novel class of antimicrobial agents that inhibit QS, and are less prone to develop bacterial resistance due to their non-growth inhibition mechanism of action which does not cause survival pressure on bacteria. DHPs can prevent bacterial colonization and quorum sensing when covalently bound to substrates. In this study, the role of orientation of DHP compounds was investigated after covalent attachment by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)/<i>N</i>-hydroxysuccinimide (NHS) coupling reaction to amine-functionalized glass surfaces via various positions of the DHP scaffold. The functionalized glass surfaces were characterized by X-ray photoelectron spectroscopy (XPS) and contact angle measurements and tested for their in vitro biological activity against <i>S. aureus</i> and <i>P. aeruginosa</i>. DHPs attached via the N-1 position resulted in the highest antibacterial activities against <i>S. aureus</i>, while no difference was observed for DHPs attached either via the N-1 position or the C-4 phenyl ring against <i>P. aeruginosa.</i> |
| first_indexed | 2024-04-12T11:31:43Z |
| format | Article |
| id | doaj.art-1252e04c7c5042109e6c0db40baabfff |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T11:31:43Z |
| publishDate | 2019-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1252e04c7c5042109e6c0db40baabfff2022-12-22T03:34:59ZengMDPI AGMolecules1420-30492019-07-012414267610.3390/molecules24142676molecules24142676The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological ActivityAditi Taunk0Renxun Chen1George Iskander2Kitty K. K. Ho3Basmah Almohaywi4David StClair Black5Mark D. P. Willcox6Naresh Kumar7School of Chemistry, University of New South Wales, Sydney 2052, AustraliaSchool of Chemistry, University of New South Wales, Sydney 2052, AustraliaSchool of Chemistry, University of New South Wales, Sydney 2052, AustraliaSchool of Chemistry, University of New South Wales, Sydney 2052, AustraliaSchool of Chemistry, University of New South Wales, Sydney 2052, AustraliaSchool of Chemistry, University of New South Wales, Sydney 2052, AustraliaSchool of Optometry and Vision Science, University of New South Wales, Sydney 2052, AustraliaSchool of Chemistry, University of New South Wales, Sydney 2052, AustraliaQuorum sensing (QS) signaling system is important for bacterial growth, adhesion, and biofilm formation resulting in numerous infectious diseases. Dihydropyrrol-2-ones (DHPs) represent a novel class of antimicrobial agents that inhibit QS, and are less prone to develop bacterial resistance due to their non-growth inhibition mechanism of action which does not cause survival pressure on bacteria. DHPs can prevent bacterial colonization and quorum sensing when covalently bound to substrates. In this study, the role of orientation of DHP compounds was investigated after covalent attachment by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)/<i>N</i>-hydroxysuccinimide (NHS) coupling reaction to amine-functionalized glass surfaces via various positions of the DHP scaffold. The functionalized glass surfaces were characterized by X-ray photoelectron spectroscopy (XPS) and contact angle measurements and tested for their in vitro biological activity against <i>S. aureus</i> and <i>P. aeruginosa</i>. DHPs attached via the N-1 position resulted in the highest antibacterial activities against <i>S. aureus</i>, while no difference was observed for DHPs attached either via the N-1 position or the C-4 phenyl ring against <i>P. aeruginosa.</i>https://www.mdpi.com/1420-3049/24/14/2676quorum sensingsurface attachment<i>Pseudomonas</i><i>Staphylococcus</i>antimicrobialbiomaterials |
| spellingShingle | Aditi Taunk Renxun Chen George Iskander Kitty K. K. Ho Basmah Almohaywi David StClair Black Mark D. P. Willcox Naresh Kumar The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological Activity Molecules quorum sensing surface attachment <i>Pseudomonas</i> <i>Staphylococcus</i> antimicrobial biomaterials |
| title | The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological Activity |
| title_full | The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological Activity |
| title_fullStr | The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological Activity |
| title_full_unstemmed | The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological Activity |
| title_short | The Role of Orientation of Surface Bound Dihydropyrrol-2-ones (DHP) on Biological Activity |
| title_sort | role of orientation of surface bound dihydropyrrol 2 ones dhp on biological activity |
| topic | quorum sensing surface attachment <i>Pseudomonas</i> <i>Staphylococcus</i> antimicrobial biomaterials |
| url | https://www.mdpi.com/1420-3049/24/14/2676 |
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