Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/84293
Title: Design and Synthesis of Lactams Derived from Mucochloric and Mucobromic Acids as Pseudomonas aeruginosa Quorum Sensing Inhibitors
Authors: Almohaywi, Basmah
Taunk, Aditi
Nizalapur, Shashidhar
Iskander, George
Griffith, Renate
Kumar, Naresh
Wenholz, Daniel S.
Biswas, Nripendra N.
Ho, Kitty K. K.
Rice, Scott A.
Black, David StC.
Keywords: Quorum Sensing
Pseudomonas Aeruginosa
Issue Date: 2018
Source: Almohaywi, B., Taunk, A., Wenholz, D. S., Nizalapur, S., Biswas, N. N., Ho, K. K. K., et al. (2018). Design and Synthesis of Lactams Derived from Mucochloric and Mucobromic Acids as Pseudomonas aeruginosa Quorum Sensing Inhibitors. Molecules, 23(5), 1106-.
Series/Report no.: Molecules
Abstract: Bacterial infections, particularly hospital-acquired infections caused by Pseudomonas aeruginosa, have become a global threat with a high mortality rate. Gram-negative bacteria including P. aeruginosa employ N-acyl homoserine lactones (AHLs) as chemical signals to regulate the expression of pathogenic phenotypes through a mechanism called quorum sensing (QS). Recently, strategies targeting bacterial behaviour or QS have received great attention due to their ability to disarm rather than kill pathogenic bacteria, which lowers the evolutionary burden on bacteria and the risk of resistance development. In the present study, we report the design and synthesis of N-alkyl- and N-aryl 3,4 dichloro- and 3,4-dibromopyrrole-2-one derivatives through the reductive amination of mucochloric and mucobromic acid with aliphatic and aromatic amines. The quorum sensing inhibition (QSI) activity of the synthesized compounds was determined against a P. aeruginosa MH602 reporter strain. The phenolic compounds exhibited the best activity with 80% and 75% QSI at 250 µM and were comparable in activity to the positive control compound Fu-30. Computational docking studies performed using the LasR receptor protein of P. aeruginosa suggested the importance of hydrogen bonding and hydrophobic interactions for QSI.
URI: https://hdl.handle.net/10356/84293
http://hdl.handle.net/10220/45109
ISSN: 1420-3049
DOI: 10.3390/molecules23051106
Rights: © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SCELSE Journal Articles

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