Heterocyclic Chemistry Applied to the Design of N-Acyl Homoserine Lactone Analogues as Bacterial Quorum Sensing Signals Mimics

N-acyl homoserine lactones (AHLs) are small signaling molecules used by many Gram-negative bacteria for coordinating their behavior as a function of their population density. This process, based on the biosynthesis and the sensing of such molecular signals, and referred to as Quorum Sensing (QS), regulates various gene expressions, including growth, virulence, biofilms formation, and toxin production. Considering the role of QS in bacterial pathogenicity, its modulation appears as a possible complementary approach in antibacterial strategies. Analogues and mimics of AHLs are therefore biologically relevant targets, including several families in which heterocyclic chemistry provides a strategic contribution in the molecular design and the synthetic approach. AHLs consist of three main sections, the homoserine lactone ring, the central amide group, and the side chain, which can vary in length and level of oxygenation. The purpose of this review is to summarize the contribution of heterocyclic chemistry in the design of AHLs analogues, insisting on the way heterocyclic building blocks can serve as replacements of the lactone moiety, as a bioisostere for the amide group, or as an additional pattern appended to the side chain. A few non-AHL-related heterocyclic compounds with AHL-like QS activity are also mentioned.     

New Optical Soliton Solutions of the Perturbed Fokas-Lenells Equation

In this article, we employ the perturbed Fokas-Lenells equation(FLE), which represents recent electronic communications. The Riccati-Bernoulli Sub-ODE method which does not depend on the balance rule is used for thefirst time to obtain the new exact and solitary wave solutions of this equation. This technique is direct, effective and reduces the large volume of calculations.     

Dynamics and control of a self-sustained electromechanical seismographs with time-varying stiffness

This paper is concerned with the nonlinear dynamics and vibration control of an electromechanical seismograph system with time-varying stiffness. The instrument consists of an electrical part coupled to mechanical one and is used to record the vibration during earthquakes. An active control method is applied to the system based on cubic velocity feedback. The electromechanical system is subjected to parametric and external excitations and modeled by a coupled nonlinear ordinary differential equations. The method of multiple scales is used to obtain approximate solutions and investigate the response of the system. The results of perturbation solution have been verified through numerical simulations, where different effects of the system parameters have been reported.     

Synthesis,Antimicrobial, Anti-Virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides

Since the synthesis of prontosil the first prodrug shares their chemical moiety, sulfonamides exhibit diverse modes of actions to serve as antimicrobials, diuretics, antidiabetics, and other clinical applications. This inspiring chemical nucleus has promoted several research groups to investigate the synthesis of new members exploring new clinical applications. In this study, a novel series of 5(4H)-oxazolone-based-sulfonamides (OBS) 9a–k were synthesized, and their antibacterial and antifungal activities were evaluated against a wide range of Gram-positive and -negative bacteria and fungi. Most of the tested compounds exhibited promising antibacterial activity against both Gram-positive and -negative bacteria particularly OBS 9b and 9f. Meanwhile, compound 9h showed the most potent antifungal activity. Moreover, the OBS 9a, 9b, and 9f that inhibited the bacterial growth at the lowest concentrations were subjected to further evaluation for their anti-virulence activities against Pseudomonas aeruginosa and Staphylococcus aureus. Interestingly, the three tested compounds reduced the biofilm formation and diminished the production of virulence factors in both P. aeruginosa and S. aureus. Bacteria use a signaling system, quorum sensing (QS), to regulate their virulence. In this context, in silico study has been conducted to assess the ability of OBS to compete with the QS receptors. The tested OBS showed marked ability to bind and hinder QS receptors, indicating that anti-virulence activities of OBS could be due to blocking QS, the system that controls the bacterial virulence. Furthermore, anticancer activity has been further performed for such derivatives. The OBS compounds showed variable anti-tumor activities, specifically 9a, 9b, 9f and 9k, against different cancer lines. Conclusively, the OBS compounds can serve as antimicrobials, anti-virulence and anti-tumor agents.     

Controlled release of indole‐3‐butyric acid (IBA)—based on polymeric matrix prepared by ionizing radiation

Polyacrylamide/polyethylene oxide (PAAm/PEO) controlled release matrices were designed to obtain a better control over the concentration of indole‐3‐butyric acid (IBA). PAAm/PEO incorporated IBA was prepared by exposing aqueous solutions of PEO, PAAm, crosslinking agent N,N′‐methylene‐bisacrylamide, and IBA mixtures to electron beam irradiation. PAAm/PEO copolymer structural property relationships that affect its controlled release behavior were determined. Analysis of the results obtained indicated that it is possible to optimize IBA controlled release by adjusting the dimensions and crosslinking degree of the copolymer as well as the concentration of the incorporated IBA. The crosslinking degree of the copolymer can be controlled by governing the irradiation dose, polymer blend composition and/or the amount of crosslinking agent. IBA release rates have been investigated as a function of environmental conditions, such as the changes in pH and temperature to determine the factors, which mostly contribute to the release of IBA. The effect of PAAm/PEO–IBA matrix on the average height of corn (Zea mayz) plant was investigated. The results obtained, revealed that PAAm/PEO‐IBA systems have a capability to deliver IBA slowly and continuously. As a result, the development of root and vegetative systems of Zea mayz plant was greatly promoted. Copyright © 2004 John Wiley & Sons, Ltd.     

An approach to biologically important S‐heterocycles,dithiocarbamyls, and their relevant phosphono derivatives

The feasibility of insertions of carbanions between two sulfur atoms has been reported when 5‐(4‐chlorophenyl)‐4‐cyano‐1,2‐dithiol‐3‐thione ( 1 ) and tetramethylthiuram disulfide ( 17 ) were allowed to react with unsaturated 2a,b and active phosphonium salts 11a,b . The reactions afforded, mainly, 1,3‐dithiols 4a,b and 14a,b together with substituted thiophenes 10a,b and 16a,b . Reactions of 1 and 17 with α‐alkylthiomethyl phosphonates 24a,b afforded the phosphonates 25a,b and 26a,b , respectively.