Assembling Anthracene-Tailored Amphiphiles: Charge-Transfer Interactions Directed Hierarchical Nanofibers with Ameliorative Antibacterial Activity toward Plant Pathogens

Abstract

The effective prevention of plant bacterial infections has been complicated and challenged by unceasing bacterial resistance. The application of traditional bactericides has achieved certain effects to alleviate this situation. However, these chemicals also have limitations, such as short half-life in reality, limited bioavailability, and pollutant emission from their formulations. These disadvantages drive the demand for promoting antibacterial therapeutics. Self-assembled nanostructures based on amphiphiles have inherently versatile characteristics, including high durability, good bioavailability, sustained release, and regenerability. As such, they have garnered wide interest because of these advantages that may serve as a feasible platform for the management of pathogenic infections. Flexible tuning of the shapes of these nanostructures by manipulating noncovalent driving forces consequently results in different levels of antibacterial activity. Herein, an antibacterial amphiphile, 1-[11-(9-anthracenylmethoxy)-11-oxoundecyl]pyridinium bromide (AP), was assembled into microfilms in screening medium. Hierarchical nanofibers were constructed by introducing an electron-deficient trinitrofluorenone (TNF) molecule into the assembling system directed by charge-transfer (CT) interactions to further investigate the contribution of aggregate shape to bioactivity. Biological evaluation revealed that antibacterial efficacy improved after CT complex formation. This study provides an innovative platform for developing versatile assembled structures for restraining the propagation of plant pathogens and an improved understanding of the actual interplay between the selfassembly and antibacterial ability of bactericides at the supramolecular level.

Functionalized Antimicrobial Nanofibers: Design Criteria and Recent Advances

“…Ideally, fiber diameters at the nanometric scale make their structure suitable to bio-mimic the natural extracellular matrix (ECM) of tissue, thus providing a friendly environment for the regeneration of the target site and facilitating repair mechanisms [ 33 , 34 , 35 ]. In addition to topographical fibers resembling native ECM architecture, they can also influence cell migration, adhesion, differentiation, and regeneration [ 36 , 37 , 38 , 39 , 40 , 41 ].…”

Photo‐Stimuli Smart Supramolecular Self‐Assembly of Azobenzene/β‐Cyclodextrin Inclusion Complex for Controlling Plant Bacterial Diseases

“…[1][2][3][4][5] The implementation of constructive and effective management for these diseases is an extremely difficult task because of limitations by variant factors including continuously changing bacterial populations, changeable climate, and unprofessional use of limited traditional pesticide. [6,7] Even worse, new and emerging bacterial resistance problems further interfere with crop management in a way that possesses few options. [8,9] For example, Xanthomonas oryzae pv.…”

Fabrication of Host–Guest Complexes between Adamantane-Functionalized 1,3,4-Oxadiazoles and β-Cyclodextrin with Improved Control Efficiency against Intractable Plant Bacterial Diseases

“…Given the practical applications in medicine, the multidimensional adamantane scaffold can be elaborately explored and modified to develop novel agricultural bactericides for managing phytopathogen infections. In our previous studies, we have flexibly manipulated noncovalent interactions to yield an array of supramolecular assemblies with diverse morphologies. − Interestingly, the achieved nanofibers formed by an anthracene-decorated amphiphile and an electron-deficient trinitrofluorenone driven by charge-transfer interactions displayed ameliorative antibacterial competences . Within our ongoing research to develop highly bioactive, eco-friendly, and biocompatible supramolecular complexes for managing agricultural bacterial infections, herein, a type of interesting adamantane-functionalized 1,3,4-oxadiazole was reasonably designed to facilitate the formation of supramolecular complexes via β-CD–adamantane host–guest interactions.…”

“…65−67 Interestingly, the achieved nanofibers formed by an anthracene-decorated amphiphile and an electron-deficient trinitrofluorenone driven by charge-transfer interactions displayed ameliorative antibacterial competences. 67 Within our ongoing research to develop highly bioactive, eco-friendly, and biocompatible supramolecular complexes for managing agricultural bacterial infections, herein, a type of interesting adamantane-functionalized 1,3,4-oxadiazole was reasonably designed to facilitate the formation of supramolecular complexes via β-CD−adamantane host−guest interactions. Next, the supramolecular binary complexes could be fabricated and simultaneously characterized by 1 H nuclear magnetic resonance (NMR), isothermal titration calorimetry (ITC), high-resolution mass spectrometry (HRMS), dynamic light scattering (DLS), and transmission electron microscopy (TEM).…”