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1.
Nano Lett ; 22(12): 4839-4847, 2022 06 22.
Article En | MEDLINE | ID: mdl-35667033

A safe, biocompatible, and stimuli-responsive cucurbit[7]uril-mediated supramolecular bactericidal nanoparticle was fabricated by encapsulating a highly bioactive carbazole-decorated imidazolium salt (A1, EC50 = 0.647 µg/mL against phytopathogen Xanthomonas oryzae pv oryzae) into the host cucurbit[7]uril (CB[7]), thereby leading to self-assembled topographies from microsheets (A1) to nanospheroidal architectures (A1@CB[7]). The assembly behaviors were elucidated by acquired single-crystal structures, 1H NMR, ITC, and X-ray powder diffraction experiments. Complex A1@CB[7] displayed lower phytotoxicity and could efficiently switch on its potent antibacterial ability via introducing a simple competitor 1-adamantanamine hydrochloride (AD). In vivo antibacterial trials against rice bacterial blight revealed that A1@CB[7] could relieve the disease symptoms after being triggered by AD and provide a workable control efficiency of 42.6% at 100 µg/mL, which was superior to bismerthiazol (33.4%). These materials can provide a viable platform for fabricating diverse stimuli-responsive supramolecular bactericides for managing bacterial infections with improved safety.


Bacterial Infections , Nanoparticles , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/therapeutic use , Bacteria , Delayed-Action Preparations , Heterocyclic Compounds, 2-Ring , Humans , Imidazolidines , Macrocyclic Compounds
2.
ACS Appl Mater Interfaces ; 14(2): 2564-2577, 2022 Jan 19.
Article En | MEDLINE | ID: mdl-34981928

Supramolecular chemistry provides huge potentials and opportunities in agricultural pest management. In an attempt to develop highly bioactive, eco-friendly, and biocompatible supramolecular complexes for managing intractable plant bacterial diseases, herein, a type of interesting adamantane-functionalized 1,3,4-oxadiazole was rationally prepared to facilitate the formation of supramolecular complexes via ß-cyclodextrin-adamantane host-guest interactions. Initial antibacterial screening revealed that most of these adamantane-decorated 1,3,4-oxadiazoles were obviously bioactive against three typically destructive phytopathogens. The lowest EC50 values could reach 0.936 (III18), 0.889 (III18), and 2.10 (III19) µg/mL against the corresponding Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac), and Pseudomonas syringae pv. actinidiae (Psa). Next, the representative supramolecular binary complex III18@ß-CD (binding mode 1:1) was successfully fabricated and characterized by 1H nuclear magnetic resonance (NMR), isothermal titration calorimetry (ITC), high-resolution mass spectrometry (HRMS), dynamic light scattering (DLS), and transmission electron microscopy (TEM). Eventually, correlative water solubility and foliar surface wettability were significantly improved after the formation of host-guest assemblies. In vivo antibacterial evaluation found that the achieved supramolecular complex could distinctly alleviate the disease symptoms and promote the control efficiencies against rice bacterial blight (from 34.6-35.7% (III18) to 40.3-43.6% (III18@ß-CD)) and kiwi canker diseases (from 41.0-42.3% (III18) to 53.9-68.0% (III18@ß-CD)) at 200 µg/mL (active ingredient). The current study can provide a feasible platform and insight for constructing biocompatible supramolecular assemblies for managing destructive bacterial infections in agriculture.


Adamantane/pharmacology , Anti-Bacterial Agents/pharmacology , Bacterial Infections/drug therapy , Biocompatible Materials/pharmacology , Oxadiazoles/pharmacology , beta-Cyclodextrins/pharmacology , Adamantane/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Biocompatible Materials/chemical synthesis , Biocompatible Materials/chemistry , Materials Testing , Microbial Sensitivity Tests , Molecular Structure , Oryza/microbiology , Oxadiazoles/chemistry , Pseudomonas/drug effects , Xanthomonas/drug effects , beta-Cyclodextrins/chemistry
3.
J Agric Food Chem ; 68(45): 12558-12568, 2020 Nov 11.
Article En | MEDLINE | ID: mdl-33140649

In recent years, naturally occurring tetrahydro-ß-carboline (THC) alkaloids and their derivatives have been of biological interest. However, few studies and developments have reported the use of such structures in managing plant bacterial diseases. Herein, an array of novel THC derivatives containing an attractive 1,3-diaminopropan-2-ol pattern were prepared to evaluate the antiphytopathogen activity in vitro and in vivo and explore innovative antibacterial frameworks. Notably, target compounds exhibited excellent activities against three rebellious phytopathogens, namely, Pseudomonas syringae pv. actinidiae (Psa), Xanthomonas axonopodis pv. citri, and Xanthomonas oryzae pv. oryzae, at related optimal EC50 values of 2.39 (II9), 2.06 (I23), and 1.69 (II9) µg/mL, respectively. These effects were superior to those of the parent structure 1,2,3,4-THC and positive controls. In vivo assays showed that II9 exhibited excellent control efficiencies of 51.89 and 65.45% at 200 µg/mL against rice bacterial blight and kiwifruit bacterial canker, respectively, and I23 substantially relieved the citrus canker on the leaves. Antibacterial mechanisms indicated that these THC compounds could induce the increment of reactive oxygen species and subsequently endow the tested bacteria with distinct apoptotic behavior. In addition, II9 could alleviate the hypersensitive response and pathogenicity of Psa. Overall, these simple THC derivatives can be further developed as versatile antibacterial agents.


Actinidia/microbiology , Anti-Bacterial Agents/pharmacology , Carbolines/pharmacology , Citrus/microbiology , Diamines/pharmacology , Oryza/microbiology , Plant Diseases/microbiology , Anti-Bacterial Agents/chemistry , Carbolines/chemistry , Diamines/chemistry , Microbial Sensitivity Tests , Molecular Structure , Pseudomonas syringae/drug effects , Xanthomonas/drug effects
4.
J Agric Food Chem ; 68(20): 5579-5585, 2020 May 20.
Article En | MEDLINE | ID: mdl-32348138

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 self-assembly and antibacterial ability of bactericides at the supramolecular level.


Anthracenes/chemistry , Anthracenes/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Plant Diseases/microbiology , Xanthomonas/drug effects , Drug Carriers/chemistry , Nanofibers/chemistry , Xanthomonas/physiology
5.
Article Zh | WPRIM | ID: wpr-313759

<p><b>OBJECTIVE</b>To analyze the clinical effects of intramedullary fixation of Kirschner pin for the treatment of distal fibula fractures.</p><p><b>METHODS</b>From April 2007 to June 2010, thirty patients with the distal fibula fractures were treated with intramedullary fixation of Kirschner pin. There were 22 males and 8 females with an average age of 35.6 years old (22 to 60 years), length of hospital stay was 10 to 30 days (means 15.8 days). There were 20 cases of Transverse fracture and 10 cases of oblique fracture. Evaluation of the function of the ankle joint is based on the American Orthopaedic Foot and Ankle Society (AOFAS) standard evaluation systems.</p><p><b>RESULTS</b>All the cases were followed up. The mean followed-up time was 15.5 months (3 to 30 months). All fractures were bone healed, no case suffered infection and nonunion, no case suffered nervus fibularis superficialis injury. According to the AOFAS (American Orthopaedic Foot and Ankle Society) evaluation systems, the total scores after operation was 96.1 +/- 4.3 (the pain was 39.0 +/- 4.0, the fracture force line was 10, the function was 47.1 +/- 2.1. Twenty-eight patients obtained excellent results, 2 good.</p><p><b>CONCLUSION</b>This method can be easily operated with the advantages of less pain and safety. It can effectively attenuate the financial burden of the patients. Thus worth being popularized in clinicic and basic level hospital.</p>


Adult , Female , Humans , Male , Middle Aged , Fibula , Wounds and Injuries , Fracture Fixation, Intramedullary , Methods
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