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1.
J Agric Food Chem ; 72(3): 1444-1453, 2024 Jan 24.
Article in English | MEDLINE | ID: mdl-38206812

ABSTRACT

1,3,4-Oxadiazole thioethers have shown exciting antibacterial activities; however, the current mechanism of action involving such substances against bacteria is limited to proteomics-mediated protein pathways and differentially expressed gene analysis. Herein, we report a series of novel 1,3,4-oxadiazole thioethers containing a carboxamide/amine moiety, most of which show good in vitro and in vivo bacteriostatic activities. Compounds A10 and A18 were screened through CoMFA models as optimums against Xanthomonas oryzae pv. oryzae (Xoo, EC50 values of 5.32 and 4.63 mg/L, respectively) and Xanthomonas oryzae pv. oryzicola (Xoc, EC50 values of 7.58 and 7.65 mg/L, respectively). Compound A10 was implemented in proteomic techniques and activity-based protein profiling (ABPP) analysis to elucidate the antibacterial mechanism and biochemical targets. The results indicate that A10 disrupts the growth and pathogenicity of Xoc by interfering with pathways associated with bacterial virulence, including the two-component regulation system, flagellar assembly, bacterial secretion system, quorum sensing, ABC transporters, and bacterial chemotaxis. Specifically, the translational regulator (CsrA) and the virulence regulator (Xoc3530) are two effective target proteins of A10. Knocking out the CsrA or Xoc3530 gene in Xoc results in a significant reduction in the motility and pathogenicity of the mutant strains. This study contributes available molecular entities, effective targets, and mechanism basis for the management of rice bacterial diseases.


Subject(s)
Oryza , Oxadiazoles , Xanthomonas , Sulfides/chemistry , Proteomics , Microbial Sensitivity Tests , Anti-Bacterial Agents/pharmacology , Oryza/microbiology , Plant Diseases/microbiology
2.
Sci China Life Sci ; 67(2): 391-402, 2024 Feb.
Article in English | MEDLINE | ID: mdl-37987940

ABSTRACT

The prevention and control of rice bacterial leaf blight (BLB) disease has not yet been achieved due to the lack of effective agrochemicals and available targets. Herein, we develop a series of novel bissulfones and a novel target with a unique mechanism to address this challenge. The developed bissulfones can control Xanthomonas oryzae pv. oryzae (Xoo), and 2-(bis(methylsulfonyl)methylene)-N-(4-chlorophenyl) hydrazine-1-carboxamide (B7) is more effective than the commercial drugs thiodiazole copper (TC) and bismerthiazol (BT). Pyruvate kinase (PYK) in Xoo has been identified for the first time as the target protein of our bissulfone B7. PYK modulates bacterial virulence via a CRP-like protein (Clp)/two-component system regulatory protein (regR) axis. The elucidation of this pathway facilitates the use of B7 to reduce PYK expression at the transcriptional level, block PYK activity at the protein level, and impair the interaction within the PYK-Clp-regR complex via competitive inhibition, thereby attenuating bacterial biology and pathogenicity. This study offers insights into the molecular and mechanistic aspects underlying anti-Xoo strategies that target PYK. We believe that these valuable discoveries will be used for bacterial disease control in the future.


Subject(s)
Oryza , Xanthomonas , Virulence , Pyruvate Kinase/metabolism , Pyruvate Kinase/pharmacology , Anti-Bacterial Agents/metabolism , Oryza/microbiology , Biology , Plant Diseases/prevention & control , Plant Diseases/microbiology
3.
Bull Entomol Res ; 113(4): 497-507, 2023 Aug.
Article in English | MEDLINE | ID: mdl-37278204

ABSTRACT

Toll-interacting protein (Tollip) participates in multiple biological processes. However, the biological functions of Tollip proteins in insects remain to be further explored. Here, the genomic sequence of tollip gene from Antheraea pernyi (named Ap-Tollip) was identified with a length of 15,060 bp, including eight exons and seven introns. The predicted Ap-Tollip protein contained conserved C2 and CUE domains and was highly homologous to those tollips from invertebrates. Ap-Tollip was highly expressed in fat body compared with other determined tissues. As far as the developmental stages were concerned, the highest expression level was found at the 14th day in eggs or the 3rd day of the 1st instar. Ap-Tollip was also obviously regulated by lipopolysaccharide, polycytidylic acid or 20E in different tissues. In addition, the interaction between Ap-Tollip and ubiquitin was confirmed by western blotting and pull-down assay. RNAi of Ap-Tollip significantly affected the expression levels of apoptosis and autophagy-related genes. These results indicated that Ap-Tollip was involved in immunity and development of A. pernyi.


Subject(s)
Moths , Animals , Moths/metabolism , RNA Interference , Insect Proteins/genetics , Insect Proteins/metabolism
4.
Fish Shellfish Immunol ; 137: 108750, 2023 Jun.
Article in English | MEDLINE | ID: mdl-37084855

ABSTRACT

An ecdysteroid-regulated 16-kDa protein homolog (named Pc-E16), encoding 150 amino acid residues with a conserved MD-2-related lipid-recognition domain, was first identified in Procambarus clarkii. Phylogenetic analyses indicated similarity between Pc-E16 and 16-kDa proteins from Aplysia californica and insects. Recombinant Pc-E16 protein was successfully expressed in BL21 (DE3) Escherichia coli cells, and polyclonal antibodies against purified Pc-E16 proteins were prepared. In comparison with other tissues, Pc-E16 was highly expressed in the intestine; real-time PCR and Western blotting results indicated that Pc-E16 expression was significantly induced by lipopolysaccharides in hepatopancreas and hemocytes. Pc-E16-mediated signaling pathways were investigated by digital gene expression analysis following RNA interference targeting Pc-E16. A total of 6103 differentially expressed genes (DEGs) were identified, of which 3318 were up- and 2785 were downregulated. Many DEGs were involved in binding and catalytic activity. Kyoto Encyclopedia of Genes and Genomes pathway enrichment analysis revealed that DEGs were clustered into 225 pathways, and 15 significantly enriched pathways were identified at the immune system level. In addition, the expression level of Pc-E16 in hemocytes and hepatopancreas was obviously downregulated at 48 h after dsRNA injection, and Pc-E16-RNAi treatment affected the expression levels of immune-related genes. Altogether, our results suggest that Pc-E16 is involved in the innate immune response of P. clarkii.


Subject(s)
Astacoidea , Ecdysteroids , Animals , Ecdysteroids/metabolism , Phylogeny , Gene Expression Profiling , Immunity, Innate/genetics , Recombinant Proteins/genetics , Hepatopancreas/metabolism , Arthropod Proteins
5.
J Agric Food Chem ; 70(30): 9356-9366, 2022 Aug 03.
Article in English | MEDLINE | ID: mdl-35862796

ABSTRACT

Rice bacterial blight and rice bacterial streak are two serious rice diseases and have caused great harm to the production of rice all over the world. To develop an efficient antibacterial agent with a novel target, a series of novel 2-oxo-N-phenylacetamide derivatives containing a dissulfone moiety were synthesized, and their antibacterial activities were evaluated. Among them, compound D14 exhibited the best antibacterial activities, especially against Xoo and Xoc with EC50 values of 0.63 and 0.79 mg/L, respectively, which were much better than the commercial control of bismerthiazol (BT) (76.59 and 83.35 mg/L, respectively) and thiodiazole copper (TC) (91.72 and 114.00 mg/L, respectively). Meanwhile, compound D14 can interact with a CRP-like protein (Clp) of Pxo99A and show strong binding activity with Xoo-Clp with a Kd value of 0.52 µM, which was far superior to the corresponding Kd values of BT (183.94 µM) and TC (222.58 µM). Treatment of D14 and deletion of the clp gene could significantly reduce the expression of the clp gene and attenuate the virulence of pathogenic bacteria. These results indicated that compound D14 could be used as a potential novel agricultural bactericide and Clp can be used as a target protein for the control of plant bacterial diseases. This work provided reliable support for developing novel antibacterial agents based on Clp as a target protein.


Subject(s)
Oryza , Xanthomonas , Acetanilides , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Microbial Sensitivity Tests , Oryza/microbiology , Oxadiazoles/chemistry , Plant Diseases/microbiology
6.
Nanoscale ; 14(3): 890-897, 2022 Jan 20.
Article in English | MEDLINE | ID: mdl-34985490

ABSTRACT

The polyethylene oxide (PEO) solid electrolyte is a promising candidate for all solid state lithium-ion batteries (ASSLIBs), but its low ionic conductivity and poor interfacial compatibility against lithium limit the rate and cycling performance of the cell. Herein, the novel and efficient TiO2@polydopamine (PDA) fillers have been synthesized by coating PDA onto the surface of the TiO2 nanofibers, which are then incorporated into PEO matrices to form the composite electrolyte. The composite electrolyte displays a higher ionic conductivity of 4.36 × 10-4 S cm-1, a wider electrochemical window up to about 5 V and a higher tLi+ of 0.190 at 55 °C compared to the PEO electrolyte. Additionally, the Li/composite electrolyte/Li batteries show a stable Li plating/stripping cycle performance, indicating good interfacial compatibility between the composite electrolyte and lithium. Thus, the LiFePO4/Li ASSLIBs display a fantastic rate performance and cycling stability, and deliver superior discharge specific capacities of 153.83 and 136.45 mA h g-1 at current densities of 0.5C and 2C, achieving good capacity retentions of 93.27% and 91.23% at 0.5C and 1C after 150 cycles, respectively. Therefore, the PEO-TiO2@PDA composite electrolyte is a potential solid electrolyte for ASSLIBs.

7.
Int J Biol Macromol ; 166: 550-556, 2021 Jan 01.
Article in English | MEDLINE | ID: mdl-33137382

ABSTRACT

Secretion-associated and ras-related protein 1 (Sar1) is a small GTPase that plays an important role in the transport of protein coated with coat protein complex II vesicles. However, its alternative roles in the biological processes of Procambarus clarkii remain unclear. Here, a sar1 gene (named as Pc-sar1) with an open reading frame of 582 bp from P. clarkii was identified. Pc-sar1 was expressed in all examined tissues with highest expression levels in muscle, which was determined by real-time PCR and western blotting. After the induction of lipopolysaccharide (LPS) and polycytidylic acid (Poly I: C), the transcriptional levels of Pc-sar1 differed in hepatopancreas, gill, muscle and intestine. In contrast, the expression of Pc-sar1 was upregulated by 20-hydroxyecdysone in these four tissues. In addition, the RNA interference of Pc-sar1 significantly affected the expression levels of immune and hormone-related genes. These results indicate that Pc-sar1 is involved in the innate immune response and ecdysteroid signaling pathway.


Subject(s)
Astacoidea/enzymology , Astacoidea/immunology , Ecdysteroids/metabolism , Monomeric GTP-Binding Proteins/metabolism , Signal Transduction , Amino Acid Sequence , Animals , Astacoidea/drug effects , Astacoidea/genetics , Ecdysterone/pharmacology , Gene Expression Regulation/drug effects , Lipopolysaccharides/pharmacology , Monomeric GTP-Binding Proteins/chemistry , Monomeric GTP-Binding Proteins/isolation & purification , Phylogeny , Poly I-C/pharmacology , RNA Interference , Tissue Distribution/drug effects
8.
J Agric Food Chem ; 68(20): 5539-5544, 2020 May 20.
Article in English | MEDLINE | ID: mdl-32323987

ABSTRACT

Tomato chlorosis virus (ToCV) has caused great harm to the production of tomato worldwide. To develop efficient anti-ToCV agents, some novel 4(3H)-quinazolinone derivatives containing dithioacetal were designed and synthesized, and their anti-ToCV activities were evaluated by microscale thermophoresis (MST) using ToCV coat protein (ToCV-CP) as a new target. The results showed that some compounds had a strong binding capacity to ToCV-CP. In particular, compounds C5 and C22 have an excellent binding capacity to ToCV-CP, with binding constant values of 0.24 and 0.25 µM, respectively. Additionally, reduced ToCV-CP gene expression levels of 81.05 and 87.59% could be achieved when tomato was treated with compounds C5 and C22, respectively, which were obviously higher than the levels after ningnanmycin (NNM) treatment (43.88%) and lead compound Xiangcaoliusuobingmi (XCLSBM) treatment (63.56%). Therefore, this work indicates that 4(3H)-quinazolinone derivatives containing dithioacetal moiety can be used as novel anti-ToCV agents.


Subject(s)
Antiviral Agents/chemical synthesis , Antiviral Agents/pharmacology , Crinivirus/drug effects , Quinazolinones/chemistry , Quinazolinones/pharmacology , Antiviral Agents/chemistry , Crinivirus/genetics , Crinivirus/physiology , Drug Design , Solanum lycopersicum/virology , Molecular Structure , Plant Diseases/virology , Structure-Activity Relationship
9.
Int J Mol Sci ; 19(12)2018 Dec 15.
Article in English | MEDLINE | ID: mdl-30558295

ABSTRACT

Plant immune activators can protect crops from plant virus pathogens by activating intrinsic immune mechanisms in plants and are widely used in agricultural production. In our previous work, we found that curcumin analogs exhibit excellent biological activity against plant viruses, especially protective activity. Inspired by these results, the active substructure of pentadienone and quinazoline were spliced to obtain curcumin analogs as potential exogenously induced resistant molecule. Bioassay results showed that compound A13 exhibited excellent protective activity for tobacco to against Tobacco mosaic virus (TMV) at 500 µg/mL, with a value of 70.4 ± 2.6% compared with control treatments, which was better than that of the plant immune activator chitosan oligosaccharide (49.0 ± 5.9%). The protective activity is due to compound A13 inducing tobacco resistance to TMV, which was related to defense-related enzymes, defense-related genes, and photosynthesis. This was confirmed by the up-regulated expression of proteins that mediate stress responses and oxidative phosphorylation.


Subject(s)
Curcumin/analogs & derivatives , Nicotiana/immunology , Nicotiana/virology , Plant Diseases/immunology , Plant Immunity , Quinazolines/immunology , Tobacco Mosaic Virus/immunology , Disease Resistance , Plant Diseases/prevention & control , Quinazolines/chemistry
10.
Data Brief ; 20: 1775-1778, 2018 Oct.
Article in English | MEDLINE | ID: mdl-30294623

ABSTRACT

The nuclear magnetic resonance, and high-resolution mass spectrometry of quinazoline derivatives containing a dithioacetal moiety, which was hosted in the research article entitled "Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety". The data include 1H nuclear magnetic resonance (1H NMR), 13C nuclear magnetic resonance (13C NMR), and high-resolution mass spectrometry. In this article, a more comprehensive data interpretation and analysis is explained.

11.
Bioorg Chem ; 80: 433-443, 2018 10.
Article in English | MEDLINE | ID: mdl-29986188

ABSTRACT

A series of novel quinazoline derivatives containing a dithioacetal moiety were designed and synthesized, and their structures were characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. Bioassay results indicated that compound 4b exhibited remarkable protective activity against cucumber mosaic virus (CMV, EC50 = 248.6 µg/mL) and curative activity against potato virus Y (EC50 = 350.5 µg/mL), which were better than those of ningnanmycin (357.7 µg/mL and 493.7 µg/mL, respectively). Moreover, compound 4b could increase the chlorophyll content in plants, improve photosynthesis, and effectively induce tobacco anti-CMV activity.


Subject(s)
Antiviral Agents/pharmacology , Cucumovirus/drug effects , Nicotiana/virology , Plant Diseases/prevention & control , Potyvirus/drug effects , Quinazolines/pharmacology , Acetals/chemical synthesis , Acetals/chemistry , Acetals/pharmacology , Antiviral Agents/chemical synthesis , Antiviral Agents/chemistry , Disease Resistance/drug effects , Drug Design , Plant Diseases/virology , Quinazolines/chemical synthesis , Quinazolines/chemistry
12.
Biomed Chromatogr ; 32(7): e4230, 2018 Jul.
Article in English | MEDLINE | ID: mdl-29500910

ABSTRACT

A simple and rapid method for enantioselective determination of dufulin in cucumber and soil was developed by liquid chromatography with tandem mass spectrometry. The enantiomers were separated on a Superchiral S-OD chiral cellulose tris(3,5-dimethylphenylcarbamate) column at 20°C, with a mixture of acetonitrile and water (0.1% formic acid; 52:48, v/v) as mobile phase at a flow rate of 0.65 mL/min. The pretreatment conditions were optimized using an orthogonal test, and the optimized method showed good linearity and sensitivity. The limits of detection and limits of quantification of two dufulin enantiomers were 0.006 and 0.02 mg/kg, respectively. The average recoveries of S-enantiomer and R-enantiomer in cucumber and soil were 80.61-99.83% and 80.97-102.96%, respectively, with relative standard deviations of 1.30-9.72%. The method was successfully applied to determine dufulin in real cucumber and soil samples. The results demonstrate that the method could facilitate further research on the differences between individual dufulin enantiomers with respect to metabolites and environmental fate and finally help reveal the complex interactions that exist between dufulin, humans and the environment.


Subject(s)
Benzothiazoles/analysis , Benzothiazoles/chemistry , Chromatography, Liquid/methods , Cucumis sativus/chemistry , Soil/chemistry , Acetonitriles , Benzothiazoles/isolation & purification , Limit of Detection , Linear Models , Reproducibility of Results , Stereoisomerism , Tandem Mass Spectrometry/methods
13.
Biomed Chromatogr ; 32(2)2018 Feb.
Article in English | MEDLINE | ID: mdl-28905410

ABSTRACT

A gas chromatography-tandem mass spectrometry method was developed and validated to simultaneously determine boscalid and fludioxonil in grape and soil samples. These samples were extracted with 10 mL of acetonitrile and purified using a mixed primary secondary amine/octadecylsilane sorbent. The method showed good linearity (R2 > 0.99) in the calibration range 0.005-2 µg/mL for both pesticides. The limits of detection and quantification for the two analytes in grape and soil were 0.006 and 0.02 mg/kg, respectively. Fungicide recoveries in grape and soil were 81.18-92.11% for boscalid and 82.73-97.67% for fludioxonil with relative standard deviations of 1.31-10.31%. The established method was successfully applied to the residual analysis of boscalid and fludioxonil in real grape and soil samples. The terminal residue concentrations of boscalid and fludioxonil in grape samples collected from Anhui and Guizhou were <5 mg/kg (the maximum residue limit set by China) 7 days after the last application and 1 mg/kg (the maximum residue limit set by USA) 14 days after the last application. These results could provide guidance for the proper and safe use of boscalid and fludioxonil in grape and help the Chinese government to establish an MRL for fludioxonil in grape.


Subject(s)
Biphenyl Compounds/analysis , Dioxoles/analysis , Fungicides, Industrial/analysis , Gas Chromatography-Mass Spectrometry/methods , Niacinamide/analogs & derivatives , Pesticide Residues/analysis , Pyrroles/analysis , Soil/chemistry , Vitis/chemistry , Analysis of Variance , Limit of Detection , Linear Models , Niacinamide/analysis , Reproducibility of Results , Tandem Mass Spectrometry
14.
Bioorg Med Chem Lett ; 27(18): 4270-4273, 2017 09 15.
Article in English | MEDLINE | ID: mdl-28866271

ABSTRACT

Based on flexible construction and broad bioactivity of ferulic acid, a series of novel α,ß-unsaturated amide derivatives bearing α-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with half-maximal effective concentration (EC50) values of 284.67µg/mL and 216.30µg/mL, which were obviously superior to that of Ningnanmycin (352.08µg/mL and 262.53µg/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus.


Subject(s)
Amides/pharmacology , Antiviral Agents/pharmacology , Cucumovirus/drug effects , Organophosphonates/pharmacology , Tobacco Mosaic Virus/drug effects , Amides/chemical synthesis , Amides/chemistry , Antiviral Agents/chemical synthesis , Antiviral Agents/chemistry , Dose-Response Relationship, Drug , Microbial Sensitivity Tests , Molecular Structure , Organophosphonates/chemistry , Structure-Activity Relationship
15.
Bioorg Med Chem Lett ; 27(17): 4096-4100, 2017 09 01.
Article in English | MEDLINE | ID: mdl-28751145

ABSTRACT

In this study, we report the synthesis and antiviral activity of trans-ferulic acid derivatives containing acylhydrazone moiety. Biological tests demonstrated that most target compounds showed potent antiviral activity against tobacco mosaic virus (TMV). Compound D4 showed remarkable inactivating activity with EC50 value of 36.59µg/mL, which was obviously superior to ribavirin (126.05µg/mL). Molecular docking results revealed that compound D4 exhibited the optimal combining capacity with five hydrogen bonds to different amino-acid residues of TMV coat protein (TMV-CP). Docking results were consistent with the inactivating activity of target compounds against TMV.


Subject(s)
Antiviral Agents/pharmacology , Coumaric Acids/pharmacology , Hydrazones/pharmacology , Molecular Docking Simulation , Tobacco Mosaic Virus/drug effects , Antiviral Agents/chemical synthesis , Antiviral Agents/chemistry , Coumaric Acids/chemical synthesis , Coumaric Acids/chemistry , Dose-Response Relationship, Drug , Hydrazones/chemistry , Microbial Sensitivity Tests , Molecular Structure , Stereoisomerism , Structure-Activity Relationship
16.
Pest Manag Sci ; 73(10): 2079-2089, 2017 Oct.
Article in English | MEDLINE | ID: mdl-28349672

ABSTRACT

BACKGROUND: Ferulic acid and quinazoline derivatives possess good antiviral activities. In order to develop novel compounds with high antiviral activities, a series of ferulic acid ester derivatives containing quinazoline were synthesized and evaluated for their antiviral activities. RESULTS: Bioassays indicated that some of the compounds exhibited good antiviral activities in vivo against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). One of the compounds demonstrated significant curative and protective activities against TMV and CMV, with EC50 values of 162.14, 114.61 and 255.49, 138.81 mg L-1 , respectively, better than those of ningnanmycin (324.51, 168.84 and 373.88, 272.70 mg L-1 ). The values of q2 and r2 for comparative molecular field analysis and comparative molecular similarity index analysis in the TMV (0.508, 0.663 and 0.992, 0.930) and CMV (0.530, 0.626 and 0.997, 0.981) models presented good predictive abilities. CONCLUSION: Some of the title compounds demonstrated good antiviral activities. Three-dimensional quantitative structure-activity relationship models revealed that the antiviral activities depend on steric and electrostatic properties. These results could provide significant structural insights for the design of highly active ferulic acid derivatives. © 2017 Society of Chemical Industry.


Subject(s)
Antiviral Agents/pharmacology , Coumaric Acids/pharmacology , Cucumovirus/drug effects , Esters/pharmacology , Quinazolines/pharmacology , Tobacco Mosaic Virus/drug effects , Antiviral Agents/chemical synthesis , Coumaric Acids/chemical synthesis , Esters/chemical synthesis , Quantitative Structure-Activity Relationship , Quinazolines/chemical synthesis
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