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1.
Pestic Biochem Physiol ; 200: 105785, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38582570

RESUMO

This study investigates the effects of chlorantraniliprole (CAP) pesticide stress on oilseed rape through comprehensive pot experiments. Assessing CAP residue variations in soil and oilseed rape (Brassia campestris L.), enzyme activities (POD, CPR, GST), and differential metabolites, we unveil significant findings. The average CAP residue levels were 18.38-13.70 mg/kg in unplanted soil, 9.94-6.30 mg/kg in planted soil, and 0-4.18 mg/kg in oilseed rape samples, respectively. Soil microbial influences and systemic pesticide translocation into oilseed rape contribute to CAP residue variations. Under the influence of CAP stress, oilseed rape displays escalated enzyme activities (POD, CPR, GST) and manifests 57 differential metabolites. Among these, 32 demonstrate considerable downregulation, mainly impacting amino acids and phenolic compounds, while 25 exhibit noteworthy overexpression, primarily affecting flavonoid compounds. This impact extends to 24 metabolic pathways, notably influencing amide biosynthesis, as well as arginine and proline metabolism. These findings underscore the discernible effects of CAP pesticide stress on oilseed rape.


Assuntos
Brassica napus , Praguicidas , ortoaminobenzoatos , Praguicidas/metabolismo , Brassica napus/metabolismo , Solo
2.
Pestic Biochem Physiol ; 200: 105830, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38582593

RESUMO

Chlorantraniliprole (CAP) is a bis-amide pesticide used for pest control mainly in agricultural production activities and rice-fish co-culture systems. CAP residues cause liver damage in non-target organism freshwater fish. However, it is unclear whether CAP-exposure-induced liver injury in fish is associated with mitochondrial dysfunction-mediated mitophagy, ferroptosis, and cytokines. Therefore, we established grass carp hepatocyte models exposed to different concentrations of CAP (20, 40, and 80 µM) in vitro. MitoSOX probe, JC-1 staining, immunofluorescence double staining, Fe2+ staining, lipid peroxidation staining, qRT-PCR, and Western blot were used to verify the physiological regulatory mechanism of CAP induced liver injury. In the present study, the CAP-treated groups exhibited down-regulation of antioxidant-related enzyme activities and accumulation of peroxides. CAP treatment induced an increase in mitochondrial reactive oxygen species (mtROS) levels and altered expression of mitochondrial fission/fusion (Drp1, Fis1, Mfn1, Mfn2, and Opa1) genes in grass carp hepatocytes. In addition, mitophagy (Parkin, Pink1, p62, LC3II/I, and Beclin-1), ferroptosis (GPX4, COX2, ACSL4, FTH, and NCOA4), and cytokine (IFN-γ, IL-18, IL-17, IL-6, IL-10, IL-1ß, IL-2, and TNF-α)-related gene expression was significantly altered. Collectively, these findings suggest that CAP exposure drives mitophagy activation, ferroptosis occurrence, and cytokine homeostasis imbalance in grass carp hepatocytes by triggering mitochondrial dysfunction mediated by the mtROS-mitochondrial fission/fusion axis. This study partly explained the physiological regulation mechanism of grass carp hepatocyte injury induced by insecticide CAP from the physiological and biochemical point of view and provided a basis for evaluating the safety of CAP environmental residues to non-target organisms.


Assuntos
Carpas , Doença Hepática Crônica Induzida por Substâncias e Drogas , Ferroptose , Doenças Mitocondriais , ortoaminobenzoatos , Animais , Citocinas/genética , Transdução de Sinais , Dinâmica Mitocondrial , Mitofagia , Hepatócitos , Homeostase
3.
Pestic Biochem Physiol ; 200: 105827, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38582591

RESUMO

In addition to the acute lethal toxicity, insecticides might affect population dynamics of insect pests by inducing life history trait changes under low concentrations, however, the underlying mechanisms remain not well understood. Here we examined systemic impacts on development and reproduction caused by low concentration exposures to cyantraniliprole in the fall armyworm (FAW), Spodoptera frugiperda, and the putative underlying mechanisms were investigated. The results showed that exposure of third-instar larvae to LC10 and LC30 of cyantraniliprole significantly extended larvae duration by 1.46 and 5.41 days, respectively. Treatment with LC30 of cyantraniliprole significantly decreased the pupae weight and pupation rate as well as the longevity, fecundity and egg hatchability of female adults. Consistently, we found that exposure of FAW to LC30 cyantraniliprole downregulated the mRNA expression of four ecdysteroid biosynthesis genes including SfNobo, SfShd, SfSpo and SfDib and one ecdysone response gene SfE75 in the larvae as well as the gene encoding vitellogenin (SfVg) in the female adults. We also found that treatment with LC30 of cyantraniliprole significantly decreased the whole body levels of glucose, trehalose, glycogen and triglyceride in the larvae. Our results indicate that low concentration of cyantraniliprole inhibited FAW development by disruption of ecdysteroid biosynthesis as well as carbohydrate and lipid metabolism, which have applied implications for the control of FAW.


Assuntos
Ecdisteroides , Inseticidas , Pirazóis , ortoaminobenzoatos , Animais , Spodoptera , Metabolismo dos Lipídeos , Larva , Inseticidas/toxicidade , Carboidratos
4.
PLoS One ; 19(4): e0302126, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38625968

RESUMO

The St. Lawrence River is an important North American waterway that is subject to anthropogenic pressures including intensive urbanization, and agricultural development. Pesticides are widely used for agricultural activities in fields surrounding the yellow perch (Perca flavescens) habitat in Lake St. Pierre (Quebec, Canada), a fluvial lake of the river where the perch population has collapsed. Clothianidin and chlorantraniliprole were two of the most detected insecticides in surface waters near perch spawning areas. The objectives of the present study were to evaluate the transcriptional and biochemical effects of these two pesticides on juvenile yellow perch exposed for 28d to environmental doses of each compound alone and in a mixture under laboratory/aquaria conditions. Hepatic mRNA-sequencing revealed an effect of chlorantraniliprole alone (37 genes) and combined with clothianidin (251 genes), but no effects of clothianidin alone were observed in perch. Dysregulated genes were mostly related to circadian rhythms and to Ca2+ signaling, the latter effect has been previously associated with chlorantraniliprole mode of action in insects. Moreover, chronic exposure to clothianidin increased the activity of acetylcholinesterase in the brain of exposed fish, suggesting a potential non-target effect of this insecticide. Further analyses of three clock genes by qRT-PCR suggested that part of the observed effects of chlorantraniliprole on the circadian gene regulation of juvenile perch could be the result of time-of-day of sacrifice. These results provide insight into biological effects of insecticides in juvenile perch and highlight the importance of considering the circadian rhythm in experimental design and results analyses.


Assuntos
Guanidinas , Inseticidas , Neonicotinoides , Percas , Tiazóis , Poluentes Químicos da Água , ortoaminobenzoatos , Animais , Percas/genética , Inseticidas/toxicidade , Inseticidas/análise , Acetilcolinesterase , Viés de Seleção , Perfilação da Expressão Gênica , Poluentes Químicos da Água/toxicidade , Poluentes Químicos da Água/análise
5.
Ecotoxicol Environ Saf ; 276: 116291, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38581910

RESUMO

Myzus persicae is an important pest that has developed resistance to nearly all currently used insecticidal products. The employment of insecticide synergists is one of the effective strategies that need to be developed for the management of this resistance. Our study showed that treatment with a combination of the antibiotic, rifampicin, with imidacloprid, cyantraniliprole, or clothianidin significantly increased their toxicities against M. persicae, by 2.72, 3.59, and 2.41 folds, respectively. Rifampicin treatment led to a noteworthy reduction in the activities of multifunctional oxidases (by 32.64%) and esterases (by 23.80%), along with a decrease in the expression of the CYP6CY3 gene (by 58.57%) in M. persicae. It also negatively impacted the fitness of the aphids, including weight, life span, number of offspring, and elongation of developmental duration. In addition, bioassays showed that the combination of rifampicin and a detoxification enzyme inhibitor, piperonyl butoxide, or dsRNA of CYP6CY3 further significantly improved the toxicity of imidacloprid against M. persicae, by 6.19- and 7.55-fold, respectively. The present study suggests that development of active ingredients such as rifampicin as candidate synergists, show promise to overcome metabolic resistance to insecticides in aphids.


Assuntos
Afídeos , Guanidinas , Inseticidas , Neonicotinoides , Nitrocompostos , Butóxido de Piperonila , Rifampina , Tiazóis , Animais , Rifampina/toxicidade , Rifampina/farmacologia , Afídeos/efeitos dos fármacos , Inseticidas/toxicidade , Neonicotinoides/toxicidade , Nitrocompostos/toxicidade , Tiazóis/toxicidade , Guanidinas/toxicidade , Butóxido de Piperonila/toxicidade , Pirazóis/toxicidade , Sinergismo Farmacológico , Resistência a Inseticidas/genética , Sinergistas de Praguicidas/toxicidade , ortoaminobenzoatos/toxicidade , Esterases/metabolismo
6.
Int Immunopharmacol ; 133: 112099, 2024 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-38643709

RESUMO

Visceral hypersensitivity resulting from compromised gut barrier with activated immune system is a key feature of irritable bowel syndrome (IBS). Corticotropin-releasing factor (CRF) and Toll-like receptor 4 (TLR4) activate proinflammatory cytokine signaling to induce these changes, which is one of the mechanisms of IBS. As activation of the NLRP3 inflammasome by lipopolysaccharide (LPS) or TLR4 leads to release interleukin (IL)-1ß, the NLRP3 inflammasome may be involved in the pathophysiology of IBS. Tranilast, an anti-allergic drug has been demonstrated to inhibit the NLRP3 inflammasome, and we evaluated the impact of tranilast on visceral hypersensitivity and colonic hyperpermeability induced by LPS or CRF (IBS rat model). Visceral pain threshold caused by colonic balloon distention was measured by monitoring abdominal muscle contractions electrophysiologically. Colonic permeability was determined by quantifying the absorbed Evans blue within the colonic tissue. Colonic protein levels of NLRP3 and IL-1ß were assessed by immunoblot or ELISA. Intragastric administration of tranilast (20-200 mg/kg) for 3 days inhibited LPS (1 mg/kg)-induced visceral hypersensitivity and colonic hyperpermeability in a dose-dependent manner. Simultaneously, tranilast also abolished these alterations induced by CRF (50 µg/kg). LPS increased colonic protein levels of NLRP3 and IL-1ß, and tranilast inhibited these changes. ß-hydroxy butyrate, an NLRP3 inhibitor, also abolished visceral hypersensitivity and colonic hyperpermeability caused by LPS. In contrast, IL-1ß induced similar GI alterations to LPS, which were not modified by tranilast. In conclusion, tranilast improved visceral pain and colonic barrier by suppression of the NLRP3 inflammasome in IBS rat models. Tranilast may be useful for IBS treating.


Assuntos
Colo , Modelos Animais de Doenças , Inflamassomos , Interleucina-1beta , Síndrome do Intestino Irritável , Lipopolissacarídeos , Proteína 3 que Contém Domínio de Pirina da Família NLR , Ratos Sprague-Dawley , ortoaminobenzoatos , Animais , Proteína 3 que Contém Domínio de Pirina da Família NLR/metabolismo , Proteína 3 que Contém Domínio de Pirina da Família NLR/antagonistas & inibidores , Síndrome do Intestino Irritável/tratamento farmacológico , Síndrome do Intestino Irritável/metabolismo , Colo/efeitos dos fármacos , Colo/metabolismo , Masculino , Inflamassomos/metabolismo , Inflamassomos/efeitos dos fármacos , ortoaminobenzoatos/farmacologia , ortoaminobenzoatos/uso terapêutico , Interleucina-1beta/metabolismo , Ratos , Permeabilidade/efeitos dos fármacos , Hiperalgesia/tratamento farmacológico , Dor Visceral/tratamento farmacológico , Dor Visceral/metabolismo
7.
Org Biomol Chem ; 22(18): 3708-3724, 2024 05 08.
Artigo em Inglês | MEDLINE | ID: mdl-38639206

RESUMO

Despite the high global prevalence, rheumatoid arthritis lacks a satisfactory treatment. Hence, the present study is undertaken to design and synthesize novel anti-inflammatory compounds. For this, quinoline and anthranilic acid, two medicinally-privileged moieties, were linked by pharmacophore hybridization, and following their computational assessments, three hybrids 5a-c were synthesized in good over all yields. The in vitro and in vivo anti-inflammatory potential of these hybrids was determined by anti-denaturation and anti-proteinase, and carrageenan-induced paw edema models. The computational studies of these hybrids revealed their drug-likeness, optimum pharmacokinetics, and less toxicity. Moreover, they demonstrated high binding affinity (-9.4 to -10.6 kcal mol-1) and suitable binding interactions for TNF-α, FLAP, and COX-II. A three-step synthetic route resulted in the hybrids 5a-c with 83-86% yield of final step. At 50 µg mL-1, the antiprotease and anti-denaturation activity of compound 5b was significantly higher than 5a and 5c. Furthermore, 5b significantly reduced the edema in the right paw of the rats that received carrageenan. The results of this study indicate the medicinal worth of the novel hybrids in treating inflammatory disorders such as rheumatoid arthritis.


Assuntos
Desenho de Fármacos , Edema , Simulação de Acoplamento Molecular , Quinolinas , ortoaminobenzoatos , Quinolinas/química , Quinolinas/farmacologia , Quinolinas/síntese química , Animais , Edema/tratamento farmacológico , Edema/induzido quimicamente , ortoaminobenzoatos/química , ortoaminobenzoatos/farmacologia , ortoaminobenzoatos/síntese química , Ratos , Carragenina , Masculino , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/síntese química , Estrutura Molecular , Ratos Wistar , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Anti-Inflamatórios não Esteroides/síntese química , Relação Dose-Resposta a Droga , Relação Estrutura-Atividade , Ciclo-Oxigenase 2/metabolismo , Ciclo-Oxigenase 2/química
8.
J Biotechnol ; 387: 44-48, 2024 May 20.
Artigo em Inglês | MEDLINE | ID: mdl-38582405

RESUMO

The biocatalytic aerobic "in-water" reduction of anthranilic acid to 2-aminobenzaldehyde by growing cultures of the basidiomycetous white-rot fungus Bjerkandera adusta has been studied. The high specific activity of Bjerkandera adusta towards the carboxylic group of anthranilic acid that allows avoiding the formation of the corresponding alcohol has been demonstrated using different substrate concentrations. The presence of ethanol as co-solvent allows increasing the yield of target product. In contrast to chemical reducing agents that usually yield 2-aminobenzyl alcohol, an overreduction of anthranilic acid is completely suppressed by the fungus and gives the target flavor compound in satisfactory preparative yields. It was shown that the activity of Bjerkandera adusta towards anthranilic acid does not apply to its m- and p-isomers.


Assuntos
Benzaldeídos , ortoaminobenzoatos , ortoaminobenzoatos/química , ortoaminobenzoatos/metabolismo , Benzaldeídos/química , Benzaldeídos/metabolismo , Oxirredução , Coriolaceae/metabolismo , Coriolaceae/química
9.
Environ Pollut ; 349: 123904, 2024 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-38565392

RESUMO

The indiscriminate and, very often, incorrect use of pesticides in Brazil, as well as in other countries, results in severe levels of environmental pollution and intoxication of human life. Herein, we studied plasma membrane models (monolayer and bilayer) of the phospholipid Dioleoyl-sn-glycerol-3-phosphocholine (DOPC) using Langmuir films, and large (LUVs) and giant (GUVs) unilamellar vesicles, to determine the effect of the pesticides chlorantraniliprole (CLTP), isoxaflutole (ISF), and simazine (SMZ), used in sugarcane. CLTP affects the lipid organization of the bioinspired models of DOPC π-A isotherms, while ISF and SMZ pesticides significantly affect the LUVs and GUVs. Furthermore, the in vivo study of the gill tissue in fish in the presence of pesticides (2.0 × 10-10 mol/L for CLTP, 8.3 × 10-9 mol/L for ISF, and SMZ at 9.9 × 10-9 mol/L) was performed using optical and fluorescence images. This investigation was motivated by the gill lipid membranes, which are vital for regulating transporter activity through transmembrane proteins, crucial for maintaining ionic balance in fish gills. In this way, the presence of phospholipids in gills offers a model for understanding their effects on fish health. Histological results show that exposure to CLTP, ISF, and SMZ may interfere with vital gill functions, leading to respiratory disorders and osmoregulation dysfunction. The results indicate that exposure to pesticides caused severe morphological alterations in fish, which could be correlated with their impact on the bioinspired membrane models. Moreover, the effect does not depend on the exposure period (24h and 96h), showing that animals exposed to pesticides for a short period suffer irreparable damage to gill tissue. In summary, we can conclude that the harm caused by pesticides, both in membrane models and in fish gills, occurs due to contamination of the aquatic system with pesticides. Therefore, water quality is vital for the preservation of ecosystems.


Assuntos
Brânquias , Praguicidas , Fosfolipídeos , Tilápia , ortoaminobenzoatos , Animais , Brânquias/efeitos dos fármacos , Brânquias/metabolismo , Fosfolipídeos/metabolismo , Praguicidas/toxicidade , Tilápia/metabolismo , ortoaminobenzoatos/toxicidade , Poluentes Químicos da Água/toxicidade , Membrana Celular/efeitos dos fármacos , Brasil
10.
Environ Geochem Health ; 46(5): 171, 2024 Apr 09.
Artigo em Inglês | MEDLINE | ID: mdl-38592558

RESUMO

Cyantraniliprole (CY), an anthranilic diamide insecticide widely used in grape farming for controlling various sucking pests, poses ecological concerns, particularly when applied as soil drenching due to the formation of more toxic and persistent metabolites. This study established the dissipation and degradation mechanisms of CY in grape rhizosphere soil using high-resolution Orbitrap-LC/MS analysis. The persistence of CY residues beyond 60 days was observed, with dissipation following biphasic first + first-order kinetics and a half-life of 15 to 21 days. The degradation mechanism of CY in the soil was elucidated, with identified metabolites such as IN-J9Z38, IN-JCZ38, IN-N7B69, and IN-QKV54. Notably, CY was found to predominantly convert to the highly persistent metabolite IN-J9Z38, raising environmental concerns. The impact of CY residues on soil enzyme activity was investigated, revealing a negative effect on dehydrogenase, alkaline phosphatase, and acid phosphatase activity, indicating significant implications for phosphorous mineralization and soil health. Furthermore, bacterial isolates were obtained from CY-enriched soil, with five isolates (CY3, CY4, CY9, CY11, and CY20) demonstrating substantial degradation potential, ranging from 66 to 92% of CY residues. These results indicate that the identified bacteria hold potential for commercial use in addressing pesticide residue contamination in soil through bioremediation techniques.


Assuntos
Pirazóis , Solo , ortoaminobenzoatos , Biodegradação Ambiental , Bactérias/genética
11.
World J Microbiol Biotechnol ; 40(6): 166, 2024 Apr 17.
Artigo em Inglês | MEDLINE | ID: mdl-38630358

RESUMO

Anthranilic acid (AA) holds significant importance in the chemical industry. It serves as a crucial building block for the amino acid tryptophan by manipulating the tryptophan biosynthesis pathway, it is possible to increase the production of anthranilic acid. In this study, we utilized metabolic engineering approaches to produce anthranilic acid from the halophilic bacterium Virgibacillus salarius MML1918. The halophilic bacteria were grown in an optimized production medium, and mass production of secondary metabolites was made in ATCC medium 1097 Proteose peptone-for halophilic bacteria and subjected to column chromatography followed by sub-column chromatography the single band for the purified compound was confirmed. Further, various spectral analyses were made for the partially purified compounds, and fluorescence microscopy for fungal cell observation was performed. The purified compound was confirmed by single crystal X-ray diffraction (XRD) analysis, and it was identified as 2-amino benzoic acid. The Fourier transform infrared Spectroscopy (FT-IR) spectrum and nuclear magnetic resonance (NMR) spectrum also confirm the structural characteristic of 2-amino benzoic acid. The UV-Vis absorption spectrum of AA shows the maximum absorption at 337.86 nm. The emission spectrum of 2-amino benzoic acid showed the maximum emission at 453 nm. The bio-imaging application of 2-amino benzoic acid was examined with fungal mycelium of Rhizoctonia solani. It was effectively bound and emitted the blue color at the concentration of 200 and 300 µg/mL. The halophilic bacterium (V. salarius), may have unique metabolic pathways and requirements compared to non-halophilic organisms, to produce AA effectively. This could have implications for industrial biotechnology, particularly in manufacturing environments where high salt concentrations are present and also it can be used as bio-imaging agent.


Assuntos
Aminoácidos , Triptofano , Virgibacillus , ortoaminobenzoatos , Espectroscopia de Infravermelho com Transformada de Fourier , Ácido Benzoico
12.
Pestic Biochem Physiol ; 201: 105888, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38685219

RESUMO

Bemisia tabaci is a formidable insect pest worldwide, and it exhibits significant resistance to various insecticides. Dimpropyridaz is a novel pyridazine pyrazolecarboxamide insecticide used against sucking insect pests, but there is little information regarding its metabolic detoxification in arthropods or cross-resistance with other insecticides. In this study, we found that dimpropyridaz shows no cross-resistance with three other popular insecticides, namely abamectin, cyantraniliprole, and flupyradifurone. After treatment of B. tabaci adults with a high dose of dimpropyridaz, higher cytochrome P450 monooxygenase (P450) activity was detected in the survivors, and the expression of the P450 gene CYP6DW4 was highly induced. Cloning and characterization of the full-length amino acid sequence of CYP6DW4 indicated that it contains conserved domains typical of P450 genes, phylogenetic analysis revealed that it was closely related to a B. tabaci protein, CYP6DW3, known to be involved in detoxification of imidacloprid. Silencing of CYP6DW4 by feeding insects with dsRNA significantly increased the susceptibility of B. tabaci to dimpropyridaz. In addition, homology modeling and molecular docking analyses showed the stable binding of dimpropyridaz to CYP6DW4, with binding free energy of -6.65 kcal/mol. Our findings indicate that CYP6DW4 plays an important role in detoxification of dimpropyridaz and possibly promotes development of resistance in B. tabaci.


Assuntos
Sistema Enzimático do Citocromo P-450 , Hemípteros , Proteínas de Insetos , Resistência a Inseticidas , Inseticidas , Ivermectina/análogos & derivados , Pirazóis , Piridazinas , ortoaminobenzoatos , Animais , Hemípteros/efeitos dos fármacos , Hemípteros/genética , Inseticidas/farmacologia , Sistema Enzimático do Citocromo P-450/genética , Sistema Enzimático do Citocromo P-450/metabolismo , Piridazinas/farmacologia , Resistência a Inseticidas/genética , Proteínas de Insetos/genética , Proteínas de Insetos/metabolismo , Proteínas de Insetos/química , Pirazóis/farmacologia , Filogenia , Neonicotinoides/farmacologia , Técnicas de Silenciamento de Genes , Simulação de Acoplamento Molecular , Sequência de Aminoácidos , Ivermectina/farmacologia , Ivermectina/toxicidade
13.
Pestic Biochem Physiol ; 201: 105891, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38685253

RESUMO

The fall armyworm (Spodoptera frugiperda) was found to have invaded China in December 2018, and in just one year, crops in 26 provinces were heavily affected. Currently, the most effective method for emergency control of fulminant pests is to use of chemical pesticides. Recently, most fall armyworm populations in China were begining to exhibite low level resistance to chlorantraniliprole. At present, it is not possible to sensitively reflect the low level resistance of S. frugiperda by detecting target mutation and detoxification enzyme activity. In this study we found that 12 successive generations of screening with chlorantraniliprole caused S. frugiperda to develop low level resistance to this insecticide, and this phenotype was not attribute to genetic mutations in S. frugiperda, but rather to a marked increase in the relative amount of the symbiotic bacteria Sphingomonas. Using FISH and qPCR assays, we determined the amount of Sphingomonas in the gut of S. frugiperda and found Sphingomonas accumulation to be highest in the 3rd-instar larvae. Additionally, Sphingomonas was observed to provide a protective effect to against chlorantraniliprole stress to S. frugiperda. With the increase of the resistance to chlorantraniliprole, the abundance of bacteria also increased, we propose Sphingomonas monitoring could be adapted into an early warning index for the development of chlorantraniliprole resistance in S. frugiperda populations, such that timely measures can be taken to delay or prevent the widespread propagation of resistance to this highly useful agricultural chemical in S. frugiperda field populations.


Assuntos
Inseticidas , Larva , Sphingomonas , Spodoptera , ortoaminobenzoatos , Animais , Spodoptera/efeitos dos fármacos , Spodoptera/microbiologia , ortoaminobenzoatos/farmacologia , Inseticidas/farmacologia , Inseticidas/toxicidade , Larva/efeitos dos fármacos , Sphingomonas/efeitos dos fármacos , Sphingomonas/genética , Resistência a Inseticidas/genética
14.
Pestic Biochem Physiol ; 201: 105892, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38685254

RESUMO

As an agricultural pest, the fall armyworm (FAW), Spodoptera frugiperda, poses a severe threat to agriculture in China. Chlorantraniliprole has been widely used to control this pest. In our previous studies, we discovered that LD10, LD20, and LD30 chlorantraniliprole promoted encapsulation in the 4th instar larvae of the FAW, with LD30 chlorantraniliprole having the most significant effect. To further investigate the molecular mechanism underlying the sublethal effects of chlorantraniliprole on encapsulation in the FAW, this study conducted the effects of encapsulation in 4th instar larvae of the FAW exposed to LD30 chlorantraniliprole. Then, we analyzed the transcriptome of the FAW hemolymph treated with LD30 chlorantraniliprole and identified genes related to encapsulation using RNAi. Our results showed that the encapsulation in the FAW was enhanced at 6, 12, 18, 24, and 48 h after exposure to LD30 chlorantraniliprole. Additionally, LD30 chlorantraniliprole significantly affected the expression of certain immune-related genes, with the heat shock protein 70 family gene SfHSP68.1 showing the most significant upregulation. Subsequent interference with SfHSP68.1 resulted in a significant inhibition of encapsulation in FAW. These findings suggested that LD30 chlorantraniliprole can promote encapsulation in the FAW by upregulating SfHSP68.1 expression. This study provides valuable insights into the sublethal effects of chlorantraniliprole on encapsulation in the FAW and the interaction between encapsulation and heat shock proteins (HSPs).


Assuntos
Proteínas de Choque Térmico HSP70 , Proteínas de Insetos , Inseticidas , Larva , Spodoptera , ortoaminobenzoatos , Animais , ortoaminobenzoatos/toxicidade , ortoaminobenzoatos/farmacologia , Spodoptera/efeitos dos fármacos , Spodoptera/genética , Inseticidas/toxicidade , Inseticidas/farmacologia , Proteínas de Choque Térmico HSP70/genética , Proteínas de Choque Térmico HSP70/metabolismo , Larva/efeitos dos fármacos , Proteínas de Insetos/genética , Proteínas de Insetos/metabolismo , Regulação para Cima/efeitos dos fármacos
15.
Insect Biochem Mol Biol ; 168: 104107, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38492676

RESUMO

The diamondback moth Plutella xylostella, a global insect pest of cruciferous vegetables, has evolved resistance to many classes of insecticides including diamides. Three point mutations (I4790M, I4790K, and G4946E) in the ryanodine receptor of P. xylostella (PxRyR) have been identified to associate with varying levels of resistance. In this study, we generated a knockin strain (I4790K-KI) of P. xylostella, using CRISPR/Cas9 to introduce the I4790K mutation into PxRyR of the susceptible IPP-S strain. Compared to IPP-S, the edited I4790K-KI strain exhibited high levels of resistance to both anthranilic diamides (chlorantraniliprole 1857-fold, cyantraniliprole 1433-fold) and the phthalic acid diamide flubendiamide (>2272-fold). Resistance to chlorantraniliprole in the I4790K-KI strain was inherited in an autosomal and recessive mode, and genetically linked with the I4790K knockin mutation. Computational modeling suggests the I4790K mutation reduces the binding of diamides to PxRyR by disrupting key hydrogen bonding interactions within the binding cavity. The approximate frequencies of the 4790M, 4790K, and 4946E alleles were assessed in ten geographical field populations of P. xylostella collected in China in 2021. The levels of chlorantraniliprole resistance (2.3- to 1444-fold) in these populations were significantly correlated with the frequencies (0.017-0.917) of the 4790K allele, but not with either 4790M (0-0.183) or 4946E (0.017-0.450) alleles. This demonstrates that the PxRyR I4790K mutation is currently the major contributing factor to chlorantraniliprole resistance in P. xylostella field populations within China. Our findings provide in vivo functional evidence for the causality of the I4790K mutation in PxRyR with high levels of diamide resistance in P. xylostella, and suggest that tracking the frequency of the I4790K allele is crucial for optimizing the monitoring and management of diamide resistance in this crop pest.


Assuntos
Diamida , Resistência a Inseticidas , Mariposas , Animais , Diamida/farmacologia , Resistência a Inseticidas/genética , Inseticidas/farmacologia , Inseticidas/metabolismo , Mariposas/genética , Mariposas/metabolismo , Mutação , ortoaminobenzoatos/farmacologia , Canal de Liberação de Cálcio do Receptor de Rianodina/genética , Canal de Liberação de Cálcio do Receptor de Rianodina/metabolismo
17.
J Agric Food Chem ; 72(14): 8072-8080, 2024 Apr 10.
Artigo em Inglês | MEDLINE | ID: mdl-38547359

RESUMO

To increase the structural diversity of insecticides and meet the needs of effective integrated insect management, the structure of chlorantraniliprole was modified based on a previously established three-dimensional quantitative structure-activity relationship (3D-QSAR) model. The pyridinyl moiety in the structure of chlorantraniliprole was replaced with a 4-fluorophenyl group. Further modifications of this 4-fluorophenyl group by introducing a halogen atom at position 2 and an electron-withdrawing group (e.g., iodine, cyano, and trifluoromethyl) at position 5 led to 34 compounds with good insecticidal efficacy against Mythimna separata, Plutella xylostella, and Spodoptera frugiperda. Among them, compound IV f against M. separata showed potency comparable to that of chlorantraniliprole. IV p against P. xylostella displayed a 4.5 times higher potency than chlorantraniliprole. In addition, IV d and chlorantraniliprole exhibited comparable potencies against S. frugiperda. Transcriptome analysis showed that the molecular target of compound IV f is the ryanodine receptor. Molecular docking was further performed to verify the mode of action and insecticidal activity against resistant P. xylostella.


Assuntos
Inseticidas , Mariposas , Animais , Inseticidas/farmacologia , Inseticidas/química , Diamida/farmacologia , Diamida/química , Simulação de Acoplamento Molecular , Mariposas/metabolismo , ortoaminobenzoatos/farmacologia , ortoaminobenzoatos/química , Relação Quantitativa Estrutura-Atividade , Canal de Liberação de Cálcio do Receptor de Rianodina/metabolismo , Larva/metabolismo
18.
Biomacromolecules ; 25(4): 2312-2322, 2024 Apr 08.
Artigo em Inglês | MEDLINE | ID: mdl-38456765

RESUMO

Local delivery of pain medication can be a beneficial strategy to address pain management after joint replacement, as it can decrease systemic opioid usage, leading to less side and long-term effects. In this study, we used ultrahigh molecular weight polyethylene (UHMWPE), commonly employed as a bearing material for joint implants, to deliver a wide set of analgesics and the nonsteroidal anti-inflammatory drug tolfenamic acid. We blended the drugs with UHMWPE and processed the blend by compression molding and sterilization by low-dose gamma irradiation. We studied the chemical stability of the eluted drugs, drug elution, tensile properties, and wear resistance of the polymer blends before and after sterilization. The incorporation of bupivacaine hydrochloride and tolfenamic acid in UHMWPE resulted in either single- or dual-drug loaded materials that can be sterilized by gamma irradiation. These compositions were found to be promising for the development of clinically relevant drug-eluting implants for joint replacement.


Assuntos
Artroplastia de Substituição , ortoaminobenzoatos , Teste de Materiais , Polietilenos/química , Analgésicos , Anti-Inflamatórios não Esteroides
19.
Cell Rep ; 43(4): 114030, 2024 Apr 23.
Artigo em Inglês | MEDLINE | ID: mdl-38551966

RESUMO

Trichoderma spp. have evolved the capacity to communicate with plants by producing various secondary metabolites (SMs). Nonhormonal SMs play important roles in plant root development, while specific SMs from rhizosphere microbes and their underlying mechanisms to control plant root branching are still largely unknown. In this study, a compound, anthranilic acid (2-AA), is identified from T. guizhouense NJAU4742 to promote lateral root development. Further studies demonstrate that 2-AA positively regulates auxin signaling and transport in the canonical auxin pathway. 2-AA also partly rescues the lateral root numbers of CASP1pro:shy2-2, which regulates endodermal cell wall remodeling via an RBOHF-induced reactive oxygen species burst. In addition, our work reports another role for microbial 2-AA in the regulation of lateral root development, which is different from its better-known role in plant indole-3-acetic acid biosynthesis. In summary, this study identifies 2-AA from T. guizhouense NJAU4742, which plays versatile roles in regulating plant root development.


Assuntos
Parede Celular , Ácidos Indolacéticos , Raízes de Plantas , Transdução de Sinais , Trichoderma , ortoaminobenzoatos , Ácidos Indolacéticos/metabolismo , Parede Celular/metabolismo , Raízes de Plantas/metabolismo , Raízes de Plantas/crescimento & desenvolvimento , Trichoderma/metabolismo , Trichoderma/crescimento & desenvolvimento , ortoaminobenzoatos/metabolismo , Arabidopsis/metabolismo , Arabidopsis/crescimento & desenvolvimento , Regulação da Expressão Gênica de Plantas , Espécies Reativas de Oxigênio/metabolismo
20.
Rapid Commun Mass Spectrom ; 38(9): e9729, 2024 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-38456250

RESUMO

RATIONALE: Ensuring the global safety and effectiveness of agrochemicals has become imperative. An in-depth understanding of impurity profiles of products is crucial, especially for high-demand agrochemicals, where impurities may be more toxic and persistent than original agrochemicals. This study focuses on the detection and identification of impurities in a commercial chlorantraniliprole (CAP), an anthranilic diamide class broad-spectrum insecticide. METHODS: Commercial CAP was collected from an agrochemical supplier in India and was analyzed using a high-performance liquid chromatography-photodiode array (HPLC-PDA) (Agilent 1260; wavelength, 220 nm) with a Zorbax RP SB-C18 (250 × 4.6 mm, 5 µm) column and liquid chromatography-mass spectrometry (LC-MS) (Agilent 6545 quadrupole time of flight (Q-TOF)) techniques to identify the impurities. The impurities were isolated by preparative HPLC using a Zorbax-DB C18 (250 × 9.4 mm, 5 µm) column. liquid chromatography- tandem mass spectrometry (LC-MS/MS) experiments (Q-TOF) were performed on CAP and its impurities to obtain their structural data. RESULTS: HPLC-PDA analysis of CAP showed four major impurities (IM-1 to IM-4) ranging from 0.76% to 4.1%. The positive ion electrospray ionization (ESI) mass spectra of CAP and its impurities showed dominant [M + H]+ ions in addition to [M + Na]+ , [M + K]+ , and [2M + Na]+ ions. High-resolution mass spectrometry (HRMS) data provided the elemental composition of the compounds, and isotopic distribution patterns revealed the number of Cl and/or Br atoms present in them. The structures of impurities were proposed based on the LC-MS/MS) data and further confirmed by nuclear magnetic resonance (NMR) data on isolated impurities/synthesis. CONCLUSION: The quality and impurities of CAP, a popular insecticide, must be assessed and described for its efficacy and safety. In this study, four impurities of CAP were detected using HPLC and successfully characterized using LC-HRMS, LC-MS/MS, and NMR data. The method is useful for verifying the purity of CAP as well as helping in the identification of its possible impurities.


Assuntos
Inseticidas , ortoaminobenzoatos , Cromatografia Líquida , Espectrometria de Massas em Tandem , Íons
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