Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea

Cai, Nan; Liu, Caixiu; Feng, Zhihui; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Ahmed, Wasim; Cui, Zi‐Ning

doi:10.3390/molecules23040740

Cited by 11 publications

(8 citation statements)

References 29 publications

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“…In a previous study, chesulfonamide was shown to effectively control B. cinerea and C. cassiicola with a strong preventive activity [27]. SYAUP-CN-26 is a derivative of chesulfonamide, which has a better activity against Botrytis cinerea than chesulfnamide [29]. Until now, there have only been a few published studies focusing on these compounds and only biological assays have been tested on SYAUP-CN-26 and other derivative, such as, inhibitory effect on mycelium growth and spore germination of B. cinerea, fungicidal activities in pot tests and control efficacy in field [30].…”

Section: Introductionmentioning

confidence: 99%

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

et al. 2019

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In recent years, Botrytis cinerea has led to serious yield losses because of its resistance to fungicides. Many sulfonamides with improved properties have been used. (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide) (abbreviation: SYAUP-CN-26) is a new sulfonamide compound that has excellent activity against B. cinerea. This study investigated the effect of SYAUP-CN-26 on electric conductivity, nucleic acids leakage, malondialdehyde (MDA) content, and reducing sugars and membrane structure reduction of B. cinerea. The results showed that the cell membrane permeability of B. cinerea increased with increasing concentrations of SYAUP-CN-26; meanwhile, the sugar content decreased, the malondialdehyde content increased, and relative electric conductivity and nucleic acid substance leakage were observed in the cell after exposure to 19.263 mg/L SYAUP-CN-26 for 24 h. After 48 h of exposure to 1.823 mg/L and 19.263 mg/L SYAUP-CN-26, the cell membranes of B. cinerea mycelia were observed to be damaged under propidium iodide (PI) and transmission electron microscopy (TEM) observations. It is assumed that SYAUP-CN-26 was responsible for the damage of cell membrane. Overall, the results indicate that SYAUP-CN-26 could inhibit the growth of B. cinerea cells by damaging the cell membranes.

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Section: Introductionmentioning

confidence: 99%

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

et al. 2019

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“…In recent studies, transcriptome analysis has been widely applied on fungicidal resistant plant pathogens, including Fusarium spp. [ 40 ], B. cinerea [ 37 ], and Penecillium didgitatum [ 46 ]. According to our transcriptome analysis the expression of lysophospholipase genes, transmembrane transporter genes, MF (multifunctional genes), MFS (super family genes) encoding, amino acid and carbohydrate metabolism genes were clearly upregulated in field mutant (M0 , M-ipro) than wild type (W0, W-ipro) with or without application of iprodione ( Supplementary Table S15 Excel sheet).…”

Section: Discussionmentioning

confidence: 99%

“…Eventually, the fold change (log fold 2 ) and FDR values used as a key indicator the expression amount of different genes among samples and represent a heat map. Functional annotation of genes was performed as described by Wang et al [ 14 ] and Cai et al [ 37 ]. GO enrichment of differential expression of genes was implemented by the GO seq R packages (1.10.1) based on Wallenius’ non-central hyper-geometric distribution.…”

Section: Methodsmentioning

confidence: 99%

Cytological and Gene Profile Expression Analysis Reveals Modification in Metabolic Pathways and Catalytic Activities Induce Resistance in Botrytis cinerea Against Iprodione Isolated From Tomato

Maqsood

Ahmar

et al. 2020

IJMS

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Grey mold is one of the most serious and catastrophic diseases, causing significant yield losses in fruits and vegetables worldwide. Iprodione is a broad spectrum agrochemical used as a foliar application as well as a seed protectant against many fungal and nematode diseases of fruits and vegetables from the last thirty years. The extensive use of agrochemicals produces resistance in plant pathogens and is the most devastating issue in food and agriculture. However, the molecular mechanism (whole transcriptomic analysis) of a resistant mutant of B. cinerea against iprodione is still unknown. In the present study, mycelial growth, sporulation, virulence, osmotic potential, cell membrane permeability, enzymatic activity, and whole transcriptomic analysis of UV (ultraviolet) mutagenic mutant and its wild type were performed to compare the fitness. The EC50 (half maximal effective concentration that inhibits the growth of mycelium) value of iprodione for 112 isolates of B. cinerea ranged from 0.07 to 0.87 µg/mL with an average (0.47 µg/mL) collected from tomato field of Guangxi Province China. Results also revealed that, among iprodione sensitive strains, only B67 strain induced two mutants, M0 and M1 after UV application. The EC50 of these induced mutants were 1025.74 μg/mL and 674.48 μg/mL, respectively, as compared to its wild type 1.12 μg/mL. Furthermore, mutant M0 showed higher mycelial growth sclerotia formation, virulence, and enzymatic activity than wild type W0 and M1 on potato dextrose agar (PDA) medium. The bctubA gene in the mutant M0 replaced TTC and GAT codon at position 593 and 599 by TTA and GAA, resulting in replacement of phenyl alanine into leucine (transversion C/A) and aspartic acid into glutamic acid (transversion T/C) respectively. In contrast, in bctubB gene, GAT codon at position 646 is replaced by AAT and aspartic acid converted into asparagine (transition G/A). RNA sequencing of the mutant and its wild type was performed without (M0, W0) and with iprodione treatment (M-ipro, W-ipro). The differential gene expression (DEG) identified 720 unigenes in mutant M-ipro than W-ipro after iprodione treatment (FDR ≤ 0.05 and log2FC ≥ 1). Seven DEGs were randomly selected for quantitative real time polymerase chain reaction to validate the RNA sequencing genes expression (log fold 2 value). The gene ontology (GO) enrichment and Kyoto encyclopedia genes and genomes (KEGG) pathway functional analyses indicated that DEG’s mainly associated with lysophopholipase, carbohydrate metabolism, amino acid metabolism, catalytic activity, multifunctional genes (MFO), glutathione-S transferase (GST), drug sensitivity, and cytochrome P450 related genes are upregulated in mutant type (M0, M-ipro) as compared to its wild type (W0, W-ipro), may be related to induce resistant in mutants of B. cinerea against iprodione.

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“…SYAUP-CN-26 (used in this study), chemically named (1 S , 2 R -((3-bromophenethyl)amino)- N -(4-chloro-2-(trifluoromethyl)phenyl)cyclohexane-1-sulfonamide), is a cycloalkyl compound containing one sulfonyl group with significant activity against B. cinerea [ 22 , 23 , 24 , 25 ] ( Figure 1 ). A previous study reported that SYAUP-CN-26 could affect the mitochondrial and cell membrane’s structure and function of B. cinerea [ 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Preliminary Study of Resistance Mechanism of Botrytis cinerea to SYAUP-CN-26

Wang¹,

Zhang²,

Zhu³

et al. 2022

Molecules

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SYAUP-CN-26 (1S, 2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) is a novel sulfonamide compound with excellent activity against Botrytis cinerea. The present study sought to explore the mutant of B.cinerea resistant to SYAUP-CN-26 using SYAUP-CN-26 plates. Moreover, the cell membrane functions of B.cinerea, histidine kinase activity, relative conductivity, triglyceride, and cell membrane structure were determined, and the target gene histidine kinase Bos1 (AF396827.2) of procymidone was amplified and sequenced. The results showed that compared to the sensitive strain, the cell membrane permeability, triglyceride, and histidine kinase activity of the resistant strain showed significant changes. The relative conductivity of the sensitive strain increased by 6.95% and 9.61%, while the relative conductivity of the resistant strain increased by 0.23% and 1.76% with 26.785 µg/mL (EC95) and 79.754 µg/mL (MIC) of SYAUP-CN-26 treatment. The triglyceride inhibition rate of the resistant strain was 23.49% and 37.80%, which was 0.23% and 1.76% higher than the sensitive strain. Compared to the sensitive strain, the histidine kinase activity of the resistant strain was increased by 23.07% and 35.61%, respectively. SYAUP-CN-26 significantly damaged the cell membrane structure of the sensitive strain. The sequencing of the Bos1 gene of the sensitive and resistant strains indicated that SYAUP-CN-26 resistance was associated with a single point mutation (P348L) in the Bos1 gene. Therefore, it was inferred that the mutant of B.cinerea resistant to SYAUP-CN-26 might be regulated by the Bos1 gene. This study will provide a theoretical basis for further research and development of sulfonamide compounds for B. cinerea and new agents for the prevention and control of resistant B. cinerea.

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Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea

Cited by 11 publications

References 29 publications

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

The Effect of (1S,2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) on Botrytis cinerea through the Membrane Damage Mechanism

Cytological and Gene Profile Expression Analysis Reveals Modification in Metabolic Pathways and Catalytic Activities Induce Resistance in Botrytis cinerea Against Iprodione Isolated From Tomato

Preliminary Study of Resistance Mechanism of Botrytis cinerea to SYAUP-CN-26

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