Design, synthesis and mechanism research of novel algicide based on bioactive fragments synthesis strategy

Huang, Shi; Zuo, Lingzi; Cheng, Guonian; He, Yanlin; Zhang, Liexiong; Han, Qiang; Feng, Lingling

doi:10.1016/j.pestbp.2023.105344

Cited by 4 publications

(5 citation statements)

References 42 publications

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“…After Synechocystis sp. PCC6803 were grown with the method described in section , untreated samples (blank control group) and compound S5 -treated metabolomics samples (experimental group) were prepared, with 3 replicates per sample as previously reported . The testing process was conducted by Anlong Kexun Technology Co., Ltd. (Wuhan, China), as described in section S1.4 of the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

“…Therefore, it is crucial to mitigate the threats of HCBs to ensure the protection of aquatic environments and the health of affected organisms . There are many ways to control HCBs, including physical control, chemical control, and biological control. − Chemical control is considered one of the most effective methods to solve the harm of HCBs. Among the existing chemical algicides, there are mainly heavy metal algicides represented by copper sulfate (CuSO 4 ), strong oxidant algicides represented by potassium permanganate and peroxide, and herbicide algicides represented by diuron and prometryn .…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, and Bioassay for the Thiadiazole-Bridged Thioacetamide Compound as Cy-FBP/SBPase Inhibitors Based on Catalytic Mechanism Virtual Screening

Zuo

Huang

et al. 2023

J. Agric. Food Chem.

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Cyanobacterial fructose-1,6-/sedoheptulose-1,7-bisphosphatase (Cy-FBP/SBPase) was an important regulatory enzyme in cyanobacterial photosynthesis and was a potential target enzyme for screening to obtain novel inhibitors against cyanobacterial blooms. In this study, we developed a novel pharmacophore screening model based on the catalytic mechanism and substrate structure of Cy-FBP/SBPase and screened 26 S series compounds with different structures and pharmacophore characteristics from the Specs database by computer-assisted drug screening. These compounds exhibited moderate inhibitory activity against Cy-FBP/SBPase, with 9 compounds inhibiting >50% at 100 μM. Among them, compound S5 showed excellent inhibitory activity against both Cy-FBP/SBPase and Synechocystis sp. PCC6803 (IC50 = 6.7 ± 0.7 μM and EC50 = 7.7 ± 1.4 μM). The binding mode of compound S5 to Cy-FBP/SBPase was predicted using the molecular docking theory and validated by sentinel mutation and enzyme activity analysis. Physiochemical, gene transcription level, and metabolomic analyses showed that compound S5 significantly reduced the quantum yield of photosystem II and the maximum electron transfer rate, downregulated transcript levels of related genes encoding the Calvin cycle and photosystem, reduced the photosynthetic efficiency of cyanobacteria, thus inhibited metabolic pathways, such as the Calvin cycle and tricarboxylic acid cycle, and eventually achieved an efficient algicide. In addition, compound S5 had a high safety profile for human-derived cells and zebrafish. In summary, the novel pharmacophore screening model obtained from the current work provides an effective solution to the cyanobacterial bloom problem.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Bioassay for the Thiadiazole-Bridged Thioacetamide Compound as Cy-FBP/SBPase Inhibitors Based on Catalytic Mechanism Virtual Screening

Zuo

Huang

et al. 2023

J. Agric. Food Chem.

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“…General Procedure for the Preparation of Intermediates 2. 18 Benzo hydrazide (2.5 g, 18.3 mmol) and KOH (1.236 g, 22.0 mmol) were dissolved in 75 mL of ethanol, and CS 2 (2.219 mL, 36 mmol) was slowly added under nitrogen protection at room temperature to obtain a yellow solution, which was heated and refluxed for 8 h after addition, cooled to room temperature, and precipitated as a white solid. Finally, the filter cake was washed with a small amount of ethanol to obtain intermediate 2 after filtration.…”

Section: Instruments and Chemicalsmentioning

confidence: 99%

“…Inhibition against Cyanobacteria in an Expanded Environment System. 18 The Microcystis aeruginosa. FACHB905 was selected as the experimental object of algae killing in an expanded environment system; it had the largest frequency and amplitude of cyanobacterial blooms.…”

Section: Generalmentioning

confidence: 99%

“…These strategies primarily involve the use of physical, chemical, and biological methods. − Physical methods mainly include cyanobacteria salvage, ultrasound, and filtration, which can alleviate the occurrence of cyanobacterial blooms by controlling the number of algae in the water . Biological methods mainly include aquatic plant control, aquatic animal control, microbial control, and biological enzyme control methods, which can control the growth of algae through nutrient competition, degradation of microcystin, or guidance of algae eaters. , Although they can effectively control cyanobacterial blooms, they have the defects of high cost, long treatment time, and limited application water. , Chemical methods are widely used in the treatment of cyanobacterial blooms because of their low cost and quick effect. , However, existing chemical algicides have some limitations, such as poor selectivity, low safety, and a large amount of use. − Therefore, it is imperative to develop an efficient, safe, and specific algicide as a substitute for the current commercial algicide.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, and Mode of Action of Thioacetamide Derivatives as the Algicide Candidate Based on Active Substructure Splicing Strategy

Huang,

Zuo,

Zhang

et al. 2024

J. Agric. Food Chem.

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Lakes and reservoirs worldwide are experiencing a growing problem with harmful cyanobacterial blooms (HCBs), which have significant implications for ecosystem health and water quality. Algaecide is an effective way to control HCBs effectively. In this study, we applied an active substructure splicing strategy for rapid discovery of algicides. Through this strategy, we first optimized the structure of the lead compound S5, designed and synthesized three series of thioacetamide derivatives (series A, B, C), and then evaluated their algicidal activities. Finally, compound A3 with excellent performance was found, which accelerated the process of discovering and developing new algicides. The biological activity assay data showed that A3 had a significant inhibitory effect on M. aeruginosa. FACHB905 (EC 50 = 0.46 μM) and Synechocystis sp. PCC6803 (EC 50 = 0.95 μM), which was better than the commercial algicide prometryn (M. aeruginosa. FACHB905, EC 50 = 6.52 μM; Synechocystis sp. PCC6803, EC 50 = 4.64 μM) as well as better than lead compound S5 (M. aeruginosa. FACHB905, EC 50 = 8.80 μM; Synechocystis sp. PCC6803, EC 50 = 7.70 μM). The relationship between the surface electrostatic potential, chemical reactivity, and global electrophilicity of the compounds and their activities was discussed by density functional theory (DFT). Physiological and biochemical studies have shown that A3 might affect the photosynthesis pathway and antioxidant system in cyanobacteria, resulting in the morphological changes of cyanobacterial cells. Our work demonstrated that A3 might be a promising candidate for the development of novel algicides and provided a new active skeleton for the development of subsequent chemical algicides.

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Natural algicidal compounds: Strategies for controlling harmful algae and application

Li,

Xing,

et al. 2024

Plant Physiology and Biochemistry

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Design, synthesis and mechanism research of novel algicide based on bioactive fragments synthesis strategy

Cited by 4 publications

References 42 publications

Design, Synthesis, and Bioassay for the Thiadiazole-Bridged Thioacetamide Compound as Cy-FBP/SBPase Inhibitors Based on Catalytic Mechanism Virtual Screening

Design, Synthesis, and Bioassay for the Thiadiazole-Bridged Thioacetamide Compound as Cy-FBP/SBPase Inhibitors Based on Catalytic Mechanism Virtual Screening

Design, Synthesis, and Mode of Action of Thioacetamide Derivatives as the Algicide Candidate Based on Active Substructure Splicing Strategy

Natural algicidal compounds: Strategies for controlling harmful algae and application

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