C–H Diselenation and Monoselenation of Electron-Deficient Alkenes via Radical Coupling at Room Temperature

Chen, Yao; Lv, Mengxia; Zhang, Yuxin; Wu, Yao; Ying, Linkun; Tang, Jielin; Gong, Xiangnan; Zhang, Jianmin; Song, Zengqiang

doi:10.1021/acs.joc.2c01567

Cited by 9 publications

(5 citation statements)

References 49 publications

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“…CY-158-11 (C 22 H 14 Cl 2 NO 2 Se 2 ) is a small molecule compound that contains N-maleimide and diphenyl diselenide ( 16 ). Maleimide motifs are found in many natural products, pharmaceuticals, bioactive molecules, and functional materials ( 17 ).…”

Section: Introductionmentioning

confidence: 99%

Small-Molecule Compound CY-158-11 Inhibits Staphylococcus aureus Biofilm Formation

et al. 2023

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Section: Introductionmentioning

confidence: 99%

Small-Molecule Compound CY-158-11 Inhibits Staphylococcus aureus Biofilm Formation

et al. 2023

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“…Based on the control studies and the reported literature, − a plausible mechanistic pathway for this novel transformation was proposed by taking enamine 1a , diphenyl diselenide 2a , and TFE 3a as examples (Scheme ). Initially, the intermediate I is generated by the reaction of PIFA and diphenyl diselenide, which undergoes thermal hemolytic cleavage to form phenyl selenide radical II and radical III .…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of β-Trifluoroethoxydimethyl Selenides as Potent Antiosteoporosis Agents

Wu,

Li,

Ying

et al. 2024

J. Med. Chem.

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An efficient protocol for the synthesis of β-trifluoroethoxydimethyl selenides was achieved under mild reaction conditions, and 39 compounds were prepared. All compounds were evaluated for their abilities to inhibit RANKL-induced osteoclastogenesis, compound 4aa exhibited the most potent activity. Further investigations revealed that 4aa could inhibit Factin ring generation, bone resorption, and osteoclast-specific gene expression in vitro. Western blot analyses demonstrated that compound 4aa abrogated the RANKL-induced mitogen-activated protein kinase and NF-kB-signaling pathways. In addition, 4aa also displayed a notable impact on the osteoblastogenesis of MC3T3-E1 preosteoblasts. In vivo experiments revealed that compound 4aa significantly ameliorated bone loss in an ovariectomized (OVX) mice model. Furthermore, the surface plasmon resonance experiment results revealed that 4aa probably bound to RANKL. Collectively, the abovementioned findings suggested that compound 4aa as a potential RANKL inhibitor averted OVX-triggered osteoporosis by regulating the inhibition of osteoclast differentiation and stimulation of osteoblast differentiation.

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“…YH7 was synthesized by the Song laboratory at the School of Pharmacy, Wenzhou Medical University. The synthesis method of YH7 was performed as described previously ( 20 ) (Fig. 1A).…”

Section: Methodsmentioning

confidence: 99%

“…Although both diphenyl diselenides and maleimide derivatives have demonstrated various medicinal properties, the antibiofilm activity and synergistic effects of mixtures of diselenide and maleimide compounds in S. aureus have not been reported. Therefore, we designed a novel diselenide maleimide hybrid, YH7, based on our previously developed metal-free and straightforward protocol for maleimide dissociation ( 20 ).…”

Section: Introductionmentioning

confidence: 99%

Novel small-molecule compound YH7 inhibits the biofilm formation of Staphylococcus aureus in a sarX -dependent manner

Xiao,

Wan,

et al. 2024

mSphere

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The emergence of antibiotic-resistant and biofilm-producing Staphylococcus aureus isolates presents major challenges for treating staphylococcal infections. Biofilm inhibition is an important anti-virulence strategy. In this study, a novel maleimide-diselenide hybrid compound (YH7) was synthesized and demonstrated remarkable antimicrobial activity against methicillin-resistant S. aureus (MRSA) and methicillin-susceptible S. aureus (MSSA) in both planktonic cultures and biofilms. The minimum inhibitory concentration (MIC) of YH7 for S. aureus isolates was 16 µg/mL. Quantification of biofilms demonstrated that the sub-MIC (4 µg/mL) of YH7 significantly inhibits biofilm formation in both MSSA and MRSA. Confocal laser scanning microscopy analysis further confirmed the biofilm inhibitory potential of YH7. YH7 also significantly suppressed bacterial adherence to A549 cells. Moreover, YH7 treatment significantly inhibited S. aureus colonization in nasal tissue of mice. Preliminary mechanistic studies revealed that YH7 exerted potent biofilm-suppressing effects by inhibiting polysaccharide intercellular adhesin (PIA) synthesis, rather than suppressing bacterial autolysis. Real-time quantitative PCR data indicated that YH7 downregulated biofilm formation-related genes ( clfA , fnbA , icaA, and icaD ) and the global regulatory gene sarX , which promotes PIA synthesis. The sarX -dependent antibiofilm potential of YH7 was validated by constructing S. aureus NCTC8325 sarX knockout and complementation strains. Importantly, YH7 demonstrated a low potential to induce drug resistance in S. aureus and exhibited non-toxic to rabbit erythrocytes, A549, and BEAS-2B cells at antibacterial concentrations. In vivo toxicity assays conducted on Galleria mellonella further confirmed that YH7 is biocompatible. Overall, YH7 demonstrated potent antibiofilm activity supports its potential as an antimicrobial agent against S. aureus biofilm-related infections. IMPORTANCE Biofilm-associated infections, characterized by antibiotic resistance and persistence, present a formidable challenge in healthcare. Traditional antibacterial agents prove inadequate against biofilms. In this study, the novel compound YH7 demonstrates potent antibiofilm properties by impeding the adhesion and the polysaccharide intercellular adhesin production of Staphylococcus aureus . Notably, its exceptional efficacy against both methicillin-resistant and methicillin-susceptible strains highlights its broad applicability. This study highlights the potential of YH7 as a novel therapeutic agent to address the pressing issue of biofilm-driven infections.

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C–H Diselenation and Monoselenation of Electron-Deficient Alkenes via Radical Coupling at Room Temperature

Cited by 9 publications

References 49 publications

Small-Molecule Compound CY-158-11 Inhibits Staphylococcus aureus Biofilm Formation

Small-Molecule Compound CY-158-11 Inhibits Staphylococcus aureus Biofilm Formation

Design, Synthesis, and Biological Evaluation of β-Trifluoroethoxydimethyl Selenides as Potent Antiosteoporosis Agents

Novel small-molecule compound YH7 inhibits the biofilm formation of Staphylococcus aureus in a sarX -dependent manner

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