In this account, we describe how some organic diselenides were successfully used in the past as reagents for asymmetric stereoselective synthesis and more recently as precursors of catalysts and reagents applied in new green protocols. A biomimetic approach offered the possibility to perform oxidative reactions using hydrogen peroxide as oxidant and water as medium affording the desired products in excellent yields under mild conditions. The umpolung of the selenium atom gave novel nucleophilic reagents having a strongly accelerated reaction rate in on water conditions. Finally, the use of diselenides to exploit specific biological activities is described here as seminal examples of a promising field of research currently under investigation in our group.
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http://dx.doi.org/10.2533/chimia.2017.592 | DOI Listing |
Chem Commun (Camb)
January 2025
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, China.
A fluorescence quenching mechanism using linear diselenides was proposed for the first time through a combination of intramolecular charge transfer (ICT) and Förster resonance energy transfer (FRET). Herein, we synthesized and screened a two-photon fluorescent probe AFC-SeSe, demonstrating a remarkable 300-fold increase in response to glutathione (GSH). Additionally, AFC-SeSe enabled real-time observation of increased thiol levels following treatment within a short timeframe in a mouse model of stroke.
View Article and Find Full Text PDFAdv Healthc Mater
January 2025
Department of Pharmacology, School of Basic Medical Sciences, Anhui Medical University, Hefei, 230032, China.
Effective glycemic control is paramount for optimal wound healing in diabetic patients. Traditional antibacterial and anti-inflammatory treatments, while important, often fall short in addressing the hyperglycemic conditions of diabetic wounds. Therefore, the development of novel therapeutic strategies for accelerating diabetic wound healing has garnered escalating attention.
View Article and Find Full Text PDFColloids Surf B Biointerfaces
December 2024
Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand; Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand. Electronic address:
Clinical diagnosis and long-term diabetes management are advanced by monitoring glycated hemoglobin A1c (HbA1c) levels. New sensitive sandwich-like immunosensors for the diagnosis of early diabetes toward detecting HbA1c and hemoglobin (Hb) are demonstrated for the first time. DNA aptamers are used for signal amplification in the sensors for the detection of HbA1c and Hb.
View Article and Find Full Text PDFACS Appl Mater Interfaces
December 2024
Collaborative Innovation Center of Advanced Microstructures, National Laboratory of Solid State Microstructure, Key Laboratory of Intelligent Optical Sensing and Manipulation, Ministry of Education, Department of Physics, Nanjing University, Nanjing, Jiangsu 210093, China.
Dynamic hydrogels are emerging as advanced materials for engineering tissue-like environments that mimic cellular microenvironments. We introduce a diselenide-cross-linked hydrogel system with light-responsive properties, designed for precise control of tumor organoid growth and light-initiated radical inactivation, particularly for dendritic cell (DC) vaccines. Diselenide exchange enables stress relaxation and hydrogel remodeling, while recombination and quenching of seleno radicals (Se) reduce cross-linking density, leading to controlled degradation.
View Article and Find Full Text PDFChem Sci
December 2024
Advanced Research Institute of Multidisciplinary Science, School of Chemistry and Chemical Engineering, Key Laboratory of Medical Molecule Science and Pharmaceutical Engineering, Ministry of Industry and Information Technology, Beijing Institute of Technology Beijing 100081 P. R. China
We report a light-promoted hydroselenation of alkenes with high -Markovnikov selectivity. Blue light activates an aryl diselenide to generate a seleno radical with subsequent addition into an alkene to form a β-seleno carbon radical. Hydrogen atom transfer (HAT) from the selenol to the carbon radical generates the linear selenide with high selectivity in preference to the branched isomer.
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