An efficient triple-click assembly using a newly designed trivalent platform is disclosed. We achieved the selective azaylide formation of 2,3,5,6-tetrafluorophenyl azides with -ester-substituted triarylphosphines leaving 2,6-dichlorophenyl azides untouched. Further rapid Staudinger reaction of dichlorophenyl azides and subsequent triazole formation allowed us to prepare trifunctionalized molecules in three steps.
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Click assembly through selective azaylide formation.
Chem Commun (Camb)
July 2024
Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan.
An efficient triple-click assembly using a newly designed trivalent platform is disclosed. We achieved the selective azaylide formation of 2,3,5,6-tetrafluorophenyl azides with -ester-substituted triarylphosphines leaving 2,6-dichlorophenyl azides untouched. Further rapid Staudinger reaction of dichlorophenyl azides and subsequent triazole formation allowed us to prepare trifunctionalized molecules in three steps.
View Article and Find Full Text PDFTrimethylsilanol Cleaves Stable Azaylides As Revealed by Unfolding of Robust "Staudinger" Single-Chain Nanoparticles.
ACS Polym Au
April 2024
Centro de Física de Materiales (CSIC - UPV/EHU) - Materials Physics Center MPC, P° Manuel Lardizabal 5, E-20018 Donostia, Spain.
Herein, we disclose a unique and selective reagent for the cleavage of stable azaylides prepared by the nonhydrolysis Staudinger reaction, enabling the on-demand unfolding of robust single-chain nanoparticles (SCNPs). SCNPs with promising use in catalysis, nanomedicine, and sensing are obtained through intrachain folding of discrete synthetic polymer chains. The unfolding of SCNPs involving reversible interactions triggered by a variety of external stimuli (e.
View Article and Find Full Text PDFAn isophorone-fused near-infrared fluorescent probe with a large Stokes shift for imaging endogenous nitroxyl in living cells and zebrafish.
Spectrochim Acta A Mol Biomol Spectrosc
February 2020
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China. Electronic address:
Nitroxyl (HNO) plays an important role in multiple physiological and pathological processes, but the detailed generation mechanism of the endogenous HNO still remained to explore and perfect further. There is an urgent need to develop an excellent fluorescent probe for selective recognition and sensitive detection of HNO in biological systems. Near-infrared (NIR) fluorescent probes with a large Stokes shift are an ideal tool for bioimaging applications.
View Article and Find Full Text PDFImaging of anti-inflammatory effects of HNO via a near-infrared fluorescent probe in cells and in rat gouty arthritis model.
J Mater Chem B
January 2019
College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, China.
Nitroxyl (HNO) plays a crucial role in anti-inflammatory effects via the inhibition of inflammatory pathways, but the details of the endogenous generation of HNO still remain challenging owing to the complex biosynthetic pathways, in which the interaction between HS and NO simultaneously generates HNO and polysulfides (HS) in mitochondria. Moreover, nearly all the available fluorescent probes for HNO are utilized for imaging HNO in cells and tissues, instead of the in situ real-time detection of the simultaneous formation of HNO and HS in mitochondria and animals. Here, we have developed a mitochondria-targeting near-infrared fluorescent probe, namely, Mito-JN, to detect the generation of HNO in cells and a rat model.
View Article and Find Full Text PDFA Chemiluminescent Probe for HNO Quantification and Real-Time Monitoring in Living Cells.
Angew Chem Int Ed Engl
January 2019
Department of Chemistry, Center for Drug Discovery, Design, and Delivery (CD4), and, Center for Global Health Impact (CGHI), Southern Methodist University, Dallas, TX, 75205-0314, USA.
Azanone (HNO) is a reactive nitrogen species with pronounced biological activity and high therapeutic potential for cardiovascular dysfunction. A critical barrier to understanding the biology of HNO and furthering clinical development is the quantification and real-time monitoring of its delivery in living systems. Herein, we describe the design and synthesis of the first chemiluminescent probe for HNO, HNOCL-1, which can detect HNO generated from concentrations of Angeli's salt as low as 138 nm with high selectivity based on the reaction with a phosphine group to form a self-cleavable azaylide intermediate.
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