Ceramide analogues containing azide groups either in the polar head or in the hydrocarbon chains are non-fluorescent. When incorporated into phospholipid bilayers, they can react in situ with a non-fluorescent 1,8-naphthalimide using click chemistry giving rise to fluorescent ceramide derivatives emitting at ≈440 nm. When incorporated into giant unilamellar vesicles, two-photon excitation at 760 nm allows visualization of the ceramide-containing bilayers. This kind of method may be of general applicability in the study of model and cell membranes.
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http://dx.doi.org/10.1007/s12154-012-0075-0 | DOI Listing |
Anal Chem
January 2025
Department of Chemistry, University of California, Davis, California 95616, United States.
Protein-protein interactions in the cell membrane are typically mediated by glycans, with terminal sialic acid often involved in these interactions. To probe the nature of the interactions, we developed quantitative cross-linking methods involving the glycans of the glycoproteins and the polypeptide moieties of proteins. We designed and synthesized biotinylated enrichable cross-linkers that were click-tagged to metabolically incorporate azido-sialic acid on cell surface glycans to allow cross-linking of the azido-glycans with lysine residues on proximal polypeptides.
View Article and Find Full Text PDFACS Appl Mater Interfaces
January 2025
Guangdong Key Laboratory for Hydrogen Energy Technologies, School of Materials and Energy, Foshan University, Foshan 528000, PR China.
Lithium metal electrodes inevitably lead to the decomposition of the liquid electrolyte and lithium dendrite growth, both of which result in the formation of unstable solid electrolyte intermediates (SEIs). Gel polymer electrolytes (GPEs) are expected to replace liquid electrolytes for optimizing the SEI issues of lithium metal. Herein, a cellulose-based gel electrolyte cross-linked by thiol-modified polyhedral oligomeric silsesquioxane (thiol-modified-POSS) was successfully obtained based on "thiol-ene" click chemistry.
View Article and Find Full Text PDFBioorg Chem
January 2025
Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002 Saudi Arabia. Electronic address:
The discovery of novel anti-cancer drugs motivated us to synthesize a new series of triple 1,2,3-triazole-based arm scaffolds featuring distinct un functionalized alkyl and/or aryl side chains with possible anti-cancer action using the click chemistry approach under both conventional and green microwave irradiation (MWI) methods. The Cu(I) catalyzed cycloaddition reaction of targeted tris-alkyne with un functionalized aliphatic and aromatic azides has been adopted as an efficient approach for synthesizing the desired click adducts. Microwave irradiation improved the synthetic processes, resulting in higher yields and faster reaction times.
View Article and Find Full Text PDFInt J Mol Sci
December 2024
Materials Research Institute, Universidad Nacional Autónoma de México, Mexico City 04510, Mexico.
Since its conceptualization, click chemistry in all its variants has proven to be a superior synthesis protocol, compared to conventional methods, for forming new covalent bonds under mild conditions, orthogonally, and with high yields. If a term like reactive resilience could be established, click reactions would be good examples, as they perform better under increasingly challenging conditions. Particularly, highly hindered couplings that perform poorly with conventional chemistry protocols-such as those used to conjugate biomacromolecules (e.
View Article and Find Full Text PDFPolymers (Basel)
December 2024
Institute of Chemistry, Federal University of Uberlândia, Uberlândia 38400-902, Brazil.
Cellulose tosylate (MCC-Tos) is a key derivative for surface modification and a crucial precursor for cellulose compatibilization in click reactions, enabling its functionalization for advanced applications. Replacing tosyl groups with alkyne groups broadens cellulose's potential in biocompatible reactions, such as thiol-yne click chemistry and protein/enzyme immobilization. To achieve this, we optimized the heterogeneous synthesis of MCC-Tos using a Doehlert matrix statistical design, evaluating the influence and interaction of the reaction conditions.
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