Inverse electron-demand aza Diels-Alder reaction of aldimine with enol ethers proceeded under the influence of a phosphoric acid diester, derived from (R)-BINOL, to give tetrahydroquinoline derivatives with excellent enantioselectivity.
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The inverse electron demand diels-alder (IEDDA): A facile bioorthogonal click reaction for development of injectable polysaccharide-based hydrogels for biomedical applications.
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Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources and International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, China. Electronic address:
The inverse electron demand Diels-Alder (IEDDA) cycloaddition between tetrazines and strained dienophiles is recognized as a fast and specific reaction. The integrating tetrazines and strained dienophiles onto the backbone of polysaccharides yield appropriate water-soluble precursors for IEDDA cycloaddition. Due to the high specificity of the IEDDA reaction and its outstanding cytocompatibility, a range of cargos (live cells, peptides and pharmaceuticals) can be effectively encapsulated in polysaccharide solutions throughout the hydrogel formation.
View Article and Find Full Text PDFClick Chemistry as an Efficient Toolbox for Coupling Sterically Hindered Molecular Systems to Obtain Advanced Materials for Nanomedicine.
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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 PDFXanthine Nucleosides with Pyrazolo[3,4-]pyrimidine Skeleton: Functionalization with Halogen Atoms, Clickable Side Chains, Pyrene, and iEDDA Cycloadducts, and Impact of Ionic Forms on Photophysical Properties.
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Xanthine nucleosides play a significant role in the expansion of the four-letter genetic code. Herein, 7-functionalized 8-aza-7-deazaxanthine ribo- and 2'-deoxyribonucleosides are described. 2-Amino-6-alkoxy nucleosides were converted to halogenated 8-aza-7-deazaxanthine nucleosides by deamination followed by hydroxy/alkoxy substitution.
View Article and Find Full Text PDFDevelopment of Amniotic Epithelial Stem Cells Secretome-Loaded Inverse Electron Demand Diels-Alder-Cross-Linked Hydrogel as a Potential Immunomodulatory Therapeutical Tool.
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Article Synopsis
- Amniotic epithelial stem cells (AEC) have regenerative potential, particularly through their conditioned medium (AEC-CM), which shows immunomodulatory and regenerative effects.
- A novel hydrogel made from hyaluronic acid and polyethylene glycol was developed to encapsulate AEC-CM, with features like fast cross-linking and sustained growth factor release over 14 days.
- Studies demonstrate that the encapsulated AEC-CM significantly enhances the suppression of peripheral blood mononuclear cells and promotes a shift towards the beneficial M2 macrophage phenotype, suggesting its viability as an immunomodulatory treatment for tissue regeneration.
Conditional Relay Activation of Theranostic Prodrug by Pretargeting Bioorthogonal Trigger and Fluorescence-Guided Visible Light Irradiation.
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Laboratory of Medicinal Chemical Biology, Jiangsu Province Engineering Research Center of Precision Diagnostics and Therapeutics Development, College of Pharmaceutical Sciences, Suzhou Medical College of Soochow University, Suzhou, 215123, China.
Bioorthogonalized light-responsive click-and-uncage platform has enabled precise cell surface engineering and timed payload release, but most of such photoactivatable prodrugs have "always-on" photoactivity leading to the dark toxicity. On the other hand, the conditionally activatable photocage is limited to the application of fluorogenic probe/photosensitizer liberation. Herein, we devise a conditionally activatable theranostic platform based on the tetrazine (Tz)-boron-dipyrromethene (BODIPY) construct, in which tetrazine serves as a quencher motif to disable both the fluorescence and photoresponsivity of BODIPY.
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