Metal-Free Click Modification of Triple Bond-Containing Polyester with Azide-Functionalized Vegetable Oil: Plasticization and Tunable Solvent Adsorption
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ABSTRACT:
SUBMITTER: Cangul K
PROVIDER: S-EPMC9281323 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:Positron emission tomography (PET) is an increasingly important biomedical imaging technique that relies on the development of radiotracers labeled with positron-emitters to achieve biochemical specificity. Fluorine-18 (t1/2 = 109.7 min) is an attractive positron-emitting radiolabel for organic radiotracers, primarily because of its longer half-life and greater availability relative to those for the main alternative, carbon-11 (t1/2 = 20.4 min). Rapid simple methods are sought for labeling prospective PET radiotracers with fluorine-18 from cyclotron-produced aqueous [18F]fluoride ion, which must often be converted first into a suitably reactive labeling synthon for use in a subsequent labelling reaction. Use of 18F-labeled synthons in 'click chemistry' attracts increasing attention for labeling PE Tradiotracers. Here we describe rapid single-step radiosyntheses of azido- or azidomethyl-bearing [18F]fluoroarenes from the reactions of diaryliodonium salts with no-carrier-added [18F]fluoride ion within a microfluidic apparatus to provide previously poorly accessible 18F-labeled click synthons in radiochemical yields of 15% for [18F]4-fluorophenyl azide and about 40% for each of the [18F](azidomethyl)-fluorobenzenes. The radiosyntheses of the latter synthons was possible under 'wet conditions', so obviating the need to dry the cyclotron-produced [18F]fluoride ion and greatly enhancing the practicality of the method.
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Project description:Multifunctionalized macromers react via a copper-free click chemistry to form an idealized 3D hydrogel. Subsequently, thiol-containing biomolecules are spatially patterned within the material with precise control over the amount and location of functionalization. Both the network formation and subsequent patterning reactions are fully cytocompatible, allowing these systems to be used to study individual cell behavior at user-defined locations throughout the material.
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Project description:A series of novel amphiphilic functionalized fibers with polarity tunable surface microenvironment were constructed by introducing hydrophilic polyamines and hydrophobic linear alkyl chain groups, aiming to selectively remove parabens from water. In addition, Fourier-transform infrared spectroscopy, X-ray powder diffraction, scanning electron microscopy, etc. were employed to determine the successful preparation of amphiphilic functionalized fibers. The adsorption experimental data indicated that the amphiphilic fibers showed excellent selectivity for parabens. In the amphiphilic fibers, hydrogen bonding and hydrophobic interaction existing in one molecular unit can effectively act together to enhance the interaction between substrate and fibers. Kinetic studies illustrated that the adsorption process was a physical adsorption with chemical characteristics. The overall initial adsorption rate together with the stepwise adsorption rate was quantified, and it is inferred that the hydrophobic interaction plays a leading role in the first step of the adsorption process. Moreover, the Freundlich model well described the sorption process with a maximum adsorption of 138.4 mg/g. What's more, the fiber still keeps excellent adsorption capacity (>90%) even after 10 adsorption/desorption cycles, which certifies it is an excellent adsorbent and can be utilized to remove paraben in practice.
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Project description:Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.
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Project description:Functionalization of nanocrystals is essential for their practical application, but synthesis on nanocrystal surfaces is limited by incompatibilities with certain key reagents. The copper-catalyzed azide-alkyne cycloaddition is among the most useful methods for ligating molecules to surfaces, but has been largely useless for semiconductor quantum dots (QDs) because Cu+ ions quickly and irreversibly quench QD fluorescence. To discover nonquenching synthetic conditions for Cu-catalyzed click reactions on QD surfaces, we developed a combinatorial fluorescence assay to screen >2000 reaction conditions to maximize cycloaddition efficiency while minimizing QD quenching. We identify conditions for complete coupling without significant quenching, which are compatible with common QD polymer surfaces and various azide/alkyne pairs. Based on insight from the combinatorial screen and mechanistic studies of Cu coordination and quenching, we find that superstoichiometric concentrations of Cu can promote full coupling if accompanied by ligands that selectively compete with the Cu from the QD surface but allow it to remain catalytically active. Applied to the conjugation of a K+ channel-specific peptidyl toxin to CdSe/ZnS QDs, we synthesize unquenched QD conjugates and image their specific and voltage-dependent affinity for K+ channels in live cells.
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Project description:The alkyne-azide cycloaddition, popularly known as the "click" reaction, has been extensively exploited in molecule/macromolecule build-up, and has offered tremendous potential in the design of nanomaterials for applications in a diverse range of disciplines, including biology. Some advantageous characteristics of this coupling include high efficiency, and adaptability to the environment in which the desired covalent linking of the alkyne and azide terminated moieties needs to be carried out. The efficient delivery of active pharmaceutical agents to specific organelles, employing nanocarriers developed through the use of "click" chemistry, constitutes a continuing topical area of research. In this review, we highlight important contributions click chemistry has made in the design of macromolecule-based nanomaterials for therapeutic intervention in mitochondria and lipid droplets.
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Project description:Novel zwitter-ionic nido-carboranyl azide 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was prepared by the reaction of 9-Cl(CH2)3Me2N-nido-7,8-C2B9H11 with NaN3. The solid-state molecular structure of nido-carboranyl azide was determined by single-crystal X-ray diffraction. 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was used for the copper(I)-catalyzed azide-alkyne cycloaddition with phenylacetylene, alkynyl-3β-cholesterol and cobalt/iron bis(dicarbollide) terminal alkynes to form the target 1,2,3-triazoles. The nido-carborane-cholesterol conjugate 9-3β-Chol-O(CH2)C-CH-N3(CH2)3Me2N-nido-7,8-C2B9H11 with charge-compensated group in a linker can be used as a precursor for preparation of liposomes for Boron Neutron Capture Therapy (BNCT). A series of novel zwitter-ionic boron-enriched cluster compounds bearing a 1,2,3-triazol-metallacarborane-carborane conjugated system was synthesized. Prepared conjugates contain a large amount of boron atom in the biomolecule and potentially can be used for BNCT.
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