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      Bioconjugation of a Near-Infrared DNA-Stabilized Silver Nanocluster to Peptides and Human Insulin by Copper-Free Click Chemistry

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          Abstract

          DNA-stabilized silver nanoclusters (DNA-AgNCs) are biocompatible emitters with intriguing properties. However, they have not been extensively used for bioimaging applications due to the lack of structural information and hence predictable conjugation strategies. Here, a copper-free click chemistry method for linking a well-characterized DNA-AgNC to molecules of interest is presented. Three different peptides and a small protein, human insulin, were tested as labeling targets. The conjugation to the target compounds was verified by MS, HPLC, and time-resolved anisotropy measurements. Moreover, the spectroscopic properties of DNA-AgNCs were found to be unaffected by the linking reactions. For DNA-AgNC-conjugated human insulin, fluorescence imaging studies were performed on Chinese hamster ovary (CHO) cells overexpressing human insulin receptor B (hIR-B). The specific staining of the CHO cell membranes demonstrates that DNA-AgNCs are great candidates for bioimaging applications, and the proposed linking strategy is easy to implement when the DNA-AgNC structure is known.

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          Most cited references43

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          Principles of Fluorescence Spectroscopy

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            A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems.

            Selective chemical reactions that are orthogonal to the diverse functionality of biological systems have become important tools in the field of chemical biology. Two notable examples are the Staudinger ligation of azides and phosphines and the Cu(I)-catalyzed [3 + 2] cycloaddition of azides and alkynes ("click chemistry"). The Staudinger ligation has sufficient biocompatibility for performance in living animals but suffers from phosphine oxidation and synthetic challenges. Click chemistry obviates the requirement of phosphines, but the Cu(I) catalyst is toxic to cells, thereby precluding in vivo applications. Here we present a strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst. The utility of the reaction was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity.
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              DNA-templated Ag nanocluster formation.

              The high affinity of Ag+ for DNA bases has enabled creation of short oligonucleotide-encapsulated Ag nanoclusters without formation of large nanoparticles. Time-dependent formation of cluster sizes ranging from Ag1 to Ag4/oligonucleotide were observed with strong, characteristic electronic transitions between 400 and 600 nm. The slow nanocluster formation kinetics enables observation of specific aqueous nanocluster absorptions that evolve over a period of 12 h. Induced circular dichroism bands confirm that the nanoclusters are associated with the chiral ss-DNA template. Fluorescence, absorption, mass, and NMR spectra all indicate that multiple species are present, but that their creation is both nucleotide- and time-dependent.
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                Author and article information

                Journal
                J Am Chem Soc
                J Am Chem Soc
                ja
                jacsat
                Journal of the American Chemical Society
                American Chemical Society
                0002-7863
                1520-5126
                13 July 2023
                02 August 2023
                13 July 2024
                : 145
                : 30
                : 16771-16777
                Affiliations
                []Department of Chemistry, University of Copenhagen , Universitetsparken 5, 2100 Copenhagen, Denmark
                []Department of Chemistry, University of Copenhagen , Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark
                [§ ]Department of Clinical Physiology and Nuclear Medicine, Copenhagen University Hospital − Rigshospitalet , Blegdamsvej 9, 2100 Copenhagen, Denmark
                []Cluster for Molecular Imaging, Department of Biomedical Sciences, University of Copenhagen , Blegdamsvej 3B, 2200 Copenhagen, Denmark
                []Department of Forensic Medicine, University of Copenhagen , Frederik V’s Vej 11, 2100 Copenhagen, Denmark
                [# ]Department of Physics, Chemistry and Pharmacy, University of Southern Denmark , Campusvej 55, 5230 Odense M, Denmark
                Author notes
                Author information
                https://orcid.org/0000-0002-7403-3118
                https://orcid.org/0000-0001-7623-5453
                https://orcid.org/0000-0002-3048-5438
                https://orcid.org/0000-0001-8187-6474
                https://orcid.org/0000-0002-2706-5547
                https://orcid.org/0000-0002-9521-8285
                https://orcid.org/0000-0003-3525-5452
                https://orcid.org/0000-0001-5435-2181
                Article
                10.1021/jacs.3c04768
                10402711
                37441791
                26253a64-cee8-4713-85f9-9f7547df0908
                © 2023 The Authors. Published by American Chemical Society

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                : 08 May 2023
                Funding
                Funded by: Villum Fonden, doi 10.13039/100008398;
                Award ID: VKR023115
                Funded by: Danmarks Frie Forskningsfond, doi 10.13039/501100004836;
                Award ID: 0136-00024B
                Funded by: Novo Nordisk, doi 10.13039/501100004191;
                Award ID: NNF16OC0021948
                Funded by: Villum Fonden, doi 10.13039/100008398;
                Award ID: VKR18333
                Categories
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                Custom metadata
                ja3c04768
                ja3c04768

                Chemistry
                Chemistry

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