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Issue 10, 2019
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Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene

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Abstract

Addition of azobenzene-derivative 1 in its E configuration to an aqueous solution containing various guanosine borate esters induces a helical G-quartet based self-organization, stabilized by intercalation of the dye. The process is driven, in a domino fashion, by the initial host–guest interaction between the dye and a specific guanosine borate diester, whose structure can be thus assigned. This inclusion complex templates the formation of G-quartets. The quartets, in turn, pile up to form a supramolecular G-quadruplex structure, in which other G species present in solution are progressively included. The G-quadruplex can be reversibly broken and reformed by photoisomerization of the dye. This hierarchical and photosensitive self-assembly is unprecedented for simple guanosine derivatives.

Graphical abstract: Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene

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Publication details

The article was received on 24 Jan 2019, accepted on 15 Feb 2019 and first published on 20 Feb 2019


Article type: Paper
DOI: 10.1039/C9OB00193J
Org. Biomol. Chem., 2019,17, 2759-2769

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    Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene

    S. Pieraccini, M. Campitiello, F. Carducci, J. T. Davis, P. Mariani and S. Masiero, Org. Biomol. Chem., 2019, 17, 2759
    DOI: 10.1039/C9OB00193J

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