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

Organic & Biomolecular Chemistry
Silvia PieracciniStefano Masiero

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.

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Citations

Oct 1, 2020·International Journal of Molecular Sciences·Concetta ImperatoreMichela Varra
May 22, 2020·Chemical Communications : Chem Comm·Songjun XiaoJeffery T Davis
Feb 14, 2021·Materials Science & Engineering. C, Materials for Biological Applications·Juliana S YonedaRosangela Itri
Mar 14, 2020·Journal of the American Chemical Society·Elisabeth WeyandtE W Meijer
Jan 15, 2020·The Journal of Organic Chemistry·Jiakun BaiRenzhong Qiao

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Methods Mentioned

BETA
NMR
irradiating
X-ray

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