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

Org Biomol Chem. 2019 Mar 6;17(10):2759-2769. doi: 10.1039/c9ob00193j.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Azo Compounds / chemistry*
  • Boric Acids / chemistry*
  • G-Quadruplexes*
  • Guanosine / chemistry*
  • Models, Molecular
  • Photochemical Processes*

Substances

  • Azo Compounds
  • Boric Acids
  • Guanosine
  • azobenzene
  • boric acid