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Issue 27, 2012
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Porphyrin-templated synthetic G-quartet (PorphySQ): a second prototype of G-quartet-based G-quadruplex ligand

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Abstract

Template-assembled synthetic G-quartet (TASQ) has been reported recently as a G-quadruplex ligand interacting with DNA according to an unprecedented, nature-inspired ‘like likes like’ approach, based on the association between two G-quartets, one being native (quadruplex) and the other one artificial (ligand). Herein, a novel TASQ-based ligand is designed, synthesized and its quadruplex-recognition properties are evaluated in vitro: PorphySQ (for porphyrin-templated synthetic G-quartet) displays enhanced quadruplex recognition properties as compared to the very first reported prototype (DOTASQ, for DOTA-templated synthetic G-quartet), since the porphyrin template insures a more stable intramolecular G-quartet fold due to self-stabilizing interactions that may take place intramolecularly between the porphyrin ring and the formed G-quartet.

Graphical abstract: Porphyrin-templated synthetic G-quartet (PorphySQ): a second prototype of G-quartet-based G-quadruplex ligand

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Publication details

The article was received on 22 Mar 2012, accepted on 17 May 2012 and first published on 18 May 2012


Article type: Paper
DOI: 10.1039/C2OB25601K
Citation: Org. Biomol. Chem., 2012,10, 5212-5218
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    Porphyrin-templated synthetic G-quartet (PorphySQ): a second prototype of G-quartet-based G-quadruplex ligand

    H. Xu, L. Stefan, R. Haudecoeur, S. Vuong, P. Richard, F. Denat, J. Barbe, C. P. Gros and D. Monchaud, Org. Biomol. Chem., 2012, 10, 5212
    DOI: 10.1039/C2OB25601K

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