NDLI: Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19

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Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19

Content Provider	Royal Society of Chemistry (RSC)
Author	Zeghida, Walid Demeunynck, Martine Dheu-Andries, Marie-Louise Dumy, Pascal Teulade-Fichou, Marie-Paule Jourdan, Muriel Monchaud, David Debray, Julien
Copyright Year	2009
Abstract	The present article reports on the design and the synthesis of a series of mono- and bis-pyrimidinoacridines and their evaluation as a novel family of quadruplex-binders. It is shown that bispyrimidinoacridines represent an interesting compromise between easy synthetic access and efficiency in terms of quadruplex interaction (both affinic and selective), as judged by G4-FID assay and molecular modelling. The present study also highlights that control of the π-stacking interactions taking place between the ligand and the accessible G-tetrad of a quadruplex-DNA is indeed essential for good recognition but not exclusively (key role of direct and water-mediated H-bonds). The introduction of additional amino side chains, valuable in the acridine series, results here in steric perturbations of the ligand/quadruplex recognition and lowers the quadruplex/duplex selectivity.
Starting Page	5219
Ending Page	5228
Page Count	10
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	24
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b912716j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Acridine Molecular modelling Ligand Power Mac G4 Quadruplex videotape
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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