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Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidines attached to acridine ligands affects their interactions with G-quadruplex DNA

DOI: 10.1039/c0ob00886a DOI Help
PMID: 21221451 PMID Help

Authors: Nancy Campbell (University of London) , Daniel L. Smith (University of St Andrews) , Anthony P. Reszka (University of London) , Stephen Neidle (University of London) , David O'hagan (University of St Andrews)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Organic & Biomolecular Chemistry , VOL 9 (5) , PAGES 3300-3315

State: Published (Approved)
Published: January 2011

Abstract: Comparative X-ray structure studies reveal that C–F bond incorporation into the peripheral pyrrolidine moieties of the G-quadruplex DNA binding ligand BSU6039 leads to a distinct pyrrolidine ring conformation, relative to the non-fluorinated analogue, and with a different binding mode involving reversal of the pyrrolidinium N+–H orientation.

Journal Keywords: Crystallography; X-Ray; Fluorine; G-Quadruplexes; Halogenation; Ligands; Pyrrolidines

Subject Areas: Biology and Bio-materials

Instruments: I04-Macromolecular Crystallography

Added On: 25/09/2015 10:07

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