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Org Biomol Chem. 2011 Mar 7;9(5):1328-31. doi: 10.1039/c0ob00886a. Epub 2011 Jan 10.

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

Author information

1
The School of Pharmacy, University of London, 29-39 Brunswick Square, London, UK WC1N 1AX.

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.

PMID:
21221451
DOI:
10.1039/c0ob00886a
[Indexed for MEDLINE]

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