Issue 5, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Nancy H. Campbell,a   Daniel L. Smith,b   Anthony P. Reszka,a   Stephen Neidle*a  and  David O'Hagan*b  

* Corresponding authors

a The School of Pharmacy, University of London, 29–39 Brunswick Square, London, UK
E-mail: stephen.neidle@pharmacy.ac.uk
Fax: +44 207 753 5969
Tel: +44 207 753 5969

b University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, UK
E-mail: do1@st-andrews.ac.uk
Fax: +44 (0)1334 463800
Tel: +44 (0)1334 467171

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.

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

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Article information

DOI
https://doi.org/10.1039/C0OB00886A
Article type
Communication
Submitted
15 Oct 2010
Accepted
01 Dec 2010
First published
10 Jan 2011

Org. Biomol. Chem., 2011,9, 1328-1331

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

N. H. Campbell, D. L. Smith, A. P. Reszka, S. Neidle and D. O'Hagan, Org. Biomol. Chem., 2011, 9, 1328 DOI: 10.1039/C0OB00886A

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