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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

62 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1328-1331
Number of pages4
JournalOrganic & Biomolecular Chemistry
Volume9
Issue number5
DOIs
Publication statusPublished - 2011

Keywords

  • SEQUENCE
  • SMALL-MOLECULE
  • RNA G-QUADRUPLEX
  • PROMOTER
  • NRAS PROTOONCOGENE
  • RECOGNITION
  • TRANSLATION
  • HUMAN TELOMERE
  • K+ SOLUTION
  • INHIBITION

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