title: Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidines attached to acridine ligands affects their interactions with G-quadruplex DNA.
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.
authors.affiliation: The School of Pharmacy, University of London, 29-39 Brunswick Square, London, UK WC1N 1AX.
authors.forename: Nancy H
authors.initials: NH
authors.lastname: Campbell
authors.forename: Daniel L
authors.initials: DL
authors.lastname: Smith
authors.forename: Anthony P
authors.initials: AP
authors.lastname: Reszka
authors.forename: Stephen
authors.initials: S
authors.lastname: Neidle
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
mesh_terms: D000166:Acridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005461:Fluorine / Q000737:chemistry*; D054856:G-Quadruplexes; D054879:Halogenation; D008024:Ligands; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: C471713:3,6-bis-(3-pyrrolidinopropionamide)acridine; D000166:Acridines; D008024:Ligands; D011759:Pyrrolidines; D005461:Fluorine