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

doi:10.1039/c0ob00886a

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 journal › Article › peer-review

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 language	English
Pages (from-to)	1328-1331
Number of pages	4
Journal	Organic & Biomolecular Chemistry
Volume	9
Issue number	5
DOIs	https://doi.org/10.1039/c0ob00886a
Publication status	Published - 2011

Keywords

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

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title = "Fluorine in medicinal chemistry: beta-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.",

keywords = "SEQUENCE, SMALL-MOLECULE, RNA G-QUADRUPLEX, PROMOTER, NRAS PROTOONCOGENE, RECOGNITION, TRANSLATION, HUMAN TELOMERE, K+ SOLUTION, INHIBITION",

author = "Campbell, {Nancy H.} and Smith, {Daniel L.} and Reszka, {Anthony P.} and Stephen Neidle and David O'Hagan",

year = "2011",

doi = "10.1039/c0ob00886a",

language = "English",

volume = "9",

pages = "1328--1331",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "5",

}

TY - JOUR

T1 - Fluorine in medicinal chemistry: beta-fluorination of peripheral pyrrolidines attached to acridine ligands affects their interactions with G-quadruplex DNA

AU - Campbell, Nancy H.

AU - Smith, Daniel L.

AU - Reszka, Anthony P.

AU - Neidle, Stephen

AU - O'Hagan, David

PY - 2011

Y1 - 2011

N2 - 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.

AB - 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.

KW - SEQUENCE

KW - SMALL-MOLECULE

KW - RNA G-QUADRUPLEX

KW - PROMOTER

KW - NRAS PROTOONCOGENE

KW - RECOGNITION

KW - TRANSLATION

KW - HUMAN TELOMERE

KW - K+ SOLUTION

KW - INHIBITION

U2 - 10.1039/c0ob00886a

DO - 10.1039/c0ob00886a

M3 - Article

SN - 1477-0520

VL - 9

SP - 1328

EP - 1331

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 5

ER -

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

Abstract

Keywords

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