PMID: 9173886Apr 1, 1997Paper

Sequence-selective binding to DNA of bis(amidinophenoxy)alkanes related to propamidine and pentamidine

The Biochemical Journal
C BaillyM J Waring

Abstract

The DNA sequences targeted by a complete homologous series of aromatic diamidines have been determined at single-nucleotide resolution via protection from cutting by the endonucleases DNase I, DNase II and micrococcal nuclease. Propamidine, pentamidine and to a lesser extent hexamidine bind selectively to nucleotide sequences composed of at least four consecutive A-T base pairs. In contrast, the binding to DNA of butamidine, heptamidine, octamidine and nonamidine is poorly sequence-selective. Sequences composed of only three consecutive A-T base pairs do not afford a potential binding site for propamidine or the longer homologues, and none of the drugs tolerate the presence of a G-C base pair within the binding site. Experiments with DNA molecules containing inosine in place of guanosine and 2,6-diaminopurine in place of adenine reveal that the lack of binding of propamidine to GC-containing sites is attributable to an obstructive effect of the exocyclic 2-amino group of guanosine. The present data support the view that the local conformation of the double helix (in particular the width of the minor groove) plays a dominant role in the binding reaction and that the capacity of diamidines to recognize AT-rich sequences selective...Continue Reading

Citations

Feb 20, 2015·Journal of Molecular Recognition : JMR·Linda CerofoliniMarco Fragai
Jan 28, 2017·International Journal of Cosmetic Science·N ParisiM E Lane
Nov 15, 2019·Cell Cycle·Eiman Abu-GaliyunOshrat Levy-Ontman
Jul 12, 2003·Journal of Biomolecular Structure & Dynamics·Kanakendu Choudhury, Michael J Leibowitz
May 12, 2007·Investigational New Drugs·Sibgat A ChoudhuryTerry Y-K Chow
Dec 2, 1999·Pharmacology & Therapeutics·B S ReddyJ W Lown
Mar 10, 2009·Journal of Medicinal Chemistry·Svetlana M BakunovaRichard R Tidwell
Sep 14, 2013·ACS Chemical Biology·Leslie A CoonrodJ Andrew Berglund
Oct 16, 2007·Journal of the American Chemical Society·Manoj MundeW David Wilson

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