Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 1, 2009
Previous Article Next Article

Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates

Author affiliations

Abstract

We have explored a series of trisubstituted acridine-peptide conjugates for their ability to recognize and discriminate between DNA quadruplexes derived from the human telomere, and the c-kit and N-ras proto-oncogenes. Quadruplex affinity was measured as the peptide sequences were varied, together with their substitution position on the acridine, and the identity of the C-terminus (acid or amide). Surface plasmon resonance measurements revealed that all compounds bound to the human telomeric quadruplex with sub-micromolar affinity. Docking calculations from molecular modelling studies were used to model the effects of substituent orientation and peptide sequence. Modelling and experiment were in agreement that placement of the peptide over the face of the acridine is detrimental to binding affinity. The highest degrees of selectivity were observed towards the N-ras quadruplex by compounds capable of forming simultaneous contacts with their acridine and peptide moieties. The ligands that bound best displayed quadruplex affinities in the 1–5 nM range and at least 10-fold discrimination between the quadruplexes studied.

Graphical abstract: Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Aug 2008, accepted on 22 Sep 2008 and first published on 30 Oct 2008


Article type: Paper
DOI: 10.1039/B814682A
Citation: Org. Biomol. Chem., 2009,7, 76-84

  •   Request permissions

    Recognition and discrimination of DNA quadruplexes by acridine-peptide conjugates

    J. E. Redman, J. M. Granadino-Roldán, J. A. Schouten, S. Ladame, A. P. Reszka, S. Neidle and S. Balasubramanian, Org. Biomol. Chem., 2009, 7, 76
    DOI: 10.1039/B814682A

Search articles by author

Spotlight

Advertisements