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Nucleic Acids Research, Vol 24, Issue 6 1127-1135, Copyright © 1996 by Oxford University Press

ARTICLES

Quinazoline-2,4(1H,3H)-dione as a substitute for thymine in triple- helix forming oligonucleotides: a reassessment

J Michel, JJ Toulme, J Vercauteren and S Moreau
INSERM U-386, Laboratoire de Biophysique Moleculaire, Universite de Bordeaux, France.

A major limitation in triple-helix formation arises from the weak energy of interaction between the third strand and the double-stranded target. We tried to increase the stacking interaction contribution within the third strand by extending the aromatic domain of thymine. We report here the use of 2,4-quinazolinedione as a substitute for thymine in the canonical TA*T triplet. The synthesis and the characterization of the quinazoline beta nucleoside Q and of its phosphoramidite derivative is described. Triple-helix- forming oligonucleotides incorporating Q have been prepared and their ability to form triplexes has been evaluated by UV-monitored thermal denaturation measurements. The introduction of one or multiple Q residues, either contiguous or remote from each other, slightly destabilized triple-stranded structures, whatever the nucleic acid base composition (pyrimidine or GT) of the third strand.
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