PMID: 8604348Mar 15, 1996Paper

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

Nucleic Acids Research
J MichelS Moreau

Abstract

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.

References

Mar 1, 1968·The Journal of Organic Chemistry·M G Stout, R K Robins

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Citations

Jan 1, 1996·Biochimie·J J ToulméE Brossalina
Jan 26, 1999·Antisense & Nucleic Acid Drug Development·F GoddeJ J Toulmé
May 25, 2005·Nucleic Acids Research·David A RuslingKeith R Fox
Apr 10, 2012·Bioorganic & Medicinal Chemistry Letters·Bastian HolzbergerAndreas Marx
Feb 26, 2009·Organic Letters·Jiarong LiJianhong Tang
Jan 30, 2004·Journal of the American Chemical Society·Haibo LiuEric T Kool
Nov 20, 2002·Accounts of Chemical Research·Eric T Kool
Nov 1, 2003·Science·Haibo LiuEric T Kool

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