Triple helices formed at oligopyrimidine*oligopurine sequences with base pair inversions: effect of a triplex-specific ligand on stability and selectivity
Open Access
- 1 May 1998
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 26 (9) , 2179-2183
- https://doi.org/10.1093/nar/26.9.2179
Abstract
Oligonucleotide-directed triple helix formation is mostly restricted to oligopyrimidine·oligopurine sequences of double helical DNA. An interruption of one or two pyrimidines in the oligopurine target strand leads to a strong triplex destabilisation. We have investigated the effect of nucleotide analogues introduced in the third strand at the site opposite the base pair inversion(s). We show that a 3-nitropyrrole derivative (M) discriminates G·C from C·G, A·T and T·A in the presence of a triplex-specific ligand (a benzo[e]pyridoindole derivative, BePI). N6-methoxy-2,6-diaminopurine (K) binds to an A·T base pair better than a T·A, G·C or C·G base pair. Some discrimination is still observed in the presence of BePI and triplex stability is markedly increased. These findings should help in designing BePI-oligonucleotide conjugates to extend the range of DNA sequences available for triplex formation.Keywords
This publication has 45 references indexed in Scilit:
- Prospects for the Therapeutic Use of Antigene OligonucleotidesCancer Investigation, 1996
- Recognition of Thymine Adenine Base Pairs by Guanine in a Pyrimidine Triple Helix MotifScience, 1989
- NMR studies of DNA (R+)n.cntdot.(Y-)n.cntdot.(Y+)n triple helixes in solution: imino and amino proton markers of T.cntdot.A.cntdot.T and C.cntdot.G.cntdot.C+ base-triple formationBiochemistry, 1989
- Inhibition of DNA Binding Proteins by Oligonucleotide-Directed Triple Helix FormationScience, 1989
- Triple-strand formation in the homopurine:homopyrimidine DNA oligonucleotides d(G-A)4 and d(T-C)4Nature, 1989
- Synthesis and duplex stability of oligonucleotides containing cytosine-thymine analoguesNucleic Acids Research, 1989
- Site-Specific Oligonucleotide Binding Represses Transcription of the Human c- myc Gene in VitroScience, 1988
- Sequence-Specific Cleavage of Double Helical DNA by Triple Helix FormationScience, 1987
- Sequence-specific recognition, photocrosslinking and cleavage of the DNA double helix by an oligo-(α]-thymidylate covalently linked to an azidoproflavine derivativeNucleic Acids Research, 1987
- The tautomeric state of N(4)-hydroxy- and of N(4)-amino-cytosine derivativesJournal of the Chemical Society C: Organic, 1968