ArticleNucleic acids research2001
The effect of amino groups on the stability of DNA duplexes and triplexes based on purines derived from inosine.
Article in Nucleic acids research, 2001. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 39 citations in OpenAlex.
- Recognition of non-standard base pairs by triplex-forming oligonucleotides containing an expanded genetic alphabet.Nature communications · 2026Article
- Recognition of Non-standard Base Pairs by Triplex-Forming Oligonucleotides Containing an Expanded Genetic Alphabet.Research square · 2026Article
- Alternative DNA structure formation in the mutagenic human c-MYC promoter.Nucleic acids research · 2017Article
- Base pairing involving artificial basesChemical science · 2016Article
- Dynamical treatment of charge transfer through duplex nucleic acids containing modified adenines.ACS nano · 2013Article
- Control of DNA minor groove width and Fis protein binding by the purine 2-amino group.Nucleic acids research · 2013Article
- C2'-pyrene-functionalized triazole-linked DNA: universal DNA/RNA hybridization probes.The Journal of organic chemistry · 2012Article
- Impact of base analogues within a CpG dinucleotide on the binding of DNA by the methyl-binding domain of MeCP2 and methylation by DNMT1.Biochemistry · 2010Article
- Structural properties of g,t-parallel duplexes.Journal of nucleic acids · 2010Article
- Recombination R-triplex: H-bonds contribution to stability as revealed with minor base substitutions for adenine.Nucleic acids research · 2006Article
- Effects of base substitutions in an RNA hairpin from molecular dynamics and free energy simulations.Biophysical journal · 2003Article
- Effects of strand and directional asymmetry on base-base coupling and charge transfer in double-helical DNA.Proceedings of the National Academy of Sciences of the United States of America · 2002Article
- Properties of triple helices formed by parallel-stranded hairpins containing 8-aminopurines.Nucleic acids research · 2002Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The effect of amino groups attached at positions 2 and 8 of the hypoxanthine moiety in the structure, reactivity and stability of DNA duplexes and triplexes is studied by means of quantum mechanical calculations, as well as extended molecular dynamics (MD) and thermodynamic integration (MD/TI) simulations. Theoretical estimates of the change in stability related to 2'-deoxyguanosine (G) --> 2'-deoxyinosine (I) --> 8-amino-2'-deoxyinosine (8AI) mutations have been experimentally verified, after synthesis of the corresponding compounds. An amino group placed at position 2 stabilizes the duplex, as expected, and surprisingly also the triplex. The presence of an amino group at position 8 of the hypoxanthine moiety stabilizes the triplex but, surprisingly, destabilizes the duplex. The subtle electronic redistribution occurring upon the introduction of an amino group on the purine seems to be responsible for this surprising behavior. Interesting 'universal base' properties are found for 8AI.
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