PMID: 11916408Mar 28, 2002Paper

Substituted 1,8-naphthyridin-2(1H)-ones are superior to thymine in the recognition of adenine in duplex as well as triplex structures

Journal of the American Chemical Society
Anne B EldrupP E Nielsen

Abstract

The synthesis and evaluation of a series of novel nucleobases based on substituted 1,8-naphthyridin-2(1H)-ones are reported. The nucleobases were designed to meet the requirements for incorporation into peptide nucleic acids (PNAs) and were evaluated as part of PNA duplex and triplex nucleic acid recognition systems. Of the various nucleobases tested, only the 7-chloro-1,8-naphthyridin-2(1H)-one (7-Cl-bT) nucleobase led to consistently increased affinity in all recognition systems, duplex (Watson-Crick) as well as triplex (Hoogsteen). For multiply modified systems, the increase in thermal stability per modification was dependent on the sequence context, ranging from 2.0 degrees C (in separate positions) to 3.5 degrees C (in adjacent positions) in PNA-DNA duplexes and from 1.2 degrees C (in separate positions) to 3.2 degrees C (in adjacent positions) in PNA-RNA duplexes. Singly mismatched oligonucleotide targets were employed to demonstrate uncompromised sequence discrimination. When part of multiply modified triplex (Hoogsteen) recognition systems, the 7-Cl-bT unit gave rise to increases in the thermal stability ranging from 2.7 to 3.5 degrees C when incorporated into separated and adjacent positions, respectively. Our results ...Continue Reading

References

May 1, 1996·Nature Structural Biology·M Eriksson, P E Nielsen
Jan 1, 1996·Bioorganic & Medicinal Chemistry·B Hyrup, P E Nielsen
Dec 1, 1996·Quarterly Reviews of Biophysics·M Eriksson, P E Nielsen
Aug 1, 1997·Antisense & Nucleic Acid Drug Development·L Good, P E Nielsen
Oct 16, 1999·Proceedings of the National Academy of Sciences of the United States of America·J LohseP E Nielsen

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Citations

Oct 10, 2002·Bioorganic & Medicinal Chemistry Letters·Caspar ChristensenPeter E Nielsen
Jul 11, 2003·Bioorganic & Medicinal Chemistry Letters·Andriy MokhirRoland Kraemer
Sep 25, 2010·PloS One·Garima Khandelwal, Jayaram Bhyravabhotla
Aug 21, 2007·Expert Opinion on Biological Therapy·Soccorsa PensatoAlessandra Romanelli
Jul 10, 2012·Artificial DNA, PNA & XNA·Alex ManicardiRoberto Corradini
Jan 21, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Hui-Miao ZhangShao-Ming Chi
Feb 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Monika WojciechowskaJoanna Trylska
Mar 8, 2016·Chemistry : a European Journal·Alexander SchadeStefan Spange
Dec 6, 2002·Organic Letters·Kallanthottathil G RajeevMuthiah Manoharan
Feb 26, 2005·The Journal of Organic Chemistry·Stephen P KeenGavin W Stewart
Jun 25, 2021·Journal of the American Chemical Society·Qi PanWangqing Kong
Nov 18, 2010·The Journal of Physical Chemistry. a·Borys OśmiałowskiReijo Kauppinen
May 8, 2015·Accounts of Chemical Research·Sofia Barluenga, Nicolas Winssinger
Aug 10, 2021·Beilstein Journal of Organic Chemistry·Nikita BrodyaginEriks Rozners
Sep 18, 2003·Bioconjugate Chemistry·Andriy A Mokhir, Roland Kraemer

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