Polyaza crown ethers as non-nucleosidic building blocks in DNA conjugates: synthesis and remarkable stabilization of dsDNA

Chembiochem : a European Journal of Chemical Biology
Katja Rohr, Stefan Vogel

Abstract

The synthesis of amphiphilic polyaza crown ether monomers X (benzyl-substituted), Y (palmityl-substituted) and Z (cholesteryl-substituted) and their incorporation into oligonucleotides are described. Their effects on thermal duplex stability were investigated by UV melting curve analysis in different alkaline metal buffer solutions. Thermal-denaturation experiments showed remarkable stabilization of dsDNA by polyaza crown ether monomers when incorporated in opposite positions. The series of polyaza crown ether monomers (X, Y and Z) with different overall lipophilicities showed a trend of increased stability of the corresponding dsDNA with increasing lipophilicity of the polyaza crown ether monomer. Multiple incorporations of benzyl-substituted polyaza crown ether monomer X as dangling ends on both sides of dsDNA resulted in strongly increased stability of the corresponding duplex.

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Citations

Jul 28, 2013·Bioconjugate Chemistry·Ulla Jakobsen, Stefan Vogel
Dec 11, 2007·Nucleosides, Nucleotides & Nucleic Acids·Ulla JakobsenStefan Vogel
Dec 11, 2007·Nucleosides, Nucleotides & Nucleic Acids·Ulla JakobsenStefan Vogel
Aug 23, 2011·Chemical Society Reviews·Minseok Kwak, Andreas Herrmann
Mar 24, 2012·The Journal of Organic Chemistry·Andreas S Madsen, Jesper Wengel
Feb 11, 2010·Bioorganic Chemistry·Mieke A CatryAnnemieke Madder
Dec 20, 2014·Photochemistry and Photobiology·Daria V BerdnikovaHeiko Ihmels
Jun 30, 2016·Organic & Biomolecular Chemistry·Ulla Jakobsen, Stefan Vogel
Jul 23, 2008·Journal of the American Chemical Society·Ulla JakobsenStefan Vogel
Feb 12, 2010·Bioconjugate Chemistry·Ching-Hui HuangJanet R Morrow

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