Hybridization-dependent fluorescence of oligodeoxynucleotides incorporating new pyrene-modified adenosine residues

Bioorganic & Medicinal Chemistry
Kohji SeioMitsuo Sekine

Abstract

We report the synthesis and properties of oligonucleotides incorporating N(6)-[N-(pyren-1-ylmethyl)carbamoyl]-deoxyadenosine (dA(pymcm)). We designed the ODN which incorporated two consecutive dA(pymcm) residues. It was revealed that on hybridization with the target DNA and RNA oligomers, the fluorescence spectra of ODNs having two consecutive dA(pymcm) molecules near the 5'-terminal position can change from the pyrene monomer emission to the excimer, depending on the chain length of the target DNA and RNA. These results indicated that dA(pymcm)-modified ODNs can be used as interesting hybridization sensors that are sensitive to the size of the target strand.

References

Nov 30, 2005·Nucleic Acids Research·Caifu ChenKarl J Guegler
Dec 20, 2005·Nucleic Acids Research·Shu-ichi NakanoNaoki Sugimoto
Jun 7, 2007·Chembiochem : a European Journal of Chemical Biology·T Santhosh KumarPatrick J Hrdlicka

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Citations

Mar 9, 2010·Chemical Reviews·Renatus W SinkeldamYitzhak Tor
May 7, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Florian Menacher, Hans-Achim Wagenknecht
Jan 17, 2016·Chemistry : a European Journal·Sina BerndlHans-Achim Wagenknecht
Feb 21, 2009·Angewandte Chemie·Sina Berndl, Hans-Achim Wagenknecht
Feb 9, 2012·Chembiochem : a European Journal of Chemical Biology·Kasper K KarlsenJesper Wengel

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