Pyrene and bis-pyrene DNA nucleobase conjugates: excimer and monomer fluorescence of linear and dendronized cytosine and 7-deazaguanine click adducts

Autor(en): Mei, Hui
Ingale, Sachin A.
Seela, Frank
Stichwörter: ARRAY; AZIDE; BRANCHED SIDE-CHAINS; Chemistry; Chemistry, Organic; Click chemistry; DNA; Duplex stability; Fluorescence; HELICAL ARRANGEMENT; INTERSTRAND STACKED PYRENES; NUCLEOSIDE; OLIGONUCLEOTIDES; PROBES; Pyrene; RNA DUPLEX; TERMINAL ALKYNES
Erscheinungsdatum: 2013
Herausgeber: PERGAMON-ELSEVIER SCIENCE LTD
Journal: TETRAHEDRON
Volumen: 69
Ausgabe: 23
Startseite: 4731
Seitenende: 4742
Zusammenfassung: 
Branched and nonbranched nucleoside pyrene click conjugates were prepared from 5-alkynyl-2'-deoxycytidines using pyrene azide in a copper(I)-catalyzed click reaction. Click chemistry was also applied to oligonucleotides to generate pyrene labeled conjugates with linear or dendronized side chains. While dendronized nucleosides carrying two proximal pyrenes show strong excimer fluorescence, single-stranded oligonucleotides containing two pyrene residues attached to a branched chain display only weak or no excimer emission. Contrary, excimer fluorescence was observed for single-stranded oligonucleotides when proximal allcynylated nucleosides were functionalized. Strong excimer fluorescence was also detected for the `dC-dG' base pair modified on both nucleobases with pyrene residues, thus having the fluorescent dye in complementary strands. In general, pyrene fluorescence is strongly quenched by the 7-deazaguanine base (charge transfer), while emission of cytosine linked pyrene is not affected. Pyrene interactions were also demonstrated by T-m increase of DNA duplexes and molecular dynamics simulation. (C) 2013 Elsevier Ltd. All rights reserved.
ISSN: 00404020
DOI: 10.1016/j.tet.2013.03.054

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