Anthraquinones as Artificial DNA Building Blocks

Abstract

Synthesis and properties of oligodeoxynucleotides containing anthraquinone-derived building blocks with flexible linkers are described. Starting from the 1,4-, 1,5-, 1,8-and 2,6-dihydroxyanthraquinone isomers, the corresponding phosphoramidites were prepared and incorporated into oligonucleotides. The site of linker attachment was found to be of critical importance for hybrid stability. Whereas the 2,6-iso-

High definition polyphosphoesters: between nucleic acids and plastics

“…4g). 90 S he DNA bases was analysed and confirmed crystallographically. 91 Among the various chromophore inserted, those which showed distinct photophysical properties arising from their position in the DNA duplex were of the greatest interest.…”

Nucleotides and Nucleic Acids; Oligo- and Polynucleotides

“…[329][330][331] Anthraquinone has been used as an artificial base in duplex DNA, and it was found that the site of linker attachment was critical for duplex stability with only the 2,6-isomer (77) stabilising duplex DNA. 332 The imidazole nucleoside (78) has been introduced into triplexforming oligonucleotides, where it forms a stable partner with a CG base pair. 333 The LNA analogues (27) and (28) also have use in TFOs, where they can stabilise a triplex even at a T:A interruption site.…”

Preparation of supramolecular chromophoric assemblies using a DNA duplex

“…They prepared clusters of phenanthrene, 54,55 pyrene, 56-59 perylenediimide 60,61 and anthraquinone. 62 Recently, they reported that oligopyrenotides, in which pyrene moieties are tethered without natural nucleobases, could form their hybrids in aqueous solution. 63 Wagenknecht and co-workers utilized (S)-1-aminopropane-2,3-diol as a linker and prepared clusters of various kinds of fluorophores.…”