Visible-light photoresponsivity of a 4-(dimethylamino)azobenzene unit incorporated into single-stranded DNA: Demonstration of a large spectral change accompanying isomerization in DMSO and detection of rapid (Z)-to-(E) isomerization in aqueous solution

Takashi Kamei, Masabumi Kudo, Haruhisa Akiyama, Momoyo Wada, Jun'ichi Nagasawa, Masahiro Funahashi, Nobuyuki Tamaoki, Taro Q.P. Uyeda

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

We demonstrate significant visible-light photoresponsivity in a synthesized oligonucleotide containing a built-in pseudonucleotide possessing a 4-(dimethylarnino)azobenzene (4-DMAzo) side chain. In dry DMSO as solvent, two clearly distinguishable spectra corresponding to the (E) and (Z) forms of the 4-DMAzo moiety tethered to the oligonucleotide were recorded with a conventional spectrophotometer before and after irradiation with 420 nm wavelength light, which induced (E)-to-(Z) isomerization. In addition, (Z)-to-(E) isomerization was accelerated by irradiation with either visible (λ = 550 nm) or UV (λ = 350 nm) light, demonstrating reversible photoresponsivity of the pseudo-ohgonucleotide. In aqueous solutions the (Z)-to-(E) thermal isomerization of the photoresponsive pseudo-ohgonucleotide was very rapid and was only detectable by laser flash photolysis.

Original languageEnglish
Pages (from-to)1846-1853
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number11
DOIs
Publication statusPublished - 2007
Externally publishedYes

Keywords

  • (E)/(Z) isomerization
  • 4-(Dimethylamino)azobenzene
  • DNA nano-devices
  • Oligonucleotides
  • Photoresponsivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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