Visible-light photocontrol of (E)/(Z) isomerization of the 4-(dimethylamino)azobenzene pseudo-nucleotide unit incorporated into an oligonucleotide and DNA hybridization in aqueous media

Takashi Kamei, Haruhisa Akiyama, Hisayuki Morii, Nobuyuki Tamaoki, Taro Q.P. Uyeda

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

We demonstrate significant photoresponsivity in aqueous media to visible light of pseudo-oligonucleotides possessing 4-(dimethylamino)azobenzene (4-DMAzo) side chains. The spectrum of the 4-DMAzo moiety during 436 nm light irradiation at pH >9 was clearly different from that of the all (E)-form, indicating the presence of the (Z)-form. Thermal (Z)-to-(E) recovery isomerization was faster at pH 9 (kZ-E = ∼101 s-1) than at pH 11; however, addition of 50% ethanol significantly slowed the thermal recovery isomerization at pH 9 (kZ-E = ∼2 s-1) and increased the magnitude of the spectral changes. Significant photoregulation of DNA hybridization by visible light was demonstrated under this condition.

Original languageEnglish
Pages (from-to)12-28
Number of pages17
JournalNucleosides, Nucleotides and Nucleic Acids
Volume28
Issue number1
DOIs
Publication statusPublished - 2009 Jan
Externally publishedYes

Keywords

  • (E)/(Z) isomerization
  • 4-(dimethylamino)azobenzene
  • Aqueous media
  • Photoregulating DNA hybridization
  • Photoresponsive oligonucleotides
  • Visible light

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

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