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Nucleosides Nucleotides Nucleic Acids. 2009;28(1):12-28. doi: 10.1080/15257770802581641.

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.

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Research Institute for Cell Engineering, National Institute of Advanced Industrial Science and Technology (AIST), Ibaraki, Japan.


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 (k(Z)(-E) = approximately 10(1) s(-1)) than at pH 11; however, addition of 50% ethanol significantly slowed the thermal recovery isomerization at pH 9 (k(Z)(-E) = approximately 2 s(-1)) and increased the magnitude of the spectral changes. Significant photoregulation of DNA hybridization by visible light was demonstrated under this condition.

[Indexed for MEDLINE]

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