Dual Crosslinking Photo-Switches for Orthogonal Photo-Control of Hybridization Between Serinol Nucleic Acid and RNA.

Wavelength-selective photo-regulation by multiple chromophores responding to different wavelengths can expand the variation of photo-manipulating systems. Herein, we report the orthogonal photo-regulation of duplex formation between serinol nucleic acid (SNA) and RNA using light-induced crosslinking reactions mediated by a new photo-reactive nucleobase 8-naphthylvinyladenine (NV A) and previously described 8-pyrenylvinyladenine (PV A). An intrastrand crosslink was induced in an SNA strand containing two adjacent NV A residues by irradiation with 340-405 nm light; the crosslink was reversed by irradiation with ≤300 nm light. In an SNA strand with adjacent NV A and PV A residues, an intrastrand crosslink resulted from irradiation with 405-465 nm light that was reversed by irradiation with ≤340 nm light. Intrastrand photo-crosslinking caused severe destabilization of an SNA/RNA duplex, resulting in dissociation to single strands. Cycloreversion resulted in duplex formation. With these NV A/NV A and NV A/PV A photo-switches, four hybridization states of two SNA/RNA duplexes could be orthogonally photo-controlled by irradiation with a suitable wavelength of light.