Azobenzene C-Nucleosides for Photocontrolled Hybridization of DNA at Room Temperature.
Herein, we report the reversible light-regulated destabilization of DNA duplexes by using azobenzene C-nucleoside photoswitches. The incorporation of two different azobenzene residues into DNA and their photoswitching properties are described. These new residues demonstrate a photoinduced destabilization effect comparable to the widely applied D-threoninol-linked azobenzene switch, which is currently the benchmark. The photoswitches presented herein show excellent photoswitching efficiencies in DNA duplexes - even at room temperature - which are superior to commonly used azobenzene-based nucleic acid photoswitches. In addition, these photoswitching residues exhibit high thermal stability and excellent fatigue resistance, thus rendering them one of the most efficient candidates for the regulation of duplex stability with light.
Institute for Organic Chemistry and Chemical Biology, Goethe University Frankfurt am Main, Max-von-Laue-Strasse 9, 60438 Frankfurt/Main (Germany), Fax: (+49) 69-798-763-42505.
Thomas
T
Goldau
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku Nagoya 464-8603 (Japan), Fax: (+81) 52-789-2528.|Venture Business Laboratory (VBL), Nagoya University, Furo-cho, Chikusa-ku Nagoya 464-8603 (Japan).
Keiji
K
Murayama
Department for Biomolecular Mechanisms, Max-Planck-Institute for Medical Research, Jahnstrasse 29, 69120 Heidelberg (Germany).
Clara
C
Brieke
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku Nagoya 464-8603 (Japan), Fax: (+81) 52-789-2528. asanuma@nubio.nagoya-u.ac.jp.
Hiroyuki
H
Asanuma
Institute for Organic Chemistry and Chemical Biology, Goethe University Frankfurt am Main, Max-von-Laue-Strasse 9, 60438 Frankfurt/Main (Germany), Fax: (+49) 69-798-763-42505. heckel@uni-frankfurt.de.
Alexander
A
Heckel
D000605:Amino Alcohols / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D020029:Base Pairing; D002072:Butylene Glycols / Q000737:chemistry*; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D006824:Hybridization, Genetic; D008027:Light; D009705:Nucleosides / Q000737:chemistry* / Q000378:metabolism; D010777:Photochemistry; D013696:Temperature
D000605:Amino Alcohols; D001391:Azo Compounds; D002072:Butylene Glycols; D009705:Nucleosides; C532652:threoninol; D004247:DNA; C009850:azobenzene
DNA; azobenzene; nucleic acids; photochemistry; photoswitches