Synthesis and properties of microenvironment-sensitive oligonucleotides containing a small fluorophore, 3-aminobenzonitrile or 3-aminobenzoic acid

Two C-nucleosides bearing small fluorescent groups as a base were synthesized by Heck-type coupling reaction and incorporated into DNA. They exhibited environment-sensitive fluorescence and opposite solvatochromic properties. The modified DNAs containing 3-aminobenzonitrile or 3-aminobenzoic acid retained the duplexes and their fluorescence reflected the microenvironment. (C) 2017 Elsevier Ltd. All rights reserved.