The fluorescently responsive 3-(naphthalen-1-ylethynyl)-3-deaza-2′-deoxyguanosine discriminates cytidine via the DNA minor groove

Abstract

A new environmentally responsive fluorescent nucleoside, 3-(naphthalen-1-ylethynyl)-3-deaza-2′-deoxyguanosine (^3nzG), has been synthesized. The nucleoside, ^3nzG, exhibited solvatochromic properties and when introduced into ODN probes it was able to recognize 2′-deoxycytidine in target strands by a distinct change in its emission wavelength through probing microenvironmental changes in the DNA minor groove. Thus, ^3nzG has the potential for use as a fluorescent probe molecule for micro-structural studies of nucleic acids including the detection of single-base alterations in target DNA sequences.