A fluorescent 3,7-bis-(naphthalen-1-ylethynylated)-2 '-deoxyadenosine analogue reports thymidine in complementary DNA by a large emission Stokes shift

作者：Yanagi Masaki; Suzuki Azusa; Hudson Robert H E; Saito Yoshio^*

来源：Organic and Biomolecular Chemistry, 2018, 16(9): 1496-1507.

DOI：10.1039/c8ob00062j

The new environmentally responsive fluorescent nucleosides, 3,7-bis-(naphthalen-1-ylethynyl)-8-aza-3,7-dideaza-2'-deoxyadenosine ((3n7nz)A, 1) and 7-(naphthalen-1-ylethynyl)-8-aza-3,7-dideaza-2'-deoxyadenosine ((37nz)A, 2), have been synthesized. Both (3n7nz)A (1) and (37nz)A (2) possess large pi-conjugated systems which extend into both the minor and major grooves or the major groove alone, respectively. The nucleosides exhibited large solvatochromic shifts ((3n7nz)A: Delta lambda = 45 nm, (37nz)A: Delta lambda = 78 nm) and were examined for their ability to fluorimetrically report hybridization events. When incorporated into ODN probes, the bis-substituted (3n7nz)A (1) selectively recognized thymidine on target strands which was reported by a distinct change in its emission wavelength in the long wavelength region, whereas (37nz)A (2) showed a preference for pairing to cytidine and a smaller wavelength shift. Thus, (3n7nz)A (1) has the potential for use as a fluorescent probe for structural studies of DNAs/RNAs including the detection of single-base alterations in target DNA sequences.

• 出版日期2018-3-7