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Metal-mediated base pairs involving artificial nucleobases have emerged as a promising means for the site-specific functionalization of nucleic acids with metal ions. In this context, a GNA-appended (GNA: glycol nucleic acid) nucleoside analogue containing the artificial nucleobase 1 H -imidazo[4,5- f ][1,10]phenanthroline ( P ) has already been applied successfully in a variety of homo- and heteroleptic metal-mediated base pairs, mainly involving Ag(I) ions. Herein, we report a thorough investigation of the Hg(II)-binding properties of  P  when incorporated into antiparallel-stranded DNA duplexes. The artificial nucleobase  P  is able to form Hg(II)-mediated homoleptic base pairs of the type  P –Hg(II)– P  with a [2 + 2] coordination environment. In addition, the heteroleptic  P –Hg(II)– T  pair was investigated. The addition of a stoichiometric amount of Hg(II) to a duplex comprising either a  P : P  pair or a  P : T  pair stabilizes the DNA duplex by 4.3 °C and 14.5 °C, respectively. The  P –Hg(II)– T  base pair, hence, represents the most stabilizing non-organometallic Hg(II)-mediated base pair reported to date. The formation of the Hg(II)-mediated base pairs was investigated by means of temperature-dependent UV spectroscopy and CD spectroscopy.    Graphic abstractElectronic supplementary material  The online version of this article (10.1007/s00775-020-01788-x) contains supplementary material, which is available to authorized users.

Stable Hg(II)-mediated base pairs with a phenanthroline-derived nucleobase surrogate in antiparallel-stranded DNA