Ethynyl-linked (pyreno)pyrrole-naphthyridine and aniline-naphthyridine molecules as fluorescent sensors of guanine via multiple hydrogen bondings.

New fluorescent molecular sensors for 9-alkylguanines were constructed by conjugation of 2-acetamido-1,8-naphthyridine with N-Boc-pyrrole, N-Boc-pyreno[2,1-b]pyrrole, or acetanilide moieties via an ethynyl bridge. In combination with the triple hydrogen-bonding motif of 2-acetamidonaphthyridine toward alkylguanine, an additional binding site was provided by the substituent properly located on the pyrrole or aniline ring to enhance the affinity of these receptor molecules. Besides the ESI-MS analyses, the binding events were readily monitored by the absorption and fluorescence changes in the visible region.