Rhodamine based colorimetric and fluorescent probe for recognition of nucleoside polyphosphates through multi-hydrogen bond

•A novel rhodamine compound was synthesized and confirmed by single crystal.•The compound contains the aminonaphthyridine as hydrogen bonding platform.•The colorimetric and fluorescent responses toward ribonucleotide were achieved.•Fluorescent imaging ribonucleotide in living cells was succeeded.

A novelty rhodamine B based chemosensor containing 2-amino-7-methyl-1, 8-naphthyridine moiety was designed and synthesized for colorimetric and fluorescent response on corresponding nucleoside polyphosphates through multi-hydrogen bond interaction in aqueous solution. The supramolecular recognition between the RBS and Cytidine-5′-diphosphate disodium hydrate (CDP) was investigated carefully: 1H nuclear magnetic resonance confirmed that the formation of multi-hydrogen bonds between naphthyridine moiety and the nucleoside base group could untie the spiro structure of RBS, and the ESI-MS spectra proved the formation of the 1:1 complexation species between RBS and CDP. The strong emission response of the RBS toward CDP and Adenosine-5′-triphosphate disodium trihydrate (ATP) ensures its application in living cells imaging.

Graphical abstractNew rhodamine compound containing 2-amino-7-methyl-1,8-naphthyridine hydrogen bonding trigger was achieved for sensing ribonucleotide polyphosphates and fluorescent imaging in cell.Figure optionsDownload full-size imageDownload as PowerPoint slide