Nitrogen-boron eight-ring rigid cis/trans BODIPY-pyrimidine isomers for in vivo and in vitro fluorescence target recognition and evaluation of inhibitory activity

Imaging technology based on fluorescent dyes is of great significance in tumor diagnosis. The fluorescent probes with antitumor effect at the same time can further expand the application of the probes in tumor. Inspired by the rigid cyclic structure of heme, the isomers cis/trans-BP with intramolecular eight-membered ring structure were obtained by innovatively combining two groups in unrelated fields, BODIPY and pyrimidine, together through substitution reaction and then by simple column chromatography. cis/trans-BP has stable spectral properties and can generate obvious fluorescence signals in organisms. The transmission electron microscope visually showed the uptake and distribution of the compounds by HeLa, and the subsequent apoptosis. The antitumor mechanisms of the compounds were further studied by flow cytometry. The results showed that trans-BP retained the function of fluorescent probe and simultaneously possessed antitumor activity. [Display omitted] •The target compound has both anticancer activity and fluorescent probe capability.•The compounds with nitrogen-boron rigid eight-membered ring structure in the molecule were synthesized.•Conformational isomers were obtained by column chromatography.•Two different domain groups of pyrimidine and BODIPY are combined on the same compound.