Synthesis, Structure, Properties, and Bioimaging of a Fluorescent Nitrogen-Linked Bisbenzothiadiazole

• Published in: Journal of organic chemistry 2016-04, Vol.81 (7), p.2958-2965
• Main Authors: Mota, Alberto A. R, Corrêa, José R, Carvalho, Pedro H. P. R, de Sousa, Núbia M. P, de Oliveira, Heibbe C. B, Gatto, Claudia C, da Silva Filho, Demétrio A, de Oliveira, Aline L, Neto, Brenno A. D
• Format: Article
• Language: English
• Subjects: Breast Neoplasms - chemistry; Crystallography, X-Ray; Fluorescent Dyes - chemistry; Humans; MCF-7 Cells; Molecular Structure; Nitrogen - chemistry; Quantum Theory; Thiadiazoles - chemical synthesis; Thiadiazoles - chemistry
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.6b00245

This paper describes the synthesis, structure, photophysical properties, and bioimaging application of a novel 2,1,3-benzothiadiazole (BTD)-based rationally designed fluorophore. The capability of undergoing efficient stabilizing processes from the excited state allowed the novel BTD derivative to be used as a stable probe for bioimaging applications. No notable photobleaching effect or degradation could be observed during the experimental time period. Before the synthesis, the molecular architecture of the novel BTD derivative was evaluated by means of DFT calculations to validate the chosen design. Single-crystal X-ray analysis revealed the nearly flat characteristics of the structure in a syn conformation. The fluorophore was successfully tested as a live-cell-imaging probe and efficiently stained MCF-7 breast cancer cell lineages.