Sensitive hydrazine detection and quantification with a fluorescent benzothiadiazole sensor: selective lipid droplets and imaging

• Published in: Organic & biomolecular chemistry 2023-06, Vol.21 (22), p.466-4619
• Main Authors: Santos, Camila O, Passos, Saulo T. A, Sorto, Jenny E. P, Machado, Daniel F. S, Correa, Jose R, da Silva Júnior, Eufrânio N, Rodrigues, Marcelo O, Neto, Brenno A. D
• Format: Article
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d3ob00007a

In this work, we describe the design, synthesis, characterization, photophysical evaluation, DFT calculations, and application of two novel fluorescent benzothiadiazole (BTD) sensors for hydrazine detection and quantification at the cellular and multicellular ( in vivo ) levels. The two probes were fully characterized, and their photophysical properties were evaluated. We tested the designed fluorogenic dye (named BTD-CHO ) as a selective sensor for the rapid, sensitive, and selective detection of hydrazine. When treated with N 2 H 4 , the probe affords a new derivative named BTD-HZN , releasing water as the only byproduct. BTD-CHO exhibited a preference for lipid droplets (LDs) and accumulated inside these organelles. Hydrazine detection in LDs could be carried out by the in situ formation of BTD-HZN inside live cells. We efficiently visualized the lipids of a challenging cellular model, microalgae ( Chlorella sorokiniana ), using these sensors. In vivo experiments indicated rapid and efficient detection of the analyte using C. elegans and zebrafish (Danio rerio) as the multicellular models. A selective hydrazine sensor in solution based on the 2,1,3-benzothiadiazole heterocycle is efficient for in vitro and in vivo analyses. This sensor generates water as the only byproduct, avoiding generation of toxic compounds and interference during in vivo applications.