Plasma membrane imaging with a fluorescent benzothiadiazole derivative

• Published in: Beilstein journal of organic chemistry Vol. 15; no. 1; pp. 2644 - 2654
• Main Authors: Carvalho, Pedro H P R, Correa, Jose R, Paiva, Karen L R, Machado, Daniel F S, Scholten, Jackson D, Neto, Brenno A D
• Format: Journal Article
• Language: English
• Published: Frankfurt am Main Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 06-11-2019; Beilstein-Institut
• Subjects: Bands; benzothiadiazole; bioprobe; cell imaging; Cell lines; Chemistry; Design; Experiments; fluorescence; Letter; Membranes; mitochondria; molecular architecture; plasma membrane; Signal transduction
• ISSN: 1860-5397; 2195-951X; 1860-5397
• DOI: 10.3762/bjoc.15.257

This work describes a novel fluorescent 2,1,3-benzothiadiazole derivative designed to act as a water-soluble and selective bioprobe for plasma membrane imaging. The new compound was efficiently synthesized in a two-step procedure with good yields. The photophysical properties were evaluated and the dye proved to have an excellent photostability in several solvents. DFT calculations were found in agreement with the experimental data and helped to understand the stabilizing intramolecular charge-transfer process from the first excited state. The new fluorescent derivative could be applied as selective bioprobe in several cell lines and displayed plasma-membrane affinity during the imaging experiments for all tested models.