Plasma membrane imaging with a fluorescent benzothiadiazole derivative

Pedro H P R Carvalho; Jose R Correa; Karen L R Paiva; Daniel F S Machado; Jackson D Scholten; Brenno A D Neto

doi:10.3762/bjoc.15.257

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

Beilstein J Org Chem. 2019 Nov 6:15:2644-2654. doi: 10.3762/bjoc.15.257. eCollection 2019.

Authors

Pedro H P R Carvalho^{1

2}, Jose R Correa¹, Karen L R Paiva¹, Daniel F S Machado¹, Jackson D Scholten², Brenno A D Neto^{1

2}

Affiliations

¹ Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), Campus Universitário Darcy Ribeiro, Brasília, Distrito Federal, 70904-970, Brazil.
² Laboratory of Molecular Catalysis, Institute of Chemistry, Graduate Program (PPGQ), Universidade Federal do Rio Grande do Sul, Porto Alegre, RS, 91501-970, Brazil.

Abstract

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.

Keywords: benzothiadiazole; bioprobe; cell imaging; fluorescence; mitochondria; molecular architecture; plasma membrane.