Multifunctional fluorescent leucomalachite green derivatives for chemodosimetric detection of Fe3+, specific imaging of lipid droplets and intracellular pH monitoring

Abstract

Three multifunctional leucomalachite green derivatives, namely BDPMBD, BInMBD and InMBD, having fluorogenic substituents on one of the phenyl rings have been synthesized and their properties were evaluated. They exhibited multifunctional properties such as selective detection of Fe³⁺, specific staining of lipid droplets and also acted as fluorescent probes for monitoring intracellular pH variations in microorganisms. Fe³⁺-mediated oxidation of these molecules to the corresponding malachite green derivatives altered their absorption/emission behaviour and these changes allowed the selective detection of Fe³⁺. The limits of detection (LOD) were estimated as 0.281 μM, 5.8 μM and 4.6 μM, respectively, for BDPMBD, BInMBD, and InMBD. The cellular uptake of these molecules was then studied in yeast, HeLa and DLD (human colon adenocarcinoma) cells. They showed efficient internalization and localization primarily in the lipid droplets, which was confirmed via co-staining with lipid droplet specific dye Nile red. Since these compounds showed pH-dependent emission switching, they were also used for monitoring intracellular pH variations in yeast, Gram-positive and Gram-negative bacteria.