Preferential Mitochondrial Localization of a Goniothalamin Fluorescent Derivative

Abstract

A fluorescent 2,1,3-benzothiadiazole-containing goniothalamin derivative, BTD−GTN (1), has been synthesized and successfully tested in bioimaging experiments in live cells. The fluorescent compound proved to be capable of transposing the cell membranes, indicating its subcellular localization. The use of the benzothiadiazole core as the fluorophore revealed the favored localization of the GTN analogue 1 in the cytoplasm of live cells, preferentially in the mitochondria, in line with previous results that indicated the loss of mitochondrial transmembrane potential upon treatment with GTN. The results described herein highlight the potential of the BTD–GTN hybrid structures for future studies regarding the cellular mechanism of action of this family of compounds.

Combined Goniothalamin And Sol-Gel Derived Bioactive Glass 45S5 Enhances Growth Inhibitory Activity Via Apoptosis Induction And Cell Cycle Arrest In Breast Cancer Cells MCF-7

“…A study conducted by Boonmuen et al, 2016 found that 5-acetyl goniothalamin (5GTN), a natural derivative of GTN was more potent than GTN in mediating the toxicity towards MCF-7 and MDA-MB-2 breast cancer cells (27). Besides, a uorescent 2,1,3-benzothiadiazole-containing goniothalamin derivative, BTD − GTN (1) hybrid, was successfully synthesised in an investigation to gain insights into the subcellular localisation and mechanism of action of MDA-MB-231 cells, which might involve a cascade of events, starting with their interaction with mitochondria (29). In a recent study, a polymeric nanosystem, in which the racemic mixture of GTN (rac-GTN) was encapsulated in pH-responsive acetalated dextran (Ac-Dex) nanoparticles (NPs), has been developed to improve the pharmacokinetic behaviour and selectivity of GTN against cancer cells including MCF-7 and MDA-MB-231 cells (30).…”

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

“…Bioimaging experiments. The bioimaging experiments were performed in a similar manner to a procedure which have already been published elsewhere [65]. Cells were seeded on 13 mm round glass coverslips on the bottom of a 24-well plate and allowed to adhere overnight.…”

When the strategies for cellular selectivity fail. Challenges and surprises in the design and application of fluorescent benzothiadiazole derivatives for mitochondrial staining

“…37 For instance, reactive oxygen species (ROS) imbalances may be a consequence of specific mitochondrial labelling by a new fluorophore, but this issue is not addressed when a new mitochondrial marker is published, unless the bioprobe is developed to detect ROS, as described in several and recent examples. [38][39][40][41][42][43][44][45][46][47][48] We have already disclosed some mitochondrial markers such as fluorescent peptoids, 49 lapachone-based structures, 50 Goniothalamin derivative, 51 multicomponent adducts 52 and benzothiadiazole derivatives. 53 2,1,3-Benzothiadiazole (BTD) is a new class of fluorescent cell markers, as we have disclosed elsewhere.…”