Indolylbenzothiadiazoles as highly tunable fluorophores for imaging lipid droplet accumulation in astrocytes and glioblastoma cells

Abstract

We present an extensive photophysical study of a series of fluorescent indolylbenzothiadiazole derivatives and their ability to specifically image lipid droplets in astrocytes and glioblastoma cells.

Photophysical characterization and fluorescence cell imaging applications of 4-N-substituted benzothiadiazoles

“…Measurements in solvents of different polarity revealed strong solvatochromism, large Stokes shis and uorescence quenching with increasing solvent polarity. Three compounds (11)(12)(13) were successfully applied as uorescent probes for imaging lipid droplets in melanoma and breast cancer cells. These dyes displayed high signal-to-background ratios, in both live and xed cells, and their lipid droplet specicity was found to correlate with high lipophilicity (log P $ 4).…”

“…[5][6][7][8][9][10] Recently, the BTD-motif has also shown its potential as a bioimaging scaffold for uorescence cell microscopy. 2,3 Our contribution to the latter has been the development of BTD-based dyes that specically stain intracellular lipid droplets (LDs), [11][12][13] lipid-rich organelles that are strongly associated with cancer progression and cancer cell survival. [14][15][16][17] LDs serve as a biomarker for cancer diagnosis and prognosis and their relative quantity can be used as a measure for therapeutic response.…”

“…Photophysical data of the 4-amino-and 4-amido-substituted BTD derivatives(1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) in solvents of different polarity…”

Fluorescent Benzothiadiazole Derivatives as Fluorescence Imaging Dyes: A Decade of New Generation Probes

“…(BTD-Ind, Figure 9) capable of LDs staining. [125] The photophysical properties could be efficiently tuned by the proper choice of the R 1 and R 2 group (see BTD-Ind structure in Figure 9) and these groups were responsible for different torsion angles between the BTD core and the substituents. Steric and electronic effects played a role in the photo response of the fluorophores.…”

“…Dyrager and co‐workers recently disclosed a series of mono‐ and disubstituted hybrid fluorescent indolyl‐BTD derivatives ( BTD‐Ind , Figure 9) capable of LDs staining [125] . The photophysical properties could be efficiently tuned by the proper choice of the R 1 and R 2 group (see BTD‐Ind structure in Figure 9) and these groups were responsible for different torsion angles between the BTD core and the substituents.…”