Acid selective pro-dye for cellular compartments

Czaplińska, Barbara; Malarz, Katarzyna; Mrozek-Wilczkiewicz, Anna; Musioł, Robert

doi:10.1038/s41598-019-50734-8

Cited by 11 publications

(5 citation statements)

References 42 publications

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“…It should be noted here that this type of decomposition does not always disturb the applications in water-based environments, e.g., biological systems. Recently, we published a report on the application of a pH-sensitive Schiff base, as a cellular probe for staining lysosomes [48].…”

Section: Influence Of Water On the Spectroscopic Propertiesmentioning

confidence: 99%

Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold

et al. 2020

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A series of novel styrylquinolines with the benzylidene imine moiety were synthesized and spectroscopically characterized for their applicability in cellular staining. The spectroscopic study revealed absorption in the ultraviolet–visible region (360–380 nm) and emission that covered the blue-green range of the light (above 500 nm). The fluorescence quantum yields were also determined, which amounted to 0.079 in the best-case scenario. The structural features that are behind these values are also discussed. An analysis of the spectroscopic properties and the theoretical calculations indicated the charge-transfer character of an emission, which was additionally evaluated using the Lippert–Mataga equation. Changes in geometry in the ground and excited states, which had a significant influence on the emission process, are also discussed. Additionally, the capability of the newly synthesized compounds for cellular staining was also investigated. These small molecules could effectively penetrate through the cellular membrane. Analyses of the images that were obtained with several of the tested styrylquinolines indicated their accumulation in organelles such as the mitochondria and the endoplasmic reticulum.

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Section: Influence Of Water On the Spectroscopic Propertiesmentioning

confidence: 99%

Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold

et al. 2020

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“…Additionally, nuclei were stained with Hoechst 33342 (Invitrogen), mitochondria with MitoTracker Green or Orange, and lysosomes with LysoTracker Yellow HCK-123 according to previously described protocols. 38 The MCF-7 cells were washed three times with PBS and mounted with DMEM without FBS or phenol red. Cellular imaging was performed using the CellInsight CX7 High Content Analysis Platform under an appropriate filter for the click reaction or dyes used and a 40× objective.…”

Section: Methodsmentioning

confidence: 99%

“…After this time, the cells were washed twice with PBS and incubated with click reaction reagents SC5 (25 μM) or HCA (25 μM), CuSO 4 (1 mM), and TCEP (1 mM) for 2 h at 37 °C. Additionally, nuclei were stained with Hoechst 33342 (Invitrogen), mitochondria with MitoTracker Green or Orange, and lysosomes with LysoTracker Yellow HCK-123 according to previously described protocols . The MCF-7 cells were washed three times with PBS and mounted with DMEM without FBS or phenol red.…”

Section: Methodsmentioning

confidence: 99%

In Situ Cellular Localization of Nonfluorescent [60]Fullerene Nanomaterial in MCF-7 Breast Cancer Cells

Serda

Malarz

Korzuch

et al. 2022

ACS Biomater. Sci. Eng.

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Cellular localization of carbon nanomaterials in cancer cells is essential information for better understanding their interaction with biological targets and a crucial factor for further evaluating their biological properties as nanovehicles or nanotherapeutics. Recently, increasing efforts to develop promising fullerene nanotherapeutics for cancer nanotechnology have been made. However, the main challenge regarding studying their cellular effects is the lack of effective methods for their visualization and determining their cellular fate due to the limited fluorescence of buckyball scaffolds. Herein, we developed a method for cellular localization of nonfluorescent and water-soluble fullerene nanomaterials using the in vitro click chemistry approach. First, we synthesized a triple-bonded fullerene probe (TBC 60 ser), which was further used as a starting material for 1,3-dipolar cycloaddition using 3-azido-7-hydroxycoumarin and sulfo-cyanine5 azide fluorophores to create fluorescent fullerene triazoles. In this work, we characterized the structurally triple-bonded [60]fullerene derivative and confirmed its high symmetry ( T h ) and the successful formation of fullerene triazoles by spectroscopic techniques (i.e., ultraviolet–visible, fluorescence, and Fourier transform infrared spectroscopies) and mass spectrometry. The created fluorescent fullerene triazoles were successfully localized in the MCF-7 breast cancer cell line using fluorescent microscopy. Overall, our findings demonstrate that TBC 60 ser localizes in the lysosomes of MCF-7 cells, with only a small affinity to mitochondria.

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“…19 The acidification of endosomes is attributed to proton transfer from the cytoplasm to the lumen through proton pumps and vacuolar H + -ATPase (V-ATPase). 20,21 BafA1 inhibits V-ATPase function, preventing LC translocation and thereby delaying botulism-induced muscle paralysis. 9,19 Monensin and nigericin are also protonophores and act as H + shunts known to delay onset times of BoNT/A-and BoNT/B-treated muscles at low concentrations.…”

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confidence: 99%

“…Several types of small molecule inhibitors of BoNT have been studied, including cellular receptor binding plant- and animal-based lectins and heavy chain (HC) binding synthetic G T1b -based glycoconjugate antagonists; , reversible, − slow-binding, and irreversible , (covalent) inhibitors of the LC active site; LC exosite (α and β) inhibitors; , pH-dependent translocation antagonists. , In particular, bafilomycin A1 (BafA1) is known to inhibit BoNT (A–G) and tetanus toxin translocation by preventing endosomal acidification . The acidification of endosomes is attributed to proton transfer from the cytoplasm to the lumen through proton pumps and vacuolar H + -ATPase (V-ATPase). , BafA1 inhibits V-ATPase function, preventing LC translocation and thereby delaying botulism-induced muscle paralysis. , …”

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confidence: 99%

Investigation of Salicylanilides as Botulinum Toxin Antagonists

et al. 2022

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Botulinum neurotoxin serotype A (BoNT/A) is recognized by the Centers for Disease Control and Prevention (CDC) as the most potent toxin and as a Tier 1 biowarfare agent. The severity and longevity of botulism stemming from BoNT/A is of significant therapeutic concern, and early administration of antitoxin–antibody therapy is the only approved pharmaceutical treatment for botulism. Small molecule therapeutic strategies have targeted both the heavy chain (HC) and the light chain (LC) catalytic active site and α-/β-exosites. The LC translocation mechanism has also been studied, but an effective, nontoxic inhibitor remains underexplored. In this work, we screened a library of salicylanilides as potential translocation inhibitors. Potential leads following a primary screen were further scrutinized to identify sal30, which has a cellular minimal concentration of a drug that is required for 50% inhibition (IC50) value of 141 nM. The inquiry of salicylanilide sal30’s mechanism of action was explored through a self-quenched fluorogenic substrate conjugated to bovine serum albumin (DQ-BSA) fluorescence, confocal microscopy, and vacuolar H+-ATPase (V-ATPase) inhibition assays. The summation of these findings imply that endolysosomal proton translocation through the protonophore mechanism of sal30 causes endosome pH to increase, which in turn prevents LC translocation into cytosol, a process that requires an acidic pH. Thus, the inhibition of BoNT/A activity by salicylanilides likely occurs through disruption of pH-dependent endosomal LC translocation. We further probed BoNT inhibition by sal30 using additivity analysis studies with bafilomycin A1, a known BoNT/A LC translocation inhibitor, which indicated the absence of synergy between the two ionophores.

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Acid selective pro-dye for cellular compartments

Cited by 11 publications

References 42 publications

Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold

Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold

In Situ Cellular Localization of Nonfluorescent [60]Fullerene Nanomaterial in MCF-7 Breast Cancer Cells

Investigation of Salicylanilides as Botulinum Toxin Antagonists

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