Tripodal cyanurates as selective transmembrane Cl<sup>−</sup> transporters

Mondal, Debashis; Sathyan, Anjana; Shinde, Sopan; Mishra, Kamal K.; Talukdar, Pinaki

doi:10.1039/c8ob01345d

Cited by 23 publications

(17 citation statements)

References 37 publications

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“…Then valinomycin was added along with 1b to monitor their cooperative effect. [10] Thei on transport rate in the absence and presence were comparable ( Figure 2F)t hat suggests the lack of cooperative transport by valinomycin and 1b.I n addition to this,the effect of different cations on the chloride efflux was also checked by varying the external cations, [28] which also supported KCl cotransport mechanism (Figure S17 C). To reassure that the M + /Cl À symport mechanism is operating in the transport process,t he EYPC liposomes, entrapping NaCl (200 mm)and 1.0 mm of lucigenin dye,were prepared.…”

Section: Ion Transport Studiesmentioning

confidence: 53%

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

et al. 2020

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Cancer cells use elevated glutathione (GSH) levels as an inner line of defense to evade apoptosis and develop drug resistance.Inthis study,wedescribe anovel 2,4-nitrobenzenesulfonyl (DNS) protected 2-hydroxyisophthalamide system that exploits GSH for its activation into free 2-hydroxyisophthalamide forming supramolecular M + /Cl À channels.Better permeation of the DNS protected compound into MCF-7 cells compared to the free 2-hydroxyisophthalamide and GSHactivatable ion transport resulted in higher cytotoxicity,w hich was associated with increased oxidative stress that further reduced the intracellular GSH levels and altered mitochondrial membrane permeability leading to the induction of the intrinsic apoptosis pathway.T he GSH-activatable transport-mediated cell death was further validated in rat insulinoma cells (INS-1E);w herein the intracellular GSH levels showed ad irect correlation to the resulting cytotoxicity.L astly,t he active compound was found to restrict the growth and proliferation of 3D spheroids of MCF-7 cells with efficiency similar to that of the anticancer drug doxorubicin.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under https://doi.

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Section: Ion Transport Studiesmentioning

confidence: 53%

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

et al. 2020

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“…This cooperativity between the two is only possible if the transport process by an anionophore 1 a occurs through an electrogenic mode and hence can be accelerated by the presence of cationophore like valinomycin. Hence, these results suggest that the transport process in lucigenin assay occurs through Cl − /NO 3 − antiport mode [18] …”

Section: Resultsmentioning

confidence: 69%

“…Hence, these results suggest that the transport process in lucigenin assay occurs through Cl À /NO 3 À antiport mode. [18] The antiport mechanism was further supported with a modified lucigenin essay. LUVs were entrapped with NaCl (200 mM) and 1 mM of lucigenin dye.…”

Section: Resultsmentioning

confidence: 88%

Reversible Stimuli‐Responsive Transmembrane Ion Transport Using Phenylhydrazone‐Based Photoswitches

et al. 2022

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Phenylhydrazone‐based synthetic receptors are reported as stimuli‐responsive anion transporters. The X‐ray crystallographic studies confirmed the preorganized anion binding E‐state and closed non‐binding Z‐state. The detailed ion transport mechanistic studies confirmed Cl−/anion exchange as the primary ion transport process. Their light‐stimulated E‐to‐Z isomerization led to a substantial decrease in the ion transport activity across the lipid bilayer membrane. Reversible “OFF” and “ON” activity switching was studied by light and acid stimuli, respectively.

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“…The ion transport rate in the absence and presence were comparable (Figure F) that suggests the lack of cooperative transport by valinomycin and 1 b . In addition to this, the effect of different cations on the chloride efflux was also checked by varying the external cations, which also supported KCl cotransport mechanism (Figure S17 C). To reassure that the M + /Cl − symport mechanism is operating in the transport process, the EYPC liposomes, entrapping NaCl (200 m m ) and 1.0 m m of lucigenin dye, were prepared.…”

Section: Resultsmentioning

confidence: 99%

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

et al. 2020

Self Cite

View full text Add to dashboard Cite

Cancer cells use elevated glutathione (GSH) levels as an inner line of defense to evade apoptosis and develop drug resistance. In this study, we describe a novel 2,4‐nitrobenzenesulfonyl (DNS) protected 2‐hydroxyisophthalamide system that exploits GSH for its activation into free 2‐hydroxyisophthalamide forming supramolecular M+/Cl− channels. Better permeation of the DNS protected compound into MCF‐7 cells compared to the free 2‐hydroxyisophthalamide and GSH‐activatable ion transport resulted in higher cytotoxicity, which was associated with increased oxidative stress that further reduced the intracellular GSH levels and altered mitochondrial membrane permeability leading to the induction of the intrinsic apoptosis pathway. The GSH‐activatable transport‐mediated cell death was further validated in rat insulinoma cells (INS‐1E); wherein the intracellular GSH levels showed a direct correlation to the resulting cytotoxicity. Lastly, the active compound was found to restrict the growth and proliferation of 3D spheroids of MCF‐7 cells with efficiency similar to that of the anticancer drug doxorubicin.

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Tripodal cyanurates as selective transmembrane Cl⁻ transporters

Abstract: Tris-carboxyamide and tris-sulfonamide-based anion receptors with cyanuric acid core are developed for transmembrane chloride transport.

Cited by 23 publications

References 37 publications

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

Reversible Stimuli‐Responsive Transmembrane Ion Transport Using Phenylhydrazone‐Based Photoswitches

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

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Tripodal cyanurates as selective transmembrane Cl− transporters

Abstract: Tris-carboxyamide and tris-sulfonamide-based anion receptors with cyanuric acid core are developed for transmembrane chloride transport.

Cited by 23 publications

References 37 publications

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

Reversible Stimuli‐Responsive Transmembrane Ion Transport Using Phenylhydrazone‐Based Photoswitches

A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels

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Tripodal cyanurates as selective transmembrane Cl⁻ transporters