Click-tambjamines as efficient and tunable bioactive anion transporters

Carreira-Barral, Israel; Mielczarek, Marcin; Alonso-Carrillo, Daniel; Capurro, Valeria; Soto‐Cerrato, Vanessa; Pérez-Tomás, Ricardo; Caci, Emanuela; Garcı́a-Valverde, Marı́a; Quesada, Roberto

doi:10.1039/d0cc00643b

Cited by 23 publications

(31 citation statements)

References 32 publications

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“…The transporters (33 c-33 h) changed the internal pH regulation which subsequently resulted in apoptosis in GLC4 cancer cell line. Inspired by the anticancer activities revealed by these transporters, the authors developed a series of "drug-like" indole based anion transporters (35)(36)(37), whose lipophilicity and transport activity were dependent on the trifluoromethyl functionalisation (Figure 10C). [41] The In vitro fluorescence and viability assay displayed that the most active transporter can be utilized as an anticancer agent by killing human melanoma A375 cancer cell line via apoptosis.…”

Section: Acyclic Anionophores Based On Urea and Thioureamentioning

confidence: 99%

“…Quesada and colleagues reported a new series of anionophores, called ‘click tambjamines’ ( 29 a – 29 i ). [35] In this design, one of the pyrrole groups of the 4‐methoxy‐2,2′‐bipyrrole core of the natural tambjamines was replaced by a 1,2,3‐ triazole ring. Few of these molecules showed significant anion transport across the liposomal membrane and displayed moderate IC 50 values (3.5 to 10.7 μM), determined on human lung (A549), breast adenocarcinoma (MCF7) and mammary epithelial (MCF10 A) cell lines.…”

Section: Anionophores and Their Biological Studiesmentioning

confidence: 99%

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Recent Advances in Bioactive Artificial Ionophores

Roy

Talukdar

2021

ChemBioChem

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Several life-threatening diseases, also known as 'Channelopathies' are linked to irregularities in ion transport proteins. Significant research efforts have fostered the development of artificial transport systems that facilitates to restore the functions of impaired natural transport proteins. Indeed, a few of these artificial ionophores demonstrate the rare combination of transmembrane ion transport and important biological activity, offering early promises of suitability in 'channel replacement therapy'. In this review, structural facets and functions of both cationophores and anionophores are discussed. Iono-phores that are toxic to various bacteria and yeast, could be exploited as antimicrobial agent. Nevertheless, few non-toxic ionophores offer the likelihood of treating a wide range of genetic diseases caused by the gene mutations. In addition, their ability to disrupt cellular homeostasis and to alter lysosomal pH endow ionophores as promising candidates for cancer treatment. Overall, critically outlining the advances in artificial ionophores in terms of in vitro ion transport, possible modes of action and biological activities enables us to propose possible future roadmaps in this research area.

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Section: Acyclic Anionophores Based On Urea and Thioureamentioning

confidence: 99%

Section: Anionophores and Their Biological Studiesmentioning

confidence: 99%

Recent Advances in Bioactive Artificial Ionophores

Roy

Talukdar

2021

ChemBioChem

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“…Usually, both are made up of NaCl (100 mM), but it is not uncommon to find works in the literature where M is Li + , Na + , K + , Rb + , Cs + or NMDG + and X is F -, Cl -, Br -, I -, NO3 -, AcO -, SCNor ClO4 -. 15,31,43,45 The intra-and extravesicular media composition may be dissimilar depending on the purpose of the experiment (pH, anion or dual gradient assay); however, regardless of the composition, the total ionic strength of both solutions must remain constant throughout a typical experiment.…”

Section: The Saltsmentioning

confidence: 99%

Supramolecular methods: the 8-hydroxypyrene-1,3,6-trisulfonic acid (HPTS) transport assay

Gilchrist

Wang

Carreira-Barral

et al. 2021

Preprint

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The vesicular anion transport activity assay, which uses 8-hydroxypyrene-1,3,6-trisulfonic acid to monitor the internal pH of the vesicles (the HPTS assay), is a widely used technique for analysing the activity of anionophore facilitated transport across a phospholipid membrane. This methods paper describes the stepwise technique to conduct this transport assay, detailing both the perks and pitfalls of using this method to determine the activity of an anionophore and the transport mechanism.

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“…Although the mode of action of tambjamines has not been elucidated yet, it seems to be closely linked to its ability to act as anion transporters, a feature that is also shared by prodiginines [ 20 , 23 ]. Furthermore, the mitochondria of T. cruzi have been regarded as a potential target, since alterations in the mitochondria have catastrophic effects on respiration and, subsequently, on the survival of the parasite [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Tambjamines and Prodiginines: Biocidal Activity against Trypanosoma cruzi

et al. 2021

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The aim of this work was to explore new therapeutic options against Chagas disease by the in vitro analysis of the biocidal activities of several tambjamine and prodiginine derivatives, against the Trypanosoma cruzi CLB strain (DTU TcVI). The compounds were initially screened against epimastigotes. The five more active compounds were assayed in intracellular forms. The tambjamine MM3 and both synthetic and natural prodigiosins displayed the highest trypanocidal profiles, with IC50 values of 4.52, 0.46, and 0.54 µM for epimastigotes and 1.9, 0.57, and 0.1 µM for trypomastigotes/amastigotes, respectively. Moreover, the combination treatment of these molecules with benznidazole showed no synergism. Finally, oxygen consumption inhibition determinations performed using high-resolution respirometry, revealed a potent effect of prodigiosin on parasite respiration (73% of inhibition at ½ IC50), suggesting that its mode of action involves the mitochondria. Moreover, its promising selectivity index (50) pointed out an interesting trypanocidal potential and highlighted the value of prodigiosin as a new candidate to fight Chagas disease.

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Click-tambjamines as efficient and tunable bioactive anion transporters

Abstract: A novel class of transmembrane anion carriers, the click-tambjamines, display remarkable anionophoric activities in model liposomes and living cells.

Cited by 23 publications

References 32 publications

Recent Advances in Bioactive Artificial Ionophores

Recent Advances in Bioactive Artificial Ionophores

Supramolecular methods: the 8-hydroxypyrene-1,3,6-trisulfonic acid (HPTS) transport assay

Tambjamines and Prodiginines: Biocidal Activity against Trypanosoma cruzi

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