A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Cd<sup>2+</sup>and Zn<sup>2+</sup>

Park, Sun Young; Yoon, Jung Hee; Hong, Chang Seop; Souane, Rachid; Kim, Jong Seung; Matthews, Susan E.; Vicens, Jacques

doi:10.1021/jo8012918

Cited by 297 publications

(117 citation statements)

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“…The two diamidines 30 a and 30 b were obtained using the Pinner methodology in 71 % and 66 % yields, respectively. [35][36][37] For the 2,4-disubstituted series (Scheme 5), 4-phenylethynylbenzonitrile (32) was formed in 98 % yield using the Sonogashira methodology between 4-bromobenzonitrile (21) and phenylacetylene (31) in the presence of palladium(II) and copper(I) iodide in dry triethylamine. [47] The triazole unit was then prepared by reaction between nitrile 32 and sodium azide in DMF.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Antimalarial Activities of a Diverse Set of Triazole‐Containing Furamidine Analogues

Berger

Kaniti

et al. 2011

ChemMedChem

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Four different series of triazole diamidines have been prepared by the Pinner method from the corresponding triazole dinitriles. Copper-catalyzed "click chemistry" was used for the synthesis of 1,4- and 4,5-substituted triazoles, aryl magnesium acetylide reagents for the 1,5-substituted triazoles, with a thermal dipolar addition reaction employed for the 2,4-substituted triazoles. In vitro antimalarial activity against two different PfCRT-modified parasite lines (Science 2002, 298, 210-213) of Plasmodium falciparum and inhibition of hemozoin formation were determined for each compound. Several diamidines with potent nanomolar antimalarial activities were identified, and selected molecules were resynthesized as their diamidoxime triazole prodrugs. One of these prodrugs, OB216, proved to be highly potent in vivo with an ED50 value of 5 mg kg(-1) (po) and an observed 100 % cure rate (CD100) of just 10 mg kg(-1) by oral (po) administration in mice infected with P. vinckei.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and Antimalarial Activities of a Diverse Set of Triazole‐Containing Furamidine Analogues

Berger

Kaniti

et al. 2011

ChemMedChem

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“…In particular the ability of derivatives to complex anions (2,3) and cations (4,5) has been exploited for the development of sensors. Recently, interest has focused on the use of calixarene derivatives in biological systems be it as drugs, drug delivery systems, or imaging agents.…”

mentioning

confidence: 99%

Stable and sensitive probes for lysosomes: Cell‐penetrating fluorescent calix[4]arenes accumulate in acidic vesicles

et al. 2010

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The uptake of a fluorescently labeled cationic calix [4] (NBDCalAm) in live, nonfixed cells has been investigated. The compound is taken into the cells rapidly and shows distinct endosomal distribution after 2 hours. This distribution pattern shows colocalization with lysosomal staining. The uptake is not altered by inhibition of clathrin or caveolae dependent pathways nor by depletion of the cellular ATP-pool. Immediately after uptake the probe is localized in the Golgi and brefeldin A treatment prevents transport to lysosomes. Pulse chase experiments with bafilomycin A1, monensin, and sodium azide showed that accumulation and retention of the probe in lysosomes is primarily driven by the activity of vacuolar ATPases. The NBD labeled calix[4]arene provides a very stable and sensitive marker for lysosomes, and has a considerable advantage over some commercially available lysosomal markers in so far that the fluorescent signal is stable even when the cells are incubated in dye-free medium after staining. ' 2010 International Society for Advancement of Cytometry Key termslysosome; calixarene; cell-penetration; immunofluorescence CALIXARENES (1) are a family of readily synthesized and functionalized macrocycles which have found applications in a number of research areas. In particular the ability of derivatives to complex anions (2,3) and cations (4,5) has been exploited for the development of sensors. Recently, interest has focused on the use of calixarene derivatives in biological systems be it as drugs, drug delivery systems, or imaging agents. In the design of drug molecules, particular attention has been paid to calixarenes as antimicrobials (6-8), as vaccines (9) and as anticancer agents (10). In the field of drug delivery, agents for nucleic acids based on single calixarenes (11-13) have shown promise and we have recently shown that larger arrays of cationic calix[4]arene, so-called multicalixarenes, are able to transfect DNA effectively (14). In addition a number of studies have combined the ability of calixarene derivatives to complex cations with their low toxicity in the development of noncovalently labeled protein MRI imaging agents (15,16).While the nontoxic (17) and non-immunogenicity (18,19) status of calixarenes has been established, less information is available on how calixarenes are processed within cells and their cellular fate, both of which are important features which must be characterized before such derivatives are taken further for clinical development. We recently demonstrated that fluorescently labeled calix [4]arene have the potential to track progress of the macrocycle in cells, as an NBD labeled cationic derivative was readily and speedily taken up into cells and provided a very stable, nontoxic read-out system to investigate cellular localization (20). The absorbance and emission spectra for the NBDCalAm showed that it can easily be visualized using a GFP filter (20).

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“…The past few years have witnessed a few numbers of sensory reports on the design and synthesis of fluorescent chemosensors for the detection of Cd II ions [29][30][31][32][33], and among them, Cd IItriggered monomer-excimer conversion is limited [34]. For the first time, we report Cd II -induced excimer formation of a biological photosensitizer, kynurenic acid (Scheme 1), a renowned antiexcitotoxic and anticonvulsant drug which is an end product of the normal metabolism of amino acid l-tryptophan [35].…”

Section: Introductionmentioning

confidence: 99%

A simple but highly selective and sensitive fluorescence reporter for toxic CdII ion via excimer formation

Samanta

Guchhait

Bhattacharya

2014

Chemical Physics Letters

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A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Cd²⁺and Zn²⁺

Cited by 297 publications

References 89 publications

Synthesis and Antimalarial Activities of a Diverse Set of Triazole‐Containing Furamidine Analogues

Synthesis and Antimalarial Activities of a Diverse Set of Triazole‐Containing Furamidine Analogues

Stable and sensitive probes for lysosomes: Cell‐penetrating fluorescent calix[4]arenes accumulate in acidic vesicles

A simple but highly selective and sensitive fluorescence reporter for toxic CdII ion via excimer formation

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A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Cd2+and Zn2+

Cited by 297 publications

References 89 publications

Synthesis and Antimalarial Activities of a Diverse Set of Triazole‐Containing Furamidine Analogues

Synthesis and Antimalarial Activities of a Diverse Set of Triazole‐Containing Furamidine Analogues

Stable and sensitive probes for lysosomes: Cell‐penetrating fluorescent calix[4]arenes accumulate in acidic vesicles

A simple but highly selective and sensitive fluorescence reporter for toxic CdII ion via excimer formation

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A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Cd²⁺and Zn²⁺